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The Info List - Adenosine


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(adenosine may be safe to the fetus in pregnant women)

Routes of administration Intravenous

ATC code

C01EB10 (WHO)

Legal status

Legal status

In general: ℞ (Prescription only)

Pharmacokinetic data

Bioavailability Rapidly cleared from circulation via cellular uptake

Protein binding No

Metabolism Rapidly converted to inosine and adenosine monophosphate

Biological half-life cleared plasma <30 seconds – half-life <10 seconds

Excretion can leave cell intact or can be degraded to hypoxanthine, xanthine, and ultimately uric acid

Identifiers

IUPAC name

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

CAS Number

58-61-7 Y

PubChem CID

60961

IUPHAR/BPS

2844

DrugBank

DB00640 Y

ChemSpider

54923 Y

UNII

K72T3FS567

KEGG

C00212 Y

ChEBI

CHEBI:16335 Y

ChEMBL

CHEMBL477 N

ECHA InfoCard 100.000.354

Chemical and physical data

Formula C10H13N5O4

Molar mass 267.241 g/mol

3D model (JSmol)

Interactive image

SMILES

n2c1c(ncnc1n(c2)[C@@H]3O[C@@H]([C@@H](O)[C@H]3O)CO)N

InChI

InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 Y

Key:OIRDTQYFTABQOQ-KQYNXXCUSA-N Y

 NY (what is this?)  (verify)

Adenosine
Adenosine
is both a chemical found in many living systems and a medication. As a medication it is used to treat certain forms of supraventricular tachycardia that do not improve with vagal maneuvers.[1] Common side effects include chest pain, feeling faint, shortness of breath along with tingling of the senses.[1] Serious side effects include a worsening dysrhythmia and low blood pressure.[1] It appears to be safe in pregnancy.[1] It is a purine nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a β-N9-glycosidic bond.[2][3][4] Derivatives of adenosine are widely found in nature and play an important role in biochemical processes, such as energy transfer—as adenosine triphosphate (ATP) and adenosine diphosphate (ADP)—as well as in signal transduction as cyclic adenosine monophosphate (cAMP). Adenosine
Adenosine
itself is a neuromodulator, believed to play a role in promoting sleep and suppressing arousal. Adenosine
Adenosine
also plays a role in regulation of blood flow to various organs through vasodilation.[5][6][7]

Contents

1 Medical uses

1.1 Supraventricular tachycardia 1.2 Nuclear stress test 1.3 Dosage

2 Drug interactions 3 Contraindications 4 Side effects 5 Pharmacological effects

5.1 Adenosine
Adenosine
receptors 5.2 Ghrelin/growth hormone secretagogue receptor 5.3 Mechanism of action

6 Metabolism 7 Research

7.1 Viruses 7.2 Anti-inflammatory properties 7.3 Central nervous system 7.4 Hair

8 See also 9 References

Medical uses[edit] Supraventricular tachycardia[edit] In individuals with supraventricular tachycardia (SVT), adenosine is used to help identify and convert the rhythm. Certain SVTs can be successfully terminated with adenosine.[8] This includes any re-entrant arrhythmias that require the AV node for the re-entry, e.g., AV reentrant tachycardia
AV reentrant tachycardia
(AVRT), AV nodal reentrant tachycardia (AVNRT). In addition, atrial tachycardia can sometimes be terminated with adenosine. Fast rhythms of the heart that are confined to the atria (e.g., atrial fibrillation, atrial flutter) or ventricles (e.g., monomorphic ventricular tachycardia) and do not involve the AV node as part of the re-entrant circuit are not typically converted by adenosine. However, the ventricular response rate is temporarily slowed with adenosine in such cases. Because of the effects of adenosine on AV node-dependent SVTs, adenosine is considered a class V antiarrhythmic agent. When adenosine is used to cardiovert an abnormal rhythm, it is normal for the heart to enter ventricular asystole for a few seconds. This can be disconcerting to a normally conscious patient, and is associated with angina-like sensations in the chest.[9] Nuclear stress test[edit] Adenosine
Adenosine
is used as an adjunct to thallous (thallium) chloride TI 201 or Tc99m myocardial perfusion scintigraphy (nuclear stress test) in patients unable to undergo adequate stress testing with exercise.[10] Dosage[edit] When given for the evaluation or treatment of a supraventricular tachycardia (SVT), the initial dose is 6 mg to 12 mg, depending on standing orders or provider preference,[11] given as a rapid parenteral infusion. Due to adenosine's extremely short half-life, the IV line is started as proximal (near) to the heart as possible, such as the antecubital fossa. The IV push is often followed with an immediate flush of 10-20 ccs of saline. If this has no effect (i.e., no evidence of transient AV block), a dose of 12 mg can be given 1–2 minutes after the first dose. Some clinicians may prefer to administer a higher dose (typically 18 mg), rather than repeat a dose that apparently had no effect.[dubious – discuss] When given to dilate the arteries, such as in a "stress test", the dosage is typically 0.14 mg/kg/min, administered for 4 or 6 minutes, depending on the protocol. The recommended dose may be increased in patients on theophylline, since methylxanthines prevent binding of adenosine at receptor sites. The dose is often decreased in patients on dipyridamole (Persantine) and diazepam (Valium) because adenosine potentiates the effects of these drugs. The recommended dose is also reduced by half in patients presenting congestive heart failure, myocardial infarction, shock, hypoxia, and/or hepatic or renal insufficiency, and in elderly patients. Drug interactions[edit] Dopamine
Dopamine
may precipitate toxicity in a person. Carbamazepine
Carbamazepine
may increase heart block. Dipyridamole
Dipyridamole
potentiates the action of adenosine, requiring the use of lower doses.

