Details of the Drug

General Information of Drug (ID: DM8OMI6)

Drug Name

Lobucavir

Synonyms

LOBUCAVIR; 127759-89-1; Cyclobut-G; C-Oxetanocin-G; C-Oxt-G; BMS-180194; Cygalovir; (+)-Cyclobut G; 2-Amino-9-((1R,2R,3S)-2,3-bis(hydroxymethyl)cyclobutyl)-1H-purin-6(9H)-one; Lobucavir [USAN:INN]; SQ 33054; UNII-8U5PYQ1R2E; SQ 34,514; DRG-0235; 126062-18-8; 8U5PYQ1R2E; SQ-34514; Bms 180194; 9-((1R,2R,3S)-2,3-Bis(hydroxymethyl)cyclobutyl)guanine; C11H15N5O3; Carbocyclic oxetanocin G; A-69992; 2-amino-9-[(1R,2R,3S)-2,3-bis(hydroxymethyl)cyclobutyl]-3H-purin-6-one

Indication

Disease Entry	ICD 11	Status	REF
Virus infection	1A24-1D9Z	Discontinued in Phase 3	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

265.27

Topological Polar Surface Area (xlogp)

-1.9

Rotatable Bond Count (rotbonds)

3

Hydrogen Bond Donor Count (hbonddonor)

4

Hydrogen Bond Acceptor Count (hbondacc)

5

Chemical Identifiers

Formula: C11H15N5O3
IUPAC Name: 2-amino-9-[(1R,2R,3S)-2,3-bis(hydroxymethyl)cyclobutyl]-1H-purin-6-one
Canonical SMILES: C1[C@@H]([C@H]([C@@H]1N2C=NC3=C2N=C(NC3=O)N)CO)CO
InChI: 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
InChIKey: GWFOVSGRNGAGDL-FSDSQADBSA-N

Cross-matching ID

PubChem CID: 135413519
CAS Number: 127759-89-1
DrugBank ID: DB12531
TTD ID: D0V4RH

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Human immunodeficiency virus Reverse transcriptase (HIV RT)	TT84ETX	POL_HV1B1	Modulator	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800002213)
2	Antiviral efficacy of lobucavir (BMS-180194), a cyclobutyl-guanosine nucleoside analogue, in the woodchuck (Marmota monax) model of chronic hepatit... Antiviral Res. 2000 Dec;48(3):197-203.
3	Antiviral drugs in current clinical use. J Clin Virol. 2004 Jun;30(2):115-33.
4	HIV-1 reverse transcriptase complex with DNA and nevirapine reveals non-nucleoside inhibition mechanism.Nat Struct Mol Biol.2012 Jan 22;19(2):253-9.
5	A peptide inhibitor of HIV-1 reverse transcriptase using alpha,beta-dehydro residues: a structure-based computer model. J Biomol Struct Dyn. 1998 Oct;16(2):347-54.
6	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
7	Quadruple nucleos(t)ide reverse transcriptase inhibitors-only regimen of tenofovir plus zidovudine/lamivudine/abacavir in heavily pre-treated HIV-1 infected patients: salvage therapy or backbone only Curr HIV Res. 2009 May;7(3):320-6.
8	Emerging antiviral drugs. Expert Opin Emerg Drugs. 2008 Sep;13(3):393-416.
9	2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.