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Zeranol

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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
3D
Similar Structures
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
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEstrogen receptorNot AvailableHumans
USex hormone-binding globulinNot AvailableHumans
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
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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.
DrugInteraction
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interactions in your software
AbciximabZeranol may decrease the anticoagulant activities of Abciximab.
AceclofenacAceclofenac may increase the thrombogenic activities of Zeranol.
AcenocoumarolZeranol may decrease the anticoagulant activities of Acenocoumarol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Zeranol.
AdalimumabZeranol may increase the thrombogenic activities of Adalimumab.
Food Interactions
Not Available

Products

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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
  1. Juniewicz PE, Welsh TH Jr, Johnson BH: Effects of zeranol upon bovine testicular function. Theriogenology. 1985 Apr;23(4):565-82. [Article]
  2. 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]
  3. McKenzie JR: Zeranol and adult steers. N Z Vet J. 1986 Jan-Feb;34(1-2):19. [Article]
  4. McKenzie JR: Zeranol and fattening bulls. N Z Vet J. 1983 Jun;31(6):104-5. [Article]
  5. Lindsay DG: Zeranol--a 'nature-identical' oestrogen? Food Chem Toxicol. 1985 Aug;23(8):767-74. [Article]
  6. 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]
  7. 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]
  8. Neumeister CE: Environmental sampling and analysis for zeranol. Am Ind Hyg Assoc J. 1987 Nov;48(11):919-21. [Article]
  9. Peck DN, Chesworth JM: Estrogenic activity in zeranol in ewes. Horm Metab Res. 1977 Nov;9(6):531-2. [Article]
  10. 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]
KEGG Drug
D06362
KEGG Compound
C14752
ChemSpider
2271133
BindingDB
32073
RxNav
1368476
ChEBI
35064
ChEMBL
CHEMBL450613
ZINC
ZINC000003831615
PDBe Ligand
27J
Wikipedia
Zeranol
PDB Entries
4mg8 / 7axh

Clinical Trials

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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
PropertyValueSource
Water Solubility0.164 mg/mLALOGPS
logP3.23ALOGPS
logP4.45Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.68Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area86.99 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity88.25 m3·mol-1Chemaxon
Polarizability34.72 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0pi0-0039000000-9c13299b0ec7a206a22e
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-03g1-1910000000-191642a2db41daa191ad
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03g1-1910000000-191642a2db41daa191ad
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0019000000-fe3bcdfefc512b4df7ba
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-21e856225667b6eaea4e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uk9-0009000000-0809a57b3508be000bf2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0029000000-f0dcdb25fff93d289e5c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000l-5091000000-045525a377a66b294c55
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06s9-0090000000-b6fd1f7ab4e7e68c39f7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-187.7615425
predicted
DarkChem Lite v0.1.0
[M-H]-187.8965425
predicted
DarkChem Lite v0.1.0
[M-H]-173.60924
predicted
DeepCCS 1.0 (2019)
[M+H]+191.5845425
predicted
DarkChem Lite v0.1.0
[M+H]+188.8585425
predicted
DarkChem Lite v0.1.0
[M+H]+175.96725
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.6975425
predicted
DarkChem Lite v0.1.0
[M+Na]+188.2322425
predicted
DarkChem Lite v0.1.0
[M+Na]+182.428
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Estrogen receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General 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 tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity)
Specific Function
14-3-3 protein binding
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. 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]
Details2. Sex hormone-binding globulin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General 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, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration
Specific Function
Androgen binding
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. 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