{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = ''N''-propyl-''N''-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide | image = Prochloraz structure.svg | image_class = skin-invert-image | width = 200px
<!--Clinical data--> | tradename = Abavit, Ascurit, Dibavit, Mirage, Octave, Omega, Prelude, Rival, Sporgon, Sportak, Sprint, Tenor<ref name="AC05372279]1997">{{cite book |title=Consolidated list of products whose consumption and/or sale have been banned, withdrawn, severely restricted or not approved by governments |year=1997 |location=New York |publisher=United Nations |isbn=978-92-1-130219-6|pages=576–}}</ref><ref name="Milne2005">{{cite book| vauthors = Milne GW |title=Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties|url=https://books.google.com/books?id=oWdc2qcb3QsC&pg=PA517|date=2 September 2005|publisher=John Wiley & Sons|isbn=978-0-471-73661-5|pages=517–}}</ref> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!-- Identifiers --> | CAS_number_Ref = | CAS_number = 67747-09-5 | CAS_supplemental = | class = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 73665 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 159925 | UNII = 99SFL01YCL | KEGG = C11182 | ChEBI = 8434 | ChEMBL = 522782 | synonyms =
<!--Chemical data--> | C=15 | H=16 | Cl=3 | N=3 | O=2 | SMILES = CCCN(CCOC1=C(C=C(C=C1Cl)Cl)Cl)C(=O)N2C=CN=C2 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = XJABPYGRRIVUOG-UHFFFAOYSA-N }}
'''Prochloraz''', brand name '''Sportak''', is an imidazole fungicide that was introduced in 1978<ref name="Carlile2006">{{cite book| vauthors = Carlile B | chapter = Chapter 3.7: Broad-spectrum systemic fungicides |title=Pesticide Selectivity, Health and the Environment| chapter-url = https://books.google.com/books?id=DV_u4w_6RLAC&pg=PA81 |date=28 September 2006|publisher=Cambridge University Press|isbn=978-1-139-45756-9|pages=81–}}</ref> and is widely used in Europe, Australia, Asia, and South America within gardening and agriculture to control the growth of fungi.<ref name="pmid16466539">{{cite journal | vauthors = Vinggaard AM, Hass U, Dalgaard M, Andersen HR, Bonefeld-Jørgensen E, Christiansen S, Laier P, Poulsen ME | display-authors = 6 | title = Prochloraz: an imidazole fungicide with multiple mechanisms of action | journal = International Journal of Andrology | volume = 29 | issue = 1 | pages = 186–192 | date = February 2006 | pmid = 16466539 | doi = 10.1111/j.1365-2605.2005.00604.x | doi-access = free }}</ref><ref name="ParanjapeGowariker2014">{{cite book| vauthors = Paranjape K, Gowariker V, Krishnamurthy VN, Gowariker S | chapter = Prochloraz fungicide |title=The Pesticide Encyclopedia| chapter-url = https://books.google.com/books?id=cnDHBgAAQBAJ&pg=PA406|date=22 December 2014|publisher=CABI|isbn=978-1-78064-014-3|pages=406–}}</ref> It is not registered for use in the United States.<ref name="ParanjapeGowariker2014" />
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.<ref name="Darbre2015">{{cite book | vauthors = Sanderson JT | chapter = Disruptors of Androgen Action and Synthesis | veditors = Darbre PD |title=Endocrine Disruption and Human Health | chapter-url = https://books.google.com/books?id=yOOcBAAAQBAJ&pg=PA86 |date=21 March 2015 |publisher=Elsevier Science |isbn=978-0-12-801120-1 |pages=86– }}</ref> 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.<ref name="ParanjapeGowariker2014" /><ref name="Milne2005" />
Like many imidazole and triazole fungicides and antifungal medications, prochloraz is not particularly selective in its actions.<ref name="pmid16466539" /><ref name="Darbre2015" /> 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.<ref name="pmid16466539" /><ref name="Darbre2015" /> In accordance, it has been shown to produce reproductive malformations in mice.<ref name="pmid16466539" /><ref name="Darbre2015" /> As such, prochloraz is considered to be an endocrine disruptor.<ref name="pmid16466539" /><ref name="Darbre2015" />
== See also == * Ketoconazole * Phenothrin * Procymidone * Vinclozolin
== References == {{Reflist|2}}
== External links == * {{PPDB|536}}
{{Androgen receptor modulators}} {{Estrogen receptor modulators}}
Category:Antiestrogens Category:Aromatase inhibitors Category:Carboxamides Category:Endocrine disruptors Category:Fungicides Category:Imidazoles Category:Nonsteroidal antiandrogens