CAS 7481-89-2|DDC|zalcitabine|4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one|DDCYD|Dideoxycytidine|HIVID|Zalcitabine|扎西他滨|Hivid|NSC 606170|2′,3′-Dideoxycytidine|2'...

基本信息

化学结构

分子式

C₉H₁₃N₃O₃

分子量

211.21782

精确质量

211.09569129

电荷

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

Canonic Smiles

Nc1ccn(c(=O)n1)[C@H]1CC[C@H](O1)CO

Isomeric Smiles

O1[C@@H](n2ccc(nc2=O)N)CC[C@H]1CO

计算属性

JChem

LogD (pH = 7.4)

-1.19

LogD (pH = 5.5)

-1.19

Log P

-1.19

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

2.88

极化表面积

88.15

极化性

20.75

摩尔折射率

52.24

LOG S

-0.73

数据来源

名称和标识

别名

DDCYDDDCZalcitabineDideoxycytidine扎西他滨2′,3′-DideoxycytidineHividNSC 6061702',3'-二脱氧胞啶Zalcitabine2',3'-Dideoxycytidine2',3'-DIDEOXYCYTIDINE2’,3’-DideoxycytidineRo 24-2027/000DDCDideoxycytidinezalcitabine4-amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-oneDDCYD2',3'-Dideoxycytidine

IUPAC传统名

zalcitabine

商标名

HIVID

IUPAC标准名

4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

API名称

Zalcitabine

国际非专利药品(INN)

zalcitabine

名称和标识

数据登录号

CAS号

7481-89-2

MDL号

MFCD00012188

PubChem SID

24278377465078792486283416096428287322635

Beilstein号

默克索引号

PubChem CID

DrugBank ID

UniProt数据库

P12502P27718P48861Q1A267Q62674P35963P12497Q9QBY3Q9Q720Q75002Q8AII1P22382P19505O89940O41798

BKMS React数据库

23785159816590715342315441227

BRENDA Ligand数据库

23781659072715342315441251598

CompTox数据库

DTXSID0023747

PubMed文献链接

119059887727578

Drug Central Database

2,856

CHEMBL

CHEMBL853

SureChEMBL数据库

SCHEMBL3598

BRENDA数据库

3.5.4.52.7.1.742.7.1.212.7.1.763.1.26.132.4.2.62.7.7.492.7.1.1457.1.1.22.7.7.317.6.2.22.7.2.3

Reaxys Registry

654956

MetaboLights数据库

MTBLS1693MTBLS379MTBLS867MTBLS926MTBLS2878MTBLS746MTBLS673

维基百科标题

SABIO-RK数据库

KEGG DRUG Database

ACToR数据库

KEGG ID

CHEBI ID

HMDB数据库

LINCS数据库

数据登录号

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB00943

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A dideoxynucleoside compound in which the 3'-hydroxyl group on the sugar moiety has been replaced by a hydrogen.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

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

308358

Application
抗病毒（如 HIV-1）1和抗癌的研究工具。2

D5782

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.

36775

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

TRC

Z140000

A pyrimidine nucleoside analogue with antiviral activity.

ChEBI

CHEBI:10101

A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.

描述信息

参考文献

PubChem文献

数据源提供

• 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

• http://en.wikipedia.org/wiki/Zalcitabine

• van der Vliet, P.C. and Kwant, M.M.: Biochemistry, 20, 2628 (1981)

• Starnes, M.C., and Cheng, Y.: J. Biol. Chem., 262, 988 (1981)

• Mitsuya, H., Broder, S.: Proc. Nat. Acad. Sci. USA, 83, 1911 (1981)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

zalcitabine

商标名

HIVID

IUPAC标准名

4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

API名称

Zalcitabine

国际非专利药品(INN)

zalcitabine

描述信息

DrugBank

DB00943

Drug Groups

approved

Description

Indication

For the treatment of Human immunovirus (HIV) infections in conjunction with other antivirals.

Pharmacology

Toxicity

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

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

Sigma Aldrich

308358

Application
抗病毒（如 HIV-1）1和抗癌的研究工具。2

D5782

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.

36775

TRC

Z140000

A pyrimidine nucleoside analogue with antiviral activity.

ChEBI

CHEBI:10101

A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.

参考文献

PubChem文献

数据源提供

• 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