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

• ChemBase编号: 522
• 分子式: C10H13N5O4
• 平均质量: 267.24132
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC传统名: adenosine; (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• 商标名: Adenocard; Adenocor; Adenoscan; Adenosin; Adensoine; Boniton; Myocol; Nucleocardyl; Sandesin; Pallacor
• 别名: 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; 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

登记号

• CAS号: 5536-17-4; 58-61-7
• EC号: 226-893-9; 200-389-9
• MDL号: MFCD00005752
• Beilstein号: 93029
• PubChem SID: 24890739; 46508728; 160963985; 24277685
• PubChem CID: 60961
• CHEBI ID: 16335
• ATC码: C01EB10
• CHEMBL: 477
• Chemspider ID: 54923
• DrugBank ID: DB00640
• IUPHAR配体索引: 2844
• KEGG ID: C00212
• 美国药典/FDA物质标识码: K72T3FS567
• 维基百科标题: Adenosine

理论计算性质

JChem

• Acid pKa: 12.454003
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): -2.2061174
• LogD (pH = 7.4): -2.09263
• Log P: -2.0909638
• 摩尔折射率: 63.1956 cm^3
• 极化性: 24.545797 Å^3
• 极化表面积: 139.54 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.21
• LOG S: -1.28
• 溶解度: 1.40e+01 g/l

分子性质

理化性质

• 溶解度: 8230 mg/L; DMSO
• 外观: Powder
• 熔点: 234-236 °C(lit.)
• 比旋光度: [α]22/D -60.2°, c = 0.7 in H2O
• 疏水性(logP): -1.6

安全信息

• 保存条件: 0°C; 0°C, Desiccate; -20°C
• RTECS编号: AU6200000; AU7175000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 2
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): III
• 澳大利亚Hazchem: 2X
• 危险公开号: R:22; R:36/37/38
• 安全公开号: S:20-25-26-37/39; S:36/37/39
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 给药途径: Intravenous, injection
• 生物利用度: Rapidly cleared from circulation via cellular uptake
• 排泄: can leave cell intact or can be degraded to hypoxanthine, xanthine, and ultimately uric acid
• 半衰期: cleared plasma <30 seconds – half life <10 seconds
• 代谢: Rapidly converted to inosine and adenosine monophosphate
• 蛋白结合率: No
• 法定药品分级: POM (UK); Rx-only (US)
• 妊娠期药物分类: C
• 相关基因信息: 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)
• 生物活性机理: Adenosine-a1-agonist; Adenosine-a2-agonist

产品相关信息

• 纯度: ≥99%; 98%
• 级别: certified reference material; USP
• 成盐信息: Free Base
• 包装: pkg of 1 g
• 适用性: suitable for cell culture
• 生物来源: Widely distributed in nature. One of the four principal nucleosides of nucleic acid
• 应用领域: Antiarrhythmic agent; Cardiac depressant; Purinergic
• Pharmacopeia Traceability: traceable to PhEur A0230200; traceable to USP 1012123
• Empirical Formula (Hill Notation): C10H13N5O4

详细说明

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
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 - 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
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。

参考文献

• 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