Caffeine's principal mode of action is as an antagonist of adenosine receptors in the brain.

Methylxanthines
Methylxanthines
(e.g., caffeine, found in coffee, or theophylline in tea, or theobromine, as found in chocolate) competitively antagonize adenosine's effects; an increased dose of adenosine may be required. By nature of caffeine's purine structure,[12] it binds to some of the same receptors as adenosine.[12] Therefore, with the proviso that theophylline and theobromine cross the blood-brain barrier very poorly (thus, have low CNS effects on the heart), the pharmacological effects of adenosine may be blunted in individuals taking large quantities of methylxanthines.[13][citation needed] Contraindications[edit] Common contraindications for adenosine include

Asthma, traditionally considered an absolute contraindication. This is being contended and it is now considered a relative contraindication (however, selective adenosine antagonists are being investigated for use in treatment of asthma)[14] Decompensated heart failure Long QT syndrome Poison/drug-induced tachycardia Second- or third-degree heart block (without a pacemaker) Severe hypotension Sick sinus syndrome
Sick sinus syndrome
(without a pacemaker)

When administered via a central lumen catheter, adenosine has been shown to initiate atrial fibrillation because of its effect on atrial tissue. In individuals with accessory pathways, the onset of atrial fibrillation can lead to a life-threatening ventricular fibrillation. However, adenosine may be administered if equipment for cardioversion is immediately available as a backup. Side effects[edit] Many individuals experience facial flushing, a temporary rash on the chest, lightheadedness, diaphoresis, or nausea after administration of adenosine due to its vasodilatory effects. Metallic taste
Metallic taste
is a hallmark side-effect of adenosine administration. These symptoms are transitory, usually lasting less than one minute. It is classically associated with a sense of "impending doom", more prosaically described as apprehension. This lasts a few seconds after administration of a bolus dose, during transient asystole induced by intravenous administration. In some cases, adenosine can make patients' limbs feel numb for about 2–5 minutes after administration intravenously depending on the dosage (usually above 12 mg). Pharmacological effects[edit] Adenosine
Adenosine
is an endogenous purine nucleoside that modulates many physiological processes. Cellular signaling by adenosine occurs through four known adenosine receptor subtypes (A1, A2A, A2B, and A3).[15] Extracellular adenosine concentrations from normal cells are approximately 300 nM; however, in response to cellular damage (e.g. in inflammatory or ischemic tissue), these concentrations are quickly elevated (600–1,200 nM). Thus, in regard to stress or injury, the function of adenosine is primarily that of cytoprotection preventing tissue damage during instances of hypoxia, ischemia, and seizure activity. Activation of A2A receptors produces a constellation of responses that in general can be classified as anti-inflammatory.[16] Adenosine
Adenosine
receptors[edit] Main article: Adenosine
Adenosine
receptor All adenosine receptor subtypes (A1, A2A, A2B, and A3) are G-protein-coupled receptors. The four receptor subtypes are further classified based on their ability to either stimulate or inhibit adenylate cyclase activity. The A1 receptors couple to Gi/o and decreases cAMP levels, while the A2 adenosine receptors couple to Gs, which stimulates adenylate cyclase activity. In addition, A1 receptors couple to Go, which has been reported to mediate adenosine inhibition of Ca2+ conductance, whereas A2B and A3 receptors also couple to Gq and stimulate phospholipase activity. Researchers at Cornell University have recently shown adenosine receptors to be key in opening the blood-brain barrier (BBB). Mice dosed with adenosine have shown increased transport across the BBB of amyloid plaque antibodies and prodrugs associated with Parkinson's disease, Alzheimer's, multiple sclerosis, and cancers of the central nervous system.[17] Ghrelin/growth hormone secretagogue receptor[edit] Adenosine
