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XANTHINE (/ˈzænθiːn/ or /ˈzænθaɪn/ ; archaically XANTHIC ACID) (3,7-dihydropurine-2,6-dione), is a purine base found in most human body tissues and fluids and in other organisms. A number of stimulants are derived from xanthine, including caffeine and theobromine .

Xanthine
Xanthine
is a product on the pathway of purine degradation .

* It is created from guanine by guanine deaminase . * It is created from hypoxanthine by xanthine oxidoreductase . * It is also created from xanthosine by purine nucleoside phosphorylase (PNP).

Xanthine
Xanthine
is subsequently converted to uric acid by the action of the xanthine oxidase enzyme.

Studies reported in 2008, based on 12C/13C isotopic ratios of organic compounds found in the Murchison meteorite , suggested that xanthine and related chemicals, including the RNA
RNA
component uracil , were formed extraterrestrially. In August 2011, a report, based on NASA studies with meteorites found on Earth, was published suggesting xanthine and related organic molecules, including the DNA
DNA
and RNA components adenine and guanine , were found in outer space .

CONTENTS

* 1 Pathology * 2 Clinical significance of xanthine derivatives * 3 Detection * 4 See also * 5 References

PATHOLOGY

People with the rare genetic disorder xanthinuria lack sufficient xanthine oxidase and cannot convert xanthine to uric acid .

CLINICAL SIGNIFICANCE OF XANTHINE DERIVATIVES

Derivatives of xanthine (known collectively as XANTHINES) are a group of alkaloids commonly used for their effects as mild stimulants and as bronchodilators , notably in the treatment of asthma symptoms. In contrast to other, more potent stimulants like sympathomimetic amines , xanthines mainly act to oppose the actions of the sleepiness-inducing adenosine , and increase alertness in the central nervous system . They also stimulate the respiratory centre, and are used for treatment of infantile apnea . Due to widespread effects, the therapeutic range of xanthines is narrow, making them merely a second-line asthma treatment. The therapeutic level is 10-20 micrograms/mL blood; signs of toxicity include tremor, nausea, nervousness, and tachycardia/arrhythmia.

Methylated xanthines (methylxanthines), which include caffeine , aminophylline , IBMX , paraxanthine , pentoxifylline , theobromine , and theophylline , affect not only the airways but stimulate heart rate, force of contraction, and cardiac arrhythmias at high concentrations. In high doses they can lead to convulsions that are resistant to anticonvulsants. Methylxanthines induce acid and pepsin secretions in the GI tract. Methylxanthines are metabolized by cytochrome P450 in the liver.

These drugs act as both:

* competitive nonselective phosphodiesterase inhibitors which raise intracellular cAMP , activate PKA , inhibit TNF-α and leukotriene synthesis, and reduce inflammation and innate immunity and * nonselective adenosine receptor antagonists which inhibit sleepiness-inducing adenosine .

But different analogues show varying potency at the numerous subtypes, and a wide range of synthetic xanthines (some nonmethylated) have been developed searching for compounds with greater selectivity for phosphodiesterase enzyme or adenosine receptor subtypes. Xanthines are also found very rarely as constituents of nucleic acids . Xanthine: R1 = R2 = R3 = H Caffeine: R1 = R2 = R3 = CH3 Theobromine: R1 = H, R2 = R3 = CH3 Theophylline: R1 = R2 = CH3, R3 = H

Examples of xanthine derivatives NAME R1 R2 R3 R8 IUPAC NOMENCLATURE FOUND IN

Xanthine H H H H 3,7-Dihydro-purine-2,6-dione Plants, animals

Caffeine
Caffeine
CH3 CH3 CH3 H 1,3,7-Trimethyl-1H-purine-2,6(3H,7H)-dione Coffee
Coffee
, guarana , yerba mate , tea , kola , guayusa , holly

Theobromine
Theobromine
H CH3 CH3 H 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione Cacao (chocolate ), yerba mate , kola , guayusa , holly

Theophylline
Theophylline
CH3 CH3 H H 1,3-Dimethyl-7H-purine-2,6-dione Tea
Tea
, cacao (chocolate ), yerba mate , kola

Paraxanthine CH3 H CH3 H 1,7-Dimethyl-7H-purine-2,6-dione Animals that have consumed caffeine

