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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
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
√Čtynodiol FrenchINN
EtynodiolGermanINN
EtynodiolumLatinINN
Salts
Name/CAS Structure Properties
Ethinodiol Diacetate
Thumb Not applicable DBSALT000942
Metrodiol Diacetate
Thumb Not applicable DBSALT000941
Brand names
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
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[8.7.0.0^{2,7}.0^{11,15}]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]
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassSteroid Esters
Direct parentSteroid Esters
Alternative parentsEstrogens and Derivatives; Ynones; Carboxylic Acid Esters; Polyamines; Enolates; Ethers
Substituentsestrane-skeleton; ynone; carboxylic acid ester; enolate; ether; polyamine; carboxylic acid derivative
Classification descriptionThis compound belongs to the steroid esters. These are compounds containing a steroid moeity which bears a carboxylic acid ester group.
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
Property Value Probability
Human Intestinal Absorption + 0.9907
Blood Brain Barrier + 0.9399
Caco-2 permeable + 0.6125
P-glycoprotein substrate Substrate 0.5754
P-glycoprotein inhibitor I Inhibitor 0.8432
P-glycoprotein inhibitor II Inhibitor 0.619
Renal organic cation transporter Non-inhibitor 0.8131
CYP450 2C9 substrate Non-substrate 0.8497
CYP450 2D6 substrate Non-substrate 0.9139
CYP450 3A4 substrate Substrate 0.7647
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.6524
CYP450 2D6 substrate Non-inhibitor 0.9519
CYP450 2C19 substrate Non-inhibitor 0.7671
CYP450 3A4 substrate Non-inhibitor 0.6564
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8322
Ames test Non AMES toxic 0.9651
Carcinogenicity Non-carcinogens 0.9119
Biodegradation Not ready biodegradable 0.963
Rat acute toxicity 2.1783 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9037
hERG inhibition (predictor II) Non-inhibitor 0.8353
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
TabletOral
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 solubility3.97e-03 g/lALOGPS
logP3.99ALOGPS
logP3.69ChemAxon
logS-5ALOGPS
pKa (strongest basic)-6.7ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area52.6ChemAxon
rotatable bond count4ChemAxon
refractivity106.62ChemAxon
polarizability44.11ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
KEGG DrugD01294
KEGG CompoundC12724
PubChem Compound9270
PubChem Substance46506993
ChemSpider8913
ChEBI31580
ChEMBL
Therapeutic Targets DatabaseDAP000856
PharmGKBPA164749157
Drug Product Database469327
RxListhttp://www.rxlist.com/cgi/generic/ethynoc.htm
WikipediaEthynodiol_diacetate
ATC CodesNot Available
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

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