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Endosulfan
Endosulfan
is an off-patent organochlorine insecticide and acaricide that is being phased out globally. The two isomers, endo and exo, are known popularly as I and II. Endosulfan
Endosulfan
sulfate is a product of oxidation containing one extra O atom attached to the S atom. Endosulfan
Endosulfan
became a highly controversial agrichemical[2] due to its acute toxicity, potential for bioaccumulation, and role as an endocrine disruptor. Because of its threats to human health and the environment, a global ban on the manufacture and use of endosulfan was negotiated under the Stockholm Convention
Stockholm Convention
in April 2011. The ban has taken effect in mid-2012, with certain uses exempted for five additional years.[3] More than 80 countries,[4] including the European Union, Australia, New Zealand, several West African nations,[5] the United States,[6][7] Brazil,[8] and Canada[9] had already banned it or announced phase-outs by the time the Stockholm Convention
Stockholm Convention
ban was agreed upon. It is still used extensively in India, China, and few other countries. It is produced by Makhteshim Agan
Makhteshim Agan
and several manufacturers in India and China. Although, the Supreme Court had, by an order dated 13.05.2011, put a ban on the production and sale of endosulfan in India till further orders.[10]

Contents

1 Uses 2 Production 3 History of commercialization and regulation 4 Health effects

4.1 Toxicity 4.2 Endocrine disruption 4.3 Reproductive and developmental effects 4.4 Endosulfan
Endosulfan
and cancer

5 Environmental fate 6 Status by region

6.1 India 6.2 New Zealand 6.3 Philippines 6.4 United States 6.5 Australia 6.6 Taiwan 6.7 Brazil

7 References 8 External links

Uses[edit] Endosulfan
Endosulfan
has been used in agriculture around the world to control insect pests including whiteflies, aphids, leafhoppers, Colorado potato beetles and cabbage worms.[11] Due to its unique mode of action, it is useful in resistance management; however, as it is not specific, it can negatively impact populations of beneficial insects.[12] It is, however, considered to be moderately toxic to honey bees,[13] and it is less toxic to bees than organophosphate insecticides.[14] Production[edit] The World Health Organization
World Health Organization
estimated worldwide annual production to be about 9,000 metric tonnes (t) in the early 1980s.[15] From 1980 to 1989, worldwide consumption averaged 10,500 tonnes per year, and for the 1990s use increased to 12,800 tonnes per year. Endosulfan
Endosulfan
is a derivative of hexachlorocyclopentadiene, and is chemically similar to aldrin, chlordane, and heptachlor. Specifically, it is produced by the Diels-Alder reaction of hexachlorocyclopentadiene with cis-butene-1,4-diol and subsequent reaction of the adduct with thionyl chloride. Technical endosulfan is a 7:3 mixture of stereoisomers, designated α and β. α- and β- Endosulfan
Endosulfan
are configurational isomers arising from the pyramidal stereochemistry of the teravalent sulfur. α- Endosulfan
Endosulfan
is the more thermodynamically stable of the two, thus β-endosulfan irreversibly converts to the α form, although the conversion is slow.[16][17] History of commercialization and regulation[edit]

Early 1950s: Endosulfan
Endosulfan
was developed. 1954: Hoechst AG
Hoechst AG
(now Sanofi) won USDA approval for the use of endosulfan in the United States.[18] 2000: Home and garden use in the United States was terminated by agreement with the EPA.[14] 2002: The U.S. Fish and Wildlife Service
U.S. Fish and Wildlife Service
recommended that endosulfan registration should be cancelled,[19] and the EPA determined that endosulfan residues on food and in water pose unacceptable risks. The agency allowed endosulfan to stay on the US market, but imposed restrictions on its agricultural uses.[14] 2007: International steps were taken to restrict the use and trade of endosulfan. It is recommended for inclusion in the Rotterdam Convention on Prior Informed Consent,[20] and the European Union proposed inclusion in the list of chemicals banned under the Stockholm Convention on Persistent Organic Pollutants. Such inclusion would ban all use and manufacture of endosulfan globally.[21] Meanwhile, the Canadian government announced that endosulfan was under consideration for phase-out,[22] and Bayer CropScience voluntarily pulled its endosulfan products from the U.S. market[23] but continues to sell the products elsewhere.[24] 2008: In February, environmental, consumer, and farm labor groups including the Natural Resources Defense Council,[25] Organic Consumers Association, and the United Farm Workers[26] called on the U.S. EPA to ban endosulfan. In May, coalitions of scientists,[27] environmental groups, and arctic tribes asked the EPA to cancel endosulfan,[28] and in July a coalition of environmental and workers groups filed a lawsuit against the EPA challenging its 2002 decision to not ban it.[29] In October, the Review Committee of the Stockholm Convention moved endosulfan along in the procedure for listing under the treaty,[30] while India blocked its addition to the Rotterdam Convention.[31] 2009: The Stockholm Convention's Persistent Organic Pollutants Review Committee (POPRC) agreed that endosulfan is a persistent organic pollutant and that "global action is warranted", setting the stage of a global ban.[32] New Zealand banned endosulfan.[33] 2010: The POPRC nominated endosulfan to be added to the Stockholm Convention at the Conference of Parties (COP) in April 2011, which would result in a global ban.[34] The EPA announced that the registration of endosulfan in the U.S. will be cancelled[7][35] Australia
Australia
banned the use of the chemical.[36] 2011: The Supreme Court of India
Supreme Court of India
banned manufacture, sale, and use of toxic pesticide endosulfan in India. The apex court said the ban would remain effective for eight weeks during which an expert committee headed by DG, ICMR, will give an interim report to the court about the harmful effect of the widely used pesticide.[37] 2011: the Argentinian Service for Sanity and Agroalimentary Quality (SENASA) decided on August 8 that the import of endosulfan into the South American country will be banned from July 1, 2012 and its commercialization and use from July 1, 2013. In the meantime, a reduced quantity can be imported and sold.[38]

