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

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SORIVUDINE (BV-araU) is an Anti-Herpes Virus Drugs, which was Withdrawn in 1995.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 8297

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Herpes zoster infections 15 Sources: http://www.chemdrug.com/article/8/3284/16419323.html	Primary		Withdrawn	Unknown Approved Use Unknown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
Antiherpesviral and anticellular effects of 1-beta-D-arabinofuranosyl-E-5-(2-halogenovinyl) uracils.	1981 Jul	6269482
Antiherpes activity of [E]-5-(1-propenyl)-2'-deoxyuridine and 5-(1-propenyl)-1-beta-D-arabinofuranosyluracil.	1981 Nov	6280606
Differential activity of potential antiviral nucleoside analogs on herpes simplex virus-induced and human cellular thymidine kinases.	1981 Sep	6272634
Inhibitory effects of antiherpesviral thymidine analogs against varicella-zoster virus.	1982 Feb	6280604
Inhibitory effect of E-5-(2-bromovinyl)-1-beta-D-arabinofuranosyluracil on herpes simplex virus replication and DNA synthesis.	1982 Jul	6287008
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 Sep	6316849
Strains of varicella-zoster virus resistant to 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil.	1984 Jun	6331298
In vitro and in vivo antiviral activity of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil (BV-araU) and related compounds.	1984 Jun	6089657
Comparison of susceptibilities of varicella-zoster virus and herpes simplex viruses to nucleoside analogs.	1986 Mar	3013088
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 Jul	2847639
Efficacies of antiherpesvirus nucleosides against two strains of herpes simplex virus type 1 in Vero and human embryo lung fibroblast cells.	1988 Jul	2847637
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 Oct	2847634
(E)-5-(2-bromovinyl)uridine requires phosphorylation by the herpes simplex virus (type 1)-induced thymidine kinase to express its antiviral activity.	1989 Jun 15	2545207
Effect of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil against herpes simplex virus type 1 infection in immunosuppressed mice.	1990 Dec	1965108
Inhibition of human herpesvirus 6 replication by 9-[4-hydroxy-2-(hydroxymethyl)butyl]guanine (2HM-HBG) and other antiviral compounds.	1990 Dec	1965107
Comparative activities of several nucleoside analogs against duck hepatitis B virus in vitro.	1990 Jul	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 May	2163240
Synthesis and antiviral activity of 1-cyclobutyl-5-(2-bromovinyl)uracil nucleoside analogues and related compounds.	1992 May 15	1316966
Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus.	1995 Apr	7649195
Antiviral activity of selected acyclic nucleoside analogues against human herpesvirus 6.	1995 Dec	8669893
Analysis of phosphorylation pathways of antiherpesvirus nucleosides by varicella-zoster virus-specific enzymes.	1996 Apr	8849252
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 Aug	9298756
A facile, alternative synthesis of 4'-thioarabinonucleosides and their biological activities.	1997 Jul 4	9216836
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 Aug	9806489
Selective activity of various antiviral compounds against HHV-7 infection.	1999 Aug	10480261
Synthesis of novel 4'-C-methyl-pyrimidine nucleosides and their biological activities.	1999 Mar 22	10206544
Design, synthesis and enzymatic activity of highly selective human mitochondrial thymidine kinase inhibitors.	2001 May 21	11392548
In vitro activity of potential anti-poxvirus agents.	2003 Jan	12615301
In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir?	2004 Mar	15168799
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 Mar 19	14985094
Synthesis and antiviral activities of 1'-carbon-substituted 4'-thiothymidines.	2004 Oct 15	15388158
Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides.	2005 Mar	15728906

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.

Name

Type

Language

SORIVUDINE

Official 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

BRAVAVIR

Brand Name

English

YN-72

Code

English

SORIVUDINE [USAN]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

92295