8-Chlorotheophylline CH3 CH3 H Cl 8-Chloro-1,3-dimethyl-7H-purine-2,6-dione Synthetic pharmaceutical ingredient

Diprophylline CH3 CH3 C3H7O2 H 7-(2,3-Dihydroxypropyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione Synthetic pharmaceutical ingredient

IBMX CH3 C4H9 H H 1-Methyl-3-(2-methylpropyl)-7H-purine-2,6-dione

Uric acid
Uric acid
H H H O 7,9-Dihydro-1H-purine-2,6,8(3H)-trione Byproduct of purine nucleotides metabolism and a normal component of urine

DETECTION

* Non-specific LC-MS * UV Spectroscopy * Fourier transform infrared spectrometry

SEE ALSO

* Murchison meteorite * Xanthene * Xanthydrol * Xanthone * Theobromine
Theobromine
poisoning * DMPX

REFERENCES

* ^ Merck Index, 11th Edition, 9968. * ^ Spiller, Gene A. (1998). Caffeine. Boca Raton: CRC Press. ISBN 0-8493-2647-8 . * ^ Voet, Donald; Voet, Judith; Pratt, Charlotte (2008). "The Major Pathways of Purine
Purine
Catabolism in Animals", Fundamentals of Biochemistry: Life at the Molecular Level, p. 840. * ^ Martins, Z.; Botta, O.; Fogel, M. L.; Sephton, M. A.; Glavin, D. P.; Watson, J. S.; Dworkin, J. P.; Schwartz, A. W.; Ehrenfreund, P. (2008). "Extraterrestrial nucleobases in the Murchison meteorite". Earth and Planetary Science Letters. 270: 130–136. arXiv :0806.2286  . Bibcode :2008E&PSL.270..130M. doi :10.1016/j.epsl.2008.03.026 . * ^ AFP Staff (13 June 2008). "We may all be space aliens: study". AFP . Archived from the original on June 17, 2008. Retrieved 2011-08-14. * ^ Callahan, M. P.; Smith, K. E.; Cleaves, H. J.; Ruzicka, J.; Stern, J. C.; Glavin, D. P.; House, C. H.; Dworkin, J. P. (2011). "Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases" . Proceedings of the National Academy of Sciences. 108 (34): 13995–8. doi :10.1073/pnas.1106493108 . PMC 3161613  . PMID 21836052 . * ^ Steigerwald, John (8 August 2011). " NASA
NASA
Researchers: DNA Building Blocks Can Be Made in Space". NASA
NASA
. Retrieved 2011-08-10. * ^ ScienceDaily Staff (9 August 2011). " DNA
DNA
Building Blocks Can Be Made in Space, NASA
NASA
Evidence Suggests". ScienceDaily . Retrieved 2011-08-09. * ^ A B Deree J, Martins JO, Melbostad H, Loomis WH, Coimbra R (2008). "Insights into the regulation of TNF-alpha production in human mononuclear cells: the effects of non-specific phosphodiesterase inhibition" . Clinics (São Paulo). 63 (3): 321–8. doi :10.1590/S1807-59322008000300006 . PMC 2664230  . PMID 18568240 . * ^ Essayan DM. (2001). "Cyclic nucleotide phosphodiesterases". J Allergy Clin Immunol. 108 (5): 671–80. doi :10.1067/mai.2001.119555 . PMID 11692087 . * ^ Marques LJ, Zheng L, Poulakis N, Guzman J, Costabel U (February 1999). " Pentoxifylline inhibits TNF-alpha production from human alveolar macrophages". Am. J. Respir. Crit. Care Med. 159 (2): 508–11. doi :10.1164/ajrccm.159.2.9804085 . PMID 9927365 . * ^ A B Peters-Golden M, Canetti C, Mancuso P, Coffey MJ (2005). "Leukotrienes: underappreciated mediators of innate immune responses". J. Immunol. 174 (2): 589–94. doi :10.4049/jimmunol.174.2.589 . PMID 15634873 . * ^ Daly JW, Jacobson KA, Ukena D (1987). " Adenosine
