NAV

Equilenin

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
 3D
Similar Structures
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

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Pharmacodynamics

Not Available

Mechanism of action
Target Actions Organism
USteroid Delta-isomerase Not Available Pseudomonas putida
USteroid Delta-isomerase Not Available Comamonas testosteroni
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/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
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Abametapir The serum concentration of Equilenin can be increased when it is combined with Abametapir.
Amiodarone 时可以减少Equilenin的新陈代谢combined with Amiodarone.
Amprenavir 时可以减少Equilenin的新陈代谢combined with Amprenavir.
Apalutamide The serum concentration of Equilenin can be decreased when it is combined with Apalutamide.
Aprepitant 时可以减少Equilenin的新陈代谢combined with Aprepitant.
Atazanavir 时可以减少Equilenin的新陈代谢combined with Atazanavir.
Avanafil The serum concentration of Avanafil can be increased when it is combined with Equilenin.
Berotralstat 时可以减少Equilenin的新陈代谢combined with Berotralstat.
Boceprevir 时可以减少Equilenin的新陈代谢combined with Boceprevir.
Carbamazepine The metabolism of Equilenin can be increased when combined with Carbamazepine.
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided byClassyfire
Description
这种化合物属于类的有机排版ounds 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…
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Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count

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
Property Value Source
Water Solubility 0.0052 mg/mL ALOGPS
logP 4.32 ALOGPS
logP 4.3 Chemaxon
logS -4.7 ALOGPS
pKa (Strongest Acidic) 9.78 Chemaxon
pKa (Strongest Basic) -5.5 Chemaxon
Physiological Charge 0 Chemaxon
Hydrogen Acceptor Count 2 Chemaxon
Hydrogen Donor Count 1 Chemaxon
Polar Surface Area 37.3 Å2 Chemaxon
Rotatable Bond Count 0 Chemaxon
Refractivity 79.04 m3·mol-1 Chemaxon
Polarizability 30.1 Å3 Chemaxon
Number of Rings 4 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter Yes Chemaxon
Veber's Rule Yes Chemaxon
MDDR-like Rule No Chemaxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9385
Caco-2 permeable + 0.8879
P-glycoprotein substrate Substrate 0.5646
P-glycoprotein inhibitor I Non-inhibitor 0.8781
P-glycoprotein inhibitor II Non-inhibitor 0.8938
Renal organic cation transporter Non-inhibitor 0.7572
CYP450 2C9 substrate Non-substrate 0.7038
CYP450 2D6 substrate Non-substrate 0.8963
CYP450 3A4 substrate Substrate 0.6896
CYP450 1A2 substrate Inhibitor 0.8458
CYP450 2C9 inhibitor Non-inhibitor 0.9438
CYP450 2D6 inhibitor Non-inhibitor 0.9583
CYP450 2C19 inhibitor Non-inhibitor 0.909
CYP450 3A4 inhibitor Non-inhibitor 0.8107
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9085
Ames test Non AMES toxic 0.916
Carcinogenicity Non-carcinogens 0.8941
Biodegradation Not ready biodegradable 0.968
Rat acute toxicity 1.7016 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8623
hERG inhibition (predictor II) Inhibitor 0.528
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Targets

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Details 1.Steroid Delta-isomerase
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
分子量
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]
Details 2.Steroid Delta-isomerase
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
分子量
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]

Enzymes

Details 1.Cytochrome P450 3A4
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
分子量
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