Identification

Generic Name
Equilenin
DrugBank Accession Number
DB03515
Background

Equilenin is an estrogenic steroid produced by horses. It has a total of five double bonds in the A- and B-ring. High concentration of equilenin is found in the urine of pregnant mares.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 266.3343
Monoisotopic: 266.13067982
Chemical Formula
C18H18O2
Synonyms
  • 3-Hydroxyestra-1,3,5(10),6,8-pentaen-17-one
  • Equilenina

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USteroid Delta-isomeraseNot AvailableComamonas testosteroni
USteroid Delta-isomeraseNot AvailablePseudomonas putida
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
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
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
AbametapirThe serum concentration of Equilenin can be increased when it is combined with Abametapir.
AbirateroneThe metabolism of Equilenin can be decreased when combined with Abiraterone.
AmiodaroneThe metabolism of Equilenin can be decreased when combined with Amiodarone.
AmprenavirThe metabolism of Equilenin can be decreased when combined with Amprenavir.
ApalutamideThe metabolism of Equilenin can be increased when combined with Apalutamide.
AprepitantThe metabolism of Equilenin can be decreased when combined with Aprepitant.
AtazanavirThe metabolism of Equilenin can be decreased when combined with Atazanavir.
BerotralstatThe metabolism of Equilenin can be decreased when combined with Berotralstat.
BoceprevirThe metabolism of Equilenin can be decreased when combined with Boceprevir.
CarbamazepineThe metabolism of Equilenin can be increased when combined with Carbamazepine.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-hydroxy delta-7-steroids / 17-oxosteroids / Delta-7-steroids / Phenanthrols / Naphthols and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / Ketones / Organic oxides / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 17-oxosteroid / 2-naphthol / 3-hydroxy-delta-7-steroid / 3-hydroxysteroid / Aromatic homopolycyclic compound / Benzenoid / Carbonyl group / Delta-7-steroid / Estrogen-skeleton
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
3-hydroxy steroid (CHEBI:34739) / Estrane and derivatives (C14303) / C18 steroids (estrogens) and derivatives (LMST02010007)
Affected organisms
Not Available

Chemical Identifiers

UNII
W8FTJ17C4J
CAS number
517-09-9
InChI Key
PDRGHUMCVRDZLQ-WMZOPIPTSA-N
InChI
InChI=1S/C18H18O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16,19H,6-9H2,1H3/t16-,18-/m0/s1
IUPAC Name
(3aS,11aS)-7-hydroxy-11a-methyl-1H,2H,3H,3aH,10H,11H,11aH-cyclopenta[a]phenanthren-1-one
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CCC1=C2C=CC2=C1C=CC(O)=C2

References

Synthesis Reference

Sigfrid Schwarz, "Equilenin derivatives, methods for producing the same and medicaments containing them." U.S. Patent US20040138194, issued July 15, 2004.

US20040138194
General References
Not Available
KEGG Compound
C14303
PubChem Compound
444865
PubChem Substance
46509080
ChemSpider
392668
BindingDB
50423545
ChEBI
34739
ChEMBL
CHEMBL225546
ZINC
ZINC000000393154
PDBe Ligand
EQU
Wikipedia
Equilenin
PDB Entries
1cqs / 1gs3 / 1ogx / 1ogz / 1oh0 / 1oho / 1qjg / 1w6y / 3fzw / 3ipt
show 14 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0052 mg/mLALOGPS
logP4.32ALOGPS
logP4.3ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.78ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.04 m3·mol-1ChemAxon
Polarizability30.1 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9385
Caco-2 permeable+0.8879
P-glycoprotein substrateSubstrate0.5646
P-glycoprotein inhibitor INon-inhibitor0.8781
P-glycoprotein inhibitor IINon-inhibitor0.8938
Renal organic cation transporterNon-inhibitor0.7572
CYP450 2C9 substrateNon-substrate0.7038
CYP450 2D6 substrateNon-substrate0.8963
CYP450 3A4 substrateSubstrate0.6896
CYP450 1A2 substrateInhibitor0.8458
CYP450 2C9 inhibitorNon-inhibitor0.9438
CYP450 2D6 inhibitorNon-inhibitor0.9583
CYP450 2C19 inhibitorNon-inhibitor0.909
CYP450 3A4 inhibitorNon-inhibitor0.8107
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9085
Ames testNon AMES toxic0.916
CarcinogenicityNon-carcinogens0.8941
BiodegradationNot ready biodegradable0.968
Rat acute toxicity1.7016 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8623
hERG inhibition (predictor II)Inhibitor0.528
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Targets

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Comamonas testosteroni
Pharmacological action
Unknown
General Function
Steroid delta-isomerase activity
Specific Function
Not Available
Gene Name
ksi
Uniprot ID
P00947
Uniprot Name
Steroid Delta-isomerase
Molecular Weight
13398.04 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Steroid delta-isomerase activity
Specific Function
Not Available
Gene Name
ksi
Uniprot ID
P07445
Uniprot Name
Steroid Delta-isomerase
Molecular Weight
14535.48 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Gherezghiher TB, Michalsen B, Chandrasena RE, Qin Z, Sohn J, Thatcher GR, Bolton JL: The naphthol selective estrogen receptor modulator (SERM), LY2066948, is oxidized to an o-quinone analogous to the naphthol equine estrogen, equilenin. Chem Biol Interact. 2012 Mar 5;196(1-2):1-10. doi: 10.1016/j.cbi.2012.01.004. Epub 2012 Jan 28. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52