Adenosine
is an endogenous agonist of the ghrelin/growth hormone secretagogue receptor.[18] However, while it is able to increase appetite, unlike other agonists of this receptor, adenosine is unable to induce the secretion of growth hormone and increase its plasma levels.[18] Mechanism of action[edit] When it is administered intravenously, adenosine causes transient heart block in the atrioventricular (AV) node. This is mediated via the A1 receptor, inhibiting adenylyl cyclase, reducing cAMP and so causing cell hyperpolarization by increasing K+ efflux via inward rectifier K+ channels, subsequently inhibiting Ca2+ current.[19] It also causes endothelial-dependent relaxation of smooth muscle as is found inside the artery walls. This causes dilation of the "normal" segments of arteries, i.e. where the endothelium is not separated from the tunica media by atherosclerotic plaque. This feature allows physicians to use adenosine to test for blockages in the coronary arteries, by exaggerating the difference between the normal and abnormal segments. The administration of adenosine also reduces blood flow to coronary arteries past the occlusion. Other coronary arteries dilate when adenosine is administered while the segment past the occlusion is already maximally dilated. This leads to less blood reaching the ischemic tissue, which in turn produces the characteristic chest pain. Metabolism[edit] Adenosine
Adenosine
used as a second messenger can be the result of de novo purine biosynthesis via adenosine monophosphate (AMP), though it is possible other pathways exist.[20] When adenosine enters the circulation, it is broken down by adenosine deaminase, which is present in red cells and the vessel wall. Dipyridamole, an inhibitor of adenosine nucleoside transporter, allows adenosine to accumulate in the blood stream. This causes an increase in coronary vasodilatation. Adenosine deaminase
Adenosine deaminase
deficiency is a known cause of immunodeficiency. Research[edit] Viruses[edit] See also: Nucleoside
Nucleoside
analogue The adenosine analog NITD008 has been reported to directly inhibit the recombinant RNA-dependent RNA polymerase
RNA polymerase
of the dengue virus by terminating its RNA chain synthesis. This suppresses peak viremia and rise in cytokines and prevented lethality in infected animals, raising the possibility of a new treatment for this flavivirus.[21] The 7-deaza-adenosine analog has been shown to inhibit the replication of the hepatitis C virus.[22] BCX4430
BCX4430
is protective against Ebola and Marburg viruses.[23] Such adenosine analogs are potentially clinically useful since they can be taken orally. Anti-inflammatory properties[edit] Adenosine
Adenosine
is believed to be an anti-inflammatory agent at the A2A receptor.[24][25] Topical treatment of adenosine to foot wounds in diabetes mellitus has been shown in lab animals to drastically increase tissue repair and reconstruction. Topical administration of adenosine for use in wound-healing deficiencies and diabetes mellitus in humans is currently under clinical investigation. Methotrexate's anti-inflammatory effect may be due to its stimulation of adenosine release.[26] Central nervous system[edit] In general, adenosine has an inhibitory effect in the central nervous system (CNS). Caffeine's stimulatory effects are credited primarily (although not entirely) to its capacity to block adenosine receptors, thereby reducing the inhibitory tonus of adenosine in the CNS. This reduction in adenosine activity leads to increased activity of the neurotransmitters dopamine and glutamate.[citation needed] Experimental evidence suggests that adenosine and adenosine agonists can activate Trk receptor phosphorylation through a mechanism that requires the adenosine A2A receptor.[27] Hair[edit] Adenosine
Adenosine
has been shown to promote thickening of hair on people with thinning hair.[28][29] A 2013 study compared topical adenosine to minoxidil in male androgenetic alopecia, finding it was not superior to minoxidil and further trials were needed.[30] See also[edit]

