This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Zeranol
Accession Number
DB11478
Type
Small Molecule
Groups
Experimental, Vet approved
Description

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.

Structure
Thumb
Synonyms
  • alpha-Zeranol
  • Zeranol
  • Zeranolum
  • α-zeranol
External IDs
MK 188 / MK-188 / P 1496 / P-1496 / P1496
International/Other Brands
Ralabol
Categories
UNII
76LO2L2V39
CAS number
26538-44-3
Weight
Average: 322.401
Monoisotopic: 322.178023937
Chemical Formula
C18H26O5
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEstrogen receptor alphaNot 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
Toxicity
Not Available
Affected organisms
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
(R)-warfarinZeranol may decrease the anticoagulant activities of (R)-warfarin.
(S)-WarfarinZeranol may decrease the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarinZeranol may decrease the anticoagulant activities of 4-hydroxycoumarin.
AbciximabZeranol may decrease the anticoagulant activities of Abciximab.
AbituzumabZeranol may increase the thrombogenic activities of Abituzumab.
AbrilumabZeranol may increase the thrombogenic activities of Abrilumab.
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.
Acetylsalicylic acidZeranol may decrease the anticoagulant activities of Acetylsalicylic acid.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

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. [PubMed:16726026]
  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. [PubMed:8440661]
  3. McKenzie JR: Zeranol and adult steers. N Z Vet J. 1986 Jan-Feb;34(1-2):19. [PubMed:16031223]
  4. McKenzie JR: Zeranol and fattening bulls. N Z Vet J. 1983 Jun;31(6):104-5. [PubMed:16030974]
  5. Lindsay DG: Zeranol--a 'nature-identical' oestrogen? Food Chem Toxicol. 1985 Aug;23(8):767-74. [PubMed:2931335]
  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. [PubMed:3701919]
  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. [PubMed:6632074]
  8. Neumeister CE: Environmental sampling and analysis for zeranol. Am Ind Hyg Assoc J. 1987 Nov;48(11):919-21. [PubMed:3425550]
  9. Peck DN, Chesworth JM: Estrogenic activity in zeranol in ewes. Horm Metab Res. 1977 Nov;9(6):531-2. [PubMed:563371]
  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. [PubMed:1229710]
External Links
KEGG Drug
D06362
KEGG Compound
C14752
ChemSpider
2271133
BindingDB
32073
ChEBI
35064
ChEMBL
CHEMBL450613
HET
27J
Wikipedia
Zeranol
PDB Entries
4mg8

Clinical Trials

Clinical Trials
Not Available

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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03g1-1910000000-191642a2db41daa191ad

Taxonomy

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
Macrolide / Dihydroxybenzoic acid / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Benzenoid / Vinylogous acid / Carboxylic acid ester / Lactone / Secondary alcohol / Carboxylic acid derivative
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
macrolide (CHEBI:35064) / Mycotoxins (C14752)

Targets

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
  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. [PubMed:19913605]
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
  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. [PubMed:25349334]

Drug created on February 25, 2016 12:06 / Updated on December 02, 2019 09:04