LOBUCAVIR

Investigational

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 8504

PubMed

Title	Date	PubMed
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 activity of potential anti-poxvirus agents.	2003-01	12615301
Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8.	2001-12-18	11747000
A novel nonnucleoside inhibitor specifically targets cytomegalovirus DNA maturation via the UL89 and UL56 gene products.	2001-10	11533171
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents.	2001-09-21	11563039
Guanosine analogues as anti-herpesvirus agents.	2001-02-24	11200257
Antiviral efficacy of lobucavir (BMS-180194), a cyclobutyl-guanosine nucleoside analogue, in the woodchuck (Marmota monax) model of chronic hepatitis B virus (HBV) infection.	2000-12	11164506
In vivo anti-papillomavirus activity of nucleoside analogues including cidofovir on CRPV-induced rabbit papillomas.	2000-11	11114415
Ribavirin and mycophenolic acid potentiate the activity of guanine- and diaminopurine-based nucleoside analogues against hepatitis B virus.	2000-11	11114413
Lamivudine, adefovir and tenofovir exhibit long-lasting anti-hepatitis B virus activity in cell culture.	2000-01	10718947
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs.	1999-12	10582877
Human cytomegalovirus: challenges, opportunities and new drug development.	1999-09	10574177
Selective activity of various antiviral compounds against HHV-7 infection.	1999-08	10480261
Susceptibility of lamivudine-resistant hepatitis B virus to other reverse transcriptase inhibitors.	1999-06	10377169
Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus.	1997-07	9210663
Susceptibility of human cytomegalovirus to two-drug combinations in vitro.	1996-12	11324826
Analysis of phosphorylation pathways of antiherpesvirus nucleosides by varicella-zoster virus-specific enzymes.	1996-04	8849252
Efficacy of BMS-180194 against experimental cytomegalovirus infections in immunocompromised mice.	1996-03	8739602
Antiviral activity of selected acyclic nucleoside analogues against human herpesvirus 6.	1995-12	8669893
Synthesis and antiviral activity of carbocyclic oxetanocin analogues (C-OXT-A, C-OXT-G) and related compounds. II.	1993-03	8386594
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.	1991-11	1804929
Antiviral activity of oxetanocins against varicella-zoster virus.	1991-07	1656865
Synthesis and antiviral activity of enantiomeric forms of cyclobutyl nucleoside analogues.	1991-04	1849998
Cyclobut-A and cyclobut-G: broad-spectrum antiviral agents with potential utility for the therapy of AIDS.	1990-05	2329551
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.	1990-02	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.	1990-01	2159261

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 `Mon Mar 31 21:34:02 GMT 2025` Edited by `admin` on `Mon Mar 31 21:34:02 GMT 2025`
Record UNII	8U5PYQ1R2E
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LOBUCAVIR

Official Name

English

BMS-180194

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C281