Adenosine
Adenosine
receptor Adenosine
Adenosine
reuptake inhibitor List of growth hormone secretagogues

References[edit]

^ a b c d "Adenosine". The American Society of Health-System Pharmacists. Retrieved Jan 12, 2015.  ^ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 106–. ISBN 978-94-011-4439-1.  ^ J. Buckingham (1987). Dictionary of Organic Compounds. CRC Press. pp. 75–. ISBN 978-0-412-54090-5.  ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 18–. ISBN 978-3-88763-075-1.  ^ Sato, A (April 2005). "Mechanism of vasodilation to adenosine in coronary arterioles from patients with heart disease". American Journal of Physiology. Heart and Circulatory Physiology. 288 (4): H1633–40. doi:10.1152/ajpheart.00575.2004. PMID 15772334.  ^ Costa, F; Biaggioni, I (May 1998). "Role of nitric oxide in adenosine-induced vasodilation in humans". Hypertension. 31 (5): 1061–4. doi:10.1161/01.HYP.31.5.1061. PMID 9576114.  ^ Morgan, JM; McCormack, DG; Griffiths, MJ; Morgan, CJ; Barnes, PJ; Evans, TW (September 1991). " Adenosine
Adenosine
as a vasodilator in primary pulmonary hypertension". Circulation. 84 (3): 1145–9. doi:10.1161/01.CIR.84.3.1145. PMID 1884445.  ^ Mitchell J, Lazarenko G (November 2008). "Wide QRS complex tachycardia. Diagnosis: Supraventricular tachycardia
Supraventricular tachycardia
with aberrant conduction; intravenous (IV) adenosine". CJEM. 10 (6): 572–3, 581. PMID 19000353.  ^ Pijls, Nico H. J.; Bernard De Bruyne (2000). Coronary Pressure. Springer. ISBN 0-7923-6170-9.  ^ O'Keefe, JH; Bateman, TM; Silverstri, R; et al. (1992). "Safety and diagnostic accuracy of adenosine thallium-201 scintigraphy in patients unable to exercise and those with left bundle branch block". Am Heart J. 124 (3): 614–21. doi:10.1016/0002-8703(92)90268-z. PMID 1514488.  ^ http://www.regionsems.com/wp-content/uploads/2016/04/2014-Guidelines.pdf ^ a b "Caffeine". Chemistry Explained.  ^ " Vitamin
Vitamin
B4". R&S Pharmchem. April 2011. Archived from the original on 2011-07-15.  ^ Brown RA, Spina D, Page CP (March 2008). " Adenosine
Adenosine
receptors and asthma". Br. J. Pharmacol. 153 Suppl 1 (S1): S446–56. doi:10.1038/bjp.2008.22. PMC 2268070 . PMID 18311158.  ^ Haskó G, Linden J, Cronstein B, Pacher P (September 2008). " Adenosine
Adenosine
receptors: therapeutic aspects for inflammatory and immune diseases". Nat Rev Drug Discov. 7 (9): 759–70. doi:10.1038/nrd2638. PMC 2568887 . PMID 18758473.  ^ Haskó, G (January 2004). "Adenosine: an endogenous regulator of innate immunity". Trends in Immunology. 25 (1): 33–39. doi:10.1016/j.it.2003.11.003. PMID 14698282.  ^ Carman, A. J.; Mills, J. H.; Krenz, A; Kim, D. G.; Bynoe, M. S. (2011). " Adenosine receptor
Adenosine receptor
signaling modulates permeability of the blood-brain barrier". J. Neurosci. 31 (37): 13272–80. doi:10.1523/JNEUROSCI.3337-11.2011. PMC 3328085 . PMID 21917810.  ^ a b Claude Kordon; I. Robinson; Jacques Hanoune; R. Dantzer (6 December 2012). Brain Somatic Cross- Talk
Talk
and the Central Control of Metabolism. Springer Science & Business Media. pp. 42–. ISBN 978-3-642-18999-9.  ^ Katzung, Bertram (2012). Basic & Clinical Pharmacology (12th ed.). McGraw Hill. p. 245. ISBN 978-0-07-176402-5.  ^ Miller-Patrick K, Vincent DL, Early RJ, et al. (1993). "Effects of the purine biosynthesis pathway inhibitors azaserine, hadacidin, and mycophenolic acid on the developing ovine corpus luteum". Chin J Physiol. 36 (4): 245–52. PMID 8020339.  ^ Yin, Z; Chen, YL; Schul, W; Wang, QY; Gu, F; Duraiswamy, J; Reddy Kondreddi, R; Niyomrattanakit, P; Lakshminarayana, SB; Goh, A; Xu, HY; Liu, W; Liu, B; Lim, JY; Ng, CY; Qing, M; Lim, CC; Yip, A; Wang, G; Chan, WL; Tan, HP; Lin, K; Zhang, B; Zou, G; Bernard, KA; Garrett, C; Beltz, K; Dong, M; Weaver, M; He, H; Pichota, A; Dartois, V; Keller, TH; Shi, PY (2009). "An adenosine nucleoside inhibitor of dengue virus". Proc Natl Acad Sci U S A. 106 (48): 20435–20439. Bibcode:2009PNAS..10620435Y. doi:10.1073/pnas.0907010106. PMC 2787148 . PMID 19918064.  ^ Olsen, DB; Eldrup, AB; Bartholomew, L; Bhat, B; Bosserman, MR; Ceccacci, A; Colwell, LF; Fay, JF; Flores, OA; Getty, K. L.; Grobler, J. A.; Lafemina, R. L.; Markel, E. J.; Migliaccio, G.; Prhavc, M.; Stahlhut, M. W.; Tomassini, J. E.; MacCoss, M.; Hazuda, D. J.; Carroll, S. S. (2004). "A 7-Deaza- Adenosine
Adenosine
Analog Is a Potent and Selective Inhibitor of Hepatitis C Virus Replication with Excellent Pharmacokinetic Properties". Antimicrobial Agents and Chemotherapy. 48 (10): 3944–53. doi:10.1128/AAC.48.10.3944-3953.2004. PMC 521892 . PMID 15388457.  ^ Warren, T. K.; Wells, J.; Panchal, R. G.; Stuthman, K. S.; Garza, N. L.; Van Tongeren, S. A.; Dong, L.; Retterer, C. J.; Eaton, B. P.; Pegoraro, G.; Honnold, S.; Bantia, S.; Kotian, P.; Chen, X.; Taubenheim, B. R.; Welch, L. S.; Minning, D. M.; Babu, Y. S.; Sheridan, W. P.; Bavari, S. (2014). "Protection against filovirus diseases by a novel broad-spectrum nucleoside analogue BCX4430". Nature. 508 (7496): 402–5. Bibcode:2014Natur.508..402W. doi:10.1038/nature13027. PMID 24590073.  ^ Nakav S, Chaimovitz C, Sufaro Y (2008). Bozza P, ed. "Anti-Inflammatory Preconditioning by Agonists of Adenosine
Adenosine
A1 Receptor". PLoS ONE. 3 (5): e2107. Bibcode:2008PLoSO...3.2107N. doi:10.1371/journal.pone.0002107. PMC 2329854 . PMID 18461129.  ^ Trevethick MA, Mantell SJ, Stuart EF, Barnard A, Wright KN, Yeadon M (October 2008). "Treating lung inflammation with agonists of the adenosine A2A receptor: promises, problems and potential solutions". Br. J. Pharmacol. 155 (4): 463–74. doi:10.1038/bjp.2008.329. PMC 2579671 . PMID 18846036.  ^ Cronstein B (2010). "How does methotrexate suppress inflammation?". Clin Exp Rheumatol. 28 (5 Suppl 61): S21–3. PMID 21044428.  ^ Lee, FS; Chao, MV; Lee (March 2001). "Activation of Trk neurotrophin receptors in the absence of neurotrophins". PNAS. 98 (6): 3555–3560. Bibcode:2001PNAS...98.3555L. doi:10.1073/pnas.061020198. PMC 30691 . PMID 11248116.  ^ Oura, H; Iino, M; Nakazawa, Y; Tajima, M; Ideta, R; Nakaya, Y; Arase, S; Kishimoto, J (December 2008). " Adenosine
Adenosine
increases anagen hair growth and thick hairs in Japanese women with female pattern hair loss: a pilot, double-blind, randomized, placebo-controlled trial". The Journal of dermatology. 35 (12): 763–7. doi:10.1111/j.1346-8138.2008.00564.x. PMID 19239555.  ^ Hwang, KA; Hwang, YL; Lee, MH; Kim, NR; Roh, SS; Lee, Y; Kim, CD; Lee, JH; Choi, KC (February 2012). " Adenosine
Adenosine
stimulates growth of dermal papilla and lengthens the anagen phase by increasing the cysteine level via fibroblast growth factors 2 and 7 in an organ culture of mouse vibrissae hair follicles". International journal of molecular medicine. 29 (2): 195–201. doi:10.3892/ijmm.2011.817. PMID 22020741.  ^ Faghihi, G; Iraji, F; Rajaee Harandi, M; Nilforoushzadeh, M. A.; Askari, G (2013). "Comparison of the efficacy of topical minoxidil 5% and adenosine 0.75% solutions on male androgenetic alopecia and measuring patient satisfaction rate". Acta Dermatovenerol Croat. 21 (3): 155–9. PMID 24183218. 

v t e

Neurotransmitters

Amino acid-derived

Major excitatory/inhibitory systems: Glutamate
Glutamate
system: Agmatine Aspartic acid
Aspartic acid
(aspartate) Cycloserine Glutamic acid
Glutamic acid
(glutamate) Glutathione Glycine GSNO GSSG Kynurenic acid NAA NAAG Proline Serine; GABA system: GABA GABOB GHB; Glycine
Glycine
system: α-Alanine β-Alanine Glycine Hypotaurine Proline Sarcosine Serine Taurine; GHB system: GHB T-HCA (GHC)

Biogenic amines: Monoamines: 6-OHM Dopamine Epinephrine
Epinephrine
(adrenaline) NAS (normelatonin) Norepinephrine
Norepinephrine
(noradrenaline) Serotonin
Serotonin
(5-HT); Trace amines: 3-Iodothyronamine N-Methylphenethylamine N-Methyltryptamine m-Octopamine p-Octopamine Phenylethanolamine Phenethylamine Synephrine Tryptamine m-Tyramine p-Tyramine; Others: Histamine

Neuropeptides: See here instead.

Lipid-derived

Endocannabinoids: 2-AG 2-AGE (noladin ether) 2-ALPI 2-OG AA-5-HT Anandamide
Anandamide
(AEA) DEA LPI NADA NAGly OEA Oleamide PEA RVD-Hpα SEA Virodhamine
Virodhamine
(O-AEA)

Neurosteroids: See here instead.

Nucleobase-derived

Nucleosides: Adenosine
Adenosine
system: Adenosine ADP AMP ATP

Vitamin-derived

Cholinergic system: Acetylcholine

Miscellaneous

Gasotransmitters: Carbon monoxide
Carbon monoxide
(CO) Hydrogen sulfide
Hydrogen sulfide
(H2S) Nitric oxide
Nitric oxide
(NO); Candidates: Acetaldehyde Ammonia
Ammonia
(NH3) Carbonyl sulfide
Carbonyl sulfide
(COS) Nitrous oxide
Nitrous oxide
(N2O) Sulfur dioxide
Sulfur dioxide
(SO2)

v t e

Nucleic acid
Nucleic acid
constituents

Nucleobase

Purine

Adenine Guanine Hypoxanthine Xanthine Purine
Purine
analogue

Pyrimidine

Uracil Thymine Cytosine Pyrimidine
Pyrimidine
analogue

Unnatural base pair (UBP)

Nucleoside

Ribonucleoside

Adenosine Guanosine 5-Methyluridine Uridine 5-Methylcytidine Cytidine Inosine Xanthosine Wybutosine

Deoxyribonucleoside

Deoxyadenosine Deoxyguanosine Thymidine Deoxyuridine Deoxycytidine Deoxyinosine Deoxyxanthosine

Nucleotide ( Nucleoside
Nucleoside
monophosphate)

Ribonucleotide

AMP GMP m5UMP UMP CMP IMP XMP

Deoxyribonucleotide

dAMP dGMP dTMP dUMP dCMP dIMP dXMP

Cyclic nucleotide

cAMP cGMP c-di-GMP c-di-AMP cADPR

Nucleoside
Nucleoside
diphosphate

ADP GDP m5UDP UDP CDP

dADP dGDP dTDP dUDP dCDP

Nucleoside
Nucleoside
triphosphate

ATP GTP m5UTP UTP CTP ITP XTP

dATP dGTP dTTP dUTP dCTP dITP dXTP

v t e

Antiarrhythmic agents
Antiarrhythmic agents
(C01B)

Channel blockers

class I (Na+ channel blockers)

class Ia (Phase 0→ and Phase 3→)

Ajmaline Disopyramide Hydroquinidine Lorajmine Prajmaline Procainamide# Quinidine# Sparteine

class Ib (Phase 3←)

IV

Lidocaine#

enteral

Aprindine Mexiletine Tocainide

class Ic (Phase 0→)

Encainide‡ Ethacizine Flecainide Indecainide‡ Lorcainide Moracizine‡ Propafenone

class III (Phase 3→, K+ channel blockers)

Amiodarone Bretylium Bunaftine Celivarone† Dofetilide Dronedarone E-4031† Ibutilide Nifekalant Sotalol Tedisamil Vernakalant

class IV (Phase 4→, Ca2+ channel blockers)

Diltiazem Verapamil#

Receptor agonists and antagonists

class II (Phase 4→, β blockers)

Nadolol Pindolol Propranolol cardioselective

Acebutolol Atenolol Esmolol Metoprolol

A1 agonist

Adenosine Benzodiazepines Barbiturates

M2

muscarinic antagonist: Atropine Disopyramide Quinidine muscarinic agonist: Digoxin

α receptors

Amiodarone Bretylium Quinidine Verapamil

Ion transporters

Na+/ K+-ATPase

Digitoxin Digoxin Ouabain

#WHO-EM ‡Withdrawn from market Clinical trials:

†Phase III §Never to phase III

v t e

Purine
Purine
receptor modulators

Receptor (ligands)

P0 (adenine)

Agonists: 8-Aminoadenine Adenine

P1 (adenosine)

Agonists: 2-(1-Hexynyl)-N-methyladenosine 2-Cl-IB-MECA 2'-MeCCPA 4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil 5'-N-ethylcarboxamidoadenosine Adenosine ADP AMP Apadenoson ATL-146e ATP BAY 60–6583 Binodenoson Capadenoson CCPA CGS-21680 CP-532,903 Evodenoson GR 79236 LUF-5835 LUF-5845 N6-Cyclopentyladenosine Namodenoson Neladenoson dalanate Piclidenoson Regadenoson SDZ WAG 994 Selodenoson Sonedenoson Tecadenoson UK-432,097

Antagonists: 8-Chlorotheophylline 8-Phenyl-1,3-dipropylxanthine 8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine
Caffeine
citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate CPX CVT-6883 Dimethazan DMPX DPCPX Dyphylline Enprofylline Etazolate Fenethylline IBMX Isovaleric acid Istradefylline KF-26777 MRE3008F20 MRS-1220 MRS-1334 MRS-1706 MRS-1754 MRS-3777 Paraxanthine Pentoxifylline Preladenant Propentofylline Proxyphylline PSB-10 PSB-11 PSB-36 PSB-603 PSB-788 PSB-1115 Reversine Rolofylline SCH-442,416 SCH-58261 Theacrine Theobromine Theodrenaline Theophylline Tozadenant Tracazolate VUF-5574 ZM-241,385

P2 (nucleotide)

P2X (ATP)

Agonists: 2-Me-SATP α,β-Me-ATP Adenosine ADP AMP Ap4A Ap5A ATP ATPγS BzATP Cibacron blue CTP D-β,γ-Me-ATP GTP HT-AMP Ivermectin L-β,γ-Me-ATP MRS-2219 PAPET-ATP UTP Zinc

Antagonists: 5-BDBD A-317491 A-438079 A-740003 A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin
Emodin
(Rheum officinale) Evans Blue GW-791343 HMA Ip5I isoPPADS JNJ-47965567 KN-04 KN-62 Magnesium MRS-2159 NF-023 NF-110 NF-157 NF-279 NF-449 Opiranserin (VVZ-149) Oxidized-ATP Phenol Red Phenolphthalein PPADS PPNDS PSB-12062 Puerarin
Puerarin
(Radix puerariae) Purotoxin 1 RB-2 Ro 0437626 Ro 51 RO-3 Sodium ferulate
Sodium ferulate
(Angelica sinensis, Ligusticum wallichii) Suramin TC-P 262 Tetramethylpyrazine
Tetramethylpyrazine
(ligustrazine) (Ligusticum wallichii) TNP-ATP Zinc

