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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
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%
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 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
AbciximabEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
AcenocoumarolEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
AcetohexamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
AcitretinMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
AgomelatineCYP1A2 Inhibitors (Moderate) may increase the serum concentration of Agomelatine.
AlogliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
AminoglutethimideMay increase the metabolism of Progestins.
AnastrozoleEstrogen Derivatives may diminish the therapeutic effect of Anastrozole.
AprepitantMay decrease the serum concentration of Contraceptives (Estrogens).
AripiprazoleCYP3A4 Inhibitors (Weak) may increase the serum concentration of ARIPiprazole.
armodafinilMay decrease the serum concentration of Contraceptives (Estrogens).
ArtemetherMay decrease the serum concentration of Contraceptives (Estrogens).
AtazanavirMay increase the serum concentration of Contraceptives (Progestins).
BatimastatMay decrease the serum concentration of Contraceptives (Estrogens).
BoceprevirMay decrease the serum concentration of Contraceptives (Estrogens).
BosentanMay decrease the serum concentration of Contraceptives (Estrogens).
ButabarbitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
ButethalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
CanagliflozinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
CarbamazepineMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
ChlorpropamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Citric AcidEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
ClobazamMay decrease the serum concentration of Contraceptives (Estrogens).
ColesevelamMay decrease the serum concentration of Contraceptives (Estrogens).
DabrafenibMay decrease the serum concentration of CYP3A4 Substrates.
DalteparinEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
DarunavirMay decrease the serum concentration of Contraceptives (Progestins).
DeferasiroxMay decrease the serum concentration of CYP3A4 Substrates.
DehydroepiandrosteroneMay enhance the adverse/toxic effect of Estrogen Derivatives.
DicoumarolEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
DofetilideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Dofetilide.
Edetic AcidEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
EfavirenzMay decrease the serum concentration of Contraceptives (Progestins).
EnoxaparinEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
Ethyl biscoumacetateEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
ExemestaneEstrogen Derivatives may diminish the therapeutic effect of Exemestane.
ExenatideMay decrease the serum concentration of Contraceptives (Estrogens).
FelbamateMay decrease the serum concentration of Contraceptives (Estrogens). Contraceptive failure is possible.
Fondaparinux sodiumEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
FosamprenavirContraceptives (Progestins) may decrease serum concentrations of the active metabolite(s) of Fosamprenavir. Fosamprenavir may decrease the serum concentration of Contraceptives (Progestins).
FosaprepitantMay decrease the serum concentration of Contraceptives (Estrogens). The active metabolite aprepitant is likely responsible for this effect.
FosphenytoinMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
GliclazideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GlimepirideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GliquidoneHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GlyburideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GriseofulvinMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
HeparinEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
HeptabarbitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
HexobarbitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
HyaluronidaseEstrogen Derivatives may diminish the therapeutic effect of Hyaluronidase.
HydrocodoneCYP3A4 Inhibitors (Weak) may increase the serum concentration of Hydrocodone.
Insulin AspartHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin DetemirHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin GlargineHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin GlulisineHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin LisproHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin RegularHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin, isophaneHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
IsoflurophateMay decrease the serum concentration of Contraceptives (Estrogens).
LamotrigineContraceptives (Estrogens) may decrease the serum concentration of LamoTRIgine.
LenalidomideEstrogen Derivatives may enhance the thrombogenic effect of Lenalidomide.
LinagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
LomitapideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Lomitapide.
LopinavirMay decrease the serum concentration of Contraceptives (Progestins). Lopinavir may increase the serum concentration of Contraceptives (Progestins).
MetforminHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
MethohexitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
MetreleptinMay decrease the serum concentration of Contraceptives (Estrogens). Metreleptin may increase the serum concentration of Contraceptives (Estrogens).
MifepristoneMay diminish the therapeutic effect of Contraceptives (Progestins). Mifepristone may increase the serum concentration of Contraceptives (Progestins).
MitotaneMay decrease the serum concentration of CYP3A4 Substrates.
ModafinilMay decrease the serum concentration of Contraceptives (Estrogens).
NafcillinMay increase the metabolism of Contraceptives (Estrogens).
NelfinavirMay decrease the serum concentration of Contraceptives (Progestins).
NevirapineMay decrease the serum concentration of Contraceptives (Estrogens).
OspemifeneEstrogen Derivatives may enhance the adverse/toxic effect of Ospemifene. Estrogen Derivatives may diminish the therapeutic effect of Ospemifene.
OxcarbazepineMay decrease the serum concentration of Contraceptives (Estrogens). Contraceptive failure is possible.
PentobarbitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
PerampanelMay decrease the serum concentration of Contraceptives (Progestins).
PhenindioneEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
PhenprocoumonEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
PhenytoinMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
PimozideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Pimozide.
PirfenidoneCYP1A2 Inhibitors (Moderate) may increase the serum concentration of Pirfenidone.
PrimidoneMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
prucaloprideMay decrease the serum concentration of Contraceptives (Estrogens).
RepaglinideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
RopiniroleEstrogen Derivatives may increase the serum concentration of ROPINIRole.
RufinamideMay decrease the serum concentration of Ethinyl Estradiol.
SaquinavirMay decrease the serum concentration of Contraceptives (Progestins).
SaxagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
SecobarbitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
SelegilineContraceptives (Estrogens) may increase the serum concentration of Selegiline.
SiltuximabMay decrease the serum concentration of CYP3A4 Substrates.
SimeprevirMay decrease the serum concentration of Contraceptives (Estrogens).
SugammadexMay decrease the serum concentration of Contraceptives (Progestins).
SulodexideEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
TelaprevirMay decrease the serum concentration of Contraceptives (Estrogens).
ThalidomideContraceptives (Estrogens) may enhance the thrombogenic effect of Thalidomide.
TipranavirEstrogen Derivatives may enhance the dermatologic adverse effect of Tipranavir. The combination of tipranavir/ritonavir and ethinyl estradiol/norethindrone was associated with a high incidence of skin rash. Tipranavir may decrease the serum concentration of Estrogen Derivatives.
TizanidineContraceptives (Estrogens) may increase the serum concentration of TiZANidine.
TocilizumabMay decrease the serum concentration of CYP3A4 Substrates.
TolbutamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
TopiramateMay decrease the serum concentration of Contraceptives (Estrogens). Contraceptive failure is possible.
Tranexamic AcidContraceptives (Progestins) may enhance the thrombogenic effect of Tranexamic Acid.
TreprostinilEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
UlipristalMay diminish the therapeutic effect of Progestins. Progestins may diminish the therapeutic effect of Ulipristal.
VildagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Vitamin CMay increase the serum concentration of Estrogen Derivatives.
VoriconazoleMay decrease the metabolism of Contraceptives (Estrogens). Contraceptives (Estrogens) may increase the serum concentration of Voriconazole.
WarfarinEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
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