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Identification
NameEquilin
Accession NumberDB02187  (EXPT01355)
TypeSmall Molecule
GroupsApproved
DescriptionAn 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
1,3,5,7-Estratetraen-3-ol-17-one
7-Dehydroestrone
Dihydroequilenin
Equilin
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII08O86EX0J4
CAS number474-86-2
WeightAverage: 268.3502
Monoisotopic: 268.146329884
Chemical FormulaC18H20O2
InChI KeyInChIKey=WKRLQDKEXYKHJB-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[8.7.0.0²,⁷.0¹¹,¹⁵]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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct ParentOxosteroids
Alternative Parents
Substituents
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • Phenanthrene
  • Naphthalene
  • Benzenoid
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
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.
Related Articles
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
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9192
Caco-2 permeable+0.875
P-glycoprotein substrateSubstrate0.6807
P-glycoprotein inhibitor INon-inhibitor0.8085
P-glycoprotein inhibitor IINon-inhibitor0.8881
Renal organic cation transporterNon-inhibitor0.6704
CYP450 2C9 substrateNon-substrate0.7245
CYP450 2D6 substrateNon-substrate0.9081
CYP450 3A4 substrateSubstrate0.7666
CYP450 1A2 substrateInhibitor0.9108
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8209
CYP450 3A4 inhibitorNon-inhibitor0.8156
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5528
Ames testNon AMES toxic0.9109
CarcinogenicityNon-carcinogens0.93
BiodegradationNot ready biodegradable0.9319
Rat acute toxicity1.8021 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7619
hERG inhibition (predictor II)Non-inhibitor0.601
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
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 Solubility0.0133 mg/mLALOGPS
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 Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.93 m3·mol-1ChemAxon
Polarizability30.55 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-014i-3940000000-b80393e552aa78600070View in MoNA
1D NMR13C NMR SpectrumNot Available
References
Synthesis ReferenceNot Available
General References
  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:9927655 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Equilin is combined with 1,10-Phenanthroline.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Equilin.
AldesleukinEquilin may decrease the antineoplastic activities of Aldesleukin.
Aluminum hydroxideThe bioavailability of Equilin can be decreased when combined with Aluminum hydroxide.
Aluminum phosphateThe bioavailability of Equilin can be decreased when combined with Aluminum phosphate.
AmbenoniumThe risk or severity of adverse effects can be increased when Equilin is combined with Ambenonium.
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Equilin.
AmiodaroneThe serum concentration of Equilin can be increased when it is combined with Amiodarone.
Amphotericin BEquilin may increase the hypokalemic activities of Amphotericin B.
AprepitantThe serum concentration of Equilin can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of Equilin can be increased when it is combined with Atazanavir.
Atracurium besylateAtracurium besylate may increase the adverse neuromuscular activities of Equilin.
BazedoxifeneThe serum concentration of Equilin can be increased when it is combined with Bazedoxifene.
BendroflumethiazideEquilin may increase the hypokalemic activities of Bendroflumethiazide.
Benzoic AcidThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Equilin.
Bismuth SubcitrateThe bioavailability of Equilin can be decreased when combined with Bismuth Subcitrate.
BoceprevirThe serum concentration of Equilin can be increased when it is combined with Boceprevir.
BumetanideEquilin may increase the hypokalemic activities of Bumetanide.
CalcitriolThe therapeutic efficacy of Calcitriol can be decreased when used in combination with Equilin.
Calcium carbonateThe bioavailability of Equilin can be decreased when combined with Calcium carbonate.
CarbamazepineThe serum concentration of Equilin can be decreased when it is combined with Carbamazepine.
CeritinibEquilin may increase the hyperglycemic activities of Ceritinib.
CeritinibThe serum concentration of Equilin can be increased when it is combined with Ceritinib.
ChlorothiazideEquilin may increase the hypokalemic activities of Chlorothiazide.
ChlorotrianiseneThe serum concentration of Equilin can be increased when it is combined with Chlorotrianisene.
ChlorthalidoneEquilin may increase the hypokalemic activities of Chlorthalidone.
CholestyramineCholestyramine can cause a decrease in the absorption of Equilin resulting in a reduced serum concentration and potentially a decrease in efficacy.
ClarithromycinThe serum concentration of Equilin can be increased when it is combined with Clarithromycin.
CobicistatThe serum concentration of Equilin can be increased when it is combined with Cobicistat.
ColesevelamColesevelam can cause a decrease in the absorption of Equilin resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Equilin resulting in a reduced serum concentration and potentially a decrease in efficacy.
Conjugated Equine EstrogensThe serum concentration of Equilin can be increased when it is combined with Conjugated Equine Estrogens.
Corticorelin ovine triflutateThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Equilin.
CoumaphosThe risk or severity of adverse effects can be increased when Equilin is combined with Coumaphos.
DarunavirThe serum concentration of Equilin can be increased when it is combined with Darunavir.
DecamethoniumThe risk or severity of adverse effects can be increased when Equilin is combined with Decamethonium.
DeferasiroxThe risk or severity of adverse effects can be increased when Equilin is combined with Deferasirox.
DemecariumThe risk or severity of adverse effects can be increased when Equilin is combined with Demecarium.
DichlorvosThe risk or severity of adverse effects can be increased when Equilin is combined with Dichlorvos.
DienestrolThe serum concentration of Equilin can be increased when it is combined with Dienestrol.
DiethylstilbestrolThe serum concentration of Equilin can be increased when it is combined with Diethylstilbestrol.
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Equilin.
DihydrotestosteroneEquilin may increase the fluid retaining activities of Dihydrotestosterone.
DonepezilThe risk or severity of adverse effects can be increased when Equilin is combined with Donepezil.
EchothiophateThe risk or severity of adverse effects can be increased when Equilin is combined with Echothiophate.
EdrophoniumThe risk or severity of adverse effects can be increased when Equilin is combined with Edrophonium.
EnzalutamideThe serum concentration of Equilin can be decreased when it is combined with Enzalutamide.
EstradiolThe serum concentration of Equilin can be increased when it is combined with Estradiol.
EstriolThe serum concentration of Equilin can be increased when it is combined with Estriol.
EstroneThe serum concentration of Equilin can be increased when it is combined with Estrone.
Etacrynic acidEquilin may increase the hypokalemic activities of Etacrynic acid.
Ethinyl EstradiolThe serum concentration of Equilin can be increased when it is combined with Ethinyl Estradiol.
FenthionThe risk or severity of adverse effects can be increased when Equilin is combined with Fenthion.
FluoxymesteroneEquilin may increase the fluid retaining activities of Fluoxymesterone.
FosaprepitantThe serum concentration of Equilin can be increased when it is combined with Fosaprepitant.
FosphenytoinThe serum concentration of Equilin can be decreased when it is combined with Fosphenytoin.
FurosemideEquilin may increase the hypokalemic activities of Furosemide.
GalantamineThe risk or severity of adverse effects can be increased when Equilin is combined with Galantamine.
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Equilin is combined with Gallamine Triethiodide.
GenisteinThe serum concentration of Equilin can be increased when it is combined with Genistein.
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Equilin is combined with Ginkgo biloba.
Glycerol PhenylbutyrateThe therapeutic efficacy of Glycerol Phenylbutyrate can be decreased when used in combination with Equilin.
HexestrolThe serum concentration of Equilin can be increased when it is combined with Hexestrol.
Huperzine AThe risk or severity of adverse effects can be increased when Equilin is combined with Huperzine A.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Equilin.
HydrochlorothiazideEquilin may increase the hypokalemic activities of Hydrochlorothiazide.
HydroflumethiazideEquilin may increase the hypokalemic activities of Hydroflumethiazide.
IdelalisibThe serum concentration of Equilin can be increased when it is combined with Idelalisib.
IndacaterolIndacaterol may increase the hypokalemic activities of Equilin.
IndapamideEquilin may increase the hypokalemic activities of Indapamide.
IndinavirThe serum concentration of Equilin can be increased when it is combined with Indinavir.
IsoflurophateThe risk or severity of adverse effects can be increased when Equilin is combined with Isoflurophate.
IsoniazidThe serum concentration of Isoniazid can be decreased when it is combined with Equilin.
ItraconazoleThe serum concentration of Equilin can be increased when it is combined with Itraconazole.
KetoconazoleThe serum concentration of Equilin can be increased when it is combined with Ketoconazole.
LopinavirThe serum concentration of Equilin can be increased when it is combined with Lopinavir.
MagaldrateThe bioavailability of Equilin can be decreased when combined with Magaldrate.
Magnesium carbonateThe bioavailability of Equilin can be decreased when combined with Magnesium carbonate.
Magnesium hydroxideThe bioavailability of Equilin can be decreased when combined with Magnesium hydroxide.
Magnesium oxideThe bioavailability of Equilin can be decreased when combined with Magnesium oxide.
Magnesium TrisilicateThe bioavailability of Equilin can be decreased when combined with Magnesium Trisilicate.
MalathionThe risk or severity of adverse effects can be increased when Equilin is combined with Malathion.
MefloquineThe risk or severity of adverse effects can be increased when Equilin is combined with Mefloquine.
MemantineThe risk or severity of adverse effects can be increased when Equilin is combined with Memantine.
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Equilin.
MestranolThe serum concentration of Equilin can be increased when it is combined with Mestranol.
MethyclothiazideEquilin may increase the hypokalemic activities of Methyclothiazide.
MethyltestosteroneEquilin may increase the fluid retaining activities of Methyltestosterone.
MetolazoneEquilin may increase the hypokalemic activities of Metolazone.
MifepristoneThe therapeutic efficacy of Equilin can be decreased when used in combination with Mifepristone.
MinaprineThe risk or severity of adverse effects can be increased when Equilin is combined with Minaprine.
MitotaneThe serum concentration of Equilin can be decreased when it is combined with Mitotane.
MivacuriumMivacurium may increase the adverse neuromuscular activities of Equilin.
NefazodoneThe serum concentration of Equilin can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Equilin can be increased when it is combined with Nelfinavir.
NeostigmineThe risk or severity of adverse effects can be increased when Equilin is combined with Neostigmine.
NevirapineThe serum concentration of Equilin can be decreased when it is combined with Nevirapine.
NicorandilThe risk or severity of adverse effects can be increased when Equilin is combined with Nicorandil.
OxandroloneEquilin may increase the fluid retaining activities of Oxandrolone.
OxymetholoneEquilin may increase the fluid retaining activities of Oxymetholone.
PentobarbitalThe serum concentration of Equilin can be decreased when it is combined with Pentobarbital.
PhenobarbitalThe serum concentration of Equilin can be decreased when it is combined with Phenobarbital.
Phenylacetic acidThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Equilin.
PhenytoinThe serum concentration of Equilin can be decreased when it is combined with Phenytoin.
PhysostigmineThe risk or severity of adverse effects can be increased when Equilin is combined with Physostigmine.
PiretanideEquilin may increase the hypokalemic activities of Piretanide.
Polyestradiol phosphateThe serum concentration of Equilin can be increased when it is combined with Polyestradiol phosphate.
PolythiazideEquilin may increase the hypokalemic activities of Polythiazide.
PosaconazoleThe serum concentration of Equilin can be increased when it is combined with Posaconazole.
PrimidoneThe serum concentration of Equilin can be decreased when it is combined with Primidone.
PyridostigmineThe risk or severity of adverse effects can be increased when Equilin is combined with Pyridostigmine.
QuinestrolThe serum concentration of Equilin can be increased when it is combined with Quinestrol.
QuinethazoneEquilin may increase the hypokalemic activities of Quinethazone.
Rabies vaccineThe risk or severity of adverse effects can be increased when Equilin is combined with Rabies vaccine.
RapacuroniumRapacuronium may increase the adverse neuromuscular activities of Equilin.
RifabutinThe serum concentration of Equilin can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Equilin can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Equilin can be decreased when it is combined with Rifapentine.
RitonavirThe serum concentration of Equilin can be increased when it is combined with Ritonavir.
RivastigmineThe risk or severity of adverse effects can be increased when Equilin is combined with Rivastigmine.
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Equilin.
SaquinavirThe serum concentration of Equilin can be increased when it is combined with Saquinavir.
Sodium phenylbutyrateThe therapeutic efficacy of Sodium phenylbutyrate can be decreased when used in combination with Equilin.
StanozololEquilin may increase the fluid retaining activities of Stanozolol.
Synthetic Conjugated Estrogens, AThe serum concentration of Equilin can be increased when it is combined with Synthetic Conjugated Estrogens, A.
Synthetic Conjugated Estrogens, BThe serum concentration of Equilin can be increased when it is combined with Synthetic Conjugated Estrogens, B.
TacrineThe risk or severity of adverse effects can be increased when Equilin is combined with Tacrine.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Equilin.
TelaprevirThe serum concentration of Equilin can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Equilin can be increased when it is combined with Telithromycin.
TestosteroneEquilin may increase the fluid retaining activities of Testosterone.
TiboloneThe serum concentration of Equilin can be increased when it is combined with Tibolone.
TorasemideEquilin may increase the hypokalemic activities of Torasemide.
TrichlorfonThe risk or severity of adverse effects can be increased when Equilin is combined with Trichlorfon.
TrichlormethiazideEquilin may increase the hypokalemic activities of Trichlormethiazide.
TubocurarineThe risk or severity of adverse effects can be increased when Equilin is combined with Tubocurarine.
VoriconazoleThe serum concentration of Equilin can be increased when it is combined with Voriconazole.
WarfarinEquilin may increase the anticoagulant activities of Warfarin.
ZeranolThe serum concentration of Equilin can be increased when it is combined with Zeranol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Testosterone dehydrogenase (nad+) activity
Specific Function:
Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name:
HSD17B1
Uniprot ID:
P14061
Molecular Weight:
34949.715 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. [PubMed:17139284 ]
  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:17016423 ]
  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:10592235 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23