Details of the Drug

General Information of Drug (ID: DMG0H8K)

Drug Name
Bictegravir, emtricitabine and tenofovir alafenamide
Synonyms S900007760; Bictegravir mixture with emtricitabine and tenofovir alafenamide
Indication
Disease Entry ICD 11 Status REF
Human immunodeficiency virus infection 1C62 Approved [1]
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski):
4		 Molecular Weight 1173.1
Topological Polar Surface Area Not Available
Rotatable Bond Count 17
Hydrogen Bond Donor Count 6
Hydrogen Bond Acceptor Count 24
Chemical Identifiers
Formula
C50H57F4N12O13PS
IUPAC Name
4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;(1S,11R,13R)-5-hydroxy-3,6-dioxo-N-[(2,4,6-trifluorophenyl)methyl]-12-oxa-2,9-diazatetracyclo[11.2.1.02,11.04,9]hexadeca-4,7-diene-7-carboxamide;propan-2-yl (2S)-2-[[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-phenoxyphosphoryl]amino]propanoate
Canonical SMILES
C[C@H](CN1C=NC2=C(N=CN=C21)N)OC[P@@](=O)(N[C@@H](C)C(=O)OC(C)C)OC3=CC=CC=C3.C1C[C@@H]2C[C@H]1N3[C@H](O2)CN4C=C(C(=O)C(=C4C3=O)O)C(=O)NCC5=C(C=C(C=C5F)F)F.C1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F
InChI
InChI=1S/C21H18F3N3O5.C21H29N6O5P.C8H10FN3O3S/c22-9-3-14(23)12(15(24)4-9)6-25-20(30)13-7-26-8-16-27(10-1-2-11(5-10)32-16)21(31)17(26)19(29)18(13)28;1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27;9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h3-4,7,10-11,16,29H,1-2,5-6,8H2,(H,25,30);5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24);1,5-6,13H,2-3H2,(H2,10,11,14)/t10-,11+,16+;15-,16+,33+;5-,6+/m010/s1
InChIKey
GMIGIKGMWTUBHA-UKQLQXPXSA-N
Cross-matching ID
PubChem CID
129626368
TTD ID
D01IRG

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human immunodeficiency virus Integrase (HIV IN) TT5FH9Y POL_HV1B1 Inhibitor [1]
Human immunodeficiency virus Reverse transcriptase (HIV RT) TT84ETX POL_HV1B1 Inhibitor [1]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
2 Antiviral drugs in current clinical use. J Clin Virol. 2004 Jun;30(2):115-33.
3 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.
4 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.
5 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
6 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.
7 Emerging antiviral drugs. Expert Opin Emerg Drugs. 2008 Sep;13(3):393-416.
8 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
9 Radium 223 dichloride for prostate cancer treatment. Drug Des Devel Ther. 2017 Sep 6;11:2643-2651.
10 2007 FDA drug approvals: a year of flux. Nat Rev Drug Discov. 2008 Feb;7(2):107-9.
11 Clinical pipeline report, company report or official report of GlaxoSmithKline (2009).
12 HIV-1 integrase inhibitors: an emerging clinical reality. Drugs R D. 2007;8(3):155-68.
13 The naphthyridinone GSK364735 is a novel, potent human immunodeficiency virus type 1 integrase inhibitor and antiretroviral. Antimicrob Agents Chemother. 2008 Mar;52(3):901-8.
14 Elvitegravir: a new HIV integrase inhibitor. Antivir Chem Chemother. 2009 Oct 19;20(2):79-85.
15 Why have ten or so nontoxic, retrovirus integrase inhibitors not been made available for AIDS treatment. Biomed Pharmacother. 1999 Dec;53(10):484-6.
16 Long-acting shot prevents infection with HIV analogue. Nature. doi:10.1038/nature.2014.14819. 04 March 2014
17 US patent application no. 8,497,270, Macrocyclic integrase inhibitors.