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Identification
Name Desogestrel
Accession Number DB00304 (APRD00762)
Type small molecule
Groups approved
Description

A synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Desogestrelum [INN-Latin]
Brand names
  • Cerazette (Organon)
Brand name mixtures
  • Cyclessa (Desogestrel + Ethinyl Estradiol)
  • Desogen (Desogestrel + Ethinyl Estradiol)
  • Kariva (Desogestrel + Ethinyl Estradiol)
  • Marvelon 21 Tab (Desogestrel + Ethinyl Estradiol)
  • Marvelon 28 Tab (Desogestrel + Ethinyl Estradiol)
  • Mircette (Desogestrel + Ethinyl Estradiol)
  • Ortho-Cept 21 Day (Desogestrel + Ethinyl Estradiol)
  • Ortho-Cept 28 Day (Desogestrel + Ethinyl Estradiol)
Categories
  • Contraceptives, Oral, Synthetic
  • Progestins
CAS number 54024-22-5
Weight Average: 310.473
Monoisotopic: 310.229665582
Chemical Formula C22H30O
InChI Key InChIKey=RPLCPCMSCLEKRS-BPIQYHPVSA-N
InChI
InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
Plain Text
IUPAC Name
(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Alkynes
  • Alcohols and Polyols
  • Cyclohexenes and Derivatives
Pharmacology
Indication For the prevention of pregnancy in women who elect to use this product as a method of contraception.
Pharmacodynamics Desogestrel is used as a female contraceptive. Desogestrel 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. Desogestrel 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 desogestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.
Absorption Following oral administration, the relative bioavailability of desogestrel, as measured by serum levels of etonogestrel, is approximately 84%. The absolute oral bioavailability is about 76%.
Volume of distribution Not Available
Protein binding 98.3%
Metabolism

Desogestrel is rapidly and completely metabolized by hydroxylation in the intestinal mucosa and on first pass through the liver. It is primarily metabolized to 3α-hydroxydesogestrel with small amounts of 3β-hydroxydesogestrel being formed. Both of these metabolites are then rapidly oxidized to its active metabolite, etonogestrel (3-ketodesogestrel). Other metabolites (e.g. 2-hydroxydesogestrel) with no pharmacologic action have also been identified. Desogestrel and some of its metabolites (e.g. 3β-hydroxydesogestrel, 15β-hydroxydesogestrel) may also undergo glucuronide and sulfate conjugation. Early in vitro studies demonstrated that CYP2C9 and possibly CYP2C19 were involved in the conversion of desogestrel to 3α-hydroxydesogestrel and 3β-hydroxydesogestrel (PMID 9864282); however, later clinical studies conducted in humans refuted this result (PMID 15963096). The latter study indicates that CYP3A4 plays an important role in metabolizing etonogestrel. Thus, strong CYP3A4 inhibitors or inducers could result in increased side effects or therapeutic failure, respectively.

Route of elimination Not Available
Half life 27.8±7.2 hours
Clearance Not Available
Toxicity Symptoms of overdose include nausea and vaginal bleeding.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Tablet Oral 75 mcg
Prices
Unit description Cost Unit
Mircette 28 0.15-0.02/0.01 mg (21/5) tablet Disp Pack 79.99 USD disp
Kariva 28 0.15-0.02/0.01 mg (21/5) tablet Disp Pack 62.38 USD disp
Cyclessa 28 tablet Disp Pack 56.39 USD disp
Desogen 28 day tablet 1.86 USD tablet
Cyclessa 28 day tablet 1.82 USD tablet
Patents Not Available
Properties
State solid
Melting point 109.5 oC
Experimental Properties
Property Value Source
logP 4 PhysProp
Predicted Properties
Property Value Source
water solubility 3.01e-03 g/l ALOGPS
logP 4.30 ALOGPS
logP 4.34 ChemAxon Molconvert
logS -5.01 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 1 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 20.23 ChemAxon Molconvert
rotatable bond count 1 ChemAxon Molconvert
refractivity 95.73 ChemAxon Molconvert
polarizability 37.54 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Korhonen T, Tolonen A, Uusitalo J, Lundgren S, Jalonen J, Laine K: The role of CYP2C and CYP3A in the disposition of 3-keto-desogestrel after administration of desogestrel. Br J Clin Pharmacol. 2005 Jul;60(1):69-75. Pubmed
  2. Gentile DM, Verhoeven CH, Shimada T, Back DJ: The role of CYP2C in the in vitro bioactivation of the contraceptive steroid desogestrel. J Pharmacol Exp Ther. 1998 Dec;287(3):975-82. Pubmed
External Links
Resource Link
KEGG Drug D02367 Link_out
KEGG Compound C07629 Link_out
PubChem Compound 40973 Link_out
PubChem Substance 46505739 Link_out
ChemSpider 37400 Link_out
ChEBI 4453 Link_out
ChEMBL 4453 Link_out
Therapeutic Targets Database DAP001209 Link_out
PharmGKB PA449238 Link_out
Drug Product Database 2042533 Link_out
RxList http://www.rxlist.com/cgi/generic/desest.htm Link_out
Wikipedia http://en.wikipedia.org/wiki/Desogestrel Link_out
ATC Codes
  • G03AC09
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 Link_out
Gene: PGR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Bergink EW, van Meel F, Turpijn EW, van der Vies J: Binding of progestagens to receptor proteins in MCF-7 cells. J Steroid Biochem. 1983 Nov;19(5):1563-70. Pubmed
  2. Fuhrmann U, Slater EP, Fritzemeier KH: Characterization of the novel progestin gestodene by receptor binding studies and transactivation assays. Contraception. 1995 Jan;51(1):45-52. Pubmed
  3. Kloosterboer HJ, Vonk-Noordegraaf CA, Turpijn EW: Selectivity in progesterone and androgen receptor binding of progestagens used in oral contraceptives. Contraception. 1988 Sep;38(3):325-32. Pubmed
  4. Macpherson AM, Archer DF, Leslie S, Charnock-Jones DS, Makkink WK, Smith SK: The effect of etonogestrel on VEGF, oestrogen and progesterone receptor immunoreactivity and endothelial cell number in human endometrium. Hum Reprod. 1999 Dec;14(12):3080-7. Pubmed
  5. Charnock-Jones DS, Macpherson AM, Archer DF, Leslie S, Makkink WK, Sharkey AM, Smith SK: The effect of progestins on vascular endothelial growth factor, oestrogen receptor and progesterone receptor immunoreactivity and endothelial cell density in human endometrium. Hum Reprod. 2000 Aug;15 Suppl 3:85-95. Pubmed
  6. 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. Fuhrmann U, Slater EP, Fritzemeier KH: Characterization of the novel progestin gestodene by receptor binding studies and transactivation assays. Contraception. 1995 Jan;51(1):45-52. Pubmed
  2. Rabe T, Bohlmann MK, Rehberger-Schneider S, Prifti S: Induction of estrogen receptor-alpha and -beta activities by synthetic progestins. Gynecol Endocrinol. 2000 Apr;14(2):118-26. Pubmed
  3. Juchem M, Pollow K: Binding of oral contraceptive progestogens to serum proteins and cytoplasmic receptor. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 2):2171-83. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on January 10, 2012 10:22

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.