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Chemistry

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Also known as: 58-61-7, Adenocard, Adenoscan, Adenine riboside, Beta-d-adenosine, Nucleocardyl
Molecular Formula
C10H13N5O4
Molecular Weight
267.24  g/mol
InChI Key
OIRDTQYFTABQOQ-KQYNXXCUSA-N
FDA UNII
K72T3FS567

Adenosine
A nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter.
Adenosine is an Adenosine Receptor Agonist. The mechanism of action of adenosine is as an Adenosine Receptor Agonist.
1 2D Structure

Adenosine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
2.1.2 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
2.1.3 InChI Key
OIRDTQYFTABQOQ-KQYNXXCUSA-N
2.1.4 Canonical SMILES
C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
2.1.5 Isomeric SMILES
C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
2.2 Other Identifiers
2.2.1 UNII
K72T3FS567
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Adenocard

2. Adenoscan

2.3.2 Depositor-Supplied Synonyms

1. 58-61-7

2. Adenocard

3. Adenoscan

4. Adenine Riboside

5. Beta-d-adenosine

6. Nucleocardyl

7. Adenosin

8. Boniton

9. Sandesin

10. Myocol

11. Adenine Nucleoside

12. Adenocor

13. Beta-adenosine

14. 9-beta-d-ribofuranosyladenine

15. 9-beta-d-ribofuranosidoadenine

16. 9-beta-d-ribofuranosyl-9h-purin-6-amine

17. Adenosin [german]

18. Usaf Cb-10

19. 9beta-d-ribofuranosyladenine

20. 6-amino-9-beta-d-ribofuranosyl-9h-purine

21. Ade-rib

22. Caswell No. 010b

23. (2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

24. Sr 96225

25. Adenosine [usan:ban]

26. Beta-d-ribofuranoside, Adenine-9

27. 6-amino-9beta-d-ribofuranosyl-9h-purine

28. (2r,3r,4s,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

29. (2r,3r,4s,5r)-2-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

30. Chebi:16335

31. Quinquefolan B

32. 3h-adenosine

33. Nsc 7652

34. Dehydran 240

35. Sr-96225

36. 9-.beta.-d-ribofuranosyladenine

37. Adenosine (adenocard)

38. Ai3-52413

39. 9h-purin-6-amine, 9beta-d-ribofuranosyl-

40. Chembl477

41. D-adenosine

42. Beta-d-ribofuranose, 1-(6-amino-9h-purin-9-yl)-1-deoxy-

43. Adenine-d-ribose

44. K72t3fs567

45. Nsc-7652

46. Ccris 2557

47. Ncgc00023673-05

48. Pallacor

49. Mfcd00005752

50. Dsstox_cid_2558

51. Dsstox_rid_76628

52. Dsstox_gsid_22558

53. 109767-06-8

54. 133248-01-8

55. 41547-82-4

56. .beta.-d-adenosine

57. Cas-58-61-7

58. Adenocard (tn)

59. Adenoscan (tn)

60. Smr000058216

61. Medr-640

62. Adenosine (jan/usp)

63. Sr-05000001981

64. Einecs 200-389-9

65. Adenine-beta-d-arabinofuranoside

66. Nsc 627048

67. Nsc7652

68. Adenogesic

69. Adenosine [usan:usp:ban]

70. Adenin Riboside

71. Unii-k72t3fs567

72. .beta.-d-ribofuranoside, Adenine-9

73. 9-.alpha.-d-arabinofuranosyladenine

74. Nsc627048

75. B-d-adenosine

76. Hsdb 7774

77. Sun-y4001

78. N6-methylado

79. 1dgm

80. 1odi

81. 2fqy

82. 2ydo

83. 3axz

84. 4cki

85. 4ckj

86. Adenosine,(s)

87. Beta-delta-adenosine

88. [u-14c]adenosine

89. 6-amino-9.beta.-d-ribofuranosyl-9h-purine

90. 2gl0

91. 3ay0

92. 4pd9

93. Adenosine, >=99%

94. Adenosine [jan]

95. Adenosine [mi]

96. 6-amino-9-.beta.-ribofuranosyl-9h-purine

97. Adenosine [hsdb]

98. Adenosine [inci]

99. Adenosine [usan]

100. Spectrum2_001257

101. Spectrum3_000288

102. Adenosine [vandf]

103. Cid_191

104. Schembl731

105. Adenosine [mart.]

106. Bmse000061

107. Bmse000996

108. Epitope Id:140947

109. Adenosine [usp-rs]

110. Adenosine [who-dd]

111. 4-aminopyrazolo[3,4-d]pyrimidine Ribonucleoside

112. 9-ss-d-ribofuranosyladenine

113. Bspbio_001796

114. .beta.-d-ribofuranose, 1-(6-amino-9h-purin-9-yl)-1-deoxy-

115. Cid_60961

116. Mls000069638

117. Mls002153227

118. Mls006010946

119. Spectrum1500107

120. Adenine-9-ss-d-ribofuranoside

121. Regid_for_cid_60961

122. Spbio_001194

123. Adenine-9beta-d-ribofuranoside

124. Gtpl2844

125. 9beta-delta-ribofuranosyladenine

126. Adenosine [ep Impurity]

127. Adenosine [orange Book]

128. Adenosine [ep Monograph]

129. Dtxsid1022558

130. Bdbm14487

131. Kbio3_001296

132. 9-beta-delta-ribofuranosyladenine

133. Adenosine [usp Monograph]

134. Ea6c60c2-6afb-4264-a2f0-541373db950e

135. 9-.beta.-d-ribofuranosidoadenine

136. 9-beta-delta-ribofuranosidoadenine

137. Adenine-9beta-delta-ribofuranoside

138. Bio1_000437

139. Bio1_000926

140. Bio1_001415

141. Hms1920a13

142. Hms2091g13

143. Hms2235e24

144. Hms3884o04

145. Pharmakon1600-01500107

146. Act02616

147. Albb-032827

148. Amy30083

149. Zinc2169830

150. 9-beta-delta-arabinofuranosyladenine

151. Tox21_110891

152. Ac7861

153. Ccg-38824

154. Nsc755857

155. S1647

156. Akos015888594

157. Tox21_110891_1

158. Ac-8229

159. Am83931

160. Db00640

161. Nsc-755857

162. Sdccgmls-0003108.p003

163. 9-?-d-ribofuranosyl-9h-purin-6-amine

164. 9beta-d-ribofuranosyl-9h-purin-6-amine

165. Ncgc00023673-03

166. Ncgc00023673-04

167. Ncgc00023673-06

168. Ncgc00023673-07

169. Ncgc00023673-10

170. Ncgc00023673-20

171. Ncgc00178869-03

172. 9-? -d-ribofuranosyl-9h-purin-6-amine

173. Ac-27494

174. As-12664

175. Adenosine, Vetec(tm) Reagent Grade, 98%

176. Sbi-0206673.p002

177. 9beta-delta-ribofuranosyl-9h-purin-6-amine

178. Db-022408

179. 6-amino-9beta-delta-ribofuranosyl-9h-purine

180. 9-.beta.-d-ribofuranosyl-9h-purin-6-amine

181. 9-beta-delta-ribofuranosyl-9h-purin-6-amine

182. A0152

183. 9h-purin-6-amine, 9-.beta.-d-ribofuranosyl-

184. C00212

185. D00045

186. Ab00384349-11

187. Ab00384349_13

188. Ab00384349_14

189. Adenosine, Bioreagent, Suitable For Cell Culture

190. Q190012

191. 6-amino-9-.beta.-d-ribofuranosyl-9h-purine

192. Sr-05000001981-1

193. Sr-05000001981-2

194. Z1741978458

195. 1-(6-amino-9h-purin-9-yl)-1-deoxy-beta-d-ribofuranose

196. Adenosine, European Pharmacopoeia (ep) Reference Standard

197. Formycin A, From Streptomyces Kaniharaensis, >=98% (hplc)

198. 1-(6-amino-9h-purin-9-yl)-1-deoxy-beta-delta-ribofuranose

199. Adenosine, United States Pharmacopeia (usp) Reference Standard

200. Adenosine, Pharmaceutical Secondary Standard; Certified Reference Material

201. (2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

202. 142796-17-6

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 267.24 g/mol
Molecular Formula C10H13N5O4
XLogP3-1.1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count2
Exact Mass267.09675391 g/mol
Monoisotopic Mass267.09675391 g/mol
Topological Polar Surface Area140 Ų
Heavy Atom Count19
Formal Charge0
Complexity335
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameAdenocard
Drug LabelAdenosine is an endogenous nucleoside occurring in all cells of the body. It is chemically 6-amino-9--D-ribofuranosyl-9-H-purine and has the following structural formula:C10H13N5O4267.24 C10H13N5O4267.24 Adenosine is...
Active IngredientAdenosine
Dosage FormInjectable
RouteInjection
Strength3mg/ml
Market StatusPrescription
CompanyAstellas

