Zeranol
Star0
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Zeranol
- DrugBank Accession Number
- DB11478
- Background
Zeranol is a non-steroidal estrogen agonist. It is a mycotoxin, derived from fungi in the Fusarium family, and may be found as a contaminant in fungus-infected crops. It is 3-4x more potent as an estrogen agonist than the related compound zearalenone.
- Type
- Small Molecule
- Groups
- Experimental, Vet approved
- Structure
- Weight
- Average: 322.401
Monoisotopic: 322.178023937 - Chemical Formula
- C18H26O5
- Synonyms
- alpha-Zeranol
- Zeranol
- Zeranolum
- α-zeranol
- External IDs
- MK 188
- MK-188
- P 1496
- P-1496
- P1496
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UEstrogen receptor alpha Not Available Humans USex hormone-binding globulin Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab Zeranol may decrease the anticoagulant activities of Abciximab. Aceclofenac Aceclofenac may increase the thrombogenic activities of Zeranol. Acenocoumarol Zeranol may decrease the anticoagulant activities of Acenocoumarol. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Zeranol. Adalimumab Zeranol may increase the thrombogenic activities of Adalimumab. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Ralabol
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Macrolides and analogues
- Sub Class
- Not Available
- Direct Parent
- Macrolides and analogues
- Alternative Parents
- Hydroxybenzoic acid derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Secondary alcohols / Lactones / Carboxylic acid esters / Polyols / Oxacyclic compounds / Monocarboxylic acids and derivatives show 2 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Aromatic heteropolycyclic compound / Benzenoid / Carboxylic acid derivative / Carboxylic acid ester / Dihydroxybenzoic acid / Hydrocarbon derivative / Lactone show 10 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- macrolide (CHEBI:35064) / Mycotoxins (C14752)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 76LO2L2V39
- CAS number
- 26538-44-3
- InChI Key
- DWTTZBARDOXEAM-GXTWGEPZSA-N
- 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
- 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
- SMILES
- C[C@H]1CCC[C@H](O)CCCCCC2=CC(O)=CC(O)=C2C(=O)O1
References
- General References
- Juniewicz PE, Welsh TH Jr, Johnson BH: Effects of zeranol upon bovine testicular function. Theriogenology. 1985 Apr;23(4):565-82. [Article]
- Pusateri AE, Kenison DC: Measurement of zeranol in plasma from three blood vessels in steers implanted with zeranol. J Anim Sci. 1993 Feb;71(2):415-9. [Article]
- McKenzie JR: Zeranol and adult steers. N Z Vet J. 1986 Jan-Feb;34(1-2):19. [Article]
- McKenzie JR: Zeranol and fattening bulls. N Z Vet J. 1983 Jun;31(6):104-5. [Article]
- Lindsay DG: Zeranol--a 'nature-identical' oestrogen? Food Chem Toxicol. 1985 Aug;23(8):767-74. [Article]
- Dixon SN, Mallinson CB: Radioimmunoassay of the anabolic agent zeranol. III. Zeranol concentrations in the faeces of steers implanted with zeranol (Ralgro). J Vet Pharmacol Ther. 1986 Mar;9(1):88-93. [Article]
- Dixon SN, Russell KL: Radioimmunoassay of the anabolic agent zeranol. II. Zeranol concentrations in urine of sheep and cattle implanted with zeranol (Ralgro). J Vet Pharmacol Ther. 1983 Sep;6(3):173-9. [Article]
- Neumeister CE: Environmental sampling and analysis for zeranol. Am Ind Hyg Assoc J. 1987 Nov;48(11):919-21. [Article]
- Peck DN, Chesworth JM: Estrogenic activity in zeranol in ewes. Horm Metab Res. 1977 Nov;9(6):531-2. [Article]
- Ingerowski GH, Hellmann E, Stan HJ: [Determination of zeranol in meat (author's transl)]. Z Lebensm Unters Forsch. 1975 Apr 7;157(4):189-95. [Article]
- External Links
- KEGG Drug
- D06362
- KEGG Compound
- C14752
- ChemSpider
- 2271133
- BindingDB
- 32073
- 1368476
- ChEBI
- 35064
- ChEMBL
- CHEMBL450613
- ZINC
- ZINC000003831615
- PDBe Ligand
- 27J
- Wikipedia
- Zeranol
- PDB Entries
- 4mg8 / 7axh
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.164 mg/mL ALOGPS logP 3.23 ALOGPS logP 4.45 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 8.68 Chemaxon pKa (Strongest Basic) -1.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 86.99 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 88.25 m3·mol-1 Chemaxon Polarizability 34.72 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 187.7615425 predictedDarkChem Lite v0.1.0 [M-H]- 187.8965425 predictedDarkChem Lite v0.1.0 [M-H]- 173.60924 predictedDeepCCS 1.0 (2019) [M+H]+ 191.5845425 predictedDarkChem Lite v0.1.0 [M+H]+ 188.8585425 predictedDarkChem Lite v0.1.0 [M+H]+ 175.96725 predictedDeepCCS 1.0 (2019) [M+Na]+ 188.6975425 predictedDarkChem Lite v0.1.0 [M+Na]+ 188.2322425 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.428 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsEstrogen receptor alpha
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- Dang Z: Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications. Toxicol Lett. 2010 Feb 15;192(3):298-315. doi: 10.1016/j.toxlet.2009.11.004. Epub 2009 Nov 12. [Article]
2. DetailsSex hormone-binding globulin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Androgen binding
- Specific Function
- Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
- Gene Name
- SHBG
- Uniprot ID
- P04278
- Uniprot Name
- Sex hormone-binding globulin
- Molecular Weight
- 43778.755 Da
References
- Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [Article]
Drug created at February 25, 2016 19:06 / Updated at February 21, 2021 18:53