Ketoconazole
SIGMA/K1003 - 99.0-101.0% (EP, titration)
Synonym: (±)-cis-
CAS Number: 65277-42-1
Empirical Formula (Hill Notation): C26H28Cl2N4O4
Molecular Weight: 531.43
EC Number: 265-667-4
MDL Number: MFCD00058579
Linear Formula: C26H28Cl2N4O4
Product Type: Chemical
| antibiotic activity spectrum | fungi |
| Gram-positive bacteria | |
| yeast | |
| assay | 99.0-101.0% (EP, titration) |
| color | white to off-white |
| description | Specific Optical Rotation (EP): (−0.10) ∼ +0.10 ° |
| form | powder |
| InChI | 1S/C26H28Cl2N4O4/c1-19(33 |
| InChI key | XMAYWYJOQHXEEK-OZXSUGGESA |
| mode of action | enzyme | inhibits |
| Quality Level | 200 ![]() |
| SMILES string | CC(=O)N1CCN(CC1)c2ccc(OC[ |
| storage temp. | 2-8°C |
| Application: | CYP3A4 inhibitor |
| Application: | Ketoconazole is a broad spectrum antifungal agent used to treat candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. It is used to identify p-glycoprotein/CYP3A-limi |
| Biochem/physiol Actions: | Antifungal agent |
| Biochem/physiol Actions: | Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme that is necessary for the conversion of lanosterol to ergosterol. This interaction inhibits ergosterol synthesis and results in increased fungal cellular permeability. Other possible mechanisms of action are the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole inhibits the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone . |
| General description: | Chemical structure: imidazole |
| Packaging: | 100 mg in glass bottle |
| Symbol | ![]() ![]() GHS06,GHS08,GHS09 |
| Signal word | Danger |
| Hazard statements | H301 - H360F - H373 - H410 |
| Precautionary statements | P201 - P202 - P260 - P264 - P273 - P301 + P310 |
| Hazard Codes | T,N |
| Risk Statements | 60-25-48/22-50/53 |
| Safety Statements | 53-45-60-61 |
| RIDADR | UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | 99.0-101.0% (EP, titration) |
| Storage Temp. | 2-8°C |
| UNSPSC | 51101500 |




