CHEBI:172943 - bictegravir

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ChEBI Name bictegravir
ChEBI ID CHEBI:172943
Definition A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2R,5S,13aR)-8-hydroxy-7,9-dioxo-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxylic acid with the amino group of 2,4,6-trifluorobenzylamine. It is a second-generation integrase strand transfer inhibitor (INSTI) and used (as its sodium salt) for the treatment of HIV-1.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter R. Stephan
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Formula C21H18F3N3O5
Net Charge 0
Average Mass 449.386
Monoisotopic Mass 449.11986
InChI InChI=1S/C21H18F3N3O5/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/h3-4,7,10-11,16,29H,1-2,5-6,8H2,(H,25,30)/t10-,11+,16+/m0/s1
InChIKey SOLUWJRYJLAZCX-LYOVBCGYSA-N
SMILES [H][C@@]12CC[C@@]([H])(C1)N1C(=O)C3=C(O)C(=O)C(=CN3C[C@@]1([H])O2)C(=O)NCC1=C(F)C=C(F)C=C1F
Roles Classification
Biological Role(s): HIV-1 integrase inhibitor
An inhibitor of HIV-1 integrase, an enzyme required for the integration of the genetic material of the retrovirus into the DNA of the infected cells.
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ChEBI Ontology
Outgoing bictegravir (CHEBI:172943) has role HIV-1 integrase inhibitor (CHEBI:67268)
bictegravir (CHEBI:172943) is a monocarboxylic acid amide (CHEBI:29347)
bictegravir (CHEBI:172943) is a organic heterotetracyclic compound (CHEBI:38163)
bictegravir (CHEBI:172943) is a secondary carboxamide (CHEBI:140325)
bictegravir (CHEBI:172943) is a trifluorobenzene (CHEBI:83576)
bictegravir (CHEBI:172943) is conjugate acid of bictegravir(1−) (CHEBI:172960)
Incoming bictegravir(1−) (CHEBI:172960) is conjugate base of bictegravir (CHEBI:172943)
IUPAC Name
(2R,5S,13aR)-8-hydroxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide
INNs Sources
bictegravir WHO MedNet
bictégravir WHO MedNet
bictegravir WHO MedNet
bictegravirum WHO MedNet
Synonyms Sources
GS-9883 ChemIDplus
GS-9883-01 ChemIDplus
Manual Xrefs Databases
44208822 ChemSpider
Bictegravir Wikipedia
D10909 KEGG DRUG
DB11799 DrugBank
KLQ PDBeChem
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Registry Number Type Source
1611493-60-7 CAS Registry Number ChemIDplus
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Last Modified
21 May 2021