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

• ChemBase ID: 522
• Molecular Formular: C10H13N5O4
• Molecular Mass: 267.24132
• Monoisotopic Mass: 267.09675392
• SMILES: O1[C@@H](n2c3ncnc(N)c3nc2)[C@H](O)[C@H](O)[C@H]1CO
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
• 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
• InChIKey: OIRDTQYFTABQOQ-KQYNXXCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: adenosine; (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Brand Name: Adenocard; Adenocor; Adenoscan; Adenosin; Adensoine; Boniton; Myocol; Nucleocardyl; Sandesin; Pallacor
• Synonyms: 2'-Deoxyadenosine; Adenine Deoxy Nucleoside; Adenine Deoxyribonucleoside; Adenine Deoxyribose; Adenine Nucleoside; Adenine Riboside; Adenyldeoxyriboside; Deoxyadenosine; Desoxyadenosine; USAF CB-10; adenosine; MEDR-640; Adenosine; 9-β-D-Ribofuranosyladenine; Adenine-9-β-D-ribofuranoside; (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol; Adenocor; Adenoscan; Adenine-9-β-D-ribofuranoside; 9-β-D-Ribofuranosyladenine; Adenine riboside, Adenine-9-β-D-ribofuranoside; ADENOSINE FREE BASE; Ara-A; Arabinosyl-adenine; Vidarabine; 9-β-D-Arabinofuranosyladenine; ADENINE-9-β-D-ARABINOFURANOSIDE; ADENOSINE, U.S.P.; Adenosine; Adenocard; 9-β-D-呋喃核糖基腺嘌呤; 腺嘌呤-9-β-D-呋喃核糖苷; 腺嘌呤核苷; 腺苷

Database IDs

• CAS Number: 58-61-7; 5536-17-4
• EC Number: 226-893-9; 200-389-9
• MDL Number: MFCD00005752
• Beilstein Number: 93029
• PubChem SID: 24890739; 46508728; 160963985; 24277685
• PubChem CID: 60961
• CHEBI ID: 16335
• ATC CODE: C01EB10
• CHEMBL: 477
• Chemspider ID: 54923
• DrugBank ID: DB00640
• IUPHAR ligand ID: 2844
• KEGG ID: C00212
• Unique Ingredient Identifier: K72T3FS567
• Wikipedia Title: Adenosine

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.454003
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.2061174
• LogD (pH = 7.4): -2.09263
• Log P: -2.0909638
• Molar Refractivity: 63.1956 cm^3
• Polarizability: 24.545797 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.21
• LOG S: -1.28
• Solubility (Water): 1.40e+01 g/l

PROPERTIES

Physical Property

• Solubility: 8230 mg/L; DMSO
• Apperance: Powder
• Melting Point: 234-236 °C(lit.)
• Optical Rotation: [α]22/D -60.2°, c = 0.7 in H2O
• Hydrophobicity(logP): -1.6

Safety Information

• Storage Condition: 0°C; 0°C, Desiccate; -20°C
• RTECS: AU6200000; AU7175000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: R:22; R:36/37/38
• Safety Statements: S:20-25-26-37/39; S:36/37/39
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Intravenous, injection
• Bioavailability: Rapidly cleared from circulation via cellular uptake
• Excretion: can leave cell intact or can be degraded to hypoxanthine, xanthine, and ultimately uric acid
• Half Life: cleared plasma <30 seconds – half life <10 seconds
• Metabolism: Rapidly converted to inosine and adenosine monophosphate
• Protein Bound: No
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: C
• Gene Information: human ... ADA(100), ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), ERBB2(2064), ERBB4(2066)rat ... Adcy2(81636), Adora1(29290), Adora2a(25369), Adora3(25370); human ... ADA(100), ADORA3(140), ERBB2(2064), ERBB4(2066)rat ... Adcy2(81636), Adora1(29290), Adora2a(25369), Adora3(25370)
• Mechanism of Action: Adenosine-a1-agonist; Adenosine-a2-agonist

Product Information

• Purity: ≥99%; 98%
• Grade: certified reference material; USP
• Salt Data: Free Base
• Packaging: pkg of 1 g
• Suitability: suitable for cell culture
• Biological Source: Widely distributed in nature. One of the four principal nucleosides of nucleic acid
• Application(s): Antiarrhythmic agent; Cardiac depressant; Purinergic
• Pharmacopeia Traceability: traceable to PhEur A0230200; traceable to USP 1012123
• Empirical Formula (Hill Notation): C10H13N5O4

DETAILS

MP Biomedicals - 05212443

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02194609

Free Base
Cell Culture Reagent

MP Biomedicals - 02100070

Crystalline
Reported to possess antiviral activity^1 and useful for metabolism studies^2