2 of 6  
Drug NameAdenoscan
PubMed HealthAdenosine (Injection)
Drug ClassesAntiarrhythmic
Drug LabelAdenosine is an endogenous nucleoside and is chemically described as 6-amino-9-beta-D-ribofuranosyl-9-H-purine. Adenosine has the following structural formula:The molecular formula for adenosine is C10H13N5O4and its molecular weight is 267.24.Adeno...
Active IngredientAdenosine
Dosage FormSolution
RouteIv (infusion)
Strength90mg/30ml (3mg/ml); 60mg/20ml (3mg/ml)
Market StatusPrescription
CompanyAstellas

3 of 6  
Drug NameAdenosine
PubMed HealthAdenosine (Injection)
Drug ClassesAntiarrhythmic
Drug LabelAdenosine is an endogenous nucleoside occurring in all cells of the body. It is chemically 6-amino-9--D-ribofuranosyl-9-H-purine and has the following structural formula: Adenosine is a white crystalline powder. It is soluble in water and practical...
Active IngredientAdenosine
Dosage FormInjectable; Solution
Routeinjection; Iv (infusion); Injection
Strength90mg/30ml (3mg/ml); 60mg/20ml (3mg/ml); 3mg/ml
Market StatusTentative Approval; Prescription
CompanyWockhardt; Sagent Strides; Bedford; Emcure Pharms; Fresenius Kabi Usa; Hospira; Gland Pharma; Hikma Maple; Luitpold; Teva Pharms Usa; Bedford Labs; Agila Speclts; Abraxis Pharm; Akorn

4 of 6  
Drug NameAdenocard
Drug LabelAdenosine is an endogenous nucleoside occurring in all cells of the body. It is chemically 6-amino-9--D-ribofuranosyl-9-H-purine and has the following structural formula:C10H13N5O4267.24 C10H13N5O4267.24 Adenosine is...
Active IngredientAdenosine
Dosage FormInjectable
RouteInjection
Strength3mg/ml
Market StatusPrescription
CompanyAstellas

5 of 6  
Drug NameAdenoscan
PubMed HealthAdenosine (Injection)
Drug ClassesAntiarrhythmic
Drug LabelAdenosine is an endogenous nucleoside and is chemically described as 6-amino-9-beta-D-ribofuranosyl-9-H-purine. Adenosine has the following structural formula:The molecular formula for adenosine is C10H13N5O4and its molecular weight is 267.24.Adeno...
Active IngredientAdenosine
Dosage FormSolution
RouteIv (infusion)
Strength90mg/30ml (3mg/ml); 60mg/20ml (3mg/ml)
Market StatusPrescription
CompanyAstellas

6 of 6  
Drug NameAdenosine
PubMed HealthAdenosine (Injection)
Drug ClassesAntiarrhythmic
Drug LabelAdenosine is an endogenous nucleoside occurring in all cells of the body. It is chemically 6-amino-9--D-ribofuranosyl-9-H-purine and has the following structural formula: Adenosine is a white crystalline powder. It is soluble in water and practical...
Active IngredientAdenosine
Dosage FormInjectable; Solution
Routeinjection; Iv (infusion); Injection
Strength90mg/30ml (3mg/ml); 60mg/20ml (3mg/ml); 3mg/ml
Market StatusTentative Approval; Prescription
CompanyWockhardt; Sagent Strides; Bedford; Emcure Pharms; Fresenius Kabi Usa; Hospira; Gland Pharma; Hikma Maple; Luitpold; Teva Pharms Usa; Bedford Labs; Agila Speclts; Abraxis Pharm; Akorn

4.2 Therapeutic Uses

Analgesics; Anti-Arrhythmia Agents; Vasodilator Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)


Intravenous Adenocard (adenosine injection) is indicated for conversion to sinus rhythm of paroxysmal supraventricular tachycardia (PSVT), including that associated with accessory bypass tracts (Wolff-Parkinson-White Syndrome). When clinically advisable, appropriate vagal maneuvers (eg, Valsalva maneuver), should be attempted prior to Adenocard administration. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Adenocard (adenosine) (January 2006). Available from, as of October 14, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1198


Adenocard does not convert atrial flutter, atrial fibrillation, or ventricular tachycardia to normal sinus rhythm. In the presence of atrial flutter or atrial fibrillation, a transient modest slowing of ventricular response may occur immediately following Adenocard administration.

