DrugBank: Ethynodiol Diacetate (DB00823)

targets (2)

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Ethinodiol Diacetate
Ethynodiol
Etynodiol

Brand names

Cervicundin
Continuin
Femulen
Luteonorm
Luto-Metrodiol
Metrodiol
Metrodiol Diacetate
Metrulen
Ovulen
Ovulen 50

Brand name mixtures

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

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

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

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Property	Value	Source
logP	5	PhysProp

Predicted Properties

Property	Value	Source
water solubility	3.97e-03 g/l	ALOGPS
logP	3.99	ALOGPS
logP	3.61	ChemAxon Molconvert
logS	-4.99	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	2	ChemAxon Molconvert
hydrogen donor count	0	ChemAxon Molconvert
polar surface area	52.60	ChemAxon Molconvert
rotatable bond count	4	ChemAxon Molconvert
refractivity	106.62	ChemAxon Molconvert
polarizability	44.11	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D01294
KEGG Compound	C12724
PubChem Compound	9270
PubChem Substance	46506993
ChemSpider	8913
ChEBI	31580
ChEMBL	31580
Therapeutic Targets Database	DAP000856
PharmGKB	PA449545
Drug Product Database	469327
RxList	http://www.rxlist.com/cgi/generic/ethynoc.htm
Wikipedia	http://en.wikipedia.org/wiki/Ethynodiol_diacetate

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

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 Gene: PGR Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed Briggs MH: Contraceptive steroid binding to the human uterine progesterone-receptor. Curr Med Res Opin. 1975;3(2):95-8. Pubmed 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 Gene: ESR1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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

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

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
Briggs MH: Contraceptive steroid binding to the human uterine progesterone-receptor. Curr Med Res Opin. 1975;3(2):95-8. Pubmed
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:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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 April 19, 2011 15:06

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.