MP Biomedicals - 02100199

Free Base
Crystalline

DrugBank - DB00640

• Drug Groups: approved; investigational
• Description: 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. [PubChem]
• Indication: Used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (PVST), including that associated with accessory bypass tracts, and is a drug of choice for terminating stable, narrow-complex supraventricular tachycardias (SVT). Also used as an adjunct to thallous chloride TI 201 myocardial perfusion scintigraphy (thallium stress test) in patients who are unable to exercise adequately, as well as an adjunct to vagal maneuvers and clinical assessment to establish a specific diagnosis of undefined, stable, narrow-complex SVT.
• Pharmacology: Adenosine is an endogenous nucleoside occurring in all cells of the body and is not chemically related to other antiarrhythmic drugs. Adenosine may exert its pharmacologic effects by activation of purine (cell surface A₁ and A₂ adenosine) receptors, as well as relax vascular smooth muscles through the reduction in calcium uptake by 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. The drug also has negative chronotropic, dromotropic, and inotropic effects on the heart by slowing conduction time throught he AV node and interrupting AV nodal reentry pathways. Adenosine is a potent vasodilator in most vascular beds, but vasoconstriction is produced in renal afferent arterioles and hepatic veins. The drug produces a net mild to moderate reduction in systolic, diastolic, and mean arterial blood pressure and a reflex increase in heart rate. Adenosine is antagonized competitively by methylxanthines such as caffeine and theophylline, and potentiated by blockers of nucleoside transport such as dipyridamole. Adenosine is not blocked by atropine.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Half Life: Less than 10 secs
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1647

Biological Activity:
Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a β-N9-glycosidic bond. [1] 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. [2]

Sigma Aldrich - A4036

Biochem/physiol Actions
腺苷受体处的内源性神经递质。心肌保护作用可能与 A1 腺苷受体的激活有关。通过 A2 腺苷受体可介导腺苷的抗血小板和抗炎作用。相比之下，腺苷在哮喘和慢性阻塞性肺部疾病 (COPD) 中起促炎介质作用。

Sigma Aldrich - A9251

包装
1, 5, 25, 100 g in poly bottle
Biochem/physiol Actions
腺苷受体处的内源性神经递质。心肌保护作用可能与 A1 腺苷受体的激活有关。通过 A2 腺苷受体可介导腺苷的抗血小板和抗炎作用。相比之下，腺苷在哮喘和慢性阻塞性肺部疾病 (COPD) 中起促炎介质作用。

Sigma Aldrich - 146595

Biochem/physiol Actions
Endogenous neurotransmitter at adenosine receptors. Cardioprotective effects may relate to activation of A1 adenosine receptors. The antiplatelet and anti-inflammatory actions of adenosine appear to be mediated via the A2 adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD).

Sigma Aldrich - PHR1138

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Biochem/physiol Actions
Endogenous neurotransmitter at adenosine receptors. Cardioprotective effects may relate to activation of A1 adenosine receptors. The antiplatelet and anti-inflammatory actions of adenosine appear to be mediated via the A2 adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD).

REFERENCES

• de Rudder, Privat de Garilhe, Antimicrob. Ag. Chemother. , 578 (1965).
• Cancer Res. , 24 : 1042 (1964).
• http://en.wikipedia.org/wiki/Adenosine
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 719C; 720A; 721A; 722C; 725B, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 222A; 224A; 227B; 229B, (nmr)
• Davoll, J. et al., J.C.S., 1948, 967-969, (synth)
• Brown, D.M. et al., J.C.S., 1950, 3299-3304, (synth)
• Biemann, K. et al., J.A.C.S., 1962, 84, 2005-2007, (ms)
• Shikata, K. et al., Acta Cryst. B, 1973, 29, 31-38, (cryst struct)
• Sarma, R.H. et al., J.A.C.S., 1974, 96, 7337-7348, (pmr, conformn)
• Earl, R.A. et al., J.O.C., 1975, 40, 1822-1828, (cmr)
• Wilson, C.C. et al., Acta Cryst. C, 1986, 42, 697-700, (cryst struct, triacetyl)
• Puech, P. et al., Handb. Exp. Pharmacol., 1989, 89, 453-460, (rev, metab, props, use)
• Adenosine and Adenosine Receptors, Williams, M., ed., Chapman and Hall, 1990, (book)
• Pinski, S.L. et al., Cleveland Clin. J. Med., 1990, 57, 383, (use)
• Reddy, A.M. et al., J. Het. Chem., 1990, 27, 1297-1305, (ms)
• Morgan, J.M. et al., Circulation, 1991, 84, 1145, (use)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 57
• Mahler, G.S., Anal. Profiles Drug Subst., 1998, 25, 1-37, (rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AEH750