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Substance Name: Ketoconazole [USAN:USP:INN:BAN:JAN]
RN: 65277-42-1
UNII: R9400W927I
InChIKey: XMAYWYJOQHXEEK-ZEQKJWHPSA-N
Note
- Broad spectrum antifungal agent used for long periods at high doses, especially in immunosuppressed patients.
Molecular Formula
- C26-H28-Cl2-N4-O4
Molecular Weight
- 531.4372
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- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- 14-alpha Demethylase Inhibitors
- Anti-Infective Agents
- Antifungal
- Antifungal Agents
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 Enzyme Inhibitors
- Drug / Therapeutic Agent
- Enzyme Inhibitors
- Hormone Antagonists
- Human Data
- Metabolic Side Effects of Drugs and Substances
- Mutation Data
- Reproductive Effect
- Steroid Synthesis Inhibitors
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Names and Synonyms
Name of Substance
- Ketoconazole
- Ketoconazole [USAN:USP:INN:BAN:JAN]
MeSH Heading
- Ketoconazole
Synonyms
- (+-)-cis-1-Acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine
- Brizoral
- BRN 4303081
- EINECS 265-667-4
- Extina
- Fungarest
- Fungoral
- HSDB 7447
- Ketoconazol
- Ketoconazol [INN-Spanish]
- Ketoconazole
- Ketoconazolum
- Ketoconazolum [INN-Latin]
- Ketoderm
- Ketoisdin
- Ketozole
- Kuric
- KW-1414
- Nizoral
- Nizoral A-D
- NSC 317629
- Onofin K
- Orifungal M
- Panfungol
- R 41,400
- R 41400
- UNII-R9400W927I
- Xolegel
Systematic Names
- Ketoconazole
- Piperazine, 1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-, cis-
Registry Numbers
CAS Registry Number
- 65277-42-1
FDA UNII
- R9400W927I
Other Registry Number
- 72093-26-6
System Generated Number
- 0065277421
Structure Descriptors
InChI
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/s1InChIKey
XMAYWYJOQHXEEK-ZEQKJWHPSA-NSmiles
CC(=O)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | TDLo | oral | 450mg/kg/90D- (450mg/kg) | ENDOCRINE: EVIDENCE OF THYROID HYPOFUNCTION | British Medical Journal. Vol. 293, Pg. 993, 1986. |
dog | LD50 | intravenous | 23300ug/kg (23.3mg/kg) | Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981. | |
dog | LD50 | oral | 178mg/kg (178mg/kg) | Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981. | |
guinea pig | LD50 | intravenous | 23300ug/kg (23.3mg/kg) | Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981. | |
guinea pig | LD50 | oral | 178mg/kg (178mg/kg) | Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981. | |
man | LDLo | oral | 45mg/kg/17D-I (45mg/kg) | BEHAVIORAL: COMA LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" | Gut. Vol. 26, Pg. 636, 1986. |
man | TDLo | oral | 49mg/kg/17D-I (49mg/kg) | LIVER: OTHER CHANGES | Gastroenterology. Vol. 86, Pg. 503, 1984. |
mouse | LD50 | intraperitoneal | 2937mg/kg (2937mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 474, 1987. | |
mouse | LD50 | intravenous | 32mg/kg (32mg/kg) | Antimicrobial Agents and Chemotherapy. Vol. 33, Pg. 895, 1989. | |
mouse | LD50 | oral | 618mg/kg (618mg/kg) | Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981. | |
mouse | LD50 | subcutaneous | > 4gm/kg (4000mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 474, 1987. | |
rat | LD50 | intraperitoneal | 1474mg/kg (1474mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 474, 1987. | |
rat | LD50 | intravenous | 86mg/kg (86mg/kg) | Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 23, Pg. 1, 1982. | |
rat | LD50 | oral | 166mg/kg (166mg/kg) | Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981. | |
rat | LD50 | subcutaneous | > 2400mg/kg (2400mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 474, 1987. | |
women | LDLo | oral | 264mg/kg/66D- (264mg/kg) | LIVER: OTHER CHANGES | Gastroenterology. Vol. 86, Pg. 503, 1984. |
women | LDLo | oral | 412mg/kg/15W- (412mg/kg) | LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" BEHAVIORAL: COMA | Gut. Vol. 26, Pg. 636, 1986. |
women | TDLo | oral | 60mg/kg (60mg/kg) | LIVER: OTHER CHANGES | Gastroenterology. Vol. 86, Pg. 503, 1984. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 146 | deg C | EXP | |
log P (octanol-water) | 4.35 | (none) | EXP | |
Water Solubility | 0.087 | mg/L | 25 | EST |
Vapor Pressure | 1.17E-15 | mm Hg | 25 | EST |
Henry's Law Constant | 5.59E-20 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 2.36E-10 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.