Adenosine
receptors: development of selective agonists and antagonists". Prog Clin Biol Res. 230 (1): 41–63. PMID 3588607 . * ^ MacCorquodale DW. THE SYNTHESIS OF SOME ALKYLXANTHINES. Journal of the American Chemical Society. 1929 July;51(7):2245–2251. doi :10.1021/ja01382a042 * ^ WO patent 1985002540, Sunshine A, Laska EM, Siegel CE, "ANALGESIC AND ANTI-INFLAMMATORY COMPOSITIONS COMPRISING XANTHINES AND METHODS OF USING SAME", granted 1989-03-22, assigned to RICHARDSON-VICKS, INC. * ^ Constantin Koulbanis, Claude Bouillon, Patrick Darmenton,"Cosmetic compositions having a slimming action", US patent 4288433, granted 1981-09-04 , assigned to L'Oréal * ^ Daly JW, Padgett WL, Shamim MT (July 1986). "Analogues of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors". Journal of Medicinal Chemistry. 29 (7): 1305–8. doi :10.1021/jm00157a035 . PMID 3806581 . * ^ Daly JW, Jacobson KA, Ukena D (1987). " Adenosine
Adenosine
receptors: development of selective agonists and antagonists". Progress in Clinical and Biological Research. 230: 41–63. PMID 3588607 . * ^ Choi OH, Shamim MT, Padgett WL, Daly JW (1988). " Caffeine
Caffeine
and theophylline analogues: correlation of behavioral effects with activity as adenosine receptor antagonists and as phosphodiesterase inhibitors". Life Sciences. 43 (5): 387–98. doi :10.1016/0024-3205(88)90517-6 . PMID 2456442 . * ^ Shamim MT, Ukena D, Padgett WL, Daly JW (June 1989). "Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions". Journal of Medicinal Chemistry. 32 (6): 1231–7. doi :10.1021/jm00126a014 . PMID 2724296 . * ^ Daly JW, Hide I, Müller CE, Shamim M (1991). "Caffeine analogs: structure-activity relationships at adenosine receptors". Pharmacology. 42 (6): 309–21. doi :10.1159/000138813 . PMID 1658821 . * ^ Ukena D, Schudt C, Sybrecht GW (February 1993). "Adenosine receptor-blocking xanthines as inhibitors of phosphodiesterase isozymes". Biochemical Pharmacology . 45 (4): 847–51. doi :10.1016/0006-2952(93)90168-V . PMID 7680859 . * ^ Daly JW (July 2000). "Alkylxanthines as research tools". Journal of the Autonomic Nervous System. 81 (1–3): 44–52. doi :10.1016/S0165-1838(00)00110-7 . PMID 10869699 . * ^ Daly JW (August 2007). " Caffeine
Caffeine
analogs: biomedical impact". Cellular and Molecular Life Sciences : CMLS. 64 (16): 2153–69. doi :10.1007/s00018-007-7051-9 . PMID 17514358 . * ^ González MP, Terán C, Teijeira M (May 2008). "Search for new antagonist ligands for adenosine receptors from QSAR point of view. How close are we?". Medicinal Research Reviews. 28 (3): 329–71. doi :10.1002/med.20108 . PMID 17668454 . * ^ Baraldi PG, Tabrizi MA, Gessi S, Borea PA (January 2008). " Adenosine
Adenosine
receptor antagonists: translating medicinal chemistry and pharmacology into clinical utility". Chemical Reviews. 108 (1): 238–63. doi :10.1021/cr0682195 . PMID 18181659 .

