SORIVUDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H13BrN2O6
Molecular Weight	349.135
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@H]([C@@H](O)[C@@H]1O)N2C=C(\C=C\Br)C(=O)NC2=O

InChI

InChIKey=GCQYYIHYQMVWLT-HQNLTJAPSA-N

InChI=1S/C11H13BrN2O6/c12-2-1-5-3-14(11(19)13-9(5)18)10-8(17)7(16)6(4-15)20-10/h1-3,6-8,10,15-17H,4H2,(H,13,18,19)/b2-1+/t6-,7-,8+,10-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C11H13BrN2O6
Molecular Weight	349.135
Charge	0
Count

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

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/2549386
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/1653394 http://www.chemdrug.com/article/8/3284/16419323.html

SORIVUDINE (BV-araU) is an Anti-Herpes Virus Drugs, which was Withdrawn in 1995. Aantiviral action of BV-araU against VZV (varicella-zoster virus) and herpes simplex virus type 1 (HSV-1) is based on the inhibition of DNA synthesis in herpesvirus-infected cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
synthesis of virus DNA 1 Target ID: synthesis of virus DNA Sources: http://www.ncbi.nlm.nih.gov/pubmed/2549386	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Herpes zoster infections 15 Sources: http://www.chemdrug.com/article/8/3284/16419323.html	Primary		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides.	2005-03	15728906
Synthesis and antiviral activities of 1'-carbon-substituted 4'-thiothymidines.	2004-10-15	15388158
Inactivity of the bicyclic pyrimidine nucleoside analogues against simian varicella virus (SVV) does not correlate with their substrate activity for SVV-encoded thymidine kinase.	2004-03-19	14985094
In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir?	2004-03	15168799
In vitro activity of potential anti-poxvirus agents.	2003-01	12615301
Design, synthesis and enzymatic activity of highly selective human mitochondrial thymidine kinase inhibitors.	2001-05-21	11392548
Selective activity of various antiviral compounds against HHV-7 infection.	1999-08	10480261
Synthesis of novel 4'-C-methyl-pyrimidine nucleosides and their biological activities.	1999-03-22	10206544
Anti-herpesvirus activity profile of 4'-thioarabinofuranosyl purine and uracil nucleosides and activity of 1-beta-D-2'-fluoro-4'-thioarabinofuranosyl guanine and 2,6-diaminopurine against clinical isolates of human cytomegalovirus.	1998-08	9806489
Structure-activity relationship of the affinity of 5-substituted uracil nucleoside analogues for varicella-zoster virus thymidine kinase and their activity against varicella-zoster virus.	1997-08	9298756
A facile, alternative synthesis of 4'-thioarabinonucleosides and their biological activities.	1997-07-04	9216836
Analysis of phosphorylation pathways of antiherpesvirus nucleosides by varicella-zoster virus-specific enzymes.	1996-04	8849252
Antiviral activity of selected acyclic nucleoside analogues against human herpesvirus 6.	1995-12	8669893
Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus.	1995-04	7649195
Synthesis and antiviral activity of 1-cyclobutyl-5-(2-bromovinyl)uracil nucleoside analogues and related compounds.	1992-05-15	1316966
Effect of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil against herpes simplex virus type 1 infection in immunosuppressed mice.	1990-12	1965108
Inhibition of human herpesvirus 6 replication by 9-[4-hydroxy-2-(hydroxymethyl)butyl]guanine (2HM-HBG) and other antiviral compounds.	1990-12	1965107
Comparative activities of several nucleoside analogs against duck hepatitis B virus in vitro.	1990-07	2201250
Effect of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil (brovavir) on experimental infections in mice with herpes simplex virus type 1 strains of different degrees of virulence.	1990-05	2163240
(E)-5-(2-bromovinyl)uridine requires phosphorylation by the herpes simplex virus (type 1)-induced thymidine kinase to express its antiviral activity.	1989-06-15	2545207
Effects of various nucleosides on antiviral activity and metabolism of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil against herpes simplex virus types 1 and 2.	1988-10	2847634
Comparison of two bromovinyl nucleoside analogs, 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil and E-5-(2-bromovinyl)-2'-deoxyuridine, with acyclovir in inhibition of Epstein-Barr virus replication.	1988-07	2847639
Efficacies of antiherpesvirus nucleosides against two strains of herpes simplex virus type 1 in Vero and human embryo lung fibroblast cells.	1988-07	2847637
Comparison of susceptibilities of varicella-zoster virus and herpes simplex viruses to nucleoside analogs.	1986-03	3013088
Strains of varicella-zoster virus resistant to 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil.	1984-06	6331298
In vitro and in vivo antiviral activity of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil (BV-araU) and related compounds.	1984-06	6089657
Antiherpes activity of (E)-5-(2-bromovinyl)- and 5-vinyl-1-beta-D-arabinofuranosyluracil and some other 5-substituted uracil arabinosyl nucleosides in two different cell lines.	1983-09	6316849
Inhibitory effect of E-5-(2-bromovinyl)-1-beta-D-arabinofuranosyluracil on herpes simplex virus replication and DNA synthesis.	1982-07	6287008
Inhibitory effects of antiherpesviral thymidine analogs against varicella-zoster virus.	1982-02	6280604
Antiherpes activity of [E]-5-(1-propenyl)-2'-deoxyuridine and 5-(1-propenyl)-1-beta-D-arabinofuranosyluracil.	1981-11	6280606
Differential activity of potential antiviral nucleoside analogs on herpes simplex virus-induced and human cellular thymidine kinases.	1981-09	6272634
Antiherpesviral and anticellular effects of 1-beta-D-arabinofuranosyl-E-5-(2-halogenovinyl) uracils.	1981-07	6269482

Patents

Sample Use Guides

In Vivo Use Guide

for mice: 5% BV-araU (SORIVUDINE) cream given 4 times daily for 5 days starting 1 day after inoculation

Route of Administration: Topical

In Vitro Use Guide

The inhibitory effect of BV-araU (SORIVUDINE) on DNA synthesis in human embryonic lung cells infected with varicella-zoster virus (VZV) or herpes simplex virus type 1 (HSV-1) was compared with that of acyclovir. he inhibitory concentration of BV-araU for DNA synthesis in VZV-infected cells was one-thousandth of that of acyclovir.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 06:57:07 GMT 2025` Edited by `admin` on `Wed Apr 02 06:57:07 GMT 2025`
Record UNII	C7VOZ162LV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SORIVUDINE

Official Name

English

BRAVAVIR

Preferred Name

English

SORIVUDINE [MART.]

Common Name

English

SQ 32,756

Code

English

SO-32756

Code

English

SORIVUDINE [JAN]

Common Name

English

SQ-32756

Code

English

SORIVUDINE [MI]

Common Name

English

Sorivudine [WHO-DD]

Common Name

English

sorivudine [INN]

Common Name

English

YN-72

Code

English

SORIVUDINE [USAN]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

92295