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Details

Stereochemistry ACHIRAL
Molecular Formula C21H15F4N5O2S
Molecular Weight 477.435
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APALUTAMIDE

SMILES

CNC(=O)C1=CC=C(C=C1F)N2C(=S)N(C(=O)C23CCC3)C4=CC(=C(N=C4)C#N)C(F)(F)F

InChI

InChIKey=HJBWBFZLDZWPHF-UHFFFAOYSA-N
InChI=1S/C21H15F4N5O2S/c1-27-17(31)13-4-3-11(8-15(13)22)30-19(33)29(18(32)20(30)5-2-6-20)12-7-14(21(23,24)25)16(9-26)28-10-12/h3-4,7-8,10H,2,5-6H2,1H3,(H,27,31)

HIDE SMILES / InChI
Molecular Formula C21H15F4N5O2S
Molecular Weight 477.435
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Sat Dec 16 04:48:59 UTC 2023
Edited
by admin
on Sat Dec 16 04:48:59 UTC 2023
Record UNII
4T36H88UA7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APALUTAMIDE
INN   WHO-DD  
INN  
Official Name English
APALUTAMIDE [ORANGE BOOK]
Common Name English
4-(7-(6-CYANO-5-(TRIFLUOROMETHYL)PYRIDIN-3-YL)-8-OXO-6-THIOXO-5,7-DIAZASPIRO(3.4)OCTAN-5-YL)-2-FLUORO-N-METHYLBENZAMIDE
Systematic Name English
Apalutamide [WHO-DD]
Common Name English
ERLEADA
Brand Name English
APALUTAMIDE [MI]
Common Name English
apalutamide [INN]
Common Name English
BENZAMIDE, 4-(7-(6-CYANO-5-(TRIFLUOROMETHYL)-3-PYRIDINYL)-8-OXO-6-THIOXO-5,7-DIAZASPIRO(3.4)OCT-5-YL)-2-FLUORO-N-METHYL-
Systematic Name English
JNJ-56021927
Code English
APALUTAMIDE [JAN]
Common Name English
ARN-509
Code English
Classification Tree Code System Code
WHO-ATC L02BB05
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
NCI_THESAURUS C146993
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
Code System Code Type Description
DRUG BANK
DB11901
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
PUBCHEM
24872560
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
INN
10118
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
DAILYMED
4T36H88UA7
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
FDA UNII
4T36H88UA7
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
SMS_ID
100000174821
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
CAS
956104-40-8
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID40241899
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
RXCUI
1999574
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
WIKIPEDIA
Apalutamide
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL3183409
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
MERCK INDEX
m12063
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
DRUG CENTRAL
5278
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
NCI_THESAURUS
C92574
Created by admin on Sat Dec 16 04:48:59 UTC 2023 , Edited by admin on Sat Dec 16 04:48:59 UTC 2023
PRIMARY
Related Record Type Details
OAT-3
TRANSPORTER -> INHIBITOR
IC50
MATE-2
TRANSPORTER -> INHIBITOR
IC50
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
Structure of APALUTAMIDE
CUMULATIVE EXCRETION
URINE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of APALUTAMIDE
CUMULATIVE EXCRETION
FECAL
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> INHIBITOR
IC50
GABAA RECEPTOR
OFF-TARGET->INHIBITOR
OFF-TARGET ACTIVITY: INHIBITING LIGAND BINDING TO THE GABAA CHLORIDE ION CHANNEL
CYTOCHROME P450 2C19
METABOLIC ENZYME -> INDUCER
