Azvudine

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NCATS

Investigational

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H11FN6O4
Molecular Weight	286.2198
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of Azvudine

Structure Search

SMILES

NC1=NC(=O)N(C=C1)[C@@H]2O[C@@](CO)(N=[N+]=[N-])[C@@H](O)[C@@H]2F

InChI

InChIKey=KTOLOIKYVCHRJW-XZMZPDFPSA-N

InChI=1S/C9H11FN6O4/c10-5-6(18)9(3-17,14-15-12)20-7(5)16-2-1-4(11)13-8(16)19/h1-2,5-7,17-18H,3H2,(H2,11,13,19)/t5-,6-,7+,9+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C9H11FN6O4
Molecular Weight	286.2198
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	1
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:20:47 GMT 2025` Edited by `admin` on `Mon Mar 31 23:20:47 GMT 2025`
Record UNII	IJ2XP0ID0K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RO 0622

Preferred Name

English

Azvudine

Official Name

English

2(1H)-PYRIMIDINONE, 4-AMINO-1-(4-C-AZIDO-2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)-

Systematic Name

English

Azvudine [WHO-DD]

Common Name

English

4-AMINO-1-(4-C-AZIDO-2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)-2(1H)-PYRIMIDINONE

Systematic Name

English

RO-0622

Common Name

English

4-AMINO-1-((2R,3S,4R,5R)-3-FLUORO-4-HYDROXY-5-(HYDROXYMETHYL)-5-((IMINO-L,5-AZANYLIDENE)AMINO)TETRAHYDROFURAN-2-YL)PYRIMIDIN-2-ONE

Systematic Name

English

FNC

Common Name

English

2'-DEOXY-2'-.BETA.-FLUORO-4'-AZIDOCYTIDINE

Systematic Name

English

Code System Code Type Description

FDA UNII

IJ2XP0ID0K

Created by admin on Mon Mar 31 23:20:47 GMT 2025 , Edited by admin on Mon Mar 31 23:20:47 GMT 2025

PRIMARY

PUBCHEM

24769759

Created by admin on Mon Mar 31 23:20:47 GMT 2025 , Edited by admin on Mon Mar 31 23:20:47 GMT 2025

PRIMARY

CAS

1011529-10-4

Created by admin on Mon Mar 31 23:20:47 GMT 2025 , Edited by admin on Mon Mar 31 23:20:47 GMT 2025

PRIMARY

WIKIPEDIA

Azvudine

Created by admin on Mon Mar 31 23:20:47 GMT 2025 , Edited by admin on Mon Mar 31 23:20:47 GMT 2025

PRIMARY

SMS_ID

300000048394

Created by admin on Mon Mar 31 23:20:47 GMT 2025 , Edited by admin on Mon Mar 31 23:20:47 GMT 2025

PRIMARY

EPA CompTox

DTXSID901027757

Created by admin on Mon Mar 31 23:20:47 GMT 2025 , Edited by admin on Mon Mar 31 23:20:47 GMT 2025

PRIMARY

Related Record Type Details


					859A956UY8

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1

TARGET ORGANISM->INHIBITOR

Amount:

Related Record Type Details


					IJ2XP0ID0K

Azvudine

ACTIVE MOIETY

Comments:

2'-deoxy-2'-beta-fluoro-4'-azidocytidine (RO-0622) and 2'-deoxy-2'-beta-hydroxy-4'-azidocytidine (RO-9187) were excellent substrates for deoxycytidine kinase and were phosphorylated with efficiencies up to 3-fold higher than deoxycytidine. As compared with previous reports on ribonucleosides, higher levels of triphosphate were formed from RO-9187 in primary human hepatocytes, and both compounds were potent inhibitors of HCV virus replication in the replicon system (IC(50) = 171 +/- 12 nM and 24 +/- 3 nM for RO-9187 and RO-0622, respectively CC(50) >1 mM for both). Both compounds inhibited RNA synthesis by HCV polymerases from either HCV genotypes 1a and 1b or containing S96T or S282T point mutations with similar potencies, suggesting no cross-resistance with either R1479 (4'-azidocytidine) or 2'-C-methyl nucleosides.

Amount:


					IJ2XP0ID0K

Azvudine

ACTIVE MOIETY

Comments:

The most potent compound, designated RO-0622, inhibited replication in the HCV replicon model with an IC50 of 24 nM, and thus was about 50-fold more potent than R1479 (the active version of R1626 in the body). RO-0622 inhibited HIV-1 replication in MT-4 cells with an antiviral IC50 of 0.4 nM, and was therefore more than 6000-fold more potent than lamivudine.

Amount:


					IJ2XP0ID0K

Azvudine

ACTIVE MOIETY

Comments:

Originator: Roche; Class: Deoxyribonucleoside; Mechanism of Action: Hepatitis C virus NS 5 protein inhibitor, Nucleoside reverse transcriptase inhibitor, RNA-directed DNA polymerase inhibitor; Highest Development Phases: Preclinical for Hepatitis C, HIV-1 infection; Most Recent Events: 26 Apr 2009 Preclinical trials in HIV-1 infections in Europe (unspecified route), 26 Apr 2009 Antimicrobial data from a preclinical study presented at the 44th Annual Meeting of the European Association for the study of the Liver (EASL-2009), 20 Feb 2006 This programme is still in active development

Amount: