U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C21H16F4N4O2S
Molecular Weight 464.436
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENZALUTAMIDE

SMILES

CNC(=O)C1=CC=C(C=C1F)N2C(=S)N(C(=O)C2(C)C)C3=CC(=C(C=C3)C#N)C(F)(F)F

InChI

InChIKey=WXCXUHSOUPDCQV-UHFFFAOYSA-N
InChI=1S/C21H16F4N4O2S/c1-20(2)18(31)28(12-5-4-11(10-26)15(8-12)21(23,24)25)19(32)29(20)13-6-7-14(16(22)9-13)17(30)27-3/h4-9H,1-3H3,(H,27,30)

HIDE SMILES / InChI
Molecular Formula C21H16F4N4O2S
Molecular Weight 464.436
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 Fri Dec 15 16:30:25 UTC 2023
Edited
by admin
on Fri Dec 15 16:30:25 UTC 2023
Record UNII
93T0T9GKNU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENZALUTAMIDE
DASH   INN   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
ENZALUTAMIDE [USAN]
Common Name English
4-(3-(4-CYANO-3-(TRIFLUOROMETHYL)PHENYL)-5,5-DIMETHYL-4-OXO-2-THIOXOIMIDAZOLIDIN-1-YL)-2-FLUORO-N-METHYLBENZAMIDE
Systematic Name English
Enzalutamide [WHO-DD]
Common Name English
ENZALUTAMIDE [JAN]
Common Name English
XTANDI
Brand Name English
MDV 3100
Common Name English
MDV-3100
Code English
enzalutamide [INN]
Common Name English
MDV3100
Code English
ENZALUTAMIDE [VANDF]
Common Name English
ENZALUTAMIDE [MI]
Common Name English
BENZAMIDE, 4-(3-(4-CYANO-3-(TRIFLUOROMETHYL)PHENYL)-5,5-DIMETHYL-4-OXO-2-THIOXO-1-IMIDAZOLIDINYL)-2-FLUORO-N-METHYL-
Systematic Name English
ENZALUTAMIDE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C146993
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
NDF-RT N0000175560
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
LIVERTOX NBK548070
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
WHO-ATC L02BB04
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
Code System Code Type Description
IUPHAR
6812
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
PUBCHEM
15951529
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
WIKIPEDIA
Enzalutamide
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID10912307
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
FDA UNII
93T0T9GKNU
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
SMS_ID
100000138095
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
DAILYMED
93T0T9GKNU
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
NDF-RT
N0000185507
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY Cytochrome P450 2C9 Inducers [MoA]
ChEMBL
CHEMBL1082407
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
DRUG BANK
DB08899
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
INN
9621
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
USAN
WW-149
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
DRUG CENTRAL
4628
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
CHEBI
68534
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
MESH
C540278
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
EVMPD
SUB77412
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
CAS
915087-33-1
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
RXCUI
1307298
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY RxNorm
NDF-RT
N0000185607
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY Cytochrome P450 2C19 Inducers [MoA]
NDF-RT
N0000185506
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY Cytochrome P450 3A4 Inducers [MoA]
NCI_THESAURUS
C71744
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
MERCK INDEX
m11683
Created by admin on Fri Dec 15 16:30:25 UTC 2023 , Edited by admin on Fri Dec 15 16:30:25 UTC 2023
PRIMARY
Related Record Type Details
CYTOCHROME P450 2C19
METABOLIC ENZYME -> INDUCER
Therefore, co-administration of enzalutamide with CYP3A4, 2C9, and 2C19 substrates with a narrow therapeutic index should be avoided.
MODERATE
ANDROGEN RECEPTOR F876L
TARGET -> INHIBITOR RESISTANT
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
Structure of DEUTENZALUTAMIDE
LABELED -> NON-LABELED
CYTOCHROME P450 3A5
METABOLIC ENZYME -> INHIBITOR
ANDROGEN RECEPTOR
TARGET -> AGONIST
BINDING
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
In vivo, the sum of enzalutamide and M2 exposure was increased by 2.2-fold and 1.3-fold when it was co-administered with gemfibrozil (strong CYP2C8 inhibitor) or itraconazole (strong CYP3A4 inhibitor), respectively.
CYTOCHROME P450 2C19
METABOLIC ENZYME -> INHIBITOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CYTOCHROME P450 2B6
METABOLIC ENZYME -> INHIBITOR
CYTOCHROME P450 2D6
METABOLIC ENZYME -> INHIBITOR
CYTOCHROME P450 2C9
METABOLIC ENZYME -> INHIBITOR
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
In vivo, the sum of enzalutamide and M2 exposure was increased by 2.2-fold and 1.3-fold when it was co-administered with gemfibrozil (strong CYP2C8 inhibitor) or itraconazole (strong CYP3A4 inhibitor), respectively. If the co-administration of enzalutamide with a strong CYP2C8 inhibitor cannot be avoided, the daily enzalutamide dose should be reduced to 80 mg.
CYTOCHROME P450 1A2
METABOLIC ENZYME -> INHIBITOR
TIME-DEPENDENT INHIBITION
ANDROGEN RECEPTOR F876L
TARGET -> AGONIST
ANDROGEN RECEPTOR
TARGET -> INHIBITOR
CYTOCHROME P450 2C9
METABOLIC ENZYME -> INDUCER
Therefore, co-administration of enzalutamide with CYP3A4, 2C9, and 2C19 substrates with a narrow therapeutic index should be avoided.
MODERATE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INDUCER
Therefore, co-administration of enzalutamide with CYP3A4, 2C9, and 2C19 substrates with a narrow therapeutic index should be avoided
STRONG
CYTOCHROME P450 2C8
METABOLIC ENZYME -> INHIBITOR
Related Record Type Details
Structure of 4-(3-(4-CYANO-3-(TRIFLUOROMETHYL)PHENYL)-5,5-DIMETHYL-2,4-DIOXO-1-IMIDAZOLIDINYL)-2-FLUOROBENZOIC ACID
METABOLITE -> PARENT
MINOR
URINE
Structure of ENZALUTAMIDE CARBOXYLIC ACID
METABOLITE INACTIVE -> PARENT
In plasma, M1 accounted for 10% of the 14C-radioactivity. In urine, the most abundant 14C-component was M1 (62.7% of dose). In feces, the most abundant 14C-components were M1 and M10, which accounted for 3.34% and 4.26% of the radioactive dose, respectively.
FECAL; PLASMA; URINE
Structure of 4-(3-(4-CARBAMOYL-3-(TRIFLUOROMETHYL)PHENYL)-5,5-DIMETHYL-4-OXO-2-THIOXO-IMIDAZOLIDIN-1-YL)-2-FLUORO-BENZOIC ACID
METABOLITE -> PARENT
In urine, M10 was a minor metabolite, which accounted for 0.67% of the dose. In feces, M10 was one of the most abundant 14C-components, and it accounted for 4.26% of the radioactive dose.
FECAL; URINE
Structure of 4-(3-(4-(AMINOCARBONYL)-3-(TRIFLUOROMETHYL)PHENYL)-5,5-DIMETHYL-4-OXO-2-THIOXO-1-IMIDAZOLIDINYL)-2-FLUORO-N-METHYLBENZAMIDE
METABOLITE -> PARENT
Metabolite M7 was trace component in plasma; accounting for ≤ 2% of the radioactivity in the 6- and 24-hour postdose plasma samples and not detected at any other time point. In urine, M7 accounted for 9.45% of the radioactive dose. In feces, M7 accounted for 1.12% of the radioactive dose.
FECAL; PLASMA; URINE
Structure of BENZAMIDE, 4-(3-(4-CYANO-3-(TRIFLUOROMETHYL)PHENYL)-5,5-DIMETHYL-4-OXO-2-THIOXO-1-IMIDAZOLIDINYL)-2-FLUORO-N-(HYDROXYMETHYL)-
METABOLITE -> PARENT
Trace amount of M6 was observed in urine (≤ 0.42% of the dose) and plasma (≤ 2% of the radioactivity in the 6- and 24-hour postdose plasma samples and not detected at any other time point).
MINOR
PLASMA; URINE
Related Record Type Details
Structure of DEFLUORO ENZALUTAMIDE
IMPURITY -> PARENT
Structure of O-METHYL (4-CYANO-3-(TRIFLUOROMETHYL)PHENYL)CARBAMOTHIOATE
IMPURITY -> PARENT
Structure of 4-ISOTHIOCYANATO-2-(TRIFLUOROMETHYL)BENZONITRILE
IMPURITY -> PARENT
Related Record Type Details
Structure of ENZALUTAMIDE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC SINGLE ORAL DOSE

Tmax PHARMACOKINETIC DOSE

ORAL ADMINISTRATION

Volume of Distribution PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966