* v * t * e

Stimulants

ADAMANTANES

* Adapromine
Adapromine
* Amantadine
Amantadine
* Bromantane * Memantine
Memantine
* Rimantadine
Rimantadine

ADENOSINE ANTAGONISTS

* 8-Chlorotheophylline * 8-Cyclopentyltheophylline * 8-Phenyltheophylline
8-Phenyltheophylline
* Aminophylline
Aminophylline
* Caffeine
Caffeine
* CGS-15943
CGS-15943
* Dimethazan * Paraxanthine * SCH-58261 * Theobromine
Theobromine
* Theophylline
Theophylline

ALKYLAMINES

* Cyclopentamine
Cyclopentamine
* Cypenamine * Cyprodenate * Heptaminol * Isometheptene * Levopropylhexedrine * Methylhexaneamine * Octodrine * Propylhexedrine * Tuaminoheptane

AMPAKINES

* CX-516
CX-516
* CX-546
CX-546
* CX-614
CX-614
* CX-691 * CX-717 * IDRA-21 * LY-404,187 * LY-503,430 * Nooglutyl
Nooglutyl
* Org 26576
Org 26576
* PEPA * S-18986 * Sunifiram * Unifiram

ARYLCYCLOHEXYLAMINES

* Benocyclidine * Dieticyclidine * Esketamine
Esketamine
* Eticyclidine * Gacyclidine * Ketamine
Ketamine
* Phencyclamine
Phencyclamine
* Phencyclidine
Phencyclidine
* Rolicyclidine
Rolicyclidine
* Tenocyclidine * Tiletamine

BENZAZEPINES

* 6-Br-APB
6-Br-APB
* SKF-77434 * SKF-81297 * SKF-82958

CHOLINERGICS

* A-84,543 * A-366,833 * ABT-202 * ABT-418 * AR-R17779 * Altinicline * Anabasine
Anabasine
* Arecoline
Arecoline
* Bradanicline * Cotinine * Cytisine
Cytisine
* Dianicline * Epibatidine * Epiboxidine * GTS-21
GTS-21
* Ispronicline * Nicotine
Nicotine
* PHA-543,613 * PNU-120,596 * PNU-282,987 * Pozanicline * Rivanicline * Sazetidine A * SIB-1553A * SSR-180,711 * TC-1698 * TC-1827 * TC-2216 * Tebanicline * UB-165 * Varenicline
Varenicline
* WAY-317,538

CONVULSANTS

* Anatoxin-a * Bicuculline * DMCM
DMCM
* Flurothyl * Gabazine * Pentetrazol * Picrotoxin * Strychnine
Strychnine
* Thujone

EUGEROICS

* Adrafinil * Armodafinil * CRL-40,940 * CRL-40,941 * Fluorenol * JZ-IV-10 * Modafinil
Modafinil

OXAZOLINES

* 4-Methylaminorex * Aminorex
Aminorex
* Clominorex
Clominorex
* Cyclazodone
Cyclazodone
* Fenozolone * Fluminorex * Pemoline * Thozalinone

