Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

Zeranol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Zeranol
Clinical data
Trade namesFrideron, Ralabol, Ralgro, Ralone, Zerano
Other namesZearanol; α-Zearalanol; Zearalanol; MK-188; P-1496
Routes of
administration
By mouth
Drug classNonsteroidal estrogen
Identifiers
  • (3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.043.411Edit this at Wikidata
Chemical and physical data
FormulaC18H26O5
Molar mass322.401 g·mol−1
3D model (JSmol)
  • C[C@H]1CCC[C@H](O)CCCCCc2cc(O)cc(O)c2C(=O)O1
  • InChI=1S/C18H26O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h10-12,14,19-21H,2-9H2,1H3/t12-,14+/m0/s1 ☒N
  • Key:DWTTZBARDOXEAM-GXTWGEPZSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Zeranol (INNTooltip International Nonproprietary Name,USANTooltip United States Adopted Name,BANTooltip British Approved Name) (brand namesFrideron,Ralabol,Ralgro,Ralone,Zerano; developmental code namesMK-188,P-1496), orzearanol, also known asα-zearalanol or simplyzearalanol, is asyntheticnonsteroidal estrogen of theresorcylic acid lactone group related tomycoestrogens found infungi in theFusariumgenus and is used mainly as ananabolicagent inveterinary medicine.[1][2][3]

Zeranol is approved for use as a growth promoter in livestock, including beef cattle, under the brand nameRalgro (byMerck Animal Health) in theUnited States.[4] InCanada, it is approved for use in beef cattle only.[5] Its application is not approved for use in theEuropean Union. However, it is marketed under the brand nameRalone inSpain.[2]

Although zeranol may increase cancer cell proliferation in already existingbreast cancer,[6] dietary exposure from the use of zeranol-containing implants in cattle is insignificant.[7] Zeranol may be found as a contaminant in fungus-infected crops. It is 3 to 4 times more potent as an estrogen than the related compoundzearalenone.[8] It is a metabolite of zearalenone.[9]

See also

[edit]

References

[edit]
  1. ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 350–.ISBN 978-1-4757-2085-3.
  2. ^abIndex Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1105–.ISBN 978-3-88763-075-1.
  3. ^Morton IK, Hall JM (6 December 2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 295–.ISBN 978-94-011-4439-1.
  4. ^Nichols W, Hutcheson J, Streeter M, Corrigan M, Nuttelman B."Implant Strategies for Finishing Cattle using Revalor® (trenbolone acetate and estradiol), Finaplix® (trenbolone) and/or Ralgro® (zeranol)"(PDF).
  5. ^Health Canada,Questions and Answers - Hormonal Growth Promoters
  6. ^Xu P, Ye W, Jen R, Lin SH, Kuo CT, Lin YC (November 2009). "Mitogenic activity of zeranol in human breast cancer cells is enhanced by leptin and suppressed by gossypol".Anticancer Research.29 (11):4621–4628.PMID 20032412.
  7. ^Lindsay DG (August 1985). "Zeranol--a 'nature-identical' oestrogen?".Food and Chemical Toxicology.23 (8):767–774.doi:10.1016/0278-6915(85)90273-x.PMID 2931335.
  8. ^Mirocha CJ, Schauerhamer B, Christensen CM, Niku-Paavola ML, Nummi M (October 1979)."Incidence of zearalenol (Fusarium mycotoxin) in animal feed".Applied and Environmental Microbiology.38 (4):749–750.Bibcode:1979ApEnM..38..749M.doi:10.1128/AEM.38.4.749-750.1979.PMC 243572.PMID 161492.
  9. ^Miles CO, Erasmuson AF, Wilkins AL, Towers NR, Smith BL, Garthwaite I, et al. (October 1996). "Ovine metabolism of zearalenone to α-zearalanol (zeranol)".Journal of Agricultural and Food Chemistry.44 (10):3244–3250.Bibcode:1996JAFC...44.3244M.doi:10.1021/jf9601325.
Bacterial
toxins
Exotoxin
Gram
positive
Bacilli
Clostridium:
Other:
Cocci
Staphylococcus
Actinomycetota
Gram
negative
Mechanisms
Endotoxin
Virulence
factor
Mycotoxins
Plant toxins
Invertebrate
toxins
Scorpion:
Spider:
Mollusca:
Vertebrate
toxins
Fish:
Amphibian:
Reptile/
Snake venom:
  • note: some toxins are produced by lower species and pass through intermediate species
Phytoestrogens
Flavanones
Flavones
Prenylflavonoids
Isoflavones
Isoflavanes
Dihydrochalcones
Isoflavenes
Coumestans
Lignans
Flavonolignans
Flavonols
Others
Mycoestrogens
Derivatives
Synthetic
Metalloestrogens
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
CARTooltip Constitutive androstane receptor
PXRTooltip Pregnane X receptor
Retrieved from "https://en.wikipedia.org/w/index.php?title=Zeranol&oldid=1253442592"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp