Prochloraz

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Prochloraz
Prochloraz.svg
Clinical data
Trade names Abavit, Ascurit, Dibavit, Mirage, Octave, Omega, Prelude, Rival, Sporgon, Sportak, Sprint, Tenor [1] [2]
Identifiers
  • N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.060.885 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H16Cl3N3O2
Molar mass 376.66 g·mol−1
3D model (JSmol)
  • CCCN(CCOC1=C(C=C(C=C1Cl)Cl)Cl)C(=O)N2C=CN=C2
  • InChI=1S/C15H16Cl3N3O2/c1-10(2)21(15(22)20-4-3-19-9-20)5-6-23-14-12(17)7-11(16)8-13(14)18/h3-4,7-10H,5-6H2,1-2H3
  • Key:XJABPYGRRIVUOG-UHFFFAOYSA-N

Prochloraz, brand name Sportak, is an imidazole fungicide that was introduced in 1978 [3] and is widely used in Europe, Australia, Asia, and South America within gardening and agriculture to control the growth of fungi. [4] [5] It is not registered for use in the United States. [5] Similarly to other azole fungicides, prochloraz is an inhibitor of the enzyme lanosterol 14α-demethylase (CYP51A1), which is necessary for the production of ergosterol – an essential component of the fungal cell membrane – from lanosterol. [6] The agent is a broad-spectrum, protective and curative fungicide, effective against Alternaria spp., Botrytis spp., Erysiphe spp., Helminthosporium spp., Fusarium spp., Pseudocerosporella spp., Pyrenophora spp., Rhynchosporium spp., and Septoria spp. [5] [2]

Contents

Like many imidazole and triazole fungicides and antifungal medications, prochloraz is not particularly selective in its actions. [4] [6] In addition to inhibition of lanosterol 14α-demethylase, prochloraz has also been found to act as an antagonist of the androgen and estrogen receptors, as an agonist of the aryl hydrocarbon receptor, and as an inhibitor of enzymes in the steroidogenesis pathway such as CYP17A1 and aromatase. [4] [6] In accordance, it has been shown to produce reproductive malformations in mice. [4] [6] As such, prochloraz is considered to be an endocrine disruptor. [4] [6]

See also

Related Research Articles

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Lanosterol 14 alpha-demethylase

Lanosterol 14α-demethylase (CYP51A1) is the animal version of a cytochrome P450 enzyme that is involved in the conversion of lanosterol to 4,4-dimethylcholesta-8(9),14,24-trien-3β-ol. The cytochrome P450 isoenzymes are a conserved group of proteins that serve as key players in the metabolism of organic substances and the biosynthesis of important steroids, lipids, and vitamins in eukaryotes. As a member of this family, lanosterol 14α-demethylase is responsible for an essential step in the biosynthesis of sterols. In particular, this protein catalyzes the removal of the C-14α-methyl group from lanosterol. This demethylation step is regarded as the initial checkpoint in the transformation of lanosterol to other sterols that are widely used within the cell.

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Sterol 14-demethylase

In enzymology, a sterol 14-demethylase (EC 1.14.13.70) is an enzyme of the Cytochrome P450 (CYP) superfamily. It is any member of the CYP51 family. It catalyzes a chemical reaction such as:

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References

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