Health effects[edit] Endosulfan
Endosulfan
is one of the most toxic pesticides on the market today[citation needed], claimed to be responsible for many fatal pesticide poisoning incidents around the world.[39] Endosulfan
Endosulfan
is also a xenoestrogen—a synthetic substance that imitates or enhances the effect of estrogens—and it can act as an endocrine disruptor, causing reproductive and developmental damage in both animals and humans.[40] It has also been found to act as an aromatase inhibitor.[40] Whether endosulfan can cause cancer is debated. With regard to consumers' intake of endosulfan from residues on food, the Food and Agriculture Organization
Food and Agriculture Organization
of United Nations has concluded that long-term exposure from food is unlikely to present a public health concern, but short-term exposure can exceed acute reference doses.[41] Toxicity[edit] Endosulfan
Endosulfan
is acutely neurotoxic to both insects and mammals, including humans. The US EPA
US EPA
classifies it as Category I: "Highly Acutely Toxic" based on a LD50 value of 30 mg/kg for female rats,[14] while the World Health Organization
World Health Organization
classifies it as Class II "Moderately Hazardous" based on a rat LD50 of 80 mg/kg.[42] It is a GABA-gated chloride channel antagonist, and a Ca2+, Mg2+ ATPase inhibitor. Both of these enzymes are involved in the transfer of nerve impulses. Symptoms of acute poisoning include hyperactivity, tremors, convulsions, lack of coordination, staggering, difficulty breathing, nausea and vomiting, diarrhea, and in severe cases, unconsciousness.[18] Doses as low as 35 mg/kg have been documented to cause death in humans,[43] and many cases of sublethal poisoning have resulted in permanent brain damage.[18] Farm workers with chronic endosulfan exposure are at risk of rashes and skin irritation.[14] EPA's acute reference dose for dietary exposure to endosulfan is 0.015 mg/kg for adults and 0.0015 mg/kg for children. For chronic dietary expsoure, the EPA references doses are 0.006 mg/(kg·day) and 0.0006 mg/(kg·day) for adults and children, respectively.[14] Endocrine disruption[edit] Theo Colborn, an expert on endocrine disruption, lists endosulfan as a known endocrine disruptor,[44] and both the EPA and the Agency for Toxic
Toxic
Substances and Disease Registry consider endosulfan to be a potential endocrine disruptor. Numerous in vitro studies have documented its potential to disrupt hormones and animal studies have demonstrated its reproductive and developmental toxicity, especially among males.[14][18] A number of studies have documented that it acts as an antiandrogen in animals.[40][45] Endosulfan
Endosulfan
has shown to affect crustacean molt cycles, which are important biological and endocrine-controlled physiological processes essential for the crustacean growth and reproduction.[46] Environmentally relevant doses of endosulfan equal to the EPA's safe dose of 0.006 mg/kg/day have been found to affect gene expression in female rats similarly to the effects of estrogen.[47] It is not known whether endosulfan is a human teratogen (an agent that causes birth defects), though it has significant teratogenic effects in laboratory rats.[48] A 2009 assessment concluded the endocrine disruption in rats occurs only at endosulfan doses that cause neurotoxicity.[49] Reproductive and developmental effects[edit] Few studies have documented that endosulfan can also affect human development. Researchers studying children from many villages in Kasargod
Kasargod
District, Kerala, India, have linked endosulfan exposure to delays in sexual maturity among boys. Endosulfan
Endosulfan
was the only pesticide applied to cashew plantations in the villages for 20 years, and had contaminated the village environment. The researchers compared the villagers to a control group of boys from a demographically similar village that lacked a history of endosulfan pollution. Relative to the control group, the exposed boys had high levels of endosulfan in their bodies, lower levels of testosterone, and delays in reaching sexual maturity. Birth defects
Birth defects
of the male reproductive system, including cryptorchidism, were also more prevalent in the study group. The researchers concluded, "our study results suggest that endosulfan exposure in male children may delay sexual maturity and interfere with sex hormone synthesis."[50] Increased incidences of cryptorchidism have been observed in other studies of endosulfan exposed populations.[51][52] A 2007 study by the California Department of Public Health found that women who lived near farm fields sprayed with endosulfan and the related organochloride pesticide dicofol during the first eight weeks of pregnancy are several times more likely to give birth to children with autism.[53] However a 2009 assessment concluded that epidemiology and rodent studies that suggest male reproductive and autism effects are open to other interpretations, and that developmental or reproductive toxicity in rats occurs only at endosulfan doses that cause neurotoxicity.[49] Endosulfan
Endosulfan
and cancer[edit] Endosulfan
Endosulfan
is not listed as known, probable, or possible carcinogen by the EPA, IARC, or other agencies. No epidemiological studies link exposure to endosulfan specifically to cancer in humans, but in vitro assays have shown that endosulfan can promote proliferation of human breast cancer cells.[54] Evidence of carcinogenicity in animals is mixed.[18] In a 2016 study[55] by the Department of Biochemistry, Indian Institute of Science, Bangalore
Bangalore
published in Carcinogenesis, Endosulfan
Endosulfan
was found to induce reactive oxygen species (ROS) in a concentration and time-dependent manner leading to double-stranded breaks in the DNA
DNA
and also found to favour subsequent erroneous DNA repair. Environmental fate[edit] Endosulfan
Endosulfan
is a ubiquitous environmental contaminant. The chemical is semivolatile and persistent to degradation processes in the environment. Endosulfan
Endosulfan
is subject to long-range atmospheric transport, i.e. it can travel long distances from where it is used. Thus, it occurs in many environmental compartments. For example, a 2008 report by the National Park Service
National Park Service
found that endosulfan commonly contaminates air, water, plants, and fish of national parks in the US. Most of these parks are far from areas where endosulfan is used.[56] Endosulfan
Endosulfan
has been found in remote locations such as the Arctic Ocean, as well as in the Antarctic atmosphere.[57] The pesticide has also been detected in dust from the Sahara Desert collected in the Caribbean
Caribbean
after being blown across the Atlantic Ocean.[58] The compound has been shown to be one of the most abundant organochlorine pesticides in the global atmosphere.[57] The compound breaks down into endosulfan sulfate, endosulfan diol, and endosulfan furan, all of which have structures similar to the parent compound and, according to the EPA, "are also of toxicological concern…The estimated half-lives for the combined toxic residues (endosulfan plus endosulfan sulfate) [range] from roughly 9 months to 6 years." The EPA concluded, "[b]ased on environmental fate laboratory studies, terrestrial field dissipation studies, available models, monitoring studies, and published literature, it can be concluded that endosulfan is a very persistent chemical which may stay in the environment for lengthy periods of time, particularly in acid media." The EPA also concluded, "[e]ndosulfan has relatively high potential to bioaccumulate in fish."[14] It is also toxic to amphibians; low levels have been found to kill tadpoles.[59] In 2009, the committee of scientific experts of the Stockholm Convention concluded, "endosulfan is likely, as a result of long range environmental transport, to lead to significant adverse human health and environmental effects such that global action is warranted."[60] In May 2011, the Stockholm Convention
Stockholm Convention
committee approved the recommendation for elimination of production and use of endosulfan and its isomers worldwide. This is, however, subject to certain exemptions. Overall, this will lead to its elimination from the global markets.[61] Status by region[edit] India[edit]

