Tioconazole
White to off-white crystalline powder.
Inhibitors/Agonists
Tioconazole is a synthetic imidazole derivative, fungicidal Terconazole inhibits cell wall synthesis by inhibiting the biosynthesis of ergosterol or other sterols, damaging the fungal cell membrane, altering its permeability, and promoting loss of essential intracellular elements. Tioconazole is active against pathogenic Candida. (NCI04)
Tioconazole, also known as vagistat-1 or gyno-trosyd, belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). Tioconazole is a drug which is used for the local treatment of vulvovaginal candidiasis (moniliasis). Tioconazole is considered to be a practically insoluble (in water) and relatively neutral molecule. Tioconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, tioconazole is primarily located in the cytoplasm and membrane (predicted from logP). Tioconazole is a potentially toxic compound.
Tioconazole is an imidazole antifungal used to treat fungal and yeast infections. Topical formulations are used for ringworm, jock itch, athlete's foot, and tinea versicolor or "sun fungus". Tioconazole interacts with 14-alpha demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the yeast membrane. In this way, tioconazole inhibits ergosterol synthesis, resulting in increased cellular permeability. 387.7 g/mol
Tioconazole, also known as vagistat-1 or gyno-trosyd, belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). Tioconazole is a drug which is used for the local treatment of vulvovaginal candidiasis (moniliasis). Tioconazole is considered to be a practically insoluble (in water) and relatively neutral molecule. Tioconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, tioconazole is primarily located in the cytoplasm and membrane (predicted from logP). Tioconazole is a potentially toxic compound.
Tioconazole is an imidazole antifungal used to treat fungal and yeast infections. Topical formulations are used for ringworm, jock itch, athlete's foot, and tinea versicolor or "sun fungus". Tioconazole interacts with 14-alpha demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the yeast membrane. In this way, tioconazole inhibits ergosterol synthesis, resulting in increased cellular permeability. 387.7 g/mol
Formulation:
387.7 g/mol
Source:
Usage:
Tioconazole
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-285370
CAS Number: 65899-73-2
Molecular Formula: C16H13Cl3N2OS
Molecular Weight: 387.7 g/mol
Purity: ≥ 98%
Inventory: In Stock
| Size | SKU | Price | |
|---|---|---|---|
| 200mg | bt-285370-200mg | $293.85 | |
| 1g | bt-285370-1g | $913.38 | |
| 5g | bt-285370-5g | $2,910.00 |
| CAS Number | 65899-73-2 |
|---|---|
| Product Name | Tioconazole |
| Molecular Formula | C16H13Cl3N2OS |
| Molecular Weight | 387.7 g/mol |
| Appearance | White to off-white crystalline powder. |
| InChI | InChI=1S/C16H13Cl3N2OS/c17-12-1-2-13(14(18)7-12)15(8-21-5-4-20-10-21)22-9-11-3-6-23-16(11)19/h1-7,10,15H,8-9H2 |
| InChI Key | QXHHHPZILQDDPS-UHFFFAOYSA-N |
| IUPAC Name | 1-[2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole |
| Canonical SMILES | C1=CC(=C(C=C1Cl)Cl)C(CN2C=CN=C2)OCC3=C(SC=C3)Cl |
| Description | Tioconazole is a synthetic imidazole derivative, fungicidal Terconazole inhibits cell wall synthesis by inhibiting the biosynthesis of ergosterol or other sterols, damaging the fungal cell membrane, altering its permeability, and promoting loss of essential intracellular elements. Tioconazole is active against pathogenic Candida. (NCI04) Tioconazole, also known as vagistat-1 or gyno-trosyd, belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). Tioconazole is a drug which is used for the local treatment of vulvovaginal candidiasis (moniliasis). Tioconazole is considered to be a practically insoluble (in water) and relatively neutral molecule. Tioconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, tioconazole is primarily located in the cytoplasm and membrane (predicted from logP). Tioconazole is a potentially toxic compound. Tioconazole is an imidazole antifungal used to treat fungal and yeast infections. Topical formulations are used for ringworm, jock itch, athlete's foot, and tinea versicolor or "sun fungus". Tioconazole interacts with 14-alpha demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the yeast membrane. In this way, tioconazole inhibits ergosterol synthesis, resulting in increased cellular permeability. |
| Other CAS Number | 65899-73-2 |
| Physical Description | Solid |
| Pictograms | Irritant;Health Hazard;Environmental Hazard |
| Shelf Life | >2 years if stored properly |
| SMILES | C1=CC(=C(C=C1Cl)Cl)C(CN2C=CN=C2)OCC3=C(SC=C3)Cl |
