Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Miconazole [USP:INN:BAN:JAN]
RN: 22916-47-8
UNII: 7NNO0D7S5M
InChIKey: BYBLEWFAAKGYCD-UHFFFAOYSA-N

Note

  • An imidazole antifungal agent that is used topically and by intravenous infusion.

Molecular Formula

  • C18-H14-Cl4-N2-O

Molecular Weight

  • 416.1336
 

Classification Codes

  • 14-alpha Demethylase Inhibitors
  • Anti-Infective Agents
  • Antifungal
  • Antifungal Agents
  • Cytochrome P-450 CYP2C9 Inhibitors
  • 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

  • Miconazole
  • Miconazole [USP:INN:BAN:JAN]

MeSH Heading

  • Miconazole

Synonyms

  • (+-)-1-(2,4-Dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole
  • 1-(2,4-Dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole
  • 1H-Imidazole, 1-2-((2,4-dichlorophenyl)-2-((2,4-dichlorophenyl))methoxy)ethyl)-, (+-)-
  • 5-23-04-00320 (Beilstein Handbook Reference)
  • BRN 0965511
  • CCRIS 7924
  • Daktarin IV
  • EINECS 245-324-5
  • Miconazol
  • Miconazol [INN-Spanish]
  • Miconazole
  • Miconazolo
  • Miconazolo [DCIT]
  • Miconazolum
  • Miconazolum [INN-Latin]
  • MJR 1762
  • Monistat
  • Monistat IV
  • NSC 170986
  • Oravig
  • R 18134
  • UNII-7NNO0D7S5M

Systematic Names

  • 1H-Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-
  • Imidazole, 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)-
  • Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)- (9CI)
  • Miconazole

Registry Numbers

CAS Registry Number

  • 22916-47-8

FDA UNII

  • 7NNO0D7S5M

Other Registry Number

  • 75319-47-0

Related Registry Number

  • 22832-87-7 (nitrate)

System Generated Number

  • 0022916478

Structure Descriptors

InChI

1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2

InChIKey

BYBLEWFAAKGYCD-UHFFFAOYSA-N

Smiles

c1cc(c(cc1Cl)Cl)COC(Cn2ccnc2)c3ccc(cc3Cl)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 60mg/kg (60mg/kg) CARDIAC: OTHER CHANGES Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 19, Pg. 7, 1980.
infant TDLo intravenous 104mg/kg/4D-I (104mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Medical Journal of Australia. Vol. 146, Pg. 57, 1987.
mammal (species unspecified) LD50 intravenous 100mg/kg (100mg/kg) CARDIAC: OTHER CHANGES Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 19, Pg. 7, 1980.
mouse LD50 intraperitoneal 220mg/kg (220mg/kg)   Drug and Chemical Toxicology. Vol. 13, Pg. 195, 1990.
mouse LD50 intravenous 80mg/kg (80mg/kg)   British UK Patent Application. Vol. #2067993,
mouse LD50 oral 519mg/kg (519mg/kg)   Drugs in Japan Vol. -, Pg. 1325, 1995.
rat LD50 intraperitoneal 349mg/kg (349mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 2145, 1981.
rat LD50 intravenous 105mg/kg (105mg/kg)   Drugs in Japan Vol. -, Pg. 1146, 1990.
rat LD50 oral 550mg/kg (550mg/kg)   Drugs in Japan Vol. -, Pg. 1325, 1995.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 6.250 (none)   EST
Atmospheric OH Rate Constant 5.97E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.