LOBUCAVIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H15N5O3
Molecular Weight	265.2685
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC2=C(N=CN2[C@@H]3C[C@H](CO)[C@H]3CO)C(=O)N1

InChI

InChIKey=GWFOVSGRNGAGDL-FSDSQADBSA-N

InChI=1S/C11H15N5O3/c12-11-14-9-8(10(19)15-11)13-4-16(9)7-1-5(2-17)6(7)3-18/h4-7,17-18H,1-3H2,(H3,12,14,15,19)/t5-,6-,7-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C11H15N5O3
Molecular Weight	265.2685
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.thebodypro.com/article/lobucavir | https://adisinsight.springer.com/drugs/800002213 | https://www.ncbi.nlm.nih.gov/pubmed/9420038

Lobucavir is a new anti-cytomegalovirus infection agent, manufactered by Bristol Myers Squibb, Inc. Lobucavir is a cyclobutyl analog of guanine with broad spectrum antiviral activity against most herpes viruses and Hepatitis B. Lobucavir was shown to inhibit herpes simplex virus (HSV) DNA polymerase after phosphorylation by the HSV thymidine kinase. The drug was well tolerated with few side effects. Lobucavir had been in phase III clinical trial for the treatment of Hepatitis B, Herpes simplex virus infections and in phase II for the treatment of Cytomegalovirus infections. All these studies were discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Viral RNA-dependent DNA polymerase 1 Target ID: Viral RNA-dependent DNA polymerase Sources: https://adisinsight.springer.com/drugs/800002213 \| Cameron, C.E., Gotte, M., Raney, K. (2009) Viral Genome Replication, page 502, retrieved from: https://books.google.ru/books?id=o_8SedCAQCAC	Inhibitor 8297

PubMed

Title	Date	PubMed
Cyclobut-A and cyclobut-G, carbocyclic oxetanocin analogs that inhibit the replication of human immunodeficiency virus in T cells and monocytes and macrophages in vitro.	1990 Feb	2327778
(+-)-(1 alpha,2 beta,3 alpha)-9-[2,3-bis(hydroxymethyl)-cyclobutyl] guanine [(+-)-BHCG or SQ 33,054]: a potent and selective inhibitor of herpesviruses.	1990 Jan	2159261
Cyclobut-A and cyclobut-G: broad-spectrum antiviral agents with potential utility for the therapy of AIDS.	1990 May	2329551
Synthesis and antiviral activity of enantiomeric forms of cyclobutyl nucleoside analogues.	1991 Apr	1849998
Antiviral activity of oxetanocins against varicella-zoster virus.	1991 Jul	1656865
Effects of purine nucleoside analogues with a cyclobutane ring and erythromycin A oxime derivatives on duck hepatitis B virus replication in vivo and in cell culture and HIV-1 in cell culture.	1991 Nov	1804929
Synthesis and antiviral activity of carbocyclic oxetanocin analogues (C-OXT-A, C-OXT-G) and related compounds. II.	1993 Mar	8386594
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
Efficacy of BMS-180194 against experimental cytomegalovirus infections in immunocompromised mice.	1996 Mar	8739602
Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus.	1997 Jul	9210663
Selective activity of various antiviral compounds against HHV-7 infection.	1999 Aug	10480261
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs.	1999 Dec	10582877
Human cytomegalovirus: challenges, opportunities and new drug development.	1999 Sep	10574177
Antiviral efficacy of lobucavir (BMS-180194), a cyclobutyl-guanosine nucleoside analogue, in the woodchuck (Marmota monax) model of chronic hepatitis B virus (HBV) infection.	2000 Dec	11164506
In vivo anti-papillomavirus activity of nucleoside analogues including cidofovir on CRPV-induced rabbit papillomas.	2000 Nov	11114415
Ribavirin and mycophenolic acid potentiate the activity of guanine- and diaminopurine-based nucleoside analogues against hepatitis B virus.	2000 Nov	11114413
Guanosine analogues as anti-herpesvirus agents.	2000 Oct-Dec	11200257
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents.	2001 Apr-Jul	11563039
Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8.	2001 Nov-Dec	11747000
In vitro activity of potential anti-poxvirus agents.	2003 Jan	12615301
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

Patents

Sample Use Guides

In Vivo Use Guide

200 mg twice daily, 200 mg four times daily and 400 mg four times daily

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:52:26 UTC 2023` Edited by `admin` on `Sat Dec 16 05:52:26 UTC 2023`
Record UNII	8U5PYQ1R2E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOBUCAVIR

Official Name

English

9-[(1R,2R,3S)-2,3-Bis(hydroxymethyl)cyclobutyl]guanine

Systematic Name

English

6H-PURIN-6-ONE, 2-AMINO-9-(2,3-BIS(HYDROXYMETHYL)CYCLOBUTYL)-1,9-DIHYDRO, (1R-(1.ALPHA.,2.BETA.,3.ALPHA.))

Common Name

English

Lobucavir [WHO-DD]

Common Name

English

SQ 34,514

Code

English

LOBUCAVIR [USAN]

Common Name

English

LOBUCAVIR [MART.]

Common Name

English

SQ-34514

Code

English

lobucavir [INN]

Common Name

English

BMS-180194

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C281