You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
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
SynonymLanguageCode
17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetateNot AvailableNot Available
17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetateNot AvailableNot Available
17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetateNot AvailableNot Available
17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetateNot AvailableNot Available
19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetateNot AvailableNot Available
3beta, 17beta-Diacetoxy-17alpha-ethynyl-4-oestreneNot AvailableNot Available
3beta,17beta-Diacetoxy-19-nor-17alpha-pregn-4-en-20-yneNot AvailableNot Available
Ethynodiol diacetateNot AvailableNot Available
EtinodiolSpanishINN
Étynodiol FrenchINN
EtynodiolGermanINN
EtynodiolumLatinINN
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
Brand NameIngredients
Demulen 30 (21 Day Pack)Ethinyl Estradiol + Ethynodiol Diacetate
Demulen 30 (28 Day Pack)Ethinyl Estradiol + Ethynodiol Diacetate
Demulen 50 (21 Day Pack)Ethinyl Estradiol + Ethynodiol Diacetate
Demulen 50 (28 Day Pack)Ethinyl Estradiol + Ethynodiol Diacetate
EdulenEtynodiol and Ethinylestradiol
KelnorEtynodiol and Ethinylestradiol
Zovia 28Etynodiol and Ethinylestradiol
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 KeyONKUMRGIYFNPJW-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%
Metabolism
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 substrateNon-inhibitor0.6524
CYP450 2D6 substrateNon-inhibitor0.9519
CYP450 2C19 substrateNon-inhibitor0.7671
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
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 ReferenceNot Available
External Links
ATC CodesG03DC06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
ArtemetherArtemether may decrease the effectiveness of ethynodiol diacetate by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
BexaroteneBexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of ethynodiol diacetate it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
ColesevelamBile Acid Sequestrants may decrease the serum concentration of Contraceptives (Progestins). Administer oral progestin-containing contraceptives at least 1-4 hours prior to or 4-6 hours after administration of a bile acid sequestrant. Consider alternatives in order to avoid this combination when possible, due to the risk for impaired contraceptive effectiveness.
ThiopentalThiopental may decrease the effect of Ethynodiol diacetate. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
TretinoinOral Tretinoin may decrease the effect of oral contraceptive, Ethynodiol Diacetate. An alternate form of contraception should be used during concomitant therapy.
WarfarinEthynodiol diacetate may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if ethynodiol diacetate is initiated, discontinued or dose
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

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on April 22, 2014 10:56