The yellow toxicity label for endosulfan in India

Although classified as a yellow label (highly toxic) pesticide by the Central Insecticides Board, India is one of the largest producers[62] and the largest consumer of endosulfan in the world.[11] Of the total volume manufactured in India, three companies — Excel Crop Care, Hindustan Insecticides Ltd, and Coromandal Fertilizers — produce 4,500 tonnes annually for domestic use and another 4,000 tonnes for export. Endosulfan
Endosulfan
is widely used in most of the plantation crops in India. The toxicity of endosulfan and health issues due to its bioaccumulation came under media attention when health issues precipitated in the Kasargod
Kasargod
District (of Kerala) were publicised.[63][64] This inspired protests, and the pesticide was banned in Kerala
Kerala
as early as 2001, following a report by the National Institute of Occupational Health. In the Stockholm Convention
Stockholm Convention
on Persistent Organic Pollutants of 2011, when an international consensus arose for the global ban of the pesticide, India opposed this move due to pressure from the endosulfan manufacturing companies.[21][65] This flared up the protest,[66][67][68] and while India still maintained its stance, the global conference decided on a global ban, for which India asked a remission for 10 years. Later, on a petition filed in the Supreme Court of India, the production, storage, sale and use of the pesticide was temporarily banned on 13 May 2011, and later permanently by the end of 2011.[69][70] The Karnataka
Karnataka
government also banned the use of endosulfan with immediate effect. Briefing presspersons after the State Cabinet meeting, Minister for Higher Education V.S. Acharya said the Cabinet discussed the harmful effects of endosulfan on the health of farmers and people living in rural areas. The government will now invoke the provisions of the Insecticides Act, 1968 (a Central act) and write a letter to the Union Government about the ban. Minister for Energy, and Food and Civil Supplies Shobha Karandlaje, who has been spearheading a movement seeking a ban on endosulfan, said, "I am grateful to Chief Minister B.S. Yeddyurappa
B.S. Yeddyurappa
and members of the Cabinet for approving the ban.[71] Rajendra Singh Rana has written a letter to Prime Minister
Prime Minister
Manmohan Singh demanding the withdrawal of the National Institute of Occupational Health (NIOH) study on Endosulfan
Endosulfan
titled "Report Of The Investigation Of Unusual Illness" allegedly produced by the Endosulfan exposure in Padre village of Kasargod
Kasargod
district in north Kerala. In his statement Mr. Rana said "The NIOH report is flawed. I'm in complete agreement with what the workers have to say on this. In fact, I have already made representation to the Prime Minister
Prime Minister
and concerned Union Ministers of health and environment demanding immediate withdrawal of the report," as reported by The Economic Times
The Economic Times
and Outlook India [72][73] Mrs. Vibhavari Dave, local leader and Member of Legislative Assembly (MLA), from Bhavnagar, Gujarat, voiced her concerns on the impact of ban of endosulfan on families and workers of Bhavnagar. She was a part of the delegation with Bhavnagar
Bhavnagar
MP, Rajendra Singh Rana, which submitted a memorandum to the district collector's office to withdraw the NIOH report calling for ban of endosulfan.[74][75] The Pollution Control Board of the Government of Kerala, prohibited the use of endosulfan in the state of Kerala
Kerala
on 10 November 2010.[76] On February 18, 2011, the Karnataka
Karnataka
government followed suit and suspended the use of endosulfan for a period of 60 days in the state.[77] Indian Union Minister of Agriculture Sharad Pawar
Sharad Pawar
has ruled out implementing a similar ban at the national level despite the fact that endosulfan has banned in 63 countries, including the European Union, Australia, and New Zealand.[78] The Government of Gujarat
Gujarat
had initiated a study in response to the workers' rally in Bhavnagar
Bhavnagar
and representations made by Sishuvihar, an NGO
NGO
based in Ahmadabad. The committee constituted for the study also included former Deputy Director of NIOH, Ahmadabad. The committee noted that the WHO, FAO, IARC and US EPA
US EPA
have indicated that endosulfan is not carcinogenic, not teratogenic, not mutagenic and not genotoxic. The highlight of this report is the farmer exposure study based on analysis of their blood reports for residues of endosulfan and the absence of any residues. This corroborates the lack of residues in worker-exposure studies.[79][80] The Supreme Court passed interim order on May 13, 2011, in a Writ Petition filed by Democratic Youth Federation of India, (DYFI), a youth wing of Communist Party of India (Marxist) in the backdrop of the incidents reported in Kasargode, Kerala, and banned the production, distribution and use of endosulfan in India because the pesticide has debilitating effects on humans and the environment.[69][70] The Centre for Science and Environment (CSE) welcomed this order, and called it a 'resounding defeat' for the pesticide industry which has been promoting this deadly toxin. A 2001 study by CSE had linked the aerial spraying of the pesticide with the growing health disorders in Kasaragode. However some scientists have called this study flawed.[81] KM Sreekumar of the Padannakkad College of Agriculture in Kasargod
Kasargod
and Prathapan KD of the Kerala
Kerala
Agricultural University in a paper claim that the extensive spread of diseases in the area cannot be solely attributed to the use of Endosulfan
Endosulfan
and criticised the CSE for inflating the level of endosulfan reported in the blood.[82] In July 2012, the Government asked the Supreme Court to allow use of the pesticide in all states except Kerala
Kerala
and Karnataka, as these states are ready to use it for pest control.[83] But the court did not consider this request. India will phase out all endosulfan use by 2017.[84] On January 10, 2017, The Supreme Court ordered the State Governments to release the remaining undisbursed payment of compensation quantified (Rupees Five lakhs each) to all the affected persons within three months.[85] New Zealand[edit] Endosulfan
Endosulfan
was banned in New Zealand by the Environmental Risk Management Authority effective January 2009[33] after a concerted campaign by environmental groups and the Green Party. See also: Pesticides in New Zealand Philippines[edit] A shipment of about 10 tonnes of endosulfan was illegally stowed on the ill-fated MV Princess of the Stars, a ferry that sank off the waters of Romblon
Romblon
(Sibuyan Island), Philippines, during a storm in June 2008. Search, rescue, and salvage efforts were suspended when the endosulfan shipment was discovered, and blood samples from divers at the scene were sent to Malaysia
Malaysia
for analysis.[86] The Department of Health of the Philippines has temporarily banned the consumption of fish caught in the area.[87] Endosulfan
Endosulfan
is classified as a "Severe Marine Pollutant" by the International Maritime Dangerous Goods Code.[20] United States[edit]

Endosulfan
Endosulfan
use in the US in pounds per square mile by county in 2013

Endosulfan
Endosulfan
use in the US in pounds per square mile by county in 2002

In the United States, endosulfan is only registered for agricultural use, and these uses are being phased out.[7] It has been used extensively on cotton, potatoes, tomatoes, and apples according to the EPA.[88] The EPA estimates that 626 thousand kg of endosulfan were used annually from 1987 to 1997.[14] The US exported more than 140,000 lb of endosulfan from 2001 to 2003, mostly to Latin America,[89] but production and export has since stopped. In California, endosulfan contamination from the San Joaquin Valley has been implicated in the extirpation of the mountain yellow-legged frog from parts of the nearby Sierra Nevada.[90] In Florida, levels of contamination the Everglades
Everglades
and Biscayne Bay
Biscayne Bay
are high enough to pose a threat to some aquatic organisms.[91][92][93] In 2007, the EPA announced it was rereviewing the safety of endosulfan.[94] The following year, Pesticide
Pesticide
Action Network and NRDC petitioned the EPA to ban endosulfan,[95] and a coalition of environmental and labor groups sued the EPA seeking to overturn its 2002 decision to not ban endosulfan.[29] In June 2010, the EPA announced it was negotiating a phaseout of all uses with the sole US manufacturer, Makhteshim Agan, and a complete ban on the compound.[7] An official statement by Makhteshim Agan
Makhteshim Agan
of North America
North America
(MANA) states, "From a scientific standpoint, MANA continues to disagree fundamentally with EPA's conclusions regarding endosulfan and believes that key uses are still eligible for re-registration." The statement adds, "However, given the fact that the endosulfan market is quite small and the cost of developing and submitting additional data high, we have decided to voluntarily negotiate an agreement with EPA that provides growers with an adequate time frame to find alternatives for the damaging insect pests currently controlled by endosulfan." [96][97] Australia[edit] Australia
Australia
banned endosulfan on October 12, 2010,[98][99][100] with a two-year phase-out for stock of endosulfan-containing products.[98] Australia
Australia
had, in 2008, announced endosulfan would not be banned.[101] Citing New Zealand's ban, the Australian Greens
Australian Greens
called for "zero tolerance" of endosulfan residue on food.[5] Taiwan[edit] US apples with endosulfan are now allowed to be exported to Taiwan, although the ROC government denied any US pressure on it.[102] Brazil[edit] Brazil decreed total ban of the substance from July 31, 2013, being forbidden imports of the product from July 31, 2011, date in which national production and utilization begins to be phased out gradually.[103] References[edit]

