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SMB00286

Sigma-Aldrich

Terconazole

≥98%

Synonym(s):

(+-)-1-{4-[cis-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-ylmethoxy]phenyl}-4-isopropylpiperazine, Triaconazole

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About This Item

Empirical Formula (Hill Notation):
C26H31Cl2N5O3
CAS Number:
67915-31-5
Molecular Weight:
532.46
EC Number:
267-751-6
UNSPSC Code:
51303407
NACRES:
NA.85

Assay

≥98%

form

powder

color

white

solubility

DMSO: 1 mg/mL

antibiotic activity spectrum

fungi

Mode of action

enzyme | interferes

storage temp.

2-8°C

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-OZXSUGGESA-N

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General description

Terconazole is a traizole ketal derivative, which is antifungal in nature. It is especially effective against Candidal spp.

Application

Terconazole could be used for the assessment of the effect of terconazole on transduction efficiency of host cells by glycoprotein of Ebola virus (EBOV), and for the assessment of the effect of terconazole on transduction efficiency of embryonic kidney cell line 293T by human coronaviruses.

Biochem/physiol Actions

Terconazole suppresses the growth of various types of yeats and mycelium-forming fungi in in vitro conditions. Its antifungal activity is an outcome of the accumulation of the membrane-disrupting 14α-demethylsterols and ergosterol depletion. This is result of inactivation of cytochrome P-450-dependent 14α-demethylase by terconazole. It is a rapidly-acting and well-tolerated antifungal used for the treatment of vulvovaginal candidiasis. It is also used for the treatment of dermatophytosis and candidosis. The drug may facilitate the accumulation of cholesterol in late endosomes.

Packaging

2MG

Storage and Stability

Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Non Combustible Solids

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place. Storage class (TRGS 510): Non Combustible Solids

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335,H413

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
084M4036V
14140706

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E L Tolman et al.
Antimicrobial agents and chemotherapy, 29(6), 986-991 (1986-06-01)
Terconazole is a new triazole ketal derivative with broad-spectrum in vitro and in vivo antifungal activities. This study further characterizes the effects of terconazole in vitro on yeast cell growth, viability, and morphology. Terconazole inhibited the growth of Candida albicans
Florian Wrensch et al.
Viruses, 6(9), 3683-3698 (2014-09-27)
The interferon-inducible transmembrane (IFITM) proteins 1, 2 and 3 inhibit the host cell entry of several enveloped viruses, potentially by promoting the accumulation of cholesterol in endosomal compartments. IFITM3 is essential for control of influenza virus infection in mice and
J Van Cutsem et al.
Chemotherapy, 29(5), 322-331 (1983-01-01)
Terconazole, a new triazole ketal, is found to be highly active in vitro on a wide range of yeasts and mycelium-forming fungi. The in vitro activity depends largely on the medium used. In vitro it is a potent antifungal agent
Heike Hofmann-Winkler et al.
The Journal of infectious diseases, 212 Suppl 2, S172-S180 (2015-04-04)
The ongoing Ebola virus (EBOV) disease (EVD) epidemic in Western Africa is the largest EVD outbreak recorded to date and requires the rapid development and deployment of antiviral measures. The viral glycoprotein (GP) facilitates host cell entry and, jointly with
Ting Li et al.
Medical mycology, 53(5), 455-461 (2015-04-17)
Terconazole is a new, broad-spectrum, triazole antifungal agent. The aim of this study was to compare the efficacy and safety of a 6-day course of a terconazole vaginal suppository (80 mg) with two doses of oral fluconazole (150 mg) for
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