DAPORINAD

Investigational

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 Search

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

Molecular Formula	C24H29N3O2
Molecular Weight	391.506
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23617784 | https://www.cancer.gov/publications/dictionaries/cancer-drug/def/daporinad | https://jamanetwork.com/journals/jamadermatology/fullarticle/2502283

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

Primary Target	Pharmacology	Condition	Potency
Nicotinamide phosphoribosyltransferase 8 Target ID: CHEMBL1744525 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23617784	Inhibitor 8504		3.0 nM [IC50]

C_max

Value	Dose	Analyte	Population
1.4 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-007-9083-2	0.018 mg/m²/h single, intravenous dose: 0.018 mg/m²/h route of administration: Intravenous experiment type: SINGLE co-administered:	DAPORINAD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.41 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-007-9083-2	0.036 mg/m²/h single, intravenous dose: 0.036 mg/m²/h route of administration: Intravenous experiment type: SINGLE co-administered:	DAPORINAD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.92 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-007-9083-2	0.072 mg/m²/h single, intravenous dose: 0.072 mg/m²/h route of administration: Intravenous experiment type: SINGLE co-administered:	DAPORINAD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.31 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-007-9083-2	0.108 mg/m²/h single, intravenous dose: 0.108 mg/m²/h route of administration: Intravenous experiment type: SINGLE co-administered:	DAPORINAD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.51 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-007-9083-2	0.126 mg/m²/h single, intravenous dose: 0.126 mg/m²/h route of administration: Intravenous experiment type: SINGLE co-administered:	DAPORINAD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
11.32 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-007-9083-2	0.144 mg/m²/h single, intravenous dose: 0.144 mg/m²/h route of administration: Intravenous experiment type: SINGLE co-administered:	DAPORINAD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
505.9 ng × h/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-007-9083-2	0.126 mg/m²/h single, intravenous dose: 0.126 mg/m²/h route of administration: Intravenous experiment type: SINGLE co-administered:		DAPORINAD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
76.5 h EXPERIMENT https://link.springer.com/article/10.1007/s10637-007-9083-2	0.018 mg/m²/h single, intravenous dose: 0.018 mg/m²/h route of administration: Intravenous experiment type: SINGLE co-administered:		DAPORINAD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.9 h EXPERIMENT https://link.springer.com/article/10.1007/s10637-007-9083-2	0.144 mg/m²/h single, intravenous dose: 0.144 mg/m²/h route of administration: Intravenous experiment type: SINGLE co-administered:		DAPORINAD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% EXPERIMENT https://link.springer.com/article/10.1007/s10637-007-9083-2	0.018 mg/m²/h single, intravenous dose: 0.018 mg/m²/h route of administration: Intravenous experiment type: SINGLE co-administered:		DAPORINAD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

PubMed

Title	Date	PubMed
Retinal toxicity, in vivo and in vitro, associated with inhibition of nicotinamide phosphoribosyltransferase.	2015-03	25505128
On-target effect of FK866, a nicotinamide phosphoribosyl transferase inhibitor, by apoptosis-mediated death in chronic lymphocytic leukemia cells.	2014-09-15	25172933
Elevated microRNA-34a in obesity reduces NAD+ levels and SIRT1 activity by directly targeting NAMPT.	2013-12	23834033
Nicotinamide phosphoribosyl transferase (Nampt) is a target of microRNA-26b in colorectal cancer cells.	2013	23922874
Inhibition of lactate dehydrogenase A induces oxidative stress and inhibits tumor progression.	2010-02-02	20133848
Detection and pharmacological modulation of nicotinamide mononucleotide (NMN) in vitro and in vivo.	2009-05-15	19426698
Crystal structure of visfatin/pre-B cell colony-enhancing factor 1/nicotinamide phosphoribosyltransferase, free and in complex with the anti-cancer agent FK-866.	2006-09-08	16901503
FK866, a highly specific noncompetitive inhibitor of nicotinamide phosphoribosyltransferase, represents a novel mechanism for induction of tumor cell apoptosis.	2003-11-01	14612543

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:44 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:44 GMT 2025`
Record UNII	V71TF6V9M7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DAPORINAD

Official Name

English

APO-866

Preferred 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

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