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Endosulfan
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Endosulfan
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Endosulfan
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(Poison Information Monograph 576), July 2000. ^ Colborn T, Dumanoski D, Meyers JP, Our Stolen Future : How We Are Threatening Our Fertility, Intelligence and Survival, 1997, Plume. ^ Wilson VS, LeBlanc GA; Leblanc (January 1998). " Endosulfan
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elevates testosterone biotransformation and clearance in CD-1 mice". Toxicol. Appl. Pharmacol. 148 (1): 158–68. doi:10.1006/taap.1997.8319. PMID 9465275.  ^ Tumburu L, Shepard EF, Strand AE, Browdy CL; Shepard; Strand; Browdy (November 2011). "Effects of endosulfan exposure and Taura Syndrome Virus infection on the survival and molting of the marine penaeid shrimp, Litopenaeus vannamei". Chemosphere. 86 (9): 912–8. doi:10.1016/j.chemosphere.2011.10.057. PMID 22119282. CS1 maint: Multiple names: authors list (link) ^ Varayoud J, Monje L, Bernhardt T, Muñoz-de-Toro M, Luque EH, Ramos JG; Monje; Bernhardt; Muñoz-De-Toro; Luque; Ramos (October 2008). " Endosulfan
Endosulfan
modulates estrogen-dependent genes like a non-uterotrophic dose of 17beta-estradiol". Reprod. Toxicol. 26 (2): 138–45. doi:10.1016/j.reprotox.2008.08.004. PMID 18790044. CS1 maint: Multiple names: authors list (link) ^ Singh ND, Sharma AK, Dwivedi P, Patil RD, Kumar M; Sharma; Dwivedi; Patil; Kumar (2007). "Citrinin and endosulfan induced teratogenic effects in Wistar rats". J Appl Toxicol. 27 (2): 143–51. doi:10.1002/jat.1185. PMID 17186572. CS1 maint: Multiple names: authors list (link) ^ a b Silva MH, Gammon D; Gammon (February 2009). "An assessment of the developmental, reproductive, and neurotoxicity of endosulfan". Birth Defects Res. B Dev. Reprod. Toxicol. 86 (1): 1–28. doi:10.1002/bdrb.20183. PMID 19243027.  ^ Saiyed H, Dewan A, Bhatnagar V; et al. (2003). "Effect of Endosulfan on Male Reproductive Development" (PDF). Environ. Health Perspect. 111: 1958–1962. doi:10.1289/ehp.6271. Archived from the original (PDF) on 2007-09-27. CS1 maint: Explicit use of et al. (link) CS1 maint: Multiple names: authors list (link) ^ Damgaard IN, Skakkebæk NE, Toppari J; et al. (2006). "Persistent Pesticides in Human Breast Milk and Cryptorchidism" (PDF). Environ. Health Perspect. 114: 1133–1138. doi:10.1289/ehp.8741. Archived from the original (PDF) on 2007-10-10. CS1 maint: Explicit use of et al. (link) CS1 maint: Multiple names: authors list (link) ^ Olea N, Olea-Serrano F, Lardelli-Claret P; et al. (1999). "Inadvertent Exposure to Xenoestrogens in Children". Toxicol. Ind. Health. 15: 151–158. doi:10.1191/074823399678846682. CS1 maint: Explicit use of et al. (link) CS1 maint: Multiple names: authors list (link) ^ (a) Roberts EM, English PB, Grether JK, Windham GC, Somberg L, Wolff C; English; Grether; Windham; Somberg; Wolff (2007). "Maternal Residence Near Agricultural Pesticide
Pesticide
Applications and Autism
Autism
Spectrum Disorders among Children in the California Central Valley". Environ. Health Perspect. 115 (10): 1482–9. doi:10.1289/ehp.10168. PMC 2022638 . PMID 17938740. Archived from the original on 2008-07-25. CS1 maint: Multiple names: authors list (link) (b) Lay Summary: Autism
Autism
and Agricultural Pesticides Archived October 20, 2007, at the Wayback Machine., Victoria McGovern, Environ. Health Perspect. 2007, 115(10):A505 ^ (a) Grunfeld HT, Bonefeld-Jorgensen EC, Effect of in vitro estrogenic pesticides on human oestrogen receptor alpha and beta mRNA levels, Toxicol. Lett., 2004, 151(3):467–80. (b) Ibarluzea JmJ, Fernandez MF, Santa-Marina L, et al., Breast cancer risk and the combined effect of environmental estrogens, Cancer Causes Control, 2004, 15(6):591–600. (c) Soto AM, Chung KL, Sonnenschein C, The pesticides endosulfan, toxaphene, and dieldrin have estrogenic effects on human estrogensensitive cells Archived September 27, 2007, at the Wayback Machine., Environ. Health Perspect., 1994, 102(4):380–383. ^ Sebastian, Robin; Raghavan, Sathees C. (August 4, 2016). "Induction of DNA
DNA
damage and erroneous repair can explain genomic instability caused by endosulfan". Carcinogenesis. 37 (10): 929–940. doi:10.1093/carcin/bgw081. PMID 27492056.  ^ Western Airborne Contaminants Assessment Project, National Park Service. ^ a b Weber Jan, Halsall Crispin J., Muir Derek, Teixeira Camilla, Small Jeff, Solomon Keith, Hermanson Mark, Hung Hayley, Bidleman Terry (2010). "Endosulfan, a global pesticide: A review of its fate in the environment and occurrence in the Arctic". Science of The Total Environment. 408: 2966–2984. doi:10.1016/j.scitotenv.2009.10.077. CS1 maint: Multiple names: authors list (link) ^ Ramnarine, Kristy (May 12, 2008). "Harmful elements in Sahara dust". Trinidad & Tobago Express. Archived from the original on March 4, 2009. Retrieved 2008-05-14.  ^ Relyea RA (2008) A cocktail of contaminants: how mixtures of pesticides at low concentrations affect aquatic communities. Oecologia (accepted: 13 October 2008) Relyea, Ra (Mar 2009). "A cocktail of contaminants: how mixtures of pesticides at low concentrations affect aquatic communities". Oecologia. 159 (2): 363–76. doi:10.1007/s00442-008-1213-9. PMID 19002502.  ^ Earth Negotiations Bulletin (19 October 2009). "Briefing Note on the 5th Meeting of the POPRC" (PDF). International Institute for Sustainable Development.  ^ United Nations Environment Programme (UNEP) (Press release). UNEP. May 3, 2011 http://hqweb.unep.org/Documents.Multilingual/Default.asp?DocumentID=2637&ArticleID=8719&l=en&t=long. Retrieved 2011-06-13.  Missing or empty title= (help) ^ Indian Chemical Council (January 9, 2009). "Form for submission of information specified in Annex E". Retrieved 2009-01-29.  ^ Uppinangady, Arun (July 14, 2009). "Beltangady: Endosulfan
Endosulfan
Affected Leading Hellish Life — Seek Succour". Daijiworld Media Network. Retrieved 2009-07-14.  ^ 'Rain man' of Indian journalism makes sure wells stay full, Frederick Noronha, IndiaENews.com, July 5th, 2007, accessed July 5th, 2007. ^ "SUMMARY OF THE FOURTH MEETING OF THE CONFERENCE OF THE PARTIES TO THE ROTTERDAM CONVENTION". Earth Negotiations Bulletin. 15 (168). November 3, 2008.  ^ http://www.indiatogether.org/2006/sep/env-endosulf.htm ^ "V.S. Achuthanandan to lead 'satyagraha'". The Hindu. Chennai, India. April 24, 2011.  ^ http://www.indianexpress.com/news/MP-govt-backs-VS-ban-demand/783265/ ^ a b "WRIT PETITION (CIVIL) NO.213 OF 2011" (PDF). Supreme Court of India - RECORD OF PROCEEDINGS. 2011 (05). May 13, 2011.  ^ a b "WRIT PETITION (CIVIL) NO.213 OF 2011" (PDF). Supreme Court of India - RECORD OF PROCEEDINGS. 2011 (09). September 30, 2011.  ^ " Karnataka
Karnataka
bans use of endosulfan". The Hindu. Chennai, India. February 18, 2011.  ^ "Rana Wants Withdrawal of NIOH Study on Endosulfan". Outlook India. November 16, 2010. [permanent dead link] ^ "Rajendra Singh Rana, MP, Bhavnagar
Bhavnagar
calls for withdrawal of NIOH report on Endosulfan". World News. December 17, 2010.  ^ "Local MLA speaks in support of Bhavnagar
Bhavnagar
Endosulfan
Endosulfan
Workers". Daily Motion. December 18, 2010.  ^ "Workers demand withdrawal of study on Endosulfan". WebIndia 123. November 16, 2010.  ^ Notification Endosulphan, accessed Nov 19th, 2010 ^ " Karnataka
Karnataka
bans use of endosulfan". Chennai, India: The Hindu. February 18, 2011.  ^ "India will not ban Endosulfan
Endosulfan
pesticide, says Sharad Pawar". Tehelka. February 22, 2011.  ^ "REPORT OF THE COMMITTEE TO EVALUATE THE SAFETY ASPECTS OF ENDOSULFAN Department" (PDF). Health and Family Welfare Department - Government of Gujarat. March 15, 2011. Archived from the original (PDF) on October 4, 2011.  ^ "REPORT OF THE COMMITTEE TO EVALUATE THE SAFETY ASPECTS OF ENDOSULFAN" (PDF). Department of Health and Family Welfare - Government of Gujarat. March 15, 2011. Retrieved March 2015.  Check date values in: access-date= (help) ^ "Bad science".  ^ "A critique of the epidemiological studies on health in allegedly endosulfan".  ^ Venkatesan, J. (27 July 2012). "Allow use of endosulfan except in Kerala
Kerala
and Karnataka". The Hindu. Chennai, India.  ^ "India to Phase Out Use of Endosulfan
Endosulfan
by 2017: Government". NDTV. NDTV Convergence Limited. 8 August 2014. Retrieved 14 February 2016. India has agreed to phase out use of Endosulfan
Endosulfan
by 2017 and all existing stock of the pesticide in the country that is past its expiry date, government said today.  ^ "WRIT PETITION (CIVIL) NO.213 OF 2011". Supreme Court of India
Supreme Court of India
- RECORD OF PROCEEDINGS. 2017 (01). January 10, 2017.  ^ "Divers' blood samples sent to Singapore for analysis". GMAnews.TV. June 27, 2008. Retrieved 2008-06-27.  ^ Aguilar, Ephraim (June 27, 2008). "DoH bans eating of fish from Romblon
Romblon
waters". Inquirer.net. Archived from the original on June 29, 2008. Retrieved 2008-06-27.  ^ Benefits of Endosulfan
Endosulfan
in Agricultural Production: Analysis of Usage Information Archived October 12, 2008, at the Wayback Machine., U.S. EPA, Docket ID NO. EPA-HQ-OPP-2002-0262-0062, 2007. ^ Smith, Carl; Kathleen Kerr and Ava Sadripour (July–September 2008). " Pesticide
Pesticide
Exports from US Ports, 2001–2003". Int. J. Occup. Environ. Health. 14 (3): 176–186. PMID 18686717.  ^ Fellers GM, McConnell LL, Pratt D, Datta S; McConnell; Pratt; Datta (September 2004). "Pesticides in mountain yellow-legged frogs (Rana muscosa) from the Sierra Nevada Mountains of California, USA". Environ. Toxicol. Chem. 23 (9): 2170–7. doi:10.1897/03-491. PMID 15378994. CS1 maint: Multiple names: authors list (link) [dead link] ^ Carriger JF, Rand GM; Rand (October 2008). "Aquatic risk assessment of pesticides in surface waters in and adjacent to the Everglades
Everglades
and Biscayne National Parks: I. Hazard assessment and problem formulation". Ecotoxicology. 17 (7): 660–79. doi:10.1007/s10646-008-0230-0. PMID 18642080.  ^ Carriger JF, Rand GM; Rand (October 2008). "Aquatic risk assessment of pesticides in surface waters in and adjacent to the Everglades
Everglades
and Biscayne National Parks: II. Probabilistic analyses". Ecotoxicology. 17 (7): 680–96. doi:10.1007/s10646-008-0231-z. PMID 18642079.  ^ Dan B. Kimball, Superintendent National Park Service
National Park Service
(October 29, 2008). "Letter to EPA re: Petitions to Revoke All Tolerances Established for Endosulfan; Federal Register: August 20, 2008 (Volume 73, Number 162). Docket ID No. EPA-HQ-OPP-2008-0615-0041.1". Retrieved 2009-01-27.  ^ ENVIRONMENTAL PROTECTION AGENCY (November 16, 2007). "Endosulfan Updated Risk Assessments, Notice of Availability, and Solicitation of Usage Information". Federal Register. 72 (221): 64624–64626. [permanent dead link] ^ ENVIRONMENTAL PROTECTION AGENCY (August 20, 2008). "Petitions to Revoke All Tolerances Established for Endosulfan; Notice of Availability". 73 (162): 49194–49196. [permanent dead link] ^ "MANA And EPA Agree To Voluntary Plan On Endosulfan". MANA Crop Protection. June 10, 2010. Archived from the original on September 7, 2012.  ^ "MANA, EPA Agree To Voluntary Plan On Endosulfan". Growing Produce. June 11, 2010.  ^ a b Australian Pesticides and Veterinary Medicines Authority (APVMA) apvma (Press release). Commonwealth of Australia. October 12, 2010 http://www.apvma.gov.au/news_media/media_releases/2010/mr2010-12.php. Retrieved 2010-10-13.  Missing or empty title= (help) ^ " Australia
Australia
finally bans endosulfan". Australia: ABC. 13 October 2010. Retrieved 2010-10-13.  ^ "Regulator finally acts to ban endosulfan". NTN blog. Australia: National Toxics Network. October 13, 2010. Archived from the original on 2011-01-04. Retrieved 2010-10-13.  ^ Burke, Kelly (January 7, 2009). " Australia
Australia
refuses to join ban on pesticide". Fairfax. Archived from the original on 2009-03-04. Retrieved 2009-01-08.  ^ Taiwan Academics slam end of pesticide ban for U.S. fruit ^ Formenti, Lígia (July 15, 2010). "Agrotóxico endosulfan será banido no Brasil em 2013; demora é criticada". Estadão. Archived from the original on 2014-05-27. Retrieved 2014-05-26. 