, coadministration of omeprazole, a CYP2C19 substrate, with multiple daily doses of 240 mg apalutamide decreased the omeprazole AUC by 85%
Structure of APALUTAMIDE
EXCRETED UNCHANGED
FECAL
ANDROGEN RECEPTOR
TARGET -> INHIBITOR
The binding affinities of apalutamide to the ligand binding domains of AR and PR, and to full-length ERα and GR demonstrate that it is relatively selective for AR (
IC50
OAT-2
TRANSPORTER -> INHIBITOR
IC50
Structure of APALUTAMIDE
EXCRETED UNCHANGED
URINE
CYTOCHROME P450 2C9
METABOLIC ENZYME -> INDUCER
coadministration of S-warfarin, a CYP2C9 substrate, with multiple daily doses of 240 mg apalutamide decreased the S-warfarin AUC by 46%
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Due to CYP3A4 auto-induction, the contribution of CYP2C8 and CYP3A4 in the metabolism of apalutamide is estimated to be 58% and 13% following single dose but changes to 40% and 37%, respectively at steady-state.
POTASSIUM VOLTAGE-GATED CHANNEL SUBFAMILY H MEMBER 2
OFF-TARGET->INHIBITOR
IC50
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INDUCER
coadministration of midazolam, a CYP3A4 substrate, with multiple daily doses of 240 mg apalutamide decreased the midazolam AUC by 92%
Related Record Type Details
Structure of 4-(7-(6-CYANO-5-(TRIFLUOROMETHYL)PYRIDIN-3-YL)-8-OXO-6-THIOXO-5,7-DIAZASPIRO(3.4)OCTAN-5-YL)-2-FLUOROBENZOIC ACID
METABOLITE -> PARENT
PLASMA
Structure of 5-(8-(3-FLUORO-4-(METHYLCARBAMOYL)PHENYL)-5-OXO-7-THIOXO-6,8-DIAZASPIRO(3.4)OCTAN-6-YL)-3-(TRIFLUOROMETHYL)PYRIDINE-2-CARBOXAMIDE
METABOLITE -> PARENT
FECAL; URINE
Structure of (2S,3S,4S,5R,6S)-6-(1-(4-CARBAMOYL-3-FLUORO-ANILINO)CYCLOBUTANECARBONYL)OXY-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
URINE
Structure of 4-THIAZOLECARBOXYLIC ACID, 2-(5-(5-(3-FLUORO-4-((METHYLAMINO)CARBONYL)PHENYL)-8-OXO-6-THIOXO-5,7-DIAZASPIRO(3.4)OCT-7-YL)-3-(TRIFLUOROMETHYL)-2-PYRIDINYL)-4,5-DIHYDRO-
METABOLITE -> PARENT
After oral administration of 240 mg of apalutamide in 0-1680 hours
URINE
Structure of 5-(8-(4-CARBAMOYL-3-FLUORO-PHENYL)-5-OXO-7-THIOXO-6,8-DIAZASPIRO(3.4)OCTAN-6-YL)-3-(TRIFLUOROMETHYL)PYRIDINE-2-CARBOXAMIDE
METABOLITE -> PARENT
TRACE
FECAL
Structure of 5-(8-(4-CARBAMOYL-3-FLUORO-PHENYL)-5-OXO-7-THIOXO-6,8-DIAZASPIRO(3.4)OCTAN-6-YL)-3-(TRIFLUOROMETHYL)PYRIDINE-2-CARBOXAMIDE
METABOLITE -> PARENT
after oral administration of 240 mg of apalutamide in 0-1680 hours
URINE
Structure of 1-((3-FLUORO-4-((METHYLAMINO)CARBONYL)PHENYL)AMINO)CYCLOBUTANECARBOXYLIC ACID
METABOLITE -> PARENT
FECAL
Structure of 4-(6-(6-CARBAMOYL-5-(TRIFLUOROMETHYL)-3-PYRIDYL)-5-OXO-7-THIOXO-6,8-DIAZASPIRO(3.4)OCTAN-8-YL)-2-FLUORO-BENZOIC ACID
METABOLITE -> PARENT
After oral administration of 240 mg of apalutamide in 0-1680 hours
FECAL
Structure of N-DESMETHYLAPALUTAMIDE
METABOLITE ACTIVE -> PARENT
Due to CYP3A4 auto-induction, the contribution of CYP2C8 and CYP3A4 in the metabolism of apalutamide is estimated to be 58% and 13% following single dose but changes to 40% and 37%, respectively at steady-state.
MAJOR
Structure of 4-THIAZOLECARBOXYLIC ACID, 2-(5-(5-(3-FLUORO-4-((METHYLAMINO)CARBONYL)PHENYL)-8-OXO-6-THIOXO-5,7-DIAZASPIRO(3.4)OCT-7-YL)-3-(TRIFLUOROMETHYL)-2-PYRIDINYL)-4,5-DIHYDRO-
METABOLITE -> PARENT
