Terconazole
Solid powder
Others
Terconazole is a synthetic triazole derivative structurally related to fluconazole, antifungal Terconazole seems to disrupt cell wall synthesis by inhibiting biosynthesis of ergosterol or other sterols, damaging the fungal cell membrane, altering its permeability, and promoting loss of essential intracellular elements. Terconazole is active against Candida sp.. (NCI04)
Terconazole, also known as terazol 3 or gyno-terazol, belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. Terconazole is a drug which is used for the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina. Terconazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Terconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, terconazole is primarily located in the membrane (predicted from logP).
(2R,4S)-terconazole is a 1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine in which positions 2 and 4 of the 1,3-dioxolane moiety have R and S configuration, respectively. It is an enantiomer of a (2S,4R)-terconazole. 532.5 g/mol
Terconazole, also known as terazol 3 or gyno-terazol, belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. Terconazole is a drug which is used for the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina. Terconazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Terconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, terconazole is primarily located in the membrane (predicted from logP).
(2R,4S)-terconazole is a 1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine in which positions 2 and 4 of the 1,3-dioxolane moiety have R and S configuration, respectively. It is an enantiomer of a (2S,4R)-terconazole. 532.5 g/mol
Formulation:
532.5 g/mol
Source:
Usage:
Terconazole
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-284224
CAS Number: 67915-31-5
Molecular Formula: C26H31Cl2N5O3
Molecular Weight: 532.5 g/mol
Purity: ≥ 99%
Inventory: In Stock
| Size | SKU | Price | |
|---|---|---|---|
| 5mg | bt-284224-5mg | $301.08 | |
| 100mg | bt-284224-100mg | $1,657.08 |
| CAS Number | 67915-31-5 |
|---|---|
| Product Name | Terconazole |
| Molecular Formula | C26H31Cl2N5O3 |
| Molecular Weight | 532.5 g/mol |
| Appearance | Solid powder |
| 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 |
| InChI Key | BLSQLHNBWJLIBQ-ZEQKJWHPSA-N |
| Isomeric SMILES | CC(C)N1CCN(CC1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=NC=N4)C5=C(C=C(C=C5)Cl)Cl |
| IUPAC Name | 1-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-propan-2-ylpiperazine |
| Canonical SMILES | CC(C)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=NC=N4)C5=C(C=C(C=C5)Cl)Cl |
| Description | Terconazole is a synthetic triazole derivative structurally related to fluconazole, antifungal Terconazole seems to disrupt cell wall synthesis by inhibiting biosynthesis of ergosterol or other sterols, damaging the fungal cell membrane, altering its permeability, and promoting loss of essential intracellular elements. Terconazole is active against Candida sp.. (NCI04) Terconazole, also known as terazol 3 or gyno-terazol, belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. Terconazole is a drug which is used for the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina. Terconazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Terconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, terconazole is primarily located in the membrane (predicted from logP). (2R,4S)-terconazole is a 1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine in which positions 2 and 4 of the 1,3-dioxolane moiety have R and S configuration, respectively. It is an enantiomer of a (2S,4R)-terconazole. |
| Melting Point | 126.3 °C 126.3°C |
| Other CAS Number | 67915-31-5 |
| Physical Description | Solid |
| Pictograms | Irritant |
| Shelf Life | >2 years if stored properly |
| SMILES | CC(C)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=NC=N4)C5=C(C=C(C=C5)Cl)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 | 1-(4-((2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-4-(1-methylethyl)piperazine Fungistat Gyno-Terazol R 42470 Terazol terconazole |
| Reference | 1. Tolman EL, Isaacson DM, Rosenthale ME, McGuire JL, Van Cutsem J, Borgers M, Van den Bossche H. Anticandidal activities of terconazole, a broad-spectrum antimycotic. Antimicrob Agents Chemother. 1986 Jun;29(6):986-91. doi: 10.1128/aac.29.6.986. PMID: 3729366; PMCID: PMC180489. 2. Sood G, Nyirjesy P, Weitz MV, Chatwani A. Terconazole cream for non-Candida albicans fungal vaginitis: results of a retrospective analysis. Infect Dis Obstet Gynecol. 2000;8(5-6):240-3. doi: 10.1155/S1064744900000351. PMID: 11220485; PMCID: PMC1784691. 3. Cauwenbergh G, Vanden Bossche H. Terconazole. Pharmacology of a new antimycotic agent. J Reprod Med. 1989 Aug;34(8 Suppl):588-92. PMID: 2677363. 4. Fromtling RA. Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. doi: 10.1128/cmr.1.2.187. PMID: 3069196; PMCID: PMC358042. 5. Maertens JA. History of the development of azole derivatives. Clin Microbiol Infect. 2004 Mar;10 Suppl 1:1-10. doi: 10.1111/j.1470-9465.2004.00841.x. PMID: 14748798. |
| PubChem Compound | Terconazole |
| Last Modified | Mar 14 2022 |