US Natl Inst Health; DailyMed. Current Medication Information for Adenocard (adenosine) (January 2006). Available from, as of October 14, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1198


Intravenous Adenoscan is indicated as an adjunct to thallium-201 myocardial perfusion scintigraphy in patients unable to exercise adequately. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Adenoscan (adenosine) injection (August 2006). Available from, as of October 14, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1532


/Experimental Therapy:/ ... It has been shown that, in Japanese men, adenosine improves androgenetic alopecia due to the thickening of thin hair due to hair follicle miniaturization. To investigate the efficacy and safety of adenosine treatment to improve hair loss in women, 30 Japanese women with female pattern hair loss were recruited for this double-blind, randomized, placebo-controlled study. Volunteers used either 0.75% adenosine lotion or a placebo lotion topically twice daily for 12 months. Efficacy was evaluated by dermatologists and by investigators and in phototrichograms. As a result, adenosine was significantly superior to the placebo according to assessments by dermatologists and investigators and by self-assessments. Adenosine significantly increased the anagen hair growth rate and the thick hair rate. No side-effects were encountered during the trial. Adenosine improved hair loss in Japanese women by stimulating hair growth and by thickening hair shafts. Adenosine is useful for treating female pattern hair loss in women as well as androgenetic alopecia in men.

PMID:19239555 Oura H et al; J Dermatol 35 (12): 763-7 (2008).


4.3 Drug Warning

Contraindications include known hypersensitivity to adenosine, second- or third-degree AV block (except in patients with a functioning artificial pacemaker), sinus node disease, such as sick sinus syndrome or symptomatic bradycardia (except in patients with a functioning artificial pacemaker), and known or suspected bronchoconstrictive or bronchospastic lung disease (eg, asthma).

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1701


Following iv injection of adenosine, new arrhythmias (ventricular premature complexes [VPCs], atrial premature complexes, atrial fibrillation, sinus bradycardia, sinus tachycardia, skipped beats, and varying degrees of AV nodal block) frequently appear at the time of conversion to normal sinus rhythm. These arrythmias generally last only a few seconds and resolve without intervention. However, transient or prolonged episodes of asystole, sometimes fatal, have been reported with iv injection of adenosine. Ventricular fibrillation has been reported rarely with iv injection of the drug, including both resuscitated and fatal events. In most cases, these adverse effects occurred in patients receiving concomitant therapy with digoxin or, less frequently, digoxin and verapamil, although a causal relationship has not been established.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1701


Some clinicians state that adenosine should not be used in patients with wide-complex tachycardias of unknown origin because of the risk of inducing potentially serious arrhythmias, including atrial fibrillation with a rapid ventricular rate or prolonged asystole with severe hypotension in preexcited tachycardias (eg, atrial flutter); the drug also may induce ventricular fibrillation in patients with severe coronary artery disease.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1701


Appropriate resuscitative measures should be readily available.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1701


For more Drug Warnings (Complete) data for Adenosine (16 total), please visit the HSDB record page.


4.4 Drug Indication

Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy in patients unable to adequately exercise. It is also indicated to convert sinus rhythm of paroxysmal supraventricular tachycardia.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy and also indicated for conversion of sinus rhythm of paroxysmal supraventricular tachycardia. Adenosine has a short duration of action as the half life is <10 seconds, and a wide therapeutic window. Patients should be counselled regarding the risk of cardiovascular side effects, bronchoconstriction, seizures, and hypersensitivity.


5.2 MeSH Pharmacological Classification

Anti-Arrhythmia Agents

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)


Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)


Purinergic P1 Receptor Agonists

Compounds that bind to and stimulate PURINERGIC P1 RECEPTORS. (See all compounds classified as Purinergic P1 Receptor Agonists.)


Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
ADENOSINE
5.3.2 FDA UNII
K72T3FS567
5.3.3 Pharmacological Classes
Adenosine Receptor Agonists [MoA]; Adenosine Receptor Agonist [EPC]
5.4 ATC Code

C01EB10

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


C - Cardiovascular system

C01 - Cardiac therapy

C01E - Other cardiac preparations

C01EB - Other cardiac preparations

C01EB10 - Adenosine


5.5 Absorption, Distribution and Excretion

Absorption

Data regarding the absorption of adenosine are not readily available.


Route of Elimination

Adenosine is predominantly eliminated in the urine as uric acid.


Volume of Distribution

Data regarding the volume of distribution of adenosine are not readily available.


Clearance

Data regarding the clearance of adenosine are not readily available.


Intravenously administered adenosine is rapidly cleared from the circulation via cellular uptake, primarily by erythrocytes and vascular endothelial cells. This process involves a specific transmembrane nucleoside carrier system that is reversible, nonconcentrative, and bidirectionally symmetrical.

US Natl Inst Health; DailyMed. Current Medication Information for Adenocard (adenosine) (January 2006). Available from, as of October 14, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1198


As Adenocard requires no hepatic or renal function for its activation or inactivation, hepatic and renal failure would not be expected to alter its effectiveness or tolerability.

US Natl Inst Health; DailyMed. Current Medication Information for Adenocard (adenosine) (January 2006). Available from, as of October 14, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1198


5.6 Metabolism/Metabolites

Adenosine can be phosphorylated by adenosine kinase to form adenosine monophosphate. From there, it is phosphorylated again by adenylate kinase 1 to form adenosine diphosphate, and again by nucleoside diphosphate kinase A or B to form adenosine triphosphate. Alternatively, adenosine can be deaminated by adenosine deaminase to form inosine. Iosine is phosphorylated by purine nucleoside phosphorylase to form hypoxanthine. Hypoxanthine undergoes oxidation by xanthine dehydrogenase twice to form the metabolites xanthine, followed by uric acid.


Intracellular adenosine is rapidly metabolized either via phosphorylation to adenosine monophosphate by adenosine kinase, or via deamination to inosine by adenosine deaminase in the cytosol. Since adenosine kinase has a lower Km and Vmax than adenosine deaminase, deamination plays a significant role only when cytosolic adenosine saturates the phosphorylation pathway.

US Natl Inst Health; DailyMed. Current Medication Information for Adenocard (adenosine) (January 2006). Available from, as of October 14, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1198


Adenosine is rapidly metabolized intracellularly to the inactive metabolites adenosine monophosphate and inosine ... The drug is cleared by cellular uptake, principally by erythrocytes and vascular endothelial cells, via a specific transmembrane nucleoside transport system.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1702


Inosine formed by deamination of adenosine can leave the cell intact or can be degraded to hypoxanthine, xanthine, and ultimately uric acid.

US Natl Inst Health; DailyMed. Current Medication Information for Adenocard (adenosine) (January 2006). Available from, as of October 14, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1198


Adenosine monophosphate formed by phosphorylation of adenosine is incorporated into the high-energy phosphate pool. While extracellular adenosine is primarily cleared by cellular uptake, ... excessive amounts may be deaminated by an ecto-form of adenosine deaminase.

US Natl Inst Health; DailyMed. Current Medication Information for Adenocard (adenosine) (January 2006). Available from, as of October 14, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1198


5.7 Biological Half-Life

The half life of adenosine in blood is less than 10 seconds.


... The plasma half-life of adenosine is less than 10 seconds.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1702


5.8 Mechanism of Action

Agonism of adenosine receptors A1 and A2 reduces conduction time in the atrioventricular node of the heart. Conduction time is decreased by inducing potassium efflux and inhibiting calcium influx through channels in nerve cells, leading to hyperpolarization and and increased threshold for calcium dependent action potentials. Decreased conduction time leads to an antiarrhythmic effect. Inhibition of calcium influx, reduces the activity of adenylate cyclase, relaxing vascular smooth muscle. Relaxed vascular smooth muscle leads to increased blood flow through normal coronary arteries but not stenotic arteries, allowing thallium-201 to be more readily uptaken in normal coronary arteries.