after oral administration of 240 mg of apalutamide in 0-1680 hours
FECAL
Structure of 4-(6-(6-CARBAMOYL-5-(TRIFLUOROMETHYL)-3-PYRIDYL)-5-OXO-7-THIOXO-6,8-DIAZASPIRO(3.4)OCTAN-8-YL)-2-FLUORO-BENZOIC ACID
METABOLITE -> PARENT
after oral administration of 240 mg of apalutamide in 0-1680 hours
URINE
Structure of 4-(7-(6-CYANO-5-(TRIFLUOROMETHYL)PYRIDIN-3-YL)-6,8-DIOXO-5,7-DIAZASPIRO(3.4)OCTAN-5-YL)-2-FLUORO-N-METHYLBENZAMIDE
METABOLITE -> PARENT
After oral administration of 240 mg of apalutamide in 0-1680 hours
URINE
Structure of 2-((2-(5-(8-(3-FLUORO-4-(METHYLCARBAMOYL)PHENYL)-5-OXO-7-THIOXO-6,8-DIAZASPIRO(3.4)OCTAN-6-YL)-3-(TRIFLUOROMETHYL)-2-PYRIDYL)-4,5-DIHYDROTHIAZOLE-4-CARBONYL)AMINO)ACETIC ACID
METABOLITE -> PARENT
TRACE
URINE
Structure of 4-(7-(6-CYANO-5-(TRIFLUOROMETHYL)PYRIDIN-3-YL)-8-OXO-6-THIOXO-5,7-DIAZASPIRO(3.4)OCTAN-5-YL)-2-FLUOROBENZOIC ACID
METABOLITE INACTIVE -> PARENT
after oral administration of 240 mg of apalutamide in 0-1680 hours
URINE
Structure of 1-((3-FLUORO-4-((METHYLAMINO)CARBONYL)PHENYL)AMINO)CYCLOBUTANECARBOXYLIC ACID
METABOLITE -> PARENT
after oral administration of 240 mg of apalutamide in 0-1680 hours
URINE
Structure of 4-(7-(6-CYANO-5-(TRIFLUOROMETHYL)PYRIDIN-3-YL)-8-OXO-6-THIOXO-5,7-DIAZASPIRO(3.4)OCTAN-5-YL)-2-FLUOROBENZOIC ACID
METABOLITE -> PARENT
after oral administration of 240 mg of apalutamide in 0-1680 hours
FECAL
Structure of N-DESMETHYLAPALUTAMIDE
METABOLITE ACTIVE -> PARENT
Due to CYP3A4 auto-induction, the contribution of CYP2C8 and CYP3A4 in the metabolism of apalutamide is estimated to be 58% and 13% following single dose but changes to 40% and 37%, respectively at steady-state.
MAJOR
Structure of 2-((2-(5-(8-(4-CARBAMOYL-3-FLUORO-PHENYL)-5-OXO-7-THIOXO-6,8-DIAZASPIRO(3.4)OCTAN-6-YL)-3-(TRIFLUOROMETHYL)-2-PYRIDYL)-4,5-DIHYDROTHIAZOLE-4-CARBONYL)AMINO)ACETIC ACID
METABOLITE -> PARENT
URINE
Structure of 2-(5-(8-(4-CARBAMOYL-3-FLUORO-PHENYL)-5-OXO-7-THIOXO-6,8-DIAZASPIRO(3.4)OCTAN-6-YL)-3-(TRIFLUOROMETHYL)-2-PYRIDYL)-4,5-DIHYDROTHIAZOLE-4-CARBOXYLIC ACID
METABOLITE -> PARENT
FECAL; URINE
Structure of 2-(5-(8-(4-CARBOXY-3-FLUORO-PHENYL)-5-OXO-7-THIOXO-6,8-DIAZASPIRO(3.4)OCTAN-6-YL)-3-(TRIFLUOROMETHYL)-2-PYRIDYL)-4,5-DIHYDROTHIAZOLE-4-CARBOXYLIC ACID
METABOLITE -> PARENT
TRACE
FECAL; URINE
Structure of 4-(7-(6-CYANO-5-(TRIFLUOROMETHYL)PYRIDIN-3-YL)-8-OXO-6-THIOXO-5,7-DIAZASPIRO(3.4)OCTAN-5-YL)-2-FLUOROBENZOIC ACID
METABOLITE -> PARENT
after oral administration of 240 mg of apalutamide in 0-1680 hours
FECAL
Structure of (2S,3S,4S,5R,6S)-6-(1-(3-FLUORO-4-(METHYLCARBAMOYL)ANILINO)CYCLOBUTANECARBONYL)OXY-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
URINE
Related Record Type Details
Structure of APALUTAMIDE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC ROUTE OF ADMINISTRATION
PHARMACOKINETIC
DOSE
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC ROUTE OF ADMINISTRATION
PHARMACOKINETIC
DOSE
PHARMACOKINETIC
Cmax PHARMACOKINETIC ROUTE OF ADMINISTRATION
PHARMACOKINETIC
DOSE
PHARMACOKINETIC
Tmax PHARMACOKINETIC ROUTE OF ADMINISTRATION
PHARMACOKINETIC
DOSE
PHARMACOKINETIC
Tmax PHARMACOKINETIC DOSE
PHARMACOKINETIC
ROUTE OF ADMINISTRATION
PHARMACOKINETIC
NIH
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