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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 67915-31-5
• PubChem SID: 160963599; 46505257
• PubChem CID: 441383

CALCULATED PROPERTIES

JChem

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 2.5630372
• LogD (pH = 7.4): 4.3256955
• Log P: 5.374221
• Molar Refractivity: 153.1894 cm^3
• Polarizability: 54.508034 Å^3
• Polar Surface Area: 64.88 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.58
• LOG S: -4.66
• Solubility (Water): 1.16e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 4.5

DETAILS

DrugBank - DB00251

• 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: Wikipedia; RxList; PDRhealth; Drugs.com