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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11N3O3
Molecular Weight 209.2019
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2',3'-DIDEHYDRO-2',3'-DIDEOXYCYTIDINE

SMILES

NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)C=C2

InChI

InChIKey=OOBICGOWICFMIX-POYBYMJQSA-N
InChI=1S/C9H11N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h1-4,6,8,13H,5H2,(H2,10,11,14)/t6-,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula C9H11N3O3
Molecular Weight 209.2019
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
1987 Aug
Synthesis and antiviral activity of various 3'-azido, 3'-amino, 2',3'-unsaturated, and 2',3'-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses.
1987 Feb
Antiviral activity of 2',3'-dideoxycytidin-2'-ene (2',3'-dideoxy-2',3'-didehydrocytidine) against human immunodeficiency virus in vitro.
1987 Feb 1
The anti-HTLV-III (anti-HIV) and cytotoxic activity of 2',3'-didehydro-2',3'-dideoxyribonucleosides: a comparison with their parental 2',3'-dideoxyribonucleosides.
1987 Jul
Inhibitory effect of 2',3'-didehydro-2',3'-dideoxynucleosides on infectivity, cytopathic effects, and replication of human immunodeficiency virus.
1987 Jun
Ribavirin antagonizes inhibitory effects of pyrimidine 2',3'-dideoxynucleosides but enhances inhibitory effects of purine 2',3'-dideoxynucleosides on replication of human immunodeficiency virus in vitro.
1987 Oct
Potent and selective in vitro activity of 3'-deoxythymidin-2'-ene (3'-deoxy-2',3'-didehydrothymidine) against human immunodeficiency virus.
1987 Sep 1
The in vitro and in vivo anti-retrovirus activity, and intracellular metabolism of 3'-azido-2',3'-dideoxythymidine and 2',3'-dideoxycytidine are highly dependent on the cell species.
1988 Mar 1
Inhibition of the replication of hepatitis B virus in vitro by 2',3'-dideoxy-3'-thiacytidine and related analogues.
1991 Oct 1
Substrate specificity of human deoxycytidine kinase toward antiviral 2',3'-dideoxynucleoside analogs.
1992 Jan 22
Potential prodrug derivatives of 2',3'-didehydro-2',3'-dideoxynucleosides. Preparations and antiviral activities.
1992 Jul 24
Novel mutation (V75T) in human immunodeficiency virus type 1 reverse transcriptase confers resistance to 2',3'-didehydro-2',3'-dideoxythymidine in cell culture.
1994 Jun
Design and synthesis of 2',3'-dideoxy-2',3'-didehydro-beta-L-cytidine (beta-L-d4C) and 2',3'-dideoxy 2',3'-didehydro-beta-L-5-fluorocytidine (beta-L-Fd4C), two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human immunodeficiency virus (HIV) in vitro.
1996 Apr 26
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
2004 Jun 17
3'-Carbon-substituted pyrimidine nucleosides having a 2',3'-dideoxy and 2',3'-didehydro-2',3'-dideoxy structure: synthesis and antiviral evaluation.
2006
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:13:13 UTC 2023
Edited
by admin
on Sat Dec 16 05:13:13 UTC 2023
Record UNII
CI9X00489L
Record Status Validated (UNII)
Record Version
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Name Type Language
2',3'-DIDEHYDRO-2',3'-DIDEOXYCYTIDINE
Systematic Name English
ZALCITABINE RELATED COMPOUND A [USP-RS]
Common Name English
ZALCITABINE RELATED COMPOUND A [USP IMPURITY]
Common Name English
ZALCITABINE RELATED COMPOUND A
USP   USP-RS  
Code English
Code System Code Type Description
RS_ITEM_NUM
1724317
Created by admin on Sat Dec 16 05:13:13 UTC 2023 , Edited by admin on Sat Dec 16 05:13:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID30225784
Created by admin on Sat Dec 16 05:13:13 UTC 2023 , Edited by admin on Sat Dec 16 05:13:13 UTC 2023
PRIMARY
CAS
7481-88-1
Created by admin on Sat Dec 16 05:13:13 UTC 2023 , Edited by admin on Sat Dec 16 05:13:13 UTC 2023
PRIMARY
FDA UNII
CI9X00489L
Created by admin on Sat Dec 16 05:13:13 UTC 2023 , Edited by admin on Sat Dec 16 05:13:13 UTC 2023
PRIMARY
PUBCHEM
64683
Created by admin on Sat Dec 16 05:13:13 UTC 2023 , Edited by admin on Sat Dec 16 05:13:13 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP