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Details

Stereochemistry RACEMIC
Molecular Formula C26H28Cl2N4O4
Molecular Weight 531.431
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KETOCONAZOLE

SMILES

CC(=O)N1CCN(CC1)C2=CC=C(OC[C@@H]3CO[C@](CN4C=CN=C4)(O3)C5=C(Cl)C=C(Cl)C=C5)C=C2

InChI

InChIKey=XMAYWYJOQHXEEK-ZEQKJWHPSA-N
InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m1/s1

HIDE SMILES / InChI
Molecular Formula C26H28Cl2N4O4
Molecular Weight 531.431
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:05:27 UTC 2023
Edited
by admin
on Fri Dec 15 18:05:27 UTC 2023
Record UNII
R9400W927I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KETOCONAZOLE
EP   HSDB   INCI   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN   INCI  
Official Name English
PIPERAZINE, 1-ACETYL-4-(4-((2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-, CIS-
Common Name English
KETOCONAZOLE [MART.]
Common Name English
R-41400
Code English
KETOCONAZOLE [USAN]
Common Name English
KETOCONAZOLE [MI]
Common Name English
KETOCONAZOLE [EP MONOGRAPH]
Common Name English
KETOCONAZOLE [INCI]
Common Name English
NSC-317629
Code English
J02AB02
Code English
KETOCONAZOLE [EP IMPURITY]
Common Name English
(±)-CIS-1-ACETYL-4-(P-((2-(2,4-DICHLOROPHENYL)-2-(IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZINE
Common Name English
KETOCONAZOLE [USP MONOGRAPH]
Common Name English
KETOCONAZOLE [USP-RS]
Common Name English
R 41,400
Code English
KETOZOLE
Brand Name English
EXTINA
Brand Name English
KETOCONAZOLE [JAN]
Common Name English
KETOCONAZOLE [ORANGE BOOK]
Common Name English
NIZORAL
Brand Name English
ketoconazole [INN]
Common Name English
Ketoconazole [WHO-DD]
Common Name English
KETOCONAZOLE [USP IMPURITY]
Common Name English
KETOCONAZOLE [VANDF]
Common Name English
XOLEGEL
Brand Name English
KETOCONAZOLE [HSDB]
Common Name English
KETOCONAZOLUM [WHO-IP LATIN]
Common Name English
Classification Tree Code System Code
WHO-VATC QG01AF11
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
EMA ASSESSMENT REPORTS KETOCONAZOLE HRA (AUTHORIZED: CUSHING SYNDROME)
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
WHO-ATC D01AC08
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
FDA ORPHAN DRUG 51990
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
WHO-VATC QJ02AB02
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
NDF-RT N0000175487
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
WHO-VATC QD01AC08
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
LIVERTOX NBK547869
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
WHO-ATC G01AF11
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
NDF-RT N0000008217
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
WHO-ATC J02AB02
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
EU-Orphan Drug EU/3/17/1857
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
NCI_THESAURUS C2018
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
Code System Code Type Description
CAS
65277-42-1
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
DRUG BANK
DB01026
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
WIKIPEDIA
KETOCONAZOLE
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
EVMPD
SUB08373MIG
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
ChEMBL
CHEMBL295698
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
RXCUI
6135
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY RxNorm
LACTMED
Ketoconazole
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
INN
4594
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
SMS_ID
100000092078
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
CHEBI
47519
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
KETOCONAZOLE
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY Description: A white or almost white powder. Solubility: Practically insoluble in water; freely soluble in dichloromethane R; soluble in methanol R; sparingly soluble in ethanol (~750 g/l) TS. Category: Antifungal drug. Storage: Ketoconazole should be kept in a well-closed container, protected from light. Requirement: Ketoconazole contains not less than 99.0% and not more than the equivalent of 101.0% of C26H28Cl2N4O4, calculated with reference to the dried substance.
DAILYMED
R9400W927I
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
IUPHAR
2568
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
HSDB
7447
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
MERCK INDEX
m6619
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY Merck Index
FDA UNII
R9400W927I
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
NDF-RT
N0000190115
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY Cytochrome P450 3A5 Inhibitors [MoA]
NSC
317629
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
NDF-RT
N0000182141
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
PUBCHEM
47576
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
DRUG CENTRAL
1527
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
NDF-RT
N0000185503
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY P-Glycoprotein Inhibitors [MoA]
CAS
79156-75-5
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
ECHA (EC/EINECS)
265-667-4
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
RS_ITEM_NUM
1356508
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
EPA CompTox
DTXSID7029879
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
MESH
D007654
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
NCI_THESAURUS
C605
Created by admin on Fri Dec 15 18:05:27 UTC 2023 , Edited by admin on Fri Dec 15 18:05:27 UTC 2023
PRIMARY
Related Record Type Details
MRP-1
TRANSPORTER -> INHIBITOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
POTENT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
LANOSTEROL 14-ALPHA DEMETHYLASE
TARGET -> INHIBITOR
Structure of KETOCONAZOLE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Structure of KETOCONAZOLE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
OAT-1
TRANSPORTER -> INHIBITOR
ALDEHYDE OXIDASE
METABOLIC ENZYME -> INHIBITOR
IC50
SODIUM/BILE ACID COTRANSPORTER
TRANSPORTER -> INHIBITOR
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
Related Record Type Details
Structure of 2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLANE-4-METHANOL, (2R,4S)-(±)--
METABOLITE INACTIVE -> PARENT
Structure of 1-(4-(((2R)-2-(4,6-DICHLOROCYCLOHEXA-2,4-DIEN-1-YL)-2-(IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZINE
METABOLITE INACTIVE -> PARENT
Structure of 4-(((2R)-2-(2,4-DICHLOROPHENYL)-2-(IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)ANILINE
METABOLITE INACTIVE -> PARENT
Structure of KETOCONAZOLE-HYDROXY
METABOLITE INACTIVE -> PARENT
Structure of N'-(4-(((2R)-2-(2,4-DICHLOROPHENYL)-2-(IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)ETHANE-1,2-DIAMINE
METABOLITE INACTIVE -> PARENT
Structure of 1-(4-((2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-2,3-PIPERAZINEDIONE, CIS-
METABOLITE INACTIVE -> PARENT
Related Record Type Details
Structure of R-049223
IMPURITY -> PARENT
EP
Structure of N-DEACETYLKETOCONAZOLE
IMPURITY -> PARENT
EP
Structure of 2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHYL 4-METHYLBENZENESULFONATE
IMPURITY -> PARENT
EP
Structure of KETOCONAZOLE, TRANS-
IMPURITY -> PARENT
EP
Structure of 1-ACETYL-4-(4-(((2RS,4SR)-2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)-3-(4-(4-ACETYLPIPERAZIN-1-YL)PHENOXY)PHENYL)PIPERAZINE
IMPURITY -> PARENT
EP
Related Record Type Details
Structure of KETOCONAZOLE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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