PHENETHYLAMINES

* 1-(4-Methylphenyl)-2-aminobutane * 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane * 2-Fuoroamphetamine * 2-Fuoromethamphetamine * 2-OH-PEA * 2-Phenyl-3-aminobutane * 2,3-MDA * 3-Fuoroamphetamine * 3-Fluoroethamphetamine * 3-Fluoromethcathinone * 3-Methoxyamphetamine * 3-Methylamphetamine * 3,4-DMMC * 4-BMC * 4-CMC * 4-Ethylamphetamine * 4-Fluoroamphetamine * 4-Fluoromethamphetamine * 4-MA * 4-Methylbuphedrone
4-Methylbuphedrone
* 4-Methylcathinone
4-Methylcathinone
* 4-MMA * 4-Methylpentedrone * 4-MTA * 6-FNE * AL-1095 * Alfetamine * a-Ethylphenethylamine * Amfecloral * Amfepentorex * Amfepramone * Amidephrine * 2-Amino-1,2-dihydronaphthalene * 2-Aminoindane * 5-(2-Aminopropyl)indole * 2-Aminotetralin * Acridorex * Amphetamine
Amphetamine
( Dextroamphetamine
Dextroamphetamine
, Levoamphetamine ) * Amphetaminil * Arbutamine
Arbutamine
* β-Methylphenethylamine * β-Phenylmethamphetamine * Benfluorex * Benzedrone * Benzphetamine * BDB * BOH * 3-Benzhydrylmorpholine * BPAP * Buphedrone * Bupropion * Butylone
Butylone
* Camfetamine * Cathine * Cathinone
Cathinone
* Chlorphentermine * Cilobamine * Cinnamedrine * Clenbuterol
Clenbuterol
* Clobenzorex * Cloforex * Clortermine * Cypenamine * D-Deprenyl * Denopamine * Dimethoxyamphetamine
Dimethoxyamphetamine
* Dimethylamphetamine
Dimethylamphetamine
* Dimethylcathinone * Dobutamine
Dobutamine
* DOPA (Dextrodopa , Levodopa ) * Dopamine
Dopamine
* Dopexamine
Dopexamine
* Droxidopa * EBDB * Ephedrine * Epinephrine
Epinephrine
* Epinine * Etafedrine * Ethcathinone * Ethylnorepinephrine * Ethylone * Etilamfetamine
Etilamfetamine
* Etilefrine * Famprofazone
Famprofazone
* Fencamfamin
Fencamfamin
* Fencamine * Fenethylline * Fenfluramine ( Dexfenfluramine , Levofenfluramine ) * Fenproporex
Fenproporex
* Feprosidnine * Flephedrone * Fludorex * Formetorex
Formetorex
* Furfenorex * Gepefrine * Hexapradol * Hexedrone * HMMA * Hordenine * 4-Hydroxyamphetamine * 5-Iodo-2-aminoindane * Ibopamine
Ibopamine
* IMP * Indanylamphetamine * Iofetamine * Isoetarine * Isoethcathinone * Isoprenaline * L-Deprenyl (Selegiline) * Lefetamine
Lefetamine
* Lisdexamfetamine
Lisdexamfetamine
* Lophophine * MBDB * MDA (tenamfetamine) * MDBU * MDEA * MDMA
MDMA
(midomafetamine) * MDMPEA * MDOH * MDPR * MDPEA * Mefenorex * Mephedrone * Mephentermine * Metanephrine
Metanephrine
* Metaraminol * Mesocarb * Methamphetamine
Methamphetamine
(Dextromethamphetamine , Levomethamphetamine ) * Methoxamine
Methoxamine
* Methoxyphenamine * MMA * Methcathinone * Methedrone * Methoxyphenamine * Methylenedioxycathinone * Methylone
Methylone
* Mexedrone * MMDA * M MDMA
MDMA
* MMMA * Morforex * N,alpha-Diethylphenylethylamine * N-Ethylbuphedrone
N-Ethylbuphedrone
* N-Ethylhexedrone * N,N-Dimethylphenethylamine * Naphthylamphetamine * Nisoxetine * Norepinephrine
Norepinephrine
* Norfenefrine * Norfenfluramine * Normetanephrine
Normetanephrine
* L-Norpseudoephedrine * Octopamine (drug) * Orciprenaline * Ortetamine * Oxifentorex * Oxilofrine
Oxilofrine
* PBA * PCA * PCMA * PHA * Pentorex * Pentedrone * Pentylone * Phenatine * Phenpromethamine * Phentermine
Phentermine
* Phenylalanine
Phenylalanine
* Phenylephrine
Phenylephrine
* Phenylpropanolamine * Pholedrine * PIA * PMA * PMEA * PMMA * PPAP * Phthalimidopropiophenone * Prenylamine * Propylamphetamine * Pseudoephedrine
Pseudoephedrine
* Ropinirole * Salbutamol
Salbutamol
( Levosalbutamol
Levosalbutamol
) * Sibutramine
Sibutramine
* Solriamfetol * Synephrine
Synephrine
* Theodrenaline * Tiflorex * Tranylcypromine * Tyramine
Tyramine
* Tyrosine
Tyrosine
* Xylopropamine * Zylofuramine

PHENYLMORPHOLINES

* 3-Fluorophenmetrazine * Fenbutrazate * Fenmetramide
Fenmetramide
* G-130
G-130
* Manifaxine * Morazone * Morforex * Oxaflozane * PD-128,907 * Phendimetrazine * Phenmetrazine * 2-Phenyl-3,6-dimethylmorpholine
2-Phenyl-3,6-dimethylmorpholine
* Pseudophenmetrazine * Radafaxine

PIPERAZINES

* 2C-B-BZP * 3C-PEP * BZP * CM156 * DBL-583 * GBR-12783 * GBR-12935 * GBR-13069 * GBR-13098 * GBR-13119 * MeOPP * MBZP * oMPP * Vanoxerine

PIPERIDINES

* 1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine * 2-Benzylpiperidine * 2-Methyl-3-phenylpiperidine * 3,4-Dichloromethylphenidate
3,4-Dichloromethylphenidate
* 4-Benzylpiperidine * 4-Fluoromethylphenidate * 4-Methylmethylphenidate * Desoxypipradrol * Difemetorex * Diphenylpyraline * Ethylnaphthidate * Ethylphenidate * Methylnaphthidate * Isopropylphenidate * Methylphenidate
Methylphenidate
( Dexmethylphenidate
Dexmethylphenidate
) * Nocaine * Phacetoperane * Pipradrol * Propylphenidate * SCH-5472

PYRROLIDINES

* 2-Diphenylmethylpyrrolidine * 5-DBFPV
5-DBFPV
* α-PPP * α-PBP * α-PHP * α-PVP * α-PVT * Diphenylprolinol * DMPVP * FPOP * FPVP * MDPPP * MDPBP * MPBP * MPHP * MPPP * MOPVP * MOPPP * Indapyrophenidone * MDPV * Naphyrone * PEP * Picilorex * Prolintane * Pyrovalerone

