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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, TRANS-

SMILES

CC(=O)N1CCN(CC1)C2=CC=C(OC[C@@H]3CO[C@@](CN4C=CN=C4)(O3)C5=CC=C(Cl)C=C5Cl)C=C2

InChI

InChIKey=XMAYWYJOQHXEEK-BVAGGSTKSA-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

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16516899 | https://www.ncbi.nlm.nih.gov/pubmed/1495014 | https://www.ncbi.nlm.nih.gov/pubmed/26363502

trans-Ketoconazole was identified as impurity of an antifungal compound cis-ketoconazole. Cis-Ketoconazole displayed broad-spectrum in vivo activity in a wide range of experimental fungal infections caused by different fungi in a variety of animal models. trans-isomer of ketoconazole is less active than cis-ketoconazole.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
38.3 µM [IC50]
6.57 µM [IC50]
0.897 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Conazoles.
2010 Jun 9
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
AZ-AHR cells were incubated for 24 h with tested compound (trans-Ketoconazole ), TCDD (5 nM) and/or vehicle (DMSO; 0.1% v/v). After the treatments, cells were lysed and luciferase activity was measured. Dose– response curve fittings and calculations of half-maximal effective concentrations (EC50) and half-maximal inhibitory concentrations (IC50) were performed using GraphPad Prism 5 software (GraphPad Software, San Diego, USA). In parallel, cell viability was determined by conventional MTT test.
Substance Class Chemical
Created
by admin
on Thu Jul 06 16:27:57 UTC 2023
Edited
by admin
on Thu Jul 06 16:27:57 UTC 2023
Record UNII
3INP7D7XI3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KETOCONAZOLE, TRANS-
Common Name English
PIPERAZINE, 1-ACETYL-4-(4-((2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-, TRANS-
Systematic Name English
PIPERAZINE, 1-ACETYL-4-(4-(((2R,4R)-2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-, REL-
Systematic Name English
TRANS-KETOCONAZOLE
Common Name English
RS-36745
Code English
1-ACETYL-4-(4-(((2RS,4RS)-2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZINE
Systematic Name English
KETOCONAZOLE IMPURITY C [EP IMPURITY]
Common Name English
R-44319
Code English
KETOCONAZOLE, TRANS-(±)-
Common Name English
Code System Code Type Description
PUBCHEM
12854713
Created by admin on Thu Jul 06 16:27:58 UTC 2023 , Edited by admin on Thu Jul 06 16:27:58 UTC 2023
PRIMARY
FDA UNII
3INP7D7XI3
Created by admin on Thu Jul 06 16:27:58 UTC 2023 , Edited by admin on Thu Jul 06 16:27:58 UTC 2023
PRIMARY
CHEBI
48342
Created by admin on Thu Jul 06 16:27:58 UTC 2023 , Edited by admin on Thu Jul 06 16:27:58 UTC 2023
PRIMARY
CAS
83374-59-8
Created by admin on Thu Jul 06 16:27:58 UTC 2023 , Edited by admin on Thu Jul 06 16:27:58 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
EP