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Identification
NameEthynodiol
Accession NumberDB00823  (APRD00760)
TypeSmall Molecule
GroupsApproved
Description

A synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive. [PubChem]

Structure
Thumb
Synonyms
17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetate
17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetate
17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetate
17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetate
19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetate
3beta, 17beta-Diacetoxy-17alpha-ethynyl-4-oestrene
3beta,17beta-Diacetoxy-19-nor-17alpha-pregn-4-en-20-yne
Ethynodiol diacetate
Etinodiol
Étynodiol
Etynodiol
Etynodiolum
External Identifiers
  • CB 8080
  • SC 11800
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
ConovaSearle
ContinuinNot Available
DernulenSearle
FemulenPfizer
LuteonormNot Available
Luto-MetrodiolNot Available
MetrodiolNot Available
Brand mixtures
NameLabellerIngredients
Demulen 30 (21 Day Pack)Pfizer Canada Inc
Demulen 30 (28 Day Pack)Pfizer Canada Inc
Demulen 50 (21 Day Pack)Pfizer Canada Inc
Demulen 50 (28 Day Pack)Pfizer Canada Inc
Kelnor 1/35Barr Laboratories Inc.
Zovia 1/35e-28Actavis Pharma, Inc.
Zovia 1/50e-28Actavis Pharma, Inc.
Salts
Name/CASStructureProperties
Ethinodiol Diacetate
ThumbNot applicableDBSALT000942
Metrodiol Diacetate
ThumbNot applicableDBSALT000941
Categories
CAS number297-76-7
WeightAverage: 384.5085
Monoisotopic: 384.230059512
Chemical FormulaC24H32O4
InChI KeyInChIKey=ONKUMRGIYFNPJW-KIEAKMPYSA-N
InChI
InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
IUPAC Name
(1S,2R,5S,10R,11S,14R,15S)-5-(acetyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl acetate
SMILES
[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CC[C@H](OC(C)=O)C=C3CC[C@@]21[H]
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Estrane-skeleton
  • Delta-4-steroid
  • Ynone
  • Acetate salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • terminal acetylenic compound (CHEBI:31580 )
  • steroid ester (CHEBI:31580 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C12724 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030124 )
Pharmacology
IndicationFor the prevention of pregnancy in women who elect to use this product as a method of contraception.
PharmacodynamicsEthynodiol Diacetate is used as a female contraceptive. Ethynodiol Diacetate is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Ethynodiol Diacetate tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.
Mechanism of actionBinds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Ethynodiol Diacetate will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.
AbsorptionNot Available
Volume of distributionNot Available
Protein binding50-85%
MetabolismNot Available
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+0.9907
Blood Brain Barrier+0.9399
Caco-2 permeable+0.6125
P-glycoprotein substrateSubstrate0.5754
P-glycoprotein inhibitor IInhibitor0.8432
P-glycoprotein inhibitor IIInhibitor0.619
Renal organic cation transporterNon-inhibitor0.8131
CYP450 2C9 substrateNon-substrate0.8497
CYP450 2D6 substrateNon-substrate0.9139
CYP450 3A4 substrateSubstrate0.7647
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.6524
CYP450 2D6 inhibitorNon-inhibitor0.9519
CYP450 2C19 inhibitorNon-inhibitor0.7671
CYP450 3A4 inhibitorNon-inhibitor0.6564
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8322
Ames testNon AMES toxic0.9651
CarcinogenicityNon-carcinogens0.9119
BiodegradationNot ready biodegradable0.963
Rat acute toxicity2.1783 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9037
hERG inhibition (predictor II)Non-inhibitor0.8353
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral
Kit
Kitoral
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point126-127Klimstra, P.D.; U.S. Patent 3,176,013; March 30, 1965; assigned to G.D. Searle & Co.
logP5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00397 mg/mLALOGPS
logP3.99ALOGPS
logP3.69ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.62 m3·mol-1ChemAxon
Polarizability44.11 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Klimstra, P.D.; U.S. Patent 3,176,013; March 30, 1965; assigned to G.D. Searle & Co.