RACETAMS

* Oxiracetam
Oxiracetam
* Phenylpiracetam * Phenylpiracetam hydrazide

TROPANES

* 4-fluorotropacocaine * 4\'-Fluorococaine * Altropane (IACFT) * Brasofensine * CFT (WIN 35,428) * β-CIT (RTI-55) * Cocaethylene * Cocaine
Cocaine
* Dichloropane (RTI-111) * Difluoropine * FE-β-CPPIT * FP-β-CPPIT * Ioflupane (123I) * Norcocaine * PIT * PTT * RTI-31 * RTI-32 * RTI-51 * RTI-112 * RTI-113 * RTI-120 * RTI-121 (IPCIT) * RTI-126 * RTI-150 * RTI-177 * RTI-229 * RTI-336 * RTI-354 * RTI-371 * RTI-386
RTI-386
* Salicylmethylecgonine * Tesofensine * Troparil (β-CPT, WIN 35,065-2) * Tropoxane * WF-23 * WF-33

TRYPTAMINES

* 4-HO-αMT * 4-Methyl-αET * 4-Methyl-αMT * 5-Chloro-αMT * 5-Fluoro-αMT * 5-MeO-αET * 5-MeO-αMT * 5-MeO-DIPT * 6-Fluoro-αMT * 7-Methyl-αET * αET * αMT

OTHERS

* 2-MDP * 3,3-Diphenylcyclobutanamine * Amfonelic acid
Amfonelic acid
* Amineptine * Amiphenazole * Atipamezole
Atipamezole
* Atomoxetine
Atomoxetine
* Bemegride * Benzydamine * BTQ * BTS 74,398 * Centanafadine * Ciclazindol * Clofenciclan * Cropropamide * Crotetamide * D-161 * Desipramine * Diclofensine * Dimethocaine
Dimethocaine
* Efaroxan * Etamivan * Fenisorex
Fenisorex
* Fenpentadiol * Gamfexine
Gamfexine
* Gilutensin
Gilutensin
* GSK1360707F * GYKI-52895 * Hexacyclonate * Idazoxan * Indanorex * Indatraline * JNJ-7925476 * Lazabemide * Leptacline * Lomevactone * LR-5182 * Mazindol * Meclofenoxate * Medifoxamine * Mefexamide * Methamnetamine * Methastyridone * Methiopropamine * Naphthylaminopropane * Nefopam * Nikethamide
Nikethamide
* Nomifensine
Nomifensine
* O-2172
O-2172
* Oxaprotiline * PNU-99,194 * PRC200-SS * Rasagiline
Rasagiline
* Rauwolscine * Rubidium chloride * Setazindol * Tametraline * Tandamine * Thiopropamine * Thiothinone * Trazium * UH-232 * Yohimbine
Yohimbine

ATC code : N06B

* v * t * e

Drugs for obstructive airway diseases : asthma /COPD (R03 )

ADRENERGICS , INHALANTS

SHORT-ACTING β2 AGONISTS

* Bitolterol * Carbuterol * Fenoterol * Isoetarine * Pirbuterol * Procaterol * Reproterol * Rimiterol * Salbutamol
Salbutamol
(albuterol) #/ Levosalbutamol
Levosalbutamol
(levalbuterol) * Terbutaline * Tulobuterol

LONG-ACTING β2 AGONISTS

* Bambuterol * Clenbuterol
Clenbuterol
* Formoterol / Arformoterol * Salmeterol * Salmefamol

ULTRA-LONG-ACTING β2 AGONISTS

* Abediterol * Carmoterol * Indacaterol * Olodaterol * Vilanterol

OTHER

* Epinephrine
Epinephrine
# * Hexoprenaline * Isoprenaline (isoproterenol) * Orciprenaline (metaproterenol)

GLUCOCORTICOIDS

* Beclometasone # * Betamethasone * Budesonide
Budesonide
* Ciclesonide * Flunisolide * Fluticasone
Fluticasone
* Mometasone * Triamcinolone
Triamcinolone

Anticholinergics / muscarinic antagonist

* Aclidinium bromide * Glycopyrronium bromide
Glycopyrronium bromide
* Ipratropium bromide # * Oxitropium bromide * Tiotropium bromide * Umeclidinium bromide

MAST CELL STABILIZERS

* Cromoglicate * Nedocromil

XANTHINES

* Acefylline * Ambuphylline * Bamifylline * Doxofylline * Enprofylline * Etamiphylline
Etamiphylline
* Proxyphylline * Theophylline
Theophylline
/ Aminophylline
Aminophylline
/ Choline theophyllinate

EICOSANOID INHIBITION

LEUKOTRIENE ANTAGONISTS

* Montelukast
Montelukast
* Pranlukast * Zafirlukast

ARACHIDONATE 5-LIPOXYGENASE INHIBITORS

* Zileuton

THROMBOXANE RECEPTOR ANTAGONISTS

* Ramatroban * Seratrodast

NON-XANTHINE PDE4 INHIBITORS

* Ibudilast * Roflumilast

OTHERS/UNKNOWN

* Amlexanox
Amlexanox
* Eprozinol
Eprozinol
* Fenspiride * Omalizumab

COMBINATION PRODUCTS

* Aclidinium/formoterol * Beclometasone/formoterol * Beclometasone/formoterol/glycopyrronium * Budesonide/formoterol
Budesonide/formoterol
* Fluticasone
Fluticasone
furoate/vilanterol * Fluticasone
Fluticasone
propionate/salmeterol * Indacaterol/glycopyrronium bromide * Ipratropium bromide/salbutamol * Mometasone/formoterol * Umeclidinium bromide/vilanterol

* #WHO-EM * ‡Withdrawn from market

* Clinical trials :

* †Phase III * §Never to phase III

* v * t * e

Nucleotide
Nucleotide
metabolic intermediates

PURINE METABOLISM

ANABOLISM

R5P →IMP :

* R5P * PRPP * PRA * GAR * FGAR * FGAM * AIR * CAIR * SAICAR * AICAR * FAICAR

IMP→AMP :

* Adenylosuccinate

IMP→GMP :

* Xanthosine monophosphate

CATABOLISM

* Hypoxanthine
Hypoxanthine
* Xanthine * Uric acid
Uric acid
* 5-Hydroxyisourate

PYRIMIDINE METABOLISM

ANABOLISM

* Carbamoyl phosphate * Carbamoyl aspartic acid * 4,5-Dihydroorotic acid * Orotic acid
Orotic acid
* Orotidine 5\'-monophosphate * Uridine monophosphate

CATABOLISM

URACIL :

* Dihydrouracil * 3-Ureidopropionic acid * β-Alanine

THYMINE :

* Dihydrothymine * β-Ureidoisobutyric acid * 3-Aminoisobutyric acid

* 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
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
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
8-Phenyltheophylline
* Acefylline * Aminophylline
Aminophylline
* ATL-444 * Bamifylline * Cafedrine * Caffeine
Caffeine
* Caffeine
Caffeine
citrate * Cartazolate * CGH-2466 * CGS-15943
CGS-15943
* Choline theophyllinate * CPX * CVT-6883 * Dimethazan * DMPX * DPCPX * Dyphylline * Enprofylline * Etazolate
Etazolate
* Fenethylline * IBMX * Isovaleric acid
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
Theobromine
* Theodrenaline * Theophylline
Theophylline
* Tozadenant * Tracazolate * VUF-5574 * ZM-241,385

P2 (nucleotide )

P2X (ATP )

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

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

P2Y

* AGONISTS: 2-Me-SADP * 2-Me-SATP * 2-Thio-UTP * 5-Br-UDP * 5-OMe-UDP * α,β-Me-ATP * Adenosine
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
Suramin
* Ticagrelor * Ticlopidine * UDP

Transporter (blockers )

CNTS

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

ENTS

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

PMAT

* Decynium-22

Enzyme
Enzyme
(inhibitors )

XO

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

OTHERS

* Aminopterin * Azathioprine
Azathioprine
* Methotrexate * Mycophenolic acid * Pemetrexed
Pemetrexed
* Pralatrexate
Pralatrexate
* Many others

OTHERS

* PRECURSORS: Adenine * Adenosine
Adenosine
* AMP * ADP * ATP * Cytosine * Cytidine * CMP * CDP * CTP * Guanine * Guanosine
Guanosine
* GMP * GDP * GTP * Hypoxanthine
Hypoxanthine
*