An imidazole antifungal
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Prochloraz

Item No. 24051

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]-1H-imidazole-1-carboxamide
CAS Number
67747-09-5
Synonyms
  • BTS-40542
Molecular Formula
C15H16Cl3N3O2
Formula Weight
376.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
SMILES
ClC1=C(OCCN(CCC)C(N2C=NC=C2)=O)C(Cl)=CC(Cl)=C1
InChi Code
InChI=1S/C15H16Cl3N3O2/c1-2-4-20(15(22)21-5-3-19-10-21)6-7-23-14-12(17)8-11(16)9-13(14)18/h3,5,8-10H,2,4,6-7H2,1H3
InChi Key
TVLSRXXIMLFWEO-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Prochloraz is an imidazole antifungal that inhibits ergosterol biosynthesis via inhibition of the cytochrome P450-dependent 14α-demethylation of lanosterol, which results in disruption of the fungal cell membrane and cell death.1 It inhibits human placenta microsomal aromatase in vitro (IC50 = 40 nM).2 Prochloraz also acts as an antagonist of the estrogen receptor (ER) and androgen receptor (AR) (IC50s = 25 and 4 μM, respectively) as well as activates the aryl hydrocarbon receptor (AhR; EC50 = 1 μM).3 In vivo, prochloraz (250 mg/kg) reduces the weight of seminal vesicles in intact male rats and of seminal vesicles, ventral prostate, and bulbourethral glands in castrated testosterone-treated male rats.4 It also reduces testosterone levels and increases progesterone levels in male rat pups following administration of a 30 mg/kg per day dose to pregnant females during gestation.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Antignac, E., Koch, B., Grolier, P., et al. Prochloraz as potent inhibitor of benzo[α]pyrene metabolism and mutagenic activity in rat liver fractions. Toxicol. Lett. 54(2-3), 309-315 (1990).

    2. Zarn, J.A., Brüschweiler, B.J., and Schlatter, J.R. Azole fungicides affect mammalian steroidogenesis by inhibiting sterol 14 α-demethylase and aromatase. Environ. Health Perspect. 111(3), 255-261 (2003).

    3. Andersen, H.R., Vinggaard, A.M., Rasmussen, T.H., et al. Effects of currently used pesticides in assays for estrogenicity, androgenicity, and aromatase activity in vitro. Toxicol. Appl. Pharmacol. 179(1), 1-12 (2002).

    4. Vinggaard, A.M., Hass, U., Dalgaard, M., et al. Prochloraz: An imidazole fungicide with multiple mechanisms of action. Int. J. Androl. 29(1), 186-192 (2006).