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7481-89-2 分子结构
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4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

ChemBase编号:819
分子式:C9H13N3O3
平均质量:211.21782
单一同位素质量:211.09569129
SMILES和InChIs

SMILES:
O1[C@@H](n2ccc(nc2=O)N)CC[C@H]1CO
Canonical SMILES:
Nc1ccn(c(=O)n1)[C@H]1CC[C@H](O1)CO
InChI:
InChI=1S/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8+/m0/s1
InChIKey:
WREGKURFCTUGRC-POYBYMJQSA-N

引用这个纪录

CBID:819 http://www.chembase.cn/molecule-819.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
IUPAC传统名
zalcitabine
商标名
HIVID
别名
2',3'-二脱氧胞啶
扎西他滨
Zalcitabine
2',3'-Dideoxycytidine
2’,3’-Dideoxycytidine
Ro 24-2027/000
Dideoxycytidine
DDC
DDCYD
Zalcitabine
Hivid
NSC 606170
2′,3′-Dideoxycytidine
2',3'-DIDEOXYCYTIDINE
CAS号
7481-89-2
MDL号
MFCD00012188
Beilstein号
654956
默克索引号
1410109
PubChem SID
46507879
24862834
160964282
24278377
PubChem CID
24066

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 14.673299  质子受体
质子供体 LogD (pH = 5.5) -1.1882305 
LogD (pH = 7.4) -1.1882266  Log P -1.1882265 
摩尔折射率 52.2402 cm3 极化性 20.097618 Å3
极化表面积 88.15 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -1.29  LOG S -1.48 
溶解度 7.05e+00 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
2.42E+004 mg/L expand 查看数据来源
DMSO expand 查看数据来源
Water expand 查看数据来源
外观
White to Off-White Solid expand 查看数据来源
熔点
201-204°C expand 查看数据来源
216-220°C expand 查看数据来源
217-218 °C(lit.) expand 查看数据来源
比旋光度
[α]20/D +75°, c = 0.6 in H2O expand 查看数据来源
+90 (c=0.5 in water) expand 查看数据来源
疏水性(logP)
-1.3 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Refrigerator expand 查看数据来源
RTECS编号
HA3870000 expand 查看数据来源
欧盟危险性物质标志
X expand 查看数据来源
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
40 expand 查看数据来源
40-62 expand 查看数据来源
安全公开号
22-36 expand 查看数据来源
36/37 expand 查看数据来源
TSCA收录
expand 查看数据来源
GHS危险品标识
GHS08 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H351 expand 查看数据来源
H351-H361 expand 查看数据来源
GHS警示性声明
P281 expand 查看数据来源
P281-P201-P202-P308+P313-P405-P501A expand 查看数据来源
个人保护装置
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand 查看数据来源
保存温度
-20°C expand 查看数据来源
2-8°C expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
≥99.0% (HPLC) expand 查看数据来源
98% expand 查看数据来源
98+% expand 查看数据来源
99% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
Empirical Formula (Hill Notation)
C9H13N3O3 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB00943 external link
Item Information
Drug Groups approved
Description A dideoxynucleoside compound in which the 3'-hydroxyl group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of 5' to 3' phosphodiester linkages, which are needed for the elongation of DNA chains, thus resulting in the termination of viral DNA growth. The compound is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy. [PubChem]
Indication For the treatment of Human immunovirus (HIV) infections in conjunction with other antivirals.
Pharmacology Zalcitabine is an analog of 2'-deoxycytidine that is pharmacologically related to but structurally different from other nucleotide reverse transcriptase inhibitors (NRTIs). Zalcitabine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA.
Toxicity Acute overdose: Inadvertent pediatric overdoses have occurred with doses up to 1.5 mg/kg zalcitabine. Chronic overdose: in an initial dose-finding study in which zalcitabine was administered at doses 25 times (0.25 mg/kg every 8 hours) the currently recommended dose, one patient discontinued zalcitabine after 1? weeks of treatment subsequent to the development of a rash and fever.
Affected Organisms
Human Immunodeficiency Virus
Biotransformation Hepatic
Absorption Bioavailability is over 80% following oral administration.
Half Life 2 hours
Protein Binding Less than 4%
Elimination Renal excretion of unchanged drug appears to be the primary route of elimination, accounting for approximately 80% of an intravenous dose and 60% of an orally administered dose within 24 hours after dosing (n=19). Renal clearance exceeds glomerular filtration rate suggesting renal tubular secretion contributes to the elimination of zalcitabine by the kidneys.
Distribution * 0.304 to 0.734 L/kg
Clearance * 285 mL/min [HIV-infected patients receiving 1.5 mg IV infusion for 1 hour]
References
Shelton MJ, O'Donnell AM, Morse GD: Zalcitabine. Ann Pharmacother. 1993 Apr;27(4):480-9. [Pubmed]
Devineni D, Gallo JM: Zalcitabine. Clinical pharmacokinetics and efficacy. Clin Pharmacokinet. 1995 May;28(5):351-60. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1719 external link
Research Area: Infection
Biological Activity:
Zalcitabine is a nucleoside analog reverse transcriptase inhibitor (NARTI).Zalcitabine is an analog of pyrimidine. It is a derivative of the naturally existing deoxycytidine, made by replacing the hydroxyl group in position 3’ with a hydrogen.It is phosphorylated in T cells and other HIV target cells into its active triphosphate form, ddCTP. This active metabolite works as a substrate for HIV reverse transcriptase, and also by incorporation into the viral DNA, hence terminating the chain elongation due to the missing hydroxyl group. Since zalcitabine is a reverse transcriptase inhibitor it possess activity only against retroviruses. [1]
Sigma Aldrich -  D5782 external link
包装
100, 250, 500 mg in poly bottle
Application
2′,3′-Dideoxycytidine is used as a DNA chain-terminating nucleotide for DNA sequencing methods based on the Sanger chain-termination method.
Sigma Aldrich -  308358 external link
Application
抗病毒(如 HIV-1)1和抗癌的研究工具。2
Sigma Aldrich -  36775 external link
Biochem/physiol Actions
Infection of NIH Swiss 3T3 cells by 334C murine leukemia virus is inhibited by 50 μM ddCyd without effecting cell growth;1 ddCyd inhibits the in vitro infectivity and cytopathic effects of human Tlymphotropic virus type III/ lymphadenopathy-associated virus (HTLV-III/LAV).2
Toronto Research Chemicals -  Z140000 external link
A pyrimidine nucleoside analogue with antiviral activity.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Devineni D, Gallo JM: Zalcitabine. Clinical pharmacokinetics and efficacy. Clin Pharmacokinet. 1995 May;28(5):351-60. Pubmed
  • Shelton MJ, O'Donnell AM, Morse GD: Zalcitabine. Ann Pharmacother. 1993 Apr;27(4):480-9. Pubmed
  • http://en.wikipedia.org/wiki/Zalcitabine
  • van der Vliet, P.C. and Kwant, M.M.: Biochemistry, 20, 2628 (1981)
  • Mitsuya, H., Broder, S.: Proc. Nat. Acad. Sci. USA, 83, 1911 (1981)
  • Starnes, M.C., and Cheng, Y.: J. Biol. Chem., 262, 988 (1981)
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专利

专利

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