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
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
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
PubMed
Title | Date | PubMed |
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(+-)-(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 |
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Antiviral activity of oxetanocins against varicella-zoster virus. | 1991 Jul |
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Synthesis and antiviral activity of carbocyclic oxetanocin analogues (C-OXT-A, C-OXT-G) and related compounds. II. | 1993 Mar |
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Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus. | 1997 Jul |
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Selective activity of various antiviral compounds against HHV-7 infection. | 1999 Aug |
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Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs. | 1999 Dec |
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Human cytomegalovirus: challenges, opportunities and new drug development. | 1999 Sep |
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Guanosine analogues as anti-herpesvirus agents. | 2000 Oct-Dec |
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Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents. | 2001 Apr-Jul |
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Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8. | 2001 Nov-Dec |
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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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.thebodypro.com/article/lobucavir
200 mg twice daily, 200 mg four times daily and 400 mg four times daily
Route of Administration:
Oral
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NCI_THESAURUS |
C281
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NCI_THESAURUS |
C1556
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C82253
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FF-63
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DB12531
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Lobucavir
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100000082549
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C063638
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7323
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127759-89-1
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ACTIVE MOIETY