Adenosine is an endogenous nucleoside present in all cells of the body. Adenosine may exert its pharmacologic effects by activation of purine (cell-surface A1 and A2 adenosine) receptors; relaxation of vascular smooth muscle may be mediated by reduction in calcium uptake through inhibition of slow inward calcium current and activation of adenylate cyclase in smooth muscle cells. Adenosine may reduce vascular tone by modulation of sympathetic neurotransmission.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1702


Adenosine has negative chronotropic, dromotropic, and inotropic effects on the heart. The drug slows conduction time through the AV node and can interrupt AV nodal reentry pathways, leading to restoration of normal sinus rhythm in patients with PSVT, including that associated with Wolff-Parkinson-White syndrome.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1702


Adenosine is a potent vasodilator in most vascular beds, except in renal afferent arterioles and hepatic veins where it produces vasoconstriction. Adenosine is thought to exert its pharmacological effects through activation of purine receptors (cell-surface A1 and A2 adenosine receptors). Although the exact mechanism by which adenosine receptor activation relaxes vascular smooth muscle is not known, there is evidence to support both inhibition of the slow inward calcium current reducing calcium uptake, and activation of adenylate cyclase through A2 receptors in smooth muscle cells. Adenosine may also lessen vascular tone by modulating sympathetic neurotransmission. The intracellular uptake of adenosine is mediated by a specific transmembrane nucleoside transport system. Once inside the cell, adenosine is rapidly phosphorylated by adenosine kinase to adenosine monophosphate, or deaminated by adenosine deaminase to inosine. These intracellular metabolites of adenosine are not vasoactive. Myocardial uptake of thallium-201 is directly proportional to coronary blood flow. Since Adenoscan significantly increases blood flow in normal coronary arteries with little or no increase in stenotic arteries, Adenoscan causes relatively less thallium-201 uptake in vascular territories supplied by stenotic coronary arteries ie, a greater difference is seen after Adenoscan between areas served by normal and areas served by stenotic vessels than is seen prior to Adenoscan.

US Natl Inst Health; DailyMed. Current Medication Information for Adenoscan (adenosine) injection (August 2006). Available from, as of October 14, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1532


... Current evidence suggests that ADO-metabolizing enzymes such as ecto-5'-nucleotidase or ADO deaminase, as well as enzymes that degrade ATP to adenosine, play an important role in the vasoconstrictor signals sent from the macula densa to the afferent arterioles when tubuloglomerular feedback is activated; increased ADO concentration induced by temporal infusion of AngII results in downregulation of A2 ADO receptors, leading to a predominant effect of A1 receptors; the alteration in the ADO receptors balance further contributes to the synergic interaction between ADO and AngII. ... The ADO-metabolizing enzymes have become important regulators of the effects of ADO on the tone of the afferent and efferent arterioles. As AngII is able to increase de-novo renal ADO content through decrease of ADO-metabolizing enzymes, accumulation of ADO induces downregulation of ADO A2 receptor population without modifying ADO A1 receptor, thereby enhancing the constrictive effects of AngII in the renal vasculature.

PMID:19077691 Franco M et al; Curr Opin Nephrol Hypertens 18 (1): 63-7 (2009). Available from, oas of November 6, 2009:


For more Mechanism of Action (Complete) data for Adenosine (7 total), please visit the HSDB record page.


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06-Jan-2021
30-Aug-2024
KGS
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Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - INJECTABLE;INJECTION - 3MG/ML **Fede...DOSAGE - INJECTABLE;INJECTION - 3MG/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19937

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DOSAGE - SOLUTION;INTRAVENOUS - 60MG/20ML (3M...DOSAGE - SOLUTION;INTRAVENOUS - 60MG/20ML (3MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20059

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DOSAGE - SOLUTION;INTRAVENOUS - 90MG/30ML (3M...DOSAGE - SOLUTION;INTRAVENOUS - 90MG/30ML (3MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20059

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Excipients by Applications

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Topical

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Solubilizers

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Thickeners and Stabilizers

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Coating Systems & Additives

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Emulsifying Agents

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Fillers, Diluents & Binders

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Parenteral

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Taste Masking

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Film Formers & Plasticizers

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Surfactant & Foaming Agents

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Controlled & Modified Release

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Direct Compression

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Co-Processed Excipients

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Rheology Modifiers

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Lubricants & Glidants

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Chewable & Orodispersible Aids

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Granulation

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Empty Capsules

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API Stability Enhancers

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Disintegrants & Superdisintegrants

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Coloring Agents

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Vegetarian Capsules

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Soft Gelatin

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NEWS #PharmaBuzz

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REF. STANDARDS & IMPURITIES

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