CHEBI:131174 - navitoclax

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ChEBI Name navitoclax
ChEBI ID CHEBI:131174
Definition A N-sulfonylcarboxamide resulting from the formal condensation of the carboxy group of 4-{4-[(4'-chloro-4,4-dimethyl-3,4,5,6-tetrahydro[biphenyl]-2-yl)methyl]piperazin-1-yl}benzoic acid with the amino group of 4-{[(2R)-4-(morpholin-4-yl)-1-(phenylsulfanyl)butan-2-yl]amino}-3-[(trifluoromethyl)sulfonyl]benzenesulfonamide. It is a BH3-mimetic drug which targets the anti-apoptotic B-cell lymphoma-2 (BCL-2) family proteins, including BCL-2, BCL-xL, and BCL-w, and induces apoptosis in cancer cells. Currently under clinical investigation as treatment for solid tumors and hematologic malignancies.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:94128
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Formula C47H55ClF3N5O6S3
Net Charge 0
Average Mass 974.610
Monoisotopic Mass 973.29551
InChI InChI=1S/C47H55ClF3N5O6S3/c1-46(2)20-18-42(34-8-12-37(48)13-9-34)36(31-46)32-55-22-24-56(25-23-55)39-14-10-35(11-15-39)45(57)53-65(60,61)41-16-17-43(44(30-41)64(58,59)47(49,50)51)52-38(19-21-54-26-28-62-29-27-54)33-63-40-6-4-3-5-7-40/h3-17,30,38,52H,18-29,31-33H2,1-2H3,(H,53,57)/t38-/m1/s1
InChIKey JLYAXFNOILIKPP-KXQOOQHDSA-N
SMILES CC1(C)CCC(=C(CN2CCN(CC2)C2=CC=C(C=C2)C(=O)NS(=O)(=O)C2=CC(=C(N[C@H](CCN3CCOCC3)CSC3=CC=CC=C3)C=C2)S(=O)(=O)C(F)(F)F)C1)C1=CC=C(Cl)C=C1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
B-cell lymphoma 2 inhibitor
Any inhibitor of B-cell lymphoma 2 protein.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing navitoclax (CHEBI:131174) has role antineoplastic agent (CHEBI:35610)
navitoclax (CHEBI:131174) has role apoptosis inducer (CHEBI:68495)
navitoclax (CHEBI:131174) has role B-cell lymphoma 2 inhibitor (CHEBI:133022)
navitoclax (CHEBI:131174) is a N-sulfonylcarboxamide (CHEBI:90852)
navitoclax (CHEBI:131174) is a aryl sulfide (CHEBI:35683)
navitoclax (CHEBI:131174) is a monochlorobenzenes (CHEBI:83403)
navitoclax (CHEBI:131174) is a morpholines (CHEBI:38785)
navitoclax (CHEBI:131174) is a organofluorine compound (CHEBI:37143)
navitoclax (CHEBI:131174) is a piperazines (CHEBI:26144)
navitoclax (CHEBI:131174) is a secondary amino compound (CHEBI:50995)
navitoclax (CHEBI:131174) is a sulfone (CHEBI:35850)
navitoclax (CHEBI:131174) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
4-{4-[(4'-chloro-4,4-dimethyl-3,4,5,6-tetrahydro[biphenyl]-2-yl)methyl]piperazin-1-yl}-N-[(4-{[(2R)-4-(morpholin-4-yl)-1-(phenylsulfanyl)butan-2-yl]amino}-3-[(trifluoromethyl)sulfonyl]phenyl)sulfonyl]benzamide
INNs Sources
navitoclax WHO MedNet
navitoclax WHO MedNet
navitoclax WHO MedNet
navitoclaxum WHO MedNet
Synonyms Sources
A-855071.0 ChemIDplus
ABT 263 ChemIDplus
ABT-263 ChemIDplus
ABT263 ChEBI
Manual Xrefs Databases
1XJ PDBeChem
21864722 ChemSpider
D09935 KEGG DRUG
DB12340 DrugBank
LSM-42776 LINCS
LSM-4738 LINCS
Navitoclax Wikipedia
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Registry Number Type Source
923564-51-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
23 November 2020