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Substance Name: Itraconazole [USAN:USP:INN:BAN:JAN]
RN: 84625-61-6
UNII: 304NUG5GF4
InChIKey: VHVPQPYKVGDNFY-AVQIMAJZSA-N

Note

  • A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.

Molecular Formula

  • C35-H38-Cl2-N8-O4

Molecular Weight

  • 705.6432
 

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
  • Metabolic Side Effects of Drugs and Substances
  • Reproductive Effect
  • Steroid Synthesis Inhibitors

Names and Synonyms

Name of Substance

  • Itraconazole
  • Itraconazole [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Itraconazole

Synonyms

  • (+-)-1-sec-Butyl-4-(p-(4-(p-(((2R*,4S*)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-delta(sup 2)-1,2,4-triazolin-5-one
  • (1)-cis-4-(4-(4-(4-((2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2,4-dihydro-2-sec-butyl-3H-1,2,4-triazol-3-one
  • BRN 6042047
  • Candistat
  • Canditral
  • cis-Itraconazole
  • EINECS 283-347-2
  • HSDB 7839
  • Hyphanox
  • Itrac
  • Itraconazol
  • Itraconazol [Spanish]
  • Itraconazole
  • Itraconazolum
  • Itraconazolum [Latin]
  • Itralek
  • Itrizole
  • Oriconazole
  • Orungal
  • R 51,211
  • R 51211
  • Sempera
  • Spherazole CR
  • Spherazole IR
  • Sporal
  • Sporamelt
  • Sporanox
  • Sporonox
  • SUBA Itraconazole
  • Traconal
  • Triasporin
  • UNII-304NUG5GF4

Systematic Name

  • 3H-1,2,4-Triazol-3-one, 4-(4-(4-(4-((2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-2,4-dihydro-2-(1-methylpropyl)-

Registry Numbers

CAS Registry Number

  • 84625-61-6

FDA UNII

  • 304NUG5GF4

Other Registry Number

  • 84604-65-9

System Generated Number

  • 0084625616

Structure Descriptors

InChI

1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m1/s1

InChIKey

VHVPQPYKVGDNFY-AVQIMAJZSA-N

Smiles

CCC(C)N1N=CN(C1=O)c2ccc(cc2)N3CCN(CC3)c4ccc(OC[C@@H]5CO[C@](Cn6cncn6)(O5)c7ccc(Cl)cc7Cl)cc4

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 200mg/kg (200mg/kg)   Reviews of Infectious Diseases. Vol. 9(Suppl,
guinea pig LD50 oral > 160mg/kg (160mg/kg)   Reviews of Infectious Diseases. Vol. 9(Suppl,
man TDLo oral 240mg/kg/6W-I (240mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

LIVER: LIVER FUNCTION TESTS IMPAIRED
Lancet. Vol. 340, Pg. 251, 1992.
mouse LD50 intravenous 46400ug/kg (46.4mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 25, Pg. 381, 1991.
mouse LD50 oral > 320mg/kg (320mg/kg)   Reviews of Infectious Diseases. Vol. 9(Suppl,
rat LD50 intravenous 40mg/kg (40mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 25, Pg. 381, 1991.
rat LD50 oral > 320mg/kg (320mg/kg)   Reviews of Infectious Diseases. Vol. 9(Suppl,
women TDLo oral 32mg/kg/8D-I (32mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER British Medical Journal. Vol. 293, Pg. 822, 1986.
women TDLo oral 140mg/kg/5W-I (140mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
Lancet. Vol. 340, Pg. 251, 1992.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 5.66 (none)   EXP
Water Solubility 4.72E-04 mg/L 25 EST
Vapor Pressure 2.60E-20 mm Hg 25 EST
Henry's Law Constant 1.26E-22 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.86E-10 cm3/molecule-sec 25 EST

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