General Information of Drug (ID: DM1K78U)

Drug Name
Apricitabine
Synonyms
Apricitabine; 160707-69-7; AVX754; AVX 754; UNII-K1YX059ML1; BCH 10618; (-)-dOTC; (-)-BCH 10652; K1YX059ML1; AVX-754; SPD-754; BCH-10618; 4-amino-1-[(2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]pyrimidin-2-one; 4-Amino-1-[(2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]-2(1H)-pyrimidinone; BCH-10652; 2(1H)-Pyrimidinone, 4-amino-1-((2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl)-; 2(1H)-Pyrimidinone, 4-amino-1-(2-(hydroxymethyl)-1,3-oxathiolan-4-yl)-, (2R-cis)-; Apricitabine [INN]; SPD754; BCH-10619; SPD 754; AC1L9S1I; (+/-)dOTC
Indication
Disease Entry ICD 11 Status REF
Human immunodeficiency virus infection 1C62 Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 229.26
Topological Polar Surface Area (xlogp) -1.2
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C8H11N3O3S
IUPAC Name
4-amino-1-[(2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]pyrimidin-2-one
Canonical SMILES
C1[C@@H](S[C@@H](O1)CO)N2C=CC(=NC2=O)N
InChI
InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-14-7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7-/m1/s1
InChIKey
RYMCFYKJDVMSIR-RNFRBKRXSA-N
Cross-matching ID
PubChem CID
455041
CAS Number
160707-69-7
DrugBank ID
DB12855
TTD ID
D0V9QR

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]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00686270) A Long Term Safety Study of Apricitabine in HIV-infected Patients. U.S. National Institutes of Health.
2 Multiple-dose pharmacokinetics of apricitabine, a novel nucleoside reverse transcriptase inhibitor, in patients with HIV-1 infection. Clin Drug Investig. 2008;28(2):129-38.
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.