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Prochloraz

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Prochloraz
Clinical data
Trade namesAbavit, 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
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.060.885Edit this at Wikidata
Chemical and physical data
FormulaC15H16Cl3N3O2
Molar mass376.66 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 nameSportak, is animidazolefungicide that was introduced in 1978[3] and is widely used inEurope,Australia,Asia, andSouth America withingardening andagriculture to control the growth offungi.[4][5] It is not registered for use in theUnited States.[5]

Similarly to otherazole fungicides, prochloraz is aninhibitor of theenzymelanosterol 14α-demethylase (CYP51A1), which is necessary for theproduction ofergosterol – an essential component of the fungalcell membrane – fromlanosterol.[6] The agent is abroad-spectrum, protective and curative fungicide, effective againstAlternaria spp.,Botrytis spp.,Erysiphe spp.,Helminthosporium spp.,Fusarium spp.,Pseudocerosporella spp.,Pyrenophora spp.,Rhynchosporium spp., andSeptoria spp.[5][2]

Like many imidazole andtriazole fungicides andantifungal 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 anantagonist of theandrogen andestrogen receptors, as anagonist of thearyl hydrocarbon receptor, and as an inhibitor of enzymes in thesteroidogenesis pathway such asCYP17A1 andaromatase.[4][6] In accordance, it has been shown to producereproductivemalformations in mice.[4][6] As such, prochloraz is considered to be anendocrine disruptor.[4][6]

See also

[edit]

References

[edit]
  1. ^Anonymous AC05372279 (1997).Consolidated list of products whose consumption and/or sale have been banned, withdrawn, severely restricted or not approved by governments / Pharmaceuticals. United Nations Publications. pp. 576–.ISBN 978-92-1-130219-6.[permanent dead link]
  2. ^abMilne GW (2 September 2005).Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties. John Wiley & Sons. pp. 517–.ISBN 978-0-471-73661-5.
  3. ^Carlile B (28 September 2006)."Chapter 3.7: Broad-spectrum systemic fungicides".Pesticide Selectivity, Health and the Environment. Cambridge University Press. pp. 81–.ISBN 978-1-139-45756-9.
  4. ^abcdeVinggaard AM, Hass U, Dalgaard M, Andersen HR, Bonefeld-Jørgensen E, Christiansen S, et al. (February 2006)."Prochloraz: an imidazole fungicide with multiple mechanisms of action".International Journal of Andrology.29 (1):186–192.doi:10.1111/j.1365-2605.2005.00604.x.PMID 16466539.
  5. ^abcParanjape K, Gowariker V, Krishnamurthy VN, Gowariker S (22 December 2014)."Prochloraz fungicide".The Pesticide Encyclopedia. CABI. pp. 406–.ISBN 978-1-78064-014-3.
  6. ^abcdeSanderson JT (21 March 2015)."Disruptors of Androgen Action and Synthesis". In Darbre PD (ed.).Endocrine Disruption and Human Health. Elsevier Science. pp. 86–.ISBN 978-0-12-801120-1.

External links

[edit]
  • Prochloraz in the Pesticide Properties DataBase (PPDB)
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
Retrieved from "https://en.wikipedia.org/w/index.php?title=Prochloraz&oldid=1297228668"
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