P2Y

Agonists: 2-Me-SADP 2-Me-SATP 2-Thio-UTP 5-Br-UDP 5-OMe-UDP α,β-Me-ATP Adenosine ADP ADPβS Ap3A AR-C 67085MX ATP ATPγS CTP dATP Denufosol Diquafosol IDP ITP INS-365 INS-37217 MRS-2365 MRS-2690 MRS-2693 MRS-2768 MRS-2957 MRS-4062 NF-546 PAPET-ATP PSB-0474 PSB-1114 UDP UDPβS UDP-galactose UDP-glucose UDP-N-acetylglucosamine Up3U UTP UTPγS

Antagonists: 2-Me-SAMP A3P5PS AMPαS Ap4A AR-C 66096 AR-C 67085MX AR-C 69931MX AR-C 118925XX ATP BzATP C1330-7 Cangrelor Clopidogrel Elinogrel Ip5I MRS-2179 MRS-2211 MRS-2279 MRS-2395 MRS-2500 MRS-2578 NF-157 NF-340 PIT PPADS Prasugrel PSB-0739 RB-2 Regrelor Suramin Ticagrelor Ticlopidine UDP

Transporter (blockers)

CNTs

6-Hydroxy-7-methoxyflavone Adenosine dMeThPmR Estradiol KGO-2142 KGO-2173 MeThPmR Phloridzin Progesterone

ENTs

Barbiturates Benzodiazepines Cilostazol Dilazep Dipyridamole Estradiol Ethanol Hexobendine NBMPR Pentoxifylline Progesterone Propentofylline

PMAT

Decynium-22

Enzyme (inhibitors)

XO

Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol Myricetin Niraxostat Oxipurinol Phytic acid Pistacia integerrima Propolis Quercetin Tisopurine Topiroxostat

Others

Aminopterin Azathioprine Methotrexate Mycophenolic acid Pemetrexed Pralatrexate Many others

Others

Precursors: Adenine Adenosine AMP ADP ATP Cytosine Cytidine CMP CDP CTP Guanine Guanosine GMP GDP GTP Hypoxanthine Inosine IMP IDP ITP Ribose Uracil Uridine UMP UDP UTP

Others: Chrysophanol
Chrysophanol
(rhubarb)

See also: Receptor/signaling modulators

v t e

GH/IGF-1 axis signaling modulators

GH (somatotropin)

Agonists: Albusomatropin Bovine somatotropin Efpegsomatropin Growth hormone Human placental lactogen Placental growth hormone
Placental growth hormone
(growth hormone variant) Somagrebove Somapacitan Somatosalm Somatotropin Somatropin pegol Somatrem Sometribove Somatrogon (MOD-4023; hGH-CTP) Somavaratan Somavubove Somidobove

Antagonists: G120K-hGH Pegvisomant

Antisense oligonucleotides: Atesidorsen

Binding proteins: GHBP

GHIH (somatostatin)

Agonists: BIM-23052 CH-275 Cortistatin-14 Depreotide Edotreotide Ilatreotide L-803,087 L-817,818 Lanreotide NNC 26-9100 Octreotate Octreotide Pasireotide Pentetreotide RC-160 Seglitide Somatostatin
Somatostatin
(GHIH) Somatostatin
Somatostatin
(1-28) SRIF-14 SRIF-28 TT-232 Vapreotide Veldoreotide

Antagonists: BIM-23056 Cyclosomatostatin CYN-154806 Satoreotide

GHRH (somatocrinin)

Agonists: Peptide: ALRN-5281 CJC-1295 Dumorelin GHRH Modified GRF (1-29) Rismorelin Sermorelin Somatorelin Tesamorelin

Antagonists: MZ-5-156

GHS (ghrelin)

Agonists: Peptide: Alexamorelin Cortistatin-14 EP-51216 Examorelin
Examorelin
(hexarelin) Ghrelin GHRP-1 GHRP-3 GHRP-4 GHRP-5 GHRP-6 Ipamorelin Lenomorelin LY-444711 Pralmorelin
Pralmorelin
(GHRP-2) Relamorelin Tabimorelin Ulimorelin; Non-peptide: Adenosine Anamorelin Capromorelin CP-464709 Ibutamoren
Ibutamoren
(MK-677) L-692,585 Macimorelin SM-130686; Unsorted: LY-426410 LY-444711

Antagonists: A-778193 Cortistatin-8 (D-Lys³)-GHRP-6 JMV2959 YIL-781

IGF-1 (somatomedin)

See here instead.

See also: Receptor/signaling modulators • Signaling peptide/protein receptor modulators

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