External links[edit]

CDC - NIOSH Pocket Guide to Chemical Hazards 2009 Environmental Justice Foundation report detailing impacts of Endosulfan, highlighting why it should be banned globally Resources on Endosulfan, India Environment Portal Pesticideinfo.org: Endosulfan Levels of endosulfan residues on food in the U.S. Endosulphan Victims in Kerala Protect Endosufan Network — Information about endosulfan from Protect Endosufan Network. State of endosulfan, Down To Earth Interim report on endosulfan submitted by expert committee to the Supreme Court of India, Aug 4, 2011 Weeping wombs of Kasaragod Tehelka Magazine, Vol 8, Issue 18, Dated 07 May 2011

v t e

Pest control: Insecticides

Carbamates

Aldicarb Bendiocarb Carbaryl Carbofuran Ethienocarb Fenobucarb Oxamyl Methomyl Propoxur

Inorganic compounds

Aluminium phosphide Boric acid Chromated copper arsenate Copper(II) arsenate Copper(I) cyanide Diatomaceous earth Lead hydrogen arsenate Paris Green Scheele's Green

Insect growth regulators

Benzoylureas Diflubenzuron Flufenoxuron Hydroprene Lufenuron Methoprene Pyriproxyfen

Neonicotinoids

Acetamiprid Clothianidin Dinotefuran Imidacloprid Nitenpyram Nithiazine Thiacloprid Thiamethoxam

Organochlorides

Aldrin Beta-HCH Carbon tetrachloride Chlordane Cyclodiene 1,2-DCB 1,4-DCB 1,1-DCE 1,2-DCE DDD DDE DDT Dicofol Dieldrin Endosulfan Endrin Heptachlor Kepone Lindane Methoxychlor Mirex Tetradifon Toxaphene

Organophosphorus

Acephate Azamethiphos Azinphos-methyl Bensulide Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Demeton-S-methyl Diazinon Dicrotophos Diisopropyl fluorophosphate Dimefox Dimethoate Dioxathion Disulfoton Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate Isoxathion Malathion Methamidophos Methidathion Mevinphos Monocrotophos Naled Omethoate Oxydemeton-methyl Parathion Parathion-methyl Phenthoate Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Quinalphos Temefos Tebupirimfos Terbufos Tetrachlorvinphos Tribufos Trichlorfon

Pyrethroids

Acrinathrin Allethrins Bifenthrin Bioallethrin Cyfluthrin Cyhalothrin Cypermethrin Cyphenothrin Deltamethrin Empenthrin Esfenvalerate Etofenprox Fenpropathrin Fenvalerate Flumethrin Imiprothrin Metofluthrin Permethrin Phenothrin Prallethrin Pyrethrin
Pyrethrin
(I, II; chrysanthemic acid) Pyrethrum Resmethrin Silafluofen Tefluthrin Tetramethrin Tralomethrin Transfluthrin

Ryanoids

Chlorantraniliprole Cyantraniliprole Flubendiamide Ryanodine Ryanodol

Other chemicals

Afoxolaner Amitraz Azadirachtin Buprofezin Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner Pyridaben Pyriprole Ryanodine Sarolaner Sesamex Spinosad Sulfluramid Tebufenozide Tebufenpyrad Veracevine Xanthone Metaflumizone

Metabolites

Oxon Malaoxon Paraoxon TCPy

Biopesticides

Bacillus thuringiensis Baculovirus Beauveria bassiana Beauveria brongniartii Metarhizium acridum Metarhizium anisopliae Nomuraea rileyi Lecanicillium lecanii Paecilomyces fumosoroseus Paenibacillus popilliae Purpureocillium
Purpureocillium
lilacinum

v t e

Neurotoxins

Animal

Batrachotoxin Bestoxin Birtoxin Bungarotoxin Charybdotoxin Conotoxin Fasciculin Huwentoxin Poneratoxin Saxitoxin Tetrodotoxin Vanillotoxin Spooky toxin (SsTx)

Bacterial

Botulinum toxin Tetanospasmin

Cyanobacteria

Anatoxin-a Anatoxin-a(S) BMAA Saxitoxin

Plant

Bicuculline Penitrem A Picrotoxin Strychnine Tutin Rotenone Ginkgotoxin Cicutoxin Oenanthotoxin

Pesticides

Fenpropathrin Tetramethylenedisulfotetramine Bromethalin Crimidine Methamidophos Endosulfan Fipronil

Nerve agents

Cyclosarin EA-3148 Novichok agent Sarin Soman Tabun VE VG VM VR VX GV

Other

Dimethylmercury Toxopyrimidine TBPS IPTBO

v t e

Convulsants

GABA receptor antagonists

Picrotoxin Gabazine Tetramethylenedisulfotetramine Cicutoxin Phenylsilatrane Tutin Pentylenetetrazol Thujone Endosulfan Bicuculline Oenanthotoxin Fipronil TBPS IPTBO EBOB

GABA synthesis inhibitors

Allylglycine Crimidine Ginkgotoxin Toxopyrimidine Isoniazid

Glycine receptor antagonists

Strychnine Tutin

Glutamate receptor agonists

AMPA NMDA Kainic acid Domoic acid Quisqualic acid Tetrazolylglycine

v t e

Xenoestrogens

Phytoestrogens

Flavanones

Hesperetin Liquiritigenin Naringenin Pinocembrin

Flavones

Acacetin 7,8-Dihydroxyflavone Mirificin

Prenylflavonoids

8-Prenylnaringenin 6-Prenylnaringenin 8-Geranylnaringenin 6,8-Diprenylnaringenin Icaritin

Isoflavones

Biochanin A Daidzein Daidzin Formononetin Genistein Genistin Glycitein Ononin Prunetin Puerarin Tectorigenin

Isoflavanes

Equol
Equol
(S-Equol) Glabridin

Dihydrochalcones

Phloretin Phlorizin

Isoflavenes

Glabrene

Coumestans

Coumestan Coumestrol Desmethylwedelolactone Wedelolactone

Lignans

Enterodiol Enterolactone

Flavonolignans

Silybin Cinchonain-Ib

Flavonols

Quercetin

Others

Deoxymiroestrol Miroestrol Resveratrol α-Isosparteine

Mycoestrogens

Zearalanone Zearalenone α-Zearalanol (zeranol) α-Zearalenol β-Zearalanol β-Zearalenol

Derivatives

D-Penicillamine

Synthetic

Alkylphenols Atrazine BHA Bisphenol
Bisphenol
A DDE DDT Dieldrin Dioxins Endosulfan Enzacamene Erythrosine Heptachlor Lindane Methoxychlor Nonylphenol Parabens PBBs PCBs Pentachlorophenol PHBA Phthalates Propyl gallate Perfluorinated compound

Metalloestrogens

Aluminium Antimony Arsenite Barium Cadmium Chromium Cobalt Copper Lead Mercury Nickel Selenite Tin Vanadate

v t e

Androgen receptor
Androgen receptor
modulators

AR

Agonists

Testosterone
Testosterone
derivatives: 4-Androstenediol 4-Dehydroepiandrosterone
4-Dehydroepiandrosterone
(4-DHEA) 4-Hydroxytestosterone 5-Androstenedione 11-Ketotestosterone 11β-Hydroxyandrostenedione Adrenosterone
Adrenosterone
(11-ketoandrostenedione, 11-oxoandrostenedione) Androstenediol (5-androstenediol)

