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Identification
NameEquilin
Accession NumberDB02187  (EXPT01355)
Typesmall molecule
Groupsapproved
Description

An estrogenic steroid produced by horses. It has a total of four double bonds in the A- and B-ring. High concentration of euilin is found in the urine of pregnant mares. [PubChem]

Equilin is one of the estrogens present in the mixture of estrogens isolated from horse urine and marketed as Premarin. Premarin became the most commonly used form of estrogen for hormone replacement therapy in the United States of America. Estrone is the major estrogen in Premarin (about 50%) and equilin is present as about 25% of the total. Estrone is a major estrogen that is normally found in women. Equilin is not normally present in women, so there has been interest in the effects of equilin on the human body. [Wikipedia]

The estrogens in Premarin are present mainly as “conjugates”, modified chemical forms in which the active estrogen is coupled to another chemical group such as sulfate. Estrone sulfate is usually the major form of estrogen in women. After being taken into a woman’s body, the conjugated estrogens of Premarin are converted to the active unconjugated estrogens or excreted from the woman’s body. Estrone can be converted to estradiol, which is thought to be the major active estrogen in women. [Wikipedia]

Structure
Thumb
Synonyms
SynonymLanguageCode
1,3,5,7-Estratetraen-3-ol-17-oneNot AvailableNot Available
7-DehydroestroneNot AvailableNot Available
DihydroequileninNot AvailableNot Available
EquilinNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixtures
Brand NameIngredients
PremarinEquilin + Equilenin + Estrone
CategoriesNot Available
CAS number474-86-2
WeightAverage: 268.3502
Monoisotopic: 268.146329884
Chemical FormulaC18H20O2
InChI KeyWKRLQDKEXYKHJB-HFTRVMKXSA-N
InChI
InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3-5,10,14,16,19H,2,6-9H2,1H3/t14-,16+,18+/m1/s1
IUPAC Name
(1S,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5,9-tetraen-14-one
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC=C21)C=C(O)C=C3
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassKetosteroids
Direct parentKetosteroids
Alternative parentsHydroxysteroids; Phenanthrenes and Derivatives; Naphthalenes; Phenols and Derivatives; Ketones; Polyamines; Enols
Substituentsphenanthrene; naphthalene; phenol derivative; benzene; ketone; polyamine; enol; carbonyl group
Classification descriptionThis compound belongs to the ketosteroids. These are steroid derivatives comprising a ketone group attached to steroid skeleton.
Pharmacology
IndicationFor the treatment of moderate to severe vasomotor symptoms associated with the menopause, atrophic vaginitis, osteoporosis, hypoestrogenism due to hypogonadism, castration, primary ovarian failure, breast cancer (for palliation only), and Advanced androgen-dependent carcinoma of the prostate (for palliation only)
PharmacodynamicsEquilin is a component of Premarin (conjugated estrogens), a mixture of the water soluble salts of sulfate esters from estrone, equilin, 17 alpha-dihydroequilin, and other related steroids, may be derived from pregnant equine urine or yam and soy plants. Estrogens are important in the development and maintenance of the female reproductive system and secondary sex characteristics. They promote growth and development of the vagina, uterus, and fallopian tubes, and enlargement of the breasts. Indirectly, they contribute to the shaping of the skeleton, maintenance of tone and elasticity of urogenital structures, changes in the epiphyses of the long bones that allow for the pubertal growth spurt and its termination, growth of axillary and pubic hair, and pigmentation of the nipples and genitals. Decline of estrogenic activity at the end of the menstrual cycle can bring on menstruation, although the cessation of progesterone secretion is the most important factor in the mature ovulatory cycle. However, in the preovulatory or nonovulatory cycle, estrogen is the primary determinant in the onset of menstruation. Estrogens also affect the release of pituitary gonadotropins. The pharmacologic effects of conjugated estrogens are similar to those of endogenous estrogens.
Mechanism of actionEstrogens enter the cells of responsive tissues (e.g., female organs, breasts, hypothalamus, pituitary) where they interact with a protein receptor, subsequently increasing the rate of synthesis of DNA, RNA, and some proteins. Estrogens decrease the secretion of gonadotropin-releasing hormone by the hypothalamus, reducing the secretion of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the pituitary.
AbsorptionWell absorbed.
Volume of distributionNot Available
Protein binding90% bound to plasma proteins
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9192
Caco-2 permeable + 0.875
P-glycoprotein substrate Substrate 0.6807
P-glycoprotein inhibitor I Non-inhibitor 0.8085
P-glycoprotein inhibitor II Non-inhibitor 0.8881
Renal organic cation transporter Non-inhibitor 0.6704
CYP450 2C9 substrate Non-substrate 0.7245
CYP450 2D6 substrate Non-substrate 0.9081
CYP450 3A4 substrate Substrate 0.7666
CYP450 1A2 substrate Inhibitor 0.9108
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Inhibitor 0.8209
CYP450 3A4 substrate Non-inhibitor 0.8156
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5528
Ames test Non AMES toxic 0.9109
Carcinogenicity Non-carcinogens 0.93
Biodegradation Not ready biodegradable 0.9319
Rat acute toxicity 1.8021 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7619
hERG inhibition (predictor II) Non-inhibitor 0.601
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
CreamTopical
Powder, for solutionIntravenous
TabletOral
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point239 °CPhysProp
water solubility1.41 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
water solubility1.33e-02 g/lALOGPS
logP3.8ALOGPS
logP3.9ChemAxon
logS-4.3ALOGPS
pKa (strongest acidic)9.41ChemAxon
pKa (strongest basic)-6ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.3ChemAxon
rotatable bond count0ChemAxon
refractivity79.93ChemAxon
polarizability30.55ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Sawicki MW, Erman M, Puranen T, Vihko P, Ghosh D: Structure of the ternary complex of human 17beta-hydroxysteroid dehydrogenase type 1 with 3-hydroxyestra-1,3,5,7-tetraen-17-one (equilin) and NADP+. Proc Natl Acad Sci U S A. 1999 Feb 2;96(3):840-5. Pubmed
External Links
ResourceLink
KEGG DrugD04041
KEGG CompoundC14392
PubChem Compound223368
PubChem Substance46506633
ChemSpider193995
ChEBI42309
ChEMBLCHEMBL323533
HETEQI
WikipediaEquilin
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Estradiol 17-beta-dehydrogenase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Estradiol 17-beta-dehydrogenase 1 P14061 Details

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. Pubmed
  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. Pubmed
  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. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17