Ethynodiol diacetate

Identification

Summary

Ethynodiol diacetate is an oral contraceptive used to prevent pregnancy.

Brand Names
Kelnor 1/35 28 Day, Kelnor 1/50 28 Day, Zovia 1/35e 28 Day, Zovia 1/50e 28 Day
Generic Name
Ethynodiol diacetate
DrugBank Accession Number
DB00823
Background

A 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, see Etynodiol).

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 384.5085
Monoisotopic: 384.230059512
Chemical Formula
C24H32O4
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 diacetate
  • Etynodiol acetate
  • Etynodiol diacetate
External IDs
  • CB 8080
  • SC 11800
  • SC-11800

Pharmacology

Indication

For the prevention of pregnancy in women who elect to use this product as a method of contraception.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageAbnormal uterine bleedingCombination Product in combination with: Ethinylestradiol (DB00977)••• •••••
Used in combination to manageDysmenorrheaCombination Product in combination with: Ethinylestradiol (DB00977)••• •••••
Used in combination to manageMenorrhagiaCombination Product in combination with: Ethinylestradiol (DB00977)••• •••••
Used in combination to managePainCombination Product in combination with: Ethinylestradiol (DB00977)••• •••••
Used in combination to managePolycystic ovarian syndromeCombination Product in combination with: Ethinylestradiol (DB00977)••• •••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Ethynodiol 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 action

Binds 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.

TargetActionsOrganism
AProgesterone receptor
agonist
Humans
AEstrogen receptor alpha
agonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

50-85%

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Ethynodiol diacetate can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of adverse effects can be increased when Ethynodiol diacetate is combined with Abciximab.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Ethynodiol diacetate.
AcenocoumarolThe risk or severity of adverse effects can be increased when Ethynodiol diacetate is combined with Acenocoumarol.
AcetaminophenThe metabolism of Ethynodiol diacetate can be increased when combined with Acetaminophen.
Food Interactions
No interactions found.

Products

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Active Moieties
NameKindUNIICASInChI Key
Etynodiolprodrug9E01C36A9S1231-93-2JYILPERKVHXLNF-QMNUTNMBSA-N
Product Images
International/Other Brands
Conova (Searle) / Continuin / Dernulen (Searle) / Femulen (Pfizer ) / Luteonorm / Luto-Metrodiol / Metrodiol
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Demulen 30 (21 Day Pack)Ethynodiol diacetate (2 mg) + Ethinylestradiol (30 mcg)TabletOralPfizer Canada Ulc1979-12-312019-07-04Canada flag
Demulen 30 (28 Day Pack)Ethynodiol diacetate (2 mg) + Ethinylestradiol (30 mcg)TabletOralPfizer Canada Ulc1979-12-312019-07-04Canada flag
Demulen 50 (21 Day Pack)Ethynodiol diacetate (1 mg) + Ethinylestradiol (50 mcg)TabletOralPfizer Canada Ulc1970-12-312005-04-01Canada flag
Demulen 50 (28 Day Pack)Ethynodiol diacetate (1 mg) + Ethinylestradiol (50 mcg)TabletOralPfizer Canada Ulc1970-12-312005-04-01Canada flag
Ethynodiol Diacetate and Ethinyl EstradiolEthynodiol diacetate (1 mg/1) + Ethinylestradiol (50 ug/1)KitOralMylan Pharmaceuticals Inc.2016-11-30Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Estrane steroids / Delta-4-steroids / Ynones / Dicarboxylic acids and derivatives / Carboxylic acid esters / Acetylides / Organic oxides / Hydrocarbon derivatives
Substituents
Acetylide / Aliphatic homopolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Delta-4-steroid / Dicarboxylic acid or derivatives / Estrane-skeleton / Hydrocarbon derivative / Organic oxide
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, steroid ester (CHEBI:31580) / C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C12724) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030124)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
62H10A1236
CAS number
297-76-7
InChI Key
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
(1R,3aS,3bR,7S,9aR,9bS,11aS)-7-(acetyloxy)-1-ethynyl-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-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]

References

Synthesis Reference

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

General References
Not Available
Human Metabolome Database
HMDB0014961
KEGG Drug
D01294
KEGG Compound
C12724
PubChem Compound
9270
PubChem Substance
46506993
ChemSpider
8913
BindingDB
50237627
RxNav
4170
ChEBI
31580
ChEMBL
CHEMBL1200624
ZINC
ZINC000003876023
Therapeutic Targets Database
DAP000856
PharmGKB
PA164749157
RxList
RxList Drug Page
Wikipedia
Etynodiol_diacetate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceTherapeutic Equivalency1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Barr Pharmaceuticals
  • Cardinal Health
  • GD Searle LLC
  • Innovative Manufacturing and Distribution Services Inc.
  • Mckesson Corp.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Watson Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral
TabletOral0.5 mg
KitOral
Kit; tabletOral
Tablet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)126-127Klimstra, 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
Polarizability44.13 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0100-1194000000-36378317102183460fae
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-024l-0039000000-35be505ff53b8230d2d3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0089-3019000000-bf25499019cf9315ad71
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-053s-3090000000-36e86216c366cf0c9aec
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0296-6096000000-a35e8a4b5db064f0b493
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0536-9013000000-5ee6167597f12a295d9a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4u-2954000000-a966d1c9bd183728a4f0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-214.7681871
predicted
DarkChem Lite v0.1.0
[M-H]-214.0796871
predicted
DarkChem Lite v0.1.0
[M-H]-213.5543871
predicted
DarkChem Lite v0.1.0
[M-H]-188.20244
predicted
DeepCCS 1.0 (2019)
[M+H]+215.9969871
predicted
DarkChem Lite v0.1.0
[M+H]+214.2975871
predicted
DarkChem Lite v0.1.0
[M+H]+214.7773871
predicted
DarkChem Lite v0.1.0
[M+H]+190.09787
predicted
DeepCCS 1.0 (2019)
[M+Na]+214.7356871
predicted
DarkChem Lite v0.1.0
[M+Na]+215.4069871
predicted
DarkChem Lite v0.1.0
[M+Na]+214.5491871
predicted
DarkChem Lite v0.1.0
[M+Na]+195.82228
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
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 ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
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. [Article]
  2. Briggs MH: Contraceptive steroid binding to the human uterine progesterone-receptor. Curr Med Res Opin. 1975;3(2):95-8. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
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 tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Gene labs [Link]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:44