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Details

Stereochemistry ACHIRAL
Molecular Formula C24H29N3O2
Molecular Weight 391.506
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DAPORINAD

SMILES

O=C(NCCCCC1CCN(CC1)C(=O)C2=CC=CC=C2)\C=C\C3=CC=CN=C3

InChI

InChIKey=KPBNHDGDUADAGP-VAWYXSNFSA-N
InChI=1S/C24H29N3O2/c28-23(12-11-21-8-6-15-25-19-21)26-16-5-4-7-20-13-17-27(18-14-20)24(29)22-9-2-1-3-10-22/h1-3,6,8-12,15,19-20H,4-5,7,13-14,16-18H2,(H,26,28)/b12-11+

HIDE SMILES / InChI
Daporinad is an inhibitor of nicotinamide phosphoribosyltransferase (NMPRTase), an enzyme that participates in the biosynthesis of nicotinamide adenine dinucleotide (NAD+) from niacinamide (vitamin B3). Inhibition of NMPRTase may deplete energy reserves in metabolically active tumor cells and induce tumor cell apoptosis. In addition, this agent may inhibit tumor cell production of vascular endothelial growth factor (VEGF), resulting in the inhibition of tumor angiogenesis. Daporinad was investigated as a treatment of B-cell chronic lymphocytic leukemia, melanoma, and cutaneous T-cell lymphoma. Clinical trials have shown that drug has low efficacy when used alone.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Detection and pharmacological modulation of nicotinamide mononucleotide (NMN) in vitro and in vivo.
2009 May 15
Name Type Language
DAPORINAD
INN   WHO-DD  
INN  
Official Name English
APO866
Code English
2-PROPENAMIDE, N-(4-(1-BENZOYL-4-PIPERIDINYL)BUTYL)-3-(3-PYRIDINYL)-, (2E)-
Systematic Name English
daporinad [INN]
Common Name English
K 22.175
Code English
Daporinad [WHO-DD]
Common Name English
APO-866
Code English
FK866
Code English
FK-866
Code English
(2E)-N-(4-(1-BENZOYLPIPERIDIN-4-YL)BUTYL)-3-(PYRIDIN-3-YL)PROP-2-ENAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
NCI_THESAURUS C1742
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
Code System Code Type Description
FDA UNII
V71TF6V9M7
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
NCI_THESAURUS
C67043
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
DRUG BANK
DB12731
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
SMS_ID
300000034105
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
CAS
658084-64-1
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
MESH
C480543
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID101026050
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
PUBCHEM
6914657
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
INN
8912
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY