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CHEBI:119573 - delavirdine

Default Structure
ChEBI IDCHEBI:119573
ChEBI Namedelavirdine
Stars
DefinitionThe amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavirdine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection.
Secondary ChEBI IDsCHEBI:4378, CHEBI:45727
Last Modified22 February 2018
DownloadsMolfile
FormulaC22H28N6O3S
Net Charge0
Average Mass456.572
Monoisotopic Mass456.19436
SMILESCC(C)Nc1cccnc1N1CCN(C(=O)c2cc3cc(NS(C)(=O)=O)ccc3n2)CC1
InChIInChI=1S/C22H28N6O3S/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20/h4-8,13-15,24-26H,9-12H2,1-3H3
InChIKeyWHBIGIKBNXZKFE-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
HIV-1 reverse transcriptase inhibitor  An entity which inhibits the activity of HIV-1 reverse transcriptase.
Application:
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
ChEBI Ontology
Outgoing Relation(s)
delavirdine (CHEBI:119573) has role antiviral drug (CHEBI:36044)
delavirdine (CHEBI:119573) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
delavirdine (CHEBI:119573) is a N-acylpiperazine (CHEBI:46844)
delavirdine (CHEBI:119573) is a aminopyridine (CHEBI:38207)
delavirdine (CHEBI:119573) is a indolecarboxamide (CHEBI:46921)
delavirdine (CHEBI:119573) is a sulfonamide (CHEBI:35358)
Incoming Relation(s)
delavirdine mesylate (CHEBI:4379) has part delavirdine (CHEBI:119573)
IUPAC Name 
N-[2-({4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl}carbonyl)-1H-indol-5-yl]methanesulfonamide
INN  Source
delavirdineChemIDplus
Synonyms  Source
1-(3-((1-methylethyl)amino)-2-pyridinyl)-4-((5-((methylsulfonyl)amino)-1H-indol-2-yl)carbonyl)piperazineChemIDplus
2-(4-(5-methanesulfonamido-1H-indol-2-ylcarbonyl)-1-piperazinyl)-N-(1-methylethyl)-3-pyridinamineChemIDplus
DelavirdineKEGG COMPOUND
N-(2-(1-(3-(isopropylamino)pyridin-2-yl)piperazine-4-carbonyl)-1H-indol-5-yl)methanesulfonamideChEMBL
(N-[2-[4-[3-(1-methylethylamino)pyridin-2-yl]piperazin-1-yl]carbonyl-1H-indol-5-yl] methanesulfonamide)ChEMBL
N-{2-[4-(3-Isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yl}-methanesulfonamideChEMBL
Manual XrefsDatabases
799DrugCentral
C06941KEGG COMPOUND
D07782KEGG DRUG
DB00705DrugBank
DelavirdineWikipedia
SPPPDBeChem
WO9109849Patent
Registry NumbersSources
Reaxys:6356813Reaxys
CAS:136817-59-9KEGG COMPOUND
CAS:136817-59-9ChemIDplus
Citations