| Solubility | Soluble in DMSO, not in water |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Synonyms | Tioconazole; UK20,349; UK-20,349; UK 20,349; Gyno-Trosyd; Monistat 1-Day; Mykontral; Trosderm; Trosid; Trosyd; Trosyl; Vagistat. |
| Reference | 1: Rosato A, Piarulli M, Schiavone BI, Montagna MT, Caggiano G, Muraglia M, Carone A, Franchini C, Corbo F. In vitro synergy testing of anidulafungin with fluconazole, tioconazole, 5-flucytosine and amphotericin B against some Candida spp. Med Chem. 2012 Jul;8(4):690-8. PubMed PMID: 22530916. 2: Grudzień M, Gajewska A, Pluciński F, Mazurek AP. Molecular properties relevant to bioavailability of tioconazole and its derivatives. Acta Pol Pharm. 2008 Nov-Dec;65(6):757-8. PubMed PMID: 19172861. 3: Grudzień M, Krakowiak N, Pluciński F, Mazurek AP. Molecular properties of oxyconazole and tioconazole as the criteria for their bioavailability estimation. Acta Pol Pharm. 2008 Jan-Feb;65(1):123-4. PubMed PMID: 18536184. 4: Sidou F, Soto P. A randomized comparison of nail surface remanence of three nail lacquers, containing amorolfine 5%, ciclopirox 8% or tioconazole 28%, in healthy volunteers. Int J Tissue React. 2004;26(1-2):17-24. Erratum in: Int J Tissue React. 2004;26(3-4):119. PubMed PMID: 15573688. 5: Sobue S, Sekiguchi K. Difference in percutaneous absorption and intracutaneous distribution in guinea pigs among topical antifungal drugs (tioconazole solution, tioconazole cream, miconazole nitrate solution and bifonazole solution). Biol Pharm Bull. 2004 Sep;27(9):1428-32. PubMed PMID: 15340231. 6: Simonetti G, Simonetti N, Villa A. Increase of activity of tioconazole against resistant microorganisms by the addition of butylated hydroxyanisole. Int J Antimicrob Agents. 2003 Oct;22(4):439-43. PubMed PMID: 14522107. 7: Pereira M, Fachin AL, Martinez-Rossi NM. The gene that determines resistance to tioconazole and to acridine derivatives in Aspergillus nidulans may have a corresponding gene in Trichophyton rubrum. Mycopathologia. 1998;143(2):71-5. PubMed PMID: 10205888. 8: Faria A, Gonçalo S, Gonçalo M, Freitas C, Baptista PP. Allergic contact dermatitis from tioconazole. Contact Dermatitis. 1996 Oct;35(4):250-2. PubMed PMID: 8957651. 9: Heikkilä H, Stubb S, Reitamo S. A study of 72 patients with contact allergy to tioconazole. Br J Dermatol. 1996 Apr;134(4):678-80. PubMed PMID: 8733370. 10: Fachin AL, Maffei CM, Martinez-Rossi NM. In vitro susceptibility of Trichophyton rubrum isolates to griseofulvin and tioconazole. Induction and isolation of a resistant mutant to both antimycotic drugs. Mutant of Trichophyton rubrum resistant to griseofulvin and tioconazole. Mycopathologia. 1996;135(3):141-3. PubMed PMID: 9066154. 11: Penn SG, Bergström ET, Goodall DM. Capillary electrophoresis with chiral selectors: optimization of separation and determination of thermodynamic parameters for binding of tioconazole enantiomers to cyclodextrins. Anal Chem. 1994 Sep 15;66(18):2866-73. PubMed PMID: 7978295. 12: Gibson G, Buckley A, Murphy GM. Allergic contact dermatitis from tioconazole without cross-sensitivity to other imidazoles. Contact Dermatitis. 1994 May;30(5):308. PubMed PMID: 8088154. 13: Quirino AP, Barros MA. Contact dermatitis from tioconazole. Contact Dermatitis. 1994 Apr;30(4):240-1. PubMed PMID: 8033553. 14: Jones RN, Bale MJ, Hoban D, Erwin ME. In vitro antimicrobial activity of tioconazole and its concentrations in vaginal fluids following topical (vagistat-1 6.5%) application. Diagn Microbiol Infect Dis. 1993 Jul;17(1):45-51. PubMed PMID: 8359005. 15: Piletta P, Pasche-Koo F, Saurat JH. Contact dermatitis from tioconazole mimicking "one hand two feet syndrome". Contact Dermatitis. 1993 May;28(5):308. PubMed PMID: 8365142. 16: Penn SG, Goodall DM, Loran JS. Differential binding of tioconazole enantiomers to hydroxypropyl-beta-cyclodextrin studied by capillary electrophoresis. J Chromatogr. 1993 Apr 23;636(1):149-52. PubMed PMID: 8491834. 17: Marren P, Powell S. Contact sensitivity to tioconazole and other imidazoles. Contact Dermatitis. 1992 Aug;27(2):129-30. PubMed PMID: 1395626. 18: Brunelli D, Vincenzi C, Morelli R, Tosti A. Contact dermatitis from tioconazole. Contact Dermatitis. 1992 Aug;27(2):120. PubMed PMID: 1395619. 19: Onayemi O, Aldridge RD, Shaw S. Allergic contact dermatitis from tioconazole. A report of 2 cases. Contact Dermatitis. 1992 Mar;26(3):193-4. PubMed PMID: 1387058. 20: Stubb S, Heikkilä H, Reitamo S, Förström L. Contact allergy to tioconazole. Contact Dermatitis. 1992 Mar;26(3):155-8. PubMed PMID: 1387056. |
| PubChem Compound | Tioconazole |
| Last Modified | Mar 14 2022 |