You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameEthynodiol diacetate
Accession NumberDB00823  (APRD00760)
TypeSmall Molecule
GroupsApproved
DescriptionA synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive. Although etynodiol or ethynodiol are sometimes used as a synonym for ethynodiol diacetate, what is usually being referred to is actually ethynodiol diacetate and not ethynodiol (which is a separate drug that has never been marketed).
Structure
Thumb
Synonyms
17α-Ethynyl-19-norandrost-4-ene-3β,17-beta-diol diacetate
17α-Ethynyl-3,17-dihydroxy-4-estrene diacetate
17α-Ethynyl-4-estrene-3β,17β-diol diacetate
17α-Ethynylestr-4-ene-3β,17β-diol acetate
19-Nor-17α-pregn-4-en-20-yne-3β,17-diol diacetate
3β, 17β-Diacetoxy-17α-ethynyl-4-oestrene
3β,17β-Diacetoxy-19-nor-17α-pregn-4-en-20-yne
Ethynodiol
Etinodiol
Étynodiol
Etynodiol
Etynodiol acetate
Etynodiolum
External Identifiers
  • CB 8080
  • SC 11800
  • SC-11800
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not 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.
SaltsNot Available
Categories
UNII62H10A1236
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[[email protected]](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.
Related Articles
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
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
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 CodesG03FA06G03AA01G03DC06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Ethynodiol diacetate.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Ethynodiol diacetate.
AicarThe therapeutic efficacy of Aicar can be decreased when used in combination with Ethynodiol diacetate.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Ethynodiol diacetate.
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Ethynodiol diacetate.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Ethynodiol diacetate.
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Ethynodiol diacetate.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Ethynodiol diacetate.
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Ethynodiol diacetate.
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Ethynodiol diacetate.
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Ethynodiol diacetate.
ExenatideThe therapeutic efficacy of Exenatide can be decreased when used in combination with Ethynodiol diacetate.
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Ethynodiol diacetate.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Ethynodiol diacetate.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Ethynodiol diacetate.
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Ethynodiol diacetate.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Ethynodiol diacetate.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Ethynodiol diacetate.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Ethynodiol diacetate.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Ethynodiol diacetate.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Ethynodiol diacetate.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Ethynodiol diacetate.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Ethynodiol diacetate.
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Ethynodiol diacetate.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Ethynodiol diacetate.
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Ethynodiol diacetate.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Ethynodiol diacetate.
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Ethynodiol diacetate.
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Ethynodiol diacetate.
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Ethynodiol diacetate.
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Ethynodiol diacetate.
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Ethynodiol diacetate.
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Ethynodiol diacetate.
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Ethynodiol diacetate.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Ethynodiol diacetate.
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Ethynodiol diacetate.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Ethynodiol diacetate.
SitagliptinThe therapeutic efficacy of Sitagliptin can be decreased when used in combination with Ethynodiol diacetate.
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Ethynodiol diacetate.
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Ethynodiol diacetate.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Ethynodiol diacetate.
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Ethynodiol diacetate.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Ethynodiol diacetate.
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Ethynodiol diacetate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial ...
Gene Name:
PGR
Uniprot ID:
P06401
Molecular Weight:
98979.96 Da
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:858280 ]
  2. Briggs MH: Contraceptive steroid binding to the human uterine progesterone-receptor. Curr Med Res Opin. 1975;3(2):95-8. [PubMed:166800 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 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. 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:4123746 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23