Details of the Drug

General Information of Drug (ID: DMM5WQL)

Drug Name

Elvucitabine

Synonyms

Elvucitabine; beta-L-Fd4C; 181785-84-2; UNII-M09BUF90C0; L-F-D4C; L-D4FC; ACH-126443; ACH-126,443; M09BUF90C0; 4-amino-5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one; ACH 126443; 4-amino-5-fluoro-1-[(2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2(1h)-one; L-Fd4C; Elvucitabine [USAN:INN]; 4-amino-5-fluoro-1-((2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)pyrimidin-2(1H)-one; ACH 126,443; AC1LAJSF; AC1Q4HKY; Elvucitabine (USAN/INN); CHEMBL38700; ZINC7048; SCHEMBL1649928; CTK4D7977

Indication

Disease Entry	ICD 11	Status	REF
Human immunodeficiency virus infection	1C62	Discontinued in Phase 2	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

227.19

Topological Polar Surface Area (xlogp)

-1.3

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

4

Chemical Identifiers

Formula: C9H10FN3O3
IUPAC Name: 4-amino-5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one
Canonical SMILES: C1=C[C@H](O[C@H]1CO)N2C=C(C(=NC2=O)N)F
InChI: InChI=1S/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7+/m1/s1
InChIKey: HSBKFSPNDWWPSL-VDTYLAMSSA-N

Cross-matching ID

PubChem CID: 469717
CAS Number: 181785-84-2
DrugBank ID: DB06236
TTD ID: D0K2PH

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 800007421)
2	Multiple-dose pharmacokinetic behavior of elvucitabine, a nucleoside reverse transcriptase inhibitor, administered over 21 days with lopinavir-ritonavir in human immunodeficiency virus type 1-infected subjects.Antimicrob Agents Chemother.2009 Feb;53(2):662-9.
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.