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
Structure for Ethynodiol diacetate (DB00823)
- 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 Therapies
- Contraindications & Blackbox Warnings
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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.
Target Actions Organism AProgesterone receptor agonistHumans AEstrogen receptor alpha agonistHumans - 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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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Ethynodiol diacetate can be increased when it is combined with Abametapir. Abciximab The risk or severity of adverse effects can be increased when Ethynodiol diacetate is combined with Abciximab. Abiraterone The metabolism of Ethynodiol diacetate can be decreased when combined with Abiraterone. Acarbose The therapeutic efficacy of Acarbose can be decreased when used in combination with Ethynodiol diacetate. Acenocoumarol The risk or severity of adverse effects can be increased when Ethynodiol diacetate is combined with Acenocoumarol. Acetaminophen The metabolism of Ethynodiol diacetate can be increased when combined with Acetaminophen. Acetazolamide The metabolism of Ethynodiol diacetate can be increased when combined with Acetazolamide. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Ethynodiol diacetate. Acitretin The therapeutic efficacy of Ethynodiol diacetate can be decreased when used in combination with Acitretin. Albiglutide The therapeutic efficacy of Albiglutide can be decreased when used in combination with Ethynodiol diacetate. 
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- No interactions found.
Products
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Name Kind UNII CAS InChI Key Etynodiol prodrug 9E01C36A9S 1231-93-2 JYILPERKVHXLNF-QMNUTNMBSA-N - Product Images
- International/Other Brands
- Conova (Searle) / Continuin / Dernulen (Searle) / Femulen (Pfizer ) / Luteonorm / Luto-Metrodiol / Metrodiol
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Demulen 30 (21 Day Pack) Ethynodiol diacetate (2 mg) + Ethinylestradiol (30 mcg) Tablet Oral Pfizer Canada Ulc 1979-12-31 2019-07-04 Canada 
Demulen 30 (28 Day Pack) Ethynodiol diacetate (2 mg) + Ethinylestradiol (30 mcg) Tablet Oral Pfizer Canada Ulc 1979-12-31 2019-07-04 Canada Demulen 50 (21 Day Pack) Ethynodiol diacetate (1 mg) + Ethinylestradiol (50 mcg) Tablet Oral Pfizer Canada Ulc 1970-12-31 2005-04-01 Canada Demulen 50 (28 Day Pack) Ethynodiol diacetate (1 mg) + Ethinylestradiol (50 mcg) Tablet Oral Pfizer Canada Ulc 1970-12-31 2005-04-01 Canada Ethynodiol Diacetate and Ethinyl Estradiol Ethynodiol diacetate (1 mg/1) + Ethinylestradiol (35 ug/1) Kit Oral Mylan Pharmaceuticals Inc. 2017-09-19 Not applicable US 
Ethynodiol Diacetate and Ethinyl Estradiol Ethynodiol diacetate (1 mg/1) + Ethinylestradiol (50 ug/1) Kit Oral Mylan Pharmaceuticals Inc. 2016-11-30 Not applicable US Kelnor 1/35 Ethynodiol diacetate (1 mg/1) + Ethinylestradiol (35 ug/1) Kit Oral Teva Pharmaceuticals USA, Inc. 2005-06-20 Not applicable US 
Kelnor 1/35 Ethynodiol diacetate (1 mg/1) + Ethinylestradiol (0.035 mg/1) Kit Oral A-S Medication Solutions 2005-06-20 Not applicable US Kelnor 1/35 Ethynodiol diacetate (1 mg/1) + Ethinylestradiol (35 ug/1) Kit Oral Physicians Total Care, Inc. 2008-09-16 Not applicable US 
Kelnor 1/50 Ethynodiol diacetate (1 mg/1) + Ethinylestradiol (50 ug/1) Oral Teva Pharmaceuticals USA, Inc. 2018-03-01 Not applicable US
Categories
- Drug Categories
- Adrenal Cortex Hormones
- Combination Contraceptives (with Estrogen and derivatives)
- Contraceptive Agents, Female
- Contraceptives, Oral
- Contraceptives, Oral, Synthetic
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Hormonal Contraceptives for Systemic Use
- Hyperglycemia-Associated Agents
- Norpregnanes
- Norpregnenes
- Norsteroids
- Progestin Contraceptives
- Progestins
- Reproductive Control Agents
- Sex Hormones and Modulators of the Genital System
- Steroids
- 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
- (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]
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
- External Links
- Human Metabolome Database
- HMDB0014961
- KEGG Drug
- D01294
- KEGG Compound
- C12724
- PubChem Compound
- 9270
- PubChem Substance
- 46506993
- ChemSpider
- 8913
- BindingDB
- 50237627
- 4170
- ChEBI
- 31580
- ChEMBL
- CHEMBL1200624
- ZINC
- ZINC000003876023
- Therapeutic Targets Database
- DAP000856
- PharmGKB
- PA164749157
- RxList
- RxList Drug Page
- Wikipedia
- Etynodiol_diacetate
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Basic Science Therapeutic Equivalency 1
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
Form Route Strength Tablet Oral Kit Oral Tablet Oral Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 126-127 Klimstra, P.D.; U.S. Patent 3,176,013; March 30, 1965; assigned to G.D. Searle & Co. logP 5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00397 mg/mL ALOGPS logP 3.99 ALOGPS logP 3.69 ChemAxon logS -5 ALOGPS pKa (Strongest Basic) -6.7 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 52.6 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 106.62 m3·mol-1 ChemAxon Polarizability 44.11 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.6524 CYP450 2D6 inhibitor Non-inhibitor 0.9519 CYP450 2C19 inhibitor Non-inhibitor 0.7671 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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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
- 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]
- Briggs MH: Contraceptive steroid binding to the human uterine progesterone-receptor. Curr Med Res Opin. 1975;3(2):95-8. [Article]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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
- Gene labs [Link]
Drug created on June 13, 2005 13:24 / Updated on April 03, 2021 09:39