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67915-31-5 molecular structure
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1-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(propan-2-yl)piperazine

ChemBase ID: 136
Molecular Formular: C26H31Cl2N5O3
Molecular Mass: 532.46204
Monoisotopic Mass: 531.18039524
SMILES and InChIs

SMILES:
Clc1c([C@@]2(O[C@H](CO2)COc2ccc(N3CCN(CC3)C(C)C)cc2)Cn2ncnc2)ccc(Cl)c1
Canonical SMILES:
Clc1ccc(c(c1)Cl)[C@]1(OC[C@@H](O1)COc1ccc(cc1)N1CCN(CC1)C(C)C)Cn1cncn1
InChI:
InChI=1S/C26H31Cl2N5O3/c1-19(2)31-9-11-32(12-10-31)21-4-6-22(7-5-21)34-14-23-15-35-26(36-23,16-33-18-29-17-30-33)24-8-3-20(27)13-25(24)28/h3-8,13,17-19,23H,9-12,14-16H2,1-2H3/t23-,26-/m0/s1
InChIKey:
BLSQLHNBWJLIBQ-OZXSUGGESA-N

Cite this record

CBID:136 http://www.chembase.cn/molecule-136.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(propan-2-yl)piperazine
IUPAC Traditional name
terconazole
Brand Name
Fungistat
Gyno-Terazol
Terazol
Terazol 3
Terazol 7
Tercospor
Synonyms
Triaconazole
Terconazole
CAS Number
67915-31-5
PubChem SID
46505257
160963599
PubChem CID
441383

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 2.5630372  LogD (pH = 7.4) 4.3256955 
Log P 5.374221  Molar Refractivity 153.1894 cm3
Polarizability 54.508034 Å3 Polar Surface Area 64.88 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Log P 4.58  LOG S -4.66 
Solubility (Water) 1.16e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
4.5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00251 external link
Item Information
Drug Groups approved
Description Terconazole is an anti-fungal medication, primarily used to treat vaginal fungal infections. [Wikipedia]
Indication For the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina.
Pharmacology Terconazole is a triazole antifungal agent available for intravaginal use. It is structurally related to imidazole-derivative antifungal agents, although terconazole and other triazoles have 3 nitrogens in the azole ring. By inhibiting the 14-alpha-demethylase (lanosterol 14-alpha-demethylase), Terconazole inhibits ergosterol synthesis. Depletion of ergosterol in fungal membrane disrupts the structure and many functions of fungal membrane leading to inhibition of fungal growth.
Toxicity The oral LD50 values were found to be 1741 and 849 mg/kg for the male and female in rat.
Affected Organisms
Fungi
Biotransformation Systemically absorbed drug appears to be rapidly and extensively metabolized. Terconazole primarily undergoes oxidatative N- and O-dealkylation, dioxolane ring cleavage, and conjugation.
Absorption Following intravaginal administration of terconazole in humans, absorption ranged from 5-8% in three hysterectomized subjects and 12-16% in two non-hysterectomized subjects with tubal ligations
Half Life 6.9 hours (range 4.0-11.3)
Protein Binding 94.9%
Elimination Following oral (30 mg) administration of 14C-labelled terconazole, excretion of radioactivity was both by renal (32-56%) and fecal (47-52%) routes.
External Links
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RxList
PDRhealth
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REFERENCES

REFERENCES

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