Androstenediol 3β-acetate Androstenediol 17β-acetate Androstenediol diacetate Androstenediol dipropionate

Androstenedione (4-androstenedione) Atamestane Boldenone

Boldenone
Boldenone
undecylenate

Boldione
Boldione
(1,4-androstadienedione) Clostebol

Clostebol
Clostebol
acetate Clostebol
Clostebol
caproate Clostebol
Clostebol
propionate

Cloxotestosterone

Cloxotestosterone
Cloxotestosterone
acetate

Dehydroandrosterone DHEA (androstenolone, prasterone; 5-DHEA)

DHEA enanthate (prasterone enanthate) DHEA sulfate

Exemestane Formestane Plomestane Quinbolone Silandrone Testosterone# (+dutasteride)

Testosterone
Testosterone
esters Polytestosterone phloretin phosphate

Dihydrotestosterone
Dihydrotestosterone
derivatives: 1-Androstenediol 1-Androstenedione 1-Androsterone
1-Androsterone
(1-andro, 1-DHEA) 1-Testosterone 3α-Androstanediol 5α-Androst-2-en-17-one 7β-Hydroxyepiandrosterone 11-Ketodihydrotestosterone Androsterone Bolazine

Bolazine
Bolazine
capronate

Dihydrofluoxymesterone Dihydrotestosterone
Dihydrotestosterone
(DHT) (androstanolone, stanolone)

Dihydrotestosterone
Dihydrotestosterone
esters

Drostanolone

Drostanolone
Drostanolone
propionate

Epiandrosterone Epitiostanol Mepitiostane Mesabolone Mesterolone

Mesterolone
Mesterolone
cipionate

Methyldiazinol Nisterime

Nisterime
Nisterime
acetate

Prostanozol Stenbolone

Stenbolone
Stenbolone
acetate

Testifenon
Testifenon
(testiphenon, testiphenone)

19-Nortestosterone derivatives: 7α-Methyl-19-norandrostenedione
7α-Methyl-19-norandrostenedione
(MENT dione, trestione) 11β-Methyl-19-nortestosterone

11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone
dodecylcarbonate

19-Nor-5-androstenediol 19-Nor-5-androstenedione 19-Nordehydroepiandrosterone Bolandiol

Bolandiol
Bolandiol
dipropionate

Bolandione
Bolandione
(19-nor-4-androstenedione) Bolmantalate
Bolmantalate
(nandrolone adamantoate) Dienedione Dienolone Dimethandrolone

Dimethandrolone
Dimethandrolone
buciclate Dimethandrolone
Dimethandrolone
dodecylcarbonate Dimethandrolone
Dimethandrolone
undecanoate

LS-1727
LS-1727
(nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate) Methoxydienone
Methoxydienone
(methoxygonadiene) Nandrolone

Nandrolone
Nandrolone
esters

Norclostebol

Norclostebol
Norclostebol
acetate

Normethandrone
Normethandrone
(methylestrenolone, normethisterone) Oxabolone

Oxabolone
Oxabolone
cipionate (oxabolone cypionate)

Trenbolone

Trenbolone
Trenbolone
acetate Trenbolone
Trenbolone
enanthate Trenbolone
Trenbolone
hexahydrobenzylcarbonate Trenbolone
Trenbolone
undecanoate

Trendione Trestolone
Trestolone
(MENT)

Trestolone
Trestolone
acetate

Dihydrotestosterone
Dihydrotestosterone
and 19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel 5α-Dihydronandrolone 5α-Dihydronorethandrolone 5α-Dihydronorethisterone 5α-Dihydronormethandrone 19-Norandrosterone

17α-Alkylated testosterone derivatives: Bolasterone Calusterone Chlorodehydromethylandrostenediol
Chlorodehydromethylandrostenediol
(CDMA) Chlorodehydromethyltestosterone
Chlorodehydromethyltestosterone
(CDMT) Chloromethylandrostenediol
Chloromethylandrostenediol
(CMA) Enestebol Ethyltestosterone Fluoxymesterone Formebolone Hydroxystenozole Metandienone
Metandienone
(methandrostenolone) Methandriol
Methandriol
(methylandrostenediol)

Methandriol
Methandriol
bisenanthoyl acetate Methandriol
Methandriol
diacetate Methandriol
Methandriol
dipropionate Methandriol
Methandriol
propionate

Methylclostebol
Methylclostebol
(chloromethyltestosterone) Methyltestosterone
Methyltestosterone
(+esterified estrogens)

Methyltestosterone
Methyltestosterone
3-hexyl ether

Oxymesterone Penmesterol Tiomesterone

17α-Alkylated dihydrotestosterone derivatives: Androisoxazole Desoxymethyltestosterone Furazabol Mebolazine
Mebolazine
(dimethazine) Mestanolone Metenolone

Metenolone
Metenolone
acetate Metenolone
Metenolone
enanthate

Methasterone Methyl-1-testosterone Methylepitiostanol Methylstenbolone Oxandrolone Oxymetholone Stanozolol

17α-Alkylated 19-nortestosterone derivatives: Bolenol Dimethyldienolone Dimethyltrienolone Ethyldienolone Ethylestrenol Methyldienolone Methylhydroxynandrolone
Methylhydroxynandrolone
(MOHN, MHN) Metribolone Mibolerone Norboletone Norethandrolone Propetandrol RU-2309 Tetrahydrogestrinone

17α- Vinyltestosterone
Vinyltestosterone
derivatives: Norvinisterone (vinylnortestosterone) Vinyltestosterone

17α-Ethynyltestosterone derivatives: Δ4-Tibolone Danazol Desogestrel Ethisterone
Ethisterone
(ethynyltestosterone) Etonogestrel Etynodiol Etynodiol
Etynodiol
diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel
Levonorgestrel
butanoate Lynestrenol Norethisterone

Norethisterone
Norethisterone
acetate Norethisterone
Norethisterone
acetate oxime Norethisterone
Norethisterone
enanthate

Norgestrel Norgestrienone Quingestanol Quingestanol
Quingestanol
acetate Tibolone

Progesterone derivatives: Medroxyprogesterone acetate Megestrol acetate

Others/unsorted: 3-Keto-5α-abiraterone 5α-Androstane Alternariol Cl-4AS-1 Drupanol ZM-182345

Mixed (SARMs)

Nonsteroidal: 198RL26 ACP-105 AC-262536 Acetothiolutamide Andarine
Andarine
(acetamidoxolutamide, androxolutamide, GTx-007, S-4) BMS-564929 DTIB Enobosarm
Enobosarm
(ostarine, MK-2866, GTx-024, S-22) FTBU-1 GSK-4336A GSK-8698 LG-121071
LG-121071
(LGD-121071) LGD-2226 LGD-2941 (LGD-122941) LGD-3303 LGD-4033 JNJ-26146900 JNJ-28330835 JNJ-37654032 ORM-11984 R-1 RAD140 RU-59063 S-1 S-23 S-40503 S-101479 Triclosan

