Zeranol

Zeranol
Clinical data
Trade names	Frideron, Ralabol, Ralgro, Ralone, Zerano
Other names	Zearanol; α-Zearalanol; Zearalanol; MK-188; P-1496
Routes of; administration	By mouth
Drug class	Nonsteroidal estrogen
Identifiers
	IUPAC name (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	26538-44-3 ;
PubChem CID	2999413;
ChemSpider	2271133 ;
UNII	76LO2L2V39;
ChEMBL	ChEMBL371463 ;
CompTox Dashboard (EPA)	DTXSID4022315 ;
ECHA InfoCard	100.043.411
Chemical and physical data
Formula	C18H26O5
Molar mass	322.401 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H]1CCC[C@H](O)CCCCCc2cc(O)cc(O)c2C(=O)O1;
	InChI 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 ; Key:DWTTZBARDOXEAM-GXTWGEPZSA-N ;
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Zeranol (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name) (brand names Frideron, Ralabol, Ralgro, Ralone, Zerano; developmental code names MK-188, P-1496), or zearanol, also known as α-zearalanol or simply zearalanol, is a synthetic nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in fungi in the Fusarium genus and is used mainly as an anabolic agent in veterinary medicine.^[1]^[2]^[3]

Zeranol is approved for use as a growth promoter in livestock, including beef cattle, under the brand name Ralgro (by Merck Animal Health) in the United States.^[4] In Canada, it is approved for use in beef cattle only.^[5] Its application is not approved for use in the European Union. However, it is marketed under the brand name Ralone in Spain.^[2]

Although zeranol may increase cancer cell proliferation in already existing breast 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 compound zearalenone.^[8] It is a metabolite of zearalenone.^[9]

References

^ 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.
^ ^a ^b Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1105–. ISBN 978-3-88763-075-1.
^ 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.
^ 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).
^ Health Canada, Questions and Answers - Hormonal Growth Promoters
^ 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.
^ 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.
^ 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.
^ 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.

[Elks2014-1] 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.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1105–. ISBN 978-3-88763-075-1.

[MortonHall2012-3] 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.

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v t e Xenobiotic-sensing receptor modulators
CARTooltip Constitutive androstane receptor	Agonists: 6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole Cyclophosphamide Cypermethrin DHEA (prasterone) Efavirenz Ellagic acid Griseofulvin Methoxychlor Mifepristone Nefazodone Nevirapine Nicardipine Octicizer Permethrin Phenobarbital Phenytoin Pregnanedione (5β-dihydroprogesterone) Reserpine TCPOBOP Telmisartan Tolnaftate Troglitazone Valproic acid Antagonists: 3,17β-Estradiol 3α-Androstanol 3α-Androstenol 3β-Androstanol 17-Androstanol AITC Ethinylestradiol Meclizine Nigramide J Okadaic acid PK-11195 S-07662 T-0901317
PXRTooltip Pregnane X receptor	Agonists: 17α-Hydroxypregnenolone 17α-Hydroxyprogesterone Δ⁴-Androstenedione Δ⁵-Androstenediol Δ⁵-Androstenedione AA-861 Allopregnanediol Allopregnanedione (5α-dihydroprogesterone) Allopregnanolone (brexanolone) Alpha-Lipoic acid Ambrisentan AMI-193 Amlodipine besylate Antimycotics Artemisinin Aurothioglucose Bile acids Bithionol Bosentan Bumecaine Cafestol Cephaloridine Cephradine Chlorpromazine Ciglitazone Clindamycin Clofenvinfos Chloroxine Clotrimazole Colforsin Corticosterone Cyclophosphamide Cyproterone acetate Demecolcine Dexamethasone DHEA (prasterone) DHEA-S (prasterone sulfate) Dibunate sodium Diclazuril Dicloxacillin Dimercaprol Dinaline Docetaxel Docusate calcium Dodecylbenzenesulfonic acid Dronabinol Droxidopa Eburnamonine Ecopipam Enzacamene Epothilone B Erythromycin Famprofazone Febantel Felodipine Fenbendazole Fentanyl Flucloxacillin Fluorometholone Griseofulvin Guggulsterone Haloprogin Hetacillin potassium Hyperforin Hypericum perforatum (St John's wort) Indinavir sulfate Lasalocid sodium Levothyroxine Linolenic acid: α-Linolenic acid and γ-linolenic acid LOE-908 Loratadine Lovastatin Meclizine Metacycline Methylprednisolone Metyrapone Mevastatin Mifepristone Nafcillin Nicardipine Nicotine Nifedipine Nilvadipine Nisoldipine Norelgestromin Omeprazole Orlistat Oxatomide Paclitaxel Phenobarbital Piperine Plicamycin Prednisolone Pregnanediol Pregnanedione (5β-dihydroprogesterone) Pregnanolone Pregnenolone Pregnenolone 16α-carbonitrile Proadifen Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine SR-12813 Suberoylanilide Sulfisoxazole Suramin Tacrolimus Tenylidone Terconazole Testosterone isocaproate Tetracycline Thiamylal sodium Thiothixene Thonzonium bromide Tianeptine Troglitazone Troleandomycin Tropanyl 3,5-dimethulbenzoate Zafirlukast Zeranol Antagonists: Ketoconazole Sesamin
See also Receptor/signaling modulators

See also

References