General ReferencesNot Available
External Links
ATC CodesG03DC06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabEthynodiol may decrease the anticoagulant activities of Abciximab.
AcenocoumarolEthynodiol may decrease the anticoagulant activities of Acenocoumarol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Ethynodiol.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Ethynodiol.
Anthrax immune globulinEthynodiol may increase the thrombogenic activities of Anthrax immune globulin.
BatimastatThe serum concentration of Ethynodiol can be decreased when it is combined with Batimastat.
BexaroteneThe serum concentration of Ethynodiol can be decreased when it is combined with Bexarotene.
BortezomibThe metabolism of Bortezomib can be decreased when combined with Ethynodiol.
ButabarbitalThe therapeutic efficacy of Ethynodiol can be decreased when used in combination with Butabarbital.
ButethalThe therapeutic efficacy of Ethynodiol can be decreased when used in combination with Butethal.
C1 Esterase Inhibitor (Human)Ethynodiol may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Ethynodiol.
CapromabEthynodiol may decrease effectiveness of Capromab as a diagnostic agent.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Ethynodiol.
Citric AcidEthynodiol may decrease the anticoagulant activities of Citric Acid.
ColesevelamThe serum concentration of Ethynodiol can be decreased when it is combined with Colesevelam.
DalteparinEthynodiol may decrease the anticoagulant activities of Dalteparin.
DicoumarolEthynodiol may decrease the anticoagulant activities of Dicoumarol.
Edetic AcidEthynodiol may decrease the anticoagulant activities of Edetic Acid.
EnoxaparinEthynodiol may decrease the anticoagulant activities of Enoxaparin.
Eslicarbazepine acetateThe serum concentration of Ethynodiol can be decreased when it is combined with Eslicarbazepine acetate.
Ethyl biscoumacetateEthynodiol may decrease the anticoagulant activities of Ethyl biscoumacetate.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Ethynodiol.
FluvoxamineThe metabolism of Fluvoxamine can be decreased when combined with Ethynodiol.
Fondaparinux sodiumEthynodiol may decrease the anticoagulant activities of Fondaparinux sodium.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Ethynodiol.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Ethynodiol.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Ethynodiol.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Ethynodiol.
HeparinEthynodiol may decrease the anticoagulant activities of Heparin.
HeptabarbitalThe therapeutic efficacy of Ethynodiol can be decreased when used in combination with Heptabarbital.
HexobarbitalThe therapeutic efficacy of Ethynodiol can be decreased when used in combination with Hexobarbital.
IcosapentIcosapent may increase the thrombogenic activities of Ethynodiol.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Ethynodiol.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Ethynodiol.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Ethynodiol.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Ethynodiol.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Ethynodiol.
Insulin RegularThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Ethynodiol.
Insulin, isophaneThe therapeutic efficacy of Insulin, isophane can be decreased when used in combination with Ethynodiol.
IsoflurophateThe serum concentration of Ethynodiol can be decreased when it is combined with Isoflurophate.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Ethynodiol.
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Ethynodiol.
LumacaftorThe serum concentration of Ethynodiol can be decreased when it is combined with Lumacaftor.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Ethynodiol.
MethohexitalThe therapeutic efficacy of Ethynodiol can be decreased when used in combination with Methohexital.
PentobarbitalThe therapeutic efficacy of Ethynodiol can be decreased when used in combination with Pentobarbital.
PhenindioneEthynodiol may decrease the anticoagulant activities of Phenindione.
PhenprocoumonEthynodiol may decrease the anticoagulant activities of Phenprocoumon.
PhenytoinThe metabolism of Ethynodiol can be increased when combined with Phenytoin.
PrimidoneThe therapeutic efficacy of Ethynodiol can be decreased when used in combination with Primidone.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Ethynodiol.
RifabutinThe serum concentration of Ethynodiol can be decreased when it is combined with Rifabutin.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Ethynodiol.
SecobarbitalThe therapeutic efficacy of Ethynodiol can be decreased when used in combination with Secobarbital.
SimeprevirThe serum concentration of Ethynodiol can be decreased when it is combined with Simeprevir.
St. John's WortThe therapeutic efficacy of Ethynodiol can be decreased when used in combination with St. John's Wort.
SulodexideEthynodiol may decrease the anticoagulant activities of Sulodexide.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Ethynodiol.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Ethynodiol.
TreprostinilEthynodiol may decrease the anticoagulant activities of Treprostinil.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Ethynodiol.
Vitamin CThe serum concentration of Ethynodiol can be increased when it is combined with Vitamin C.
WarfarinEthynodiol may decrease the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

1. Progesterone receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Progesterone receptor P06401 Details

References:

  1. Tamaya T, Nioka S, Furuta N, Shimura T, Takano N: Contribution of functional groups of 19-nor-progestogens to binding to progesterone and estradiol-17beta receptors in rabbit uterus. Endocrinology. 1977 Jun;100(6):1579-84. Pubmed
  2. Briggs MH: Contraceptive steroid binding to the human uterine progesterone-receptor. Curr Med Res Opin. 1975;3(2):95-8. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Estrogen receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Estrogen receptor P03372 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. Kappus H, Bolt HM, Remmer H: Affinity of ethynyl-estradiol and mestranol for the uterine estrogen receptor and for the microsomal mixed function oxidase of the liver. J Steroid Biochem. 1973 Mar;4(2):121-8. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 22, 2014 10:56