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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
 

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
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Steroid Synthesis Inhibitors

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

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

InChIKey

XMAYWYJOQHXEEK-ZEQKJWHPSA-N

Smiles

CC(=O)N1CCN(CC1)c2ccc(cc2)OC[C@@H]3CO[C@@](O3)(Cn4ccnc4)c5ccc(cc5Cl)Cl

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) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BEHAVIORAL: COMA
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.