Synonym
R42,470; R-42,470; R 42,470; R42470; R-42470; R 42470; Terconazole; (+/-)-Terconazole; Gyno-Terazol;
IUPAC/Chemical Name
Piperazine, 1-[4-[[(2R ,4S )-2-(2,4-dichlorophenyl)-2-(1H -1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-(1-methylethyl)-, rel-
InChi Key
BLSQLHNBWJLIBQ-MKNUCDGGNA-N
InChi Code
InChI=1/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(2
7)13-25(24)28/h3-8,13,17-19,23H,9-12,14-16H2,1-2H3/t23-,26-/s2
SMILES Code
C([C@]1(O[C@@H](COC2=CC=C(C=C2)N3CCN(C(C)C)CC3)CO1)C4=C(Cl)C=C(Cl)C=C4)N5C=NC=N5
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Terconazole is a broad-spectrum antifungal medication for the treatment of vaginal yeast infection.
In vitro activity:
In this work, the trypanocidal activity of terconazole was evaluated using in vitro assays. In epimastigotes of two parasites strains from different discrete typing units (Y and Dm28c) the calculated IC50 were 25.7 μM and 21.9 μM, respectively. In trypomastigotes and amastigotes (the clinically relevant life-stages of T. cruzi) a higher drug susceptibility was observed with IC50 values of 4.6 μM and 5.9 μM, respectively. Finally, the molecular docking simulations suggest that terconazole inhibits the T. cruzi cytochrome P450 14-α-demethylase, interacting in a similar way that other triazole drugs.
Reference: Heliyon. 2019 Jun 12;5(6):e01947. https://pubmed.ncbi.nlm.nih.gov/31211266/
In vivo activity:
A 3-day once-daily intravaginal application of terconazole 0.8% was usually sufficient to provide a functional therapeutic period of 7 days because of prolonged high biologically active antifungal levels in the rat vagina. No side effects were observed at any concentration of terconazole.
Reference: Am J Obstet Gynecol. 1991 Oct;165(4 Pt 2):1200-6. https://pubmed.ncbi.nlm.nih.gov/1951575/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
5.0 |
9.39 |
| DMF:PBS (pH 7.2) (1:1) |
0.5 |
0.94 |
| DMSO |
27.0 |
50.71 |
| Ethanol |
50.5 |
94.84 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
532.47
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Reigada C, Sayé M, Valera-Vera E, Miranda MR, Pereira CA. Repurposing of terconazole as an anti Trypanosoma cruzi agent. Heliyon. 2019 Jun 12;5(6):e01947. doi: 10.1016/j.heliyon.2019.e01947. PMID: 31211266; PMCID: PMC6562323.
2. 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.
3. Van Cutsem J. The in vitro activity of terconazole against yeasts: its topical long-acting therapeutic efficacy in experimental vaginal candidiasis in rats. Am J Obstet Gynecol. 1991 Oct;165(4 Pt 2):1200-6. doi: 10.1016/s0002-9378(12)90727-9. PMID: 1951575.
In vitro protocol:
1. Reigada C, Sayé M, Valera-Vera E, Miranda MR, Pereira CA. Repurposing of terconazole as an anti Trypanosoma cruzi agent. Heliyon. 2019 Jun 12;5(6):e01947. doi: 10.1016/j.heliyon.2019.e01947. PMID: 31211266; PMCID: PMC6562323.
2. 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.
In vivo protocol:
1. Van Cutsem J. The in vitro activity of terconazole against yeasts: its topical long-acting therapeutic efficacy in experimental vaginal candidiasis in rats. Am J Obstet Gynecol. 1991 Oct;165(4 Pt 2):1200-6. doi: 10.1016/s0002-9378(12)90727-9. PMID: 1951575.
1: Iavazzo C, Gkegkes ID, Zarkada IM, Falagas ME. Boric acid for recurrent vulvovaginal candidiasis: the clinical evidence. J Womens Health (Larchmt). 2011 Aug;20(8):1245-55. doi: 10.1089/jwh.2010.2708. Epub 2011 Jul 20. Review. PubMed PMID: 21774671.
2: Ekiert RJ, Krzek J, Talik P. Chromatographic and electrophoretic techniques used in the analysis of triazole antifungal agents-a review. Talanta. 2010 Sep 15;82(4):1090-100. doi: 10.1016/j.talanta.2010.06.056. Epub 2010 Jul 22. Review. PubMed PMID: 20801303.
3: Young GL, Jewell D. Topical treatment for vaginal candidiasis (thrush) in pregnancy. Cochrane Database Syst Rev. 2001;(4):CD000225. Review. PubMed PMID: 11687074.
4: Ringdahl EN. Treatment of recurrent vulvovaginal candidiasis. Am Fam Physician. 2000 Jun 1;61(11):3306-12, 3317. Review. PubMed PMID: 10865926.
5: Cullins VA, Dominguez L, Guberski T, Secor RM, Wysocki SJ. Treating vaginitis. Nurse Pract. 1999 Oct;24(10):46, 49-50, 53-8 passim; quiz 64-5. Review. PubMed PMID: 10546257.
6: Sobel JD. Vulvovaginitis in healthy women. Compr Ther. 1999 Jun-Jul;25(6-7):335-46. Review. PubMed PMID: 10470518.
7: Edelman DA, Grant S. One-day therapy for vaginal candidiasis. A review. J Reprod Med. 1999 Jun;44(6):543-7. Review. PubMed PMID: 10394549.
8: Degreef H. [New antifungal agents in the treatment of superficial dermatomycoses]. Ann Dermatol Venereol. 1993;120(1):21-31. Review. French. PubMed PMID: 8393313.
9: Torres-Rodríguez JM. New topical antifungal drugs. Arch Med Res. 1993 Winter;24(4):371-5. Review. PubMed PMID: 8118161.
10: Horowitz BJ, Giaquinta D, Ito S. Evolving pathogens in vulvovaginal candidiasis: implications for patient care. J Clin Pharmacol. 1992 Mar;32(3):248-55. Review. PubMed PMID: 1564129.
11: Doering PL, Santiago TM. Drugs for treatment of vulvovaginal candidiasis: comparative efficacy of agents and regimens. DICP. 1990 Nov;24(11):1078-83. Review. PubMed PMID: 2275233.
12: Vanden Bossche H, Marichal P, Gorrens J, Coene MC. Biochemical basis for the activity and selectivity of oral antifungal drugs. Br J Clin Pract Suppl. 1990 Sep;71:41-6. Review. PubMed PMID: 2091733.
13: Weisberg M. Terconazole--a new antifungal agent for vulvovaginal candidiasis. Clin Ther. 1989 Sep-Oct;11(5):659-68. Review. PubMed PMID: 2680088.
14: Cauwenbergh G, Vanden Bossche H. Terconazole. Pharmacology of a new antimycotic agent. J Reprod Med. 1989 Aug;34(8 Suppl):588-92. Review. PubMed PMID: 2677363.
15: Fromtling RA. Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. Review. PubMed PMID: 3069196; PubMed Central PMCID: PMC358042.