Steroidal: MK-0773 TFM-4AS-1 YK-11

Antagonists

Steroidal: 7α-Thioprogesterone 7α-Thiospironolactone 7α-Thiomethylspironolactone 9,11-Dehydrocortexolone 17α-butyrate
9,11-Dehydrocortexolone 17α-butyrate
(CB-03-04) 11α-Hydroxyprogesterone 15β-Hydroxycyproterone acetate Abiraterone Abiraterone
Abiraterone
acetate Allyltestosterone Benorterone BOMT Canrenoic acid Canrenone Chlormadinone acetate Clometerone Cortexolone 17α-propionate
Cortexolone 17α-propionate
(CB-03-01) Cyproterone Cyproterone
Cyproterone
acetate Delanterone Delmadinone acetate Dicirenone Dienogest Drospirenone Edogestrone Epitestosterone Galeterone Guggulsterone Medrogestone Megestrol acetate Mespirenone Metogest Mexrenone Mifepristone Nomegestrol acetate Nordinone Osaterone Osaterone
Osaterone
acetate Oxendolone Potassium canrenoate Promegestone Prorenone Rosterolone SC-5233
SC-5233
(spirolactone) Spironolactone Spirorenone Spiroxasone Topterone Trimegestone Trimethyltrienolone
Trimethyltrienolone
(R-2956) Zanoterone

Nonsteroidal: 5N-Bicalutamide AA560 Antarlides Arabilin Apalutamide Atraric acid AZD-3514 Bakuchiol BAY-1024767 Bicalutamide Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S) BMS-641988 Cimetidine Cioteronel Darolutamide DDT
DDT
(via metabolite p,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 Fenarimol Flutamide Hydroxyflutamide Inocoterone Inocoterone
Inocoterone
acetate Ketoconazole Lavender oil LG-105 LG-120907 Linuron Methiocarb N-Butylbenzenesulfonamide N-Desmethylapalutamide N-Desmethylenzalutamide Nilutamide ONC1-13B ORM-15341 Pentomone PF-998425 Phenothrin Prochloraz Procymidone Proxalutamide Ralaniten
Ralaniten
(EPI-002) Ralaniten
Ralaniten
acetate (EPI-506) RD-162 Ro 2-7239 Ro 5-2537 RU-22930 RU-56187 RU-57073 RU-58642 RU-58841 Seviteronel Thalidomide Topilutamide
Topilutamide
(fluridil) Valproic acid Vinclozolin YM-580 YM-92088 YM-175735

GPRC6A

Agonists

Cations (incl. aluminum, calcium, gadolinium, magnesium, strontium, zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin SHBG Testosterone

See also Receptor/signaling modulators Androgens and antiandrogens Estrogen
Estrogen
receptor modulators Progesterone receptor modulators List of androgens/anabolic steroids

v t e

Estrogen
Estrogen
receptor modulators

ER

Agonists

Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one
10β,17β-Dihydroxyestra-1,4-dien-3-one
(DHED) 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodo-E2 16α-LE2 16β,17α-Epiestriol
16β,17α-Epiestriol
(16β-hydroxy-17α-estradiol) 17α- Estradiol
Estradiol
(alfatradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol
17α-Epiestriol
(16α-hydroxy-17α-estradiol) 17β-Dihydroequilenin 17β-Dihydroequilin Abiraterone Abiraterone
Abiraterone
acetate Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol
Bolandiol
dipropionate Butolame Clomestrone Cloxestradiol

Cloxestradiol
Cloxestradiol
acetate

Conjugated estrogens DHEA DHEA-S Epiestriol
Epiestriol
(16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin

Equilin
Equilin
acetate Equilin
Equilin
benzoate

ERA-63
ERA-63
(ORG-37663) Esterified estrogens Estetrol Estradiol

Estradiol
Estradiol
esters Lipoidal estradiol Polyestradiol phosphate

Estramustine Estramustine
Estramustine
phosphate Estrapronicate Estrazinol Estriol

Estriol
Estriol
esters

Estrofurate Estromustine Estrone

Estrone
Estrone
esters Estrone
Estrone
methyl ether Estropipate

Etamestrol
Etamestrol
(eptamestrol) Ethinylestradiol

Ethinylestradiol
Ethinylestradiol
3-benzoate Ethinylestradiol
Ethinylestradiol
sulfonate

Ethinylestriol Ethylestradiol Etynodiol Etynodiol
Etynodiol
diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone

Nonsteroidal: (R,R)-THC (S,S)-THC 2,8-DHHHC AC-186 Allenestrol Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol

Dienestrol
Dienestrol
diacetate

Diethylstilbestrol

Diethylstilbestrol
Diethylstilbestrol
esters

Dimestrol
Dimestrol
(dianisylhexene) Doisynoestrol
Doisynoestrol
(fenocycline) Doisynolic acid Efavirenz ERB-196
ERB-196
(WAY-202196) Erteberel
Erteberel
(SERBA-1, LY-500307) Estrobin
Estrobin
(DBE) Fenestrel FERb 033 Fosfestrol
Fosfestrol
(diethylstilbestrol diphosphate) Furostilbestrol
Furostilbestrol
(diethylstilbestrol difuroate) GTx-758 Hexestrol

Hexestrol
Hexestrol
esters

ICI-85966
ICI-85966
(Stilbostat) Mestilbol Methallenestril Methestrol Methestrol
Methestrol
dipropionate Paroxypropione Pentafluranol Phenestrol Prinaberel
Prinaberel
(ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene
Triphenylmethylethylene
(triphenylpropene) WAY-166818 WAY-200070 WAY-214156

Unknown/unsorted: ERB-26 ERA-45 ERB-79

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole) Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Coumestans
Coumestans
(e.g., coumestrol, psoralidin) Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Lavender oil Lignans
Lignans
(e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol)) Metalloestrogens (e.g., cadmium) Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, methiocarb, methoxychlor, triclocarban, triclosan) Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone) Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol)) Steroid-like (e.g., deoxymiroestrol, miroestrol) Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Others (e.g., agnuside, rotundifuran)

Mixed (SERMs)

2-Phenylbenzofuran 2-Phenylbenzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Elacestrant Chlorotrianisene Clomifene Clomifenoxide Cyclofenil D-15413 Droloxifene Enclomifene Endoxifen Etacstil
Etacstil
(GW-5638, DPC-974) Ethamoxytriphetol
Ethamoxytriphetol
(MER-25) Femarelle Fispemifene GW-7604 ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LN-1643 LN-2299 LY-117018 Menerba Miproxifene Miproxifene
Miproxifene
phosphate Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Pipendoxifene Raloxifene Spironolactone SS1010 Tamoxifen TAS-108
TAS-108
(SR-16234) Toremifene Trioxifene TZE-5323 Y-134 Zindoxifene Zuclomifene

Antagonists

(R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrol acetate EM-800 Epitiostanol ERA-90 ERB-88 Fulvestrant
Fulvestrant
(ICI-182780) Glyceollins (I, II, III, IV) ICI-164384 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-58668 SS1020 TAS-108
TAS-108
(SR-16234) ZB716 ZK-164015 ZK-191703

GPER

Agonists

2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene
Afimoxifene
(4-hydroxytamoxifen) Atrazine Bisphenol
Bisphenol
A Daidzein DDT
DDT
(p,p'-DDT, o',p'-DDE) Equol Estradiol Ethinylestradiol Fulvestrant
Fulvestrant
(ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol Tamoxifen Tectoridin Zearalanone Zearalenol Zearalenone Zeranol
Zeranol
(zearalanol))

Antagonists

CCL18 Estriol G-15 G-36 MIBE

See also Receptor/signaling modulators Estrogens and antiestrogens Androgen receptor
Androgen receptor
modulators Progesterone receptor modulators

.