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
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Formulation: 532.5 g/mol
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Terconazole - 67915-31-5

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%

Size SKU Price
5mg bt-284224-5mg $304.62
100mg bt-284224-100mg $1,676.62

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