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84625-61-6 molecular structure
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1-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one

ChemBase ID: 1038
Molecular Formular: C35H38Cl2N8O4
Molecular Mass: 705.63342
Monoisotopic Mass: 704.2393071
SMILES and InChIs

SMILES:
Clc1c([C@@]2(O[C@H](CO2)COc2ccc(N3CCN(CC3)c3ccc(n4c(=O)n(nc4)C(CC)C)cc3)cc2)Cn2ncnc2)ccc(Cl)c1
Canonical SMILES:
CCC(n1ncn(c1=O)c1ccc(cc1)N1CCN(CC1)c1ccc(cc1)OC[C@H]1CO[C@](O1)(Cn1cncn1)c1ccc(cc1Cl)Cl)C
InChI:
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-/m0/s1
InChIKey:
VHVPQPYKVGDNFY-ZPGVKDDISA-N

Cite this record

CBID:1038 http://www.chembase.cn/molecule-1038.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one
IUPAC Traditional name
itraconazole
Brand Name
Itrizole
Oriconazole
Sporal
Sporanos
Sporanox
Sporonox
Triasporn
Hyphanox
Synonyms
ITC
ITCZ
ITR
Itraconazol [Spanish]
Itraconazolum [Latin]
ITZ
itraconazole
Itraconazole
Sporanox
1-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one
(+/-)-4-[4-[4-[4-[[(2R,4S)-(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)-3H-1,2,4-triazol-3-one
Itrizole
Oriconazole
R-51211
Sporamelt
Triasporin
CAS Number
84625-61-6
MDL Number
MFCD00865619
PubChem SID
46505954
160964501
PubChem CID
55283
CHEBI ID
6076
ATC CODE
J02AC02
CHEMBL
22587
Chemspider ID
49927
DrugBank ID
DB01167
KEGG ID
D00350
Unique Ingredient Identifier
304NUG5GF4
Wikipedia Title
Itraconazole
Medline Plus
a692049

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 7.3001556  LogD (pH = 7.4) 7.3112283 
Log P 7.3113713  Molar Refractivity 200.4 cm3
Polarizability 71.596016 Å3 Polar Surface Area 100.79 Å2
Rotatable Bonds 11  Lipinski's Rule of Five false 
Log P 5.48  LOG S -4.86 
Solubility (Water) 9.64e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Insoluble expand Show data source
Apperance
White and Off-White Solid expand Show data source
Melting Point
164-166°C expand Show data source
Hydrophobicity(logP)
5.99 expand Show data source
6.5 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Admin Routes
Oral and i.v. (US), Oral only (UK) expand Show data source
Bioavailability
55%, maximal if taken with full meal expand Show data source
Half Life
21 hours expand Show data source
Metabolism
hepatic (CYP3A4) expand Show data source
Protein Bound
99.8% expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
Pregnancy Category
C (safety unknown) expand Show data source
Purity
95% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia TRC TRC
DrugBank - DB01167 external link
Item Information
Drug Groups approved; investigational
Description One of the triazole antifungal agents that inhibits cytochrome P-450-dependent enzymes resulting in impairment of ergosterol synthesis. It has been used against histoplasmosis, blastomycosis, cryptococcal meningitis & aspergillosis. [PubChem]
Indication For the treatment of the following fungal infections in immunocompromised and non-immunocompromised patients: pulmonary and extrapulmonary blastomycosis, histoplasmosis, aspergillosis, and onychomycosis.
Pharmacology Itraconazole is an imidazole/triazole type antifungal agent. Itraconazole is a highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethylation via the inhibition of the enzyme cytochrome P450 14α-demethylase. This enzyme converts lanosterol to ergosterol, and is required in fungal cell wall synthesis. The subsequent loss of normal sterols correlates with the accumulation of 14 α-methyl sterols in fungi and may be partly responsible for the fungistatic activity of fluconazole. Mammalian cell demethylation is much less sensitive to fluconazole inhibition. Itraconazole exhibits in vitro activity against Cryptococcus neoformans and Candida spp. Fungistatic activity has also been demonstrated in normal and immunocompromised animal models for systemic and intracranial fungal infections due to Cryptococcus neoformans and for systemic infections due to Candida albicans.
Toxicity No significant lethality was observed when itraconazole was administered orally to mice and rats at dosage levels of 320 mg/kg or to dogs at 200 mg/kg.
Affected Organisms
Fungi, yeast and protozoans
Biotransformation Itraconazole is extensively metabolized by the liver into a large number of metabolites, including hydroxyitraconazole, the major metabolite. The main metabolic pathways are oxidative scission of the dioxolane ring, aliphatic oxidation at the 1-methylpropyl substituent, N-dealkylation of this 1-methylpropyl substituent, oxidative degradation of the piperazine ring and triazolone scission.
Absorption The absolute oral bioavailability of itraconazole is 55%, and is maximal when taken with a full meal.
Half Life 21 hours
Protein Binding 99.8%
Elimination Itraconazole is metabolized predominately by the cytochrome P450 3A4 isoenzyme system (CYP3A4) in the liver, resulting in the formation of several metabolites, including hydroxyitraconazole, the major metabolite. Fecal excretion of the parent drug varies between 3-18% of the dose. Renal excretion of the parent drug is less than 0.03% of the dose. About 40% of the dose is excreted as inactive metabolites in the urine. No single excreted metabolite represents more than 5% of a dose.
Distribution * 796 ± 185 L
Clearance * 381 +/- 95 mL/minute [IV administration]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S2476 external link
Research Area: Infection
Biological Activity:
Itraconazole(Sporanox) is a triazole antifungal agent. It has a broader spectrum of activity than fluconazole (but not as broad as voriconazole or posaconazole). In particular, it is active against Aspergillus, which fluconazole is not. It inhibits the fungal cytochrome P450 oxidase-mediated synthesis of ergosterol. Because of its ability to inhibit cytochrome P450 3A4 CC-3, caution should be used when considering interactions with other medications. [1]
Toronto Research Chemicals - I937500 external link
An orally active antimycotic structurally related to Ketoconazole. Antifungal.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Itraconazole
  • • Espinel-Ingroff, A., et al.: Antimicrob. Agents Chemother., 26, 5 (1984)
  • • Heykants, J., et al.: Mycoses, 32, Suppl 1, 67 (1984)
  • • Sugar, A.M.,et al.: Curr. Clin. Top. Infect. Dis., 13, 74 (1984)
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PATENTS

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