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Identification
Name Ethynodiol Diacetate
Accession Number DB00823 (APRD00760)
Type small molecule
Groups approved
Description

A synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Ethinodiol Diacetate
Ethynodiol
Etynodiol
Salts Not Available
Brand names
Name Company
Cervicundin
Continuin
Femulen
Luteonorm
Luto-Metrodiol
Metrodiol
Metrodiol Diacetate
Metrulen
Ovulen
Ovulen 50
Brand mixtures
Brand Name Ingredients
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
Categories
  • Contraceptives, Oral, Synthetic
CAS number 297-76-7
Weight Average: 384.5085
Monoisotopic: 384.230059512
Chemical Formula C24H32O4
InChI Key InChIKey=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
Plain Text
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]
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Carboxylic Acids and Derivatives
  • Alkanes and Alkenes
  • Acetates
  • Alkynes
  • Ethers
  • Cyclohexenes and Derivatives
Pharmacology
Indication For the prevention of pregnancy in women who elect to use this product as a method of contraception.
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.
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
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 5 Not Available
Predicted Properties
Property Value Source
water solubility 3.97e-03 g/l 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 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 106.62 ChemAxon
polarizability 44.11 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01294 Link_out
KEGG Compound C12724 Link_out
PubChem Compound 9270 Link_out
PubChem Substance 46506993 Link_out
ChemSpider 8913 Link_out
ChEBI 31580 Link_out
ChEMBL 31580 Link_out
Therapeutic Targets Database DAP000856 Link_out
PharmGKB PA164749157 Link_out
Drug Product Database 469327 Link_out
RxList http://www.rxlist.com/cgi/generic/ethynoc.htm Link_out
Wikipedia http://en.wikipedia.org/wiki/Ethynodiol_diacetate Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Artemether Artemether may decrease the effectiveness of ethynodiol diacetate by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
Bexarotene Bexarotene 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).
Colesevelam Bile 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.
Thiopental Thiopental may decrease the effect of Ethynodiol diacetate. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
Tretinoin Oral Tretinoin may decrease the effect of oral contraceptive, Ethynodiol Diacetate. An alternate form of contraception should be used during concomitant therapy.
Warfarin Ethynodiol 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 Interactions Not Available
Targets

1. Progesterone receptor

Pharmacological action: yes
Actions: agonist

The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues

Organism class: human
UniProt ID: P06401 Link_out
Gene: PGR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P03372 Link_out
Gene: ESR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19