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Identification
NameDesogestrel
Accession NumberDB00304  (APRD00762)
TypeSmall Molecule
GroupsApproved
Description

A synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents. [PubChem]

Structure
Thumb
Synonyms
13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol
Cerazette
Desogestrelum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CerazetteOrganon
MarvelonAdcock Ingram Pharmaceuticals
Brand mixtures
NameLabellerIngredients
ApriBarr Laboratories Inc.
Apri 21Teva Canada Limited
Apri 28Teva Canada Limited
CaziantWatson Pharma, Inc.
CyclessaOrganon USA Inc.
CyredAfaxys Inc.
DesogenOrganon USA Inc.
Desogestrel and Ethinyl EstradiolNorthstar Rx LLC
EmoquetteQualitest Pharmaceuticals
EnskyceLupin Pharmaceuticals, Inc.
Freya 21Mylan Pharmaceuticals Ulc
Freya 28Mylan Pharmaceuticals Ulc
JuleberNorthstar Rx LLC
KimidessQualitest Pharmaceuticals
Linessa 21Aspen Pharma Trading Limited
Linessa 28Aspen Pharma Trading Limited
Marfem 21Novopharm Limited
Marfem 28Novopharm Limited
Marvelon 21Merck Canada Inc
Marvelon 28Merck Canada Inc
Mirvala 21Apotex Inc
Mirvala 28Apotex Inc
Ortho CeptJanssen Pharmaceuticals, Inc.
Ortho-cept Tablets (21 Day)Janssen Inc
Ortho-cept Tablets (28 Day)Janssen Inc
ReclipsenWatson Pharma, Inc.
Reclipsen 21Actavis Pharma Company
Reclipsen 28Actavis Pharma Company
Velivet Triphasic RegimenBarr Laboratories Inc.
SaltsNot Available
Categories
UNII81K9V7M3A3
CAS number54024-22-5
WeightAverage: 310.473
Monoisotopic: 310.229665582
Chemical FormulaC22H30O
InChI KeyInChIKey=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
IUPAC Name
(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidenetetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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]
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Estrane-skeleton
  • Delta-4-steroid
  • Ynone
  • Tertiary alcohol
  • Cyclic alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • terminal acetylenic compound (CHEBI:4453 )
  • 17beta-hydroxy steroid (CHEBI:4453 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C07629 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030104 )
Pharmacology
IndicationFor the prevention of pregnancy in women who elect to use this product as a method of contraception.
PharmacodynamicsDesogestrel 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 actionBinds 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.
Related Articles
AbsorptionFollowing 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 distributionNot Available
Protein binding98.3%
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.

SubstrateEnzymesProduct
Desogestrel
Not Available
15b-hydroxydesogestrelDetails
Desogestrel
Not Available
2-hydroxydesogestrelDetails
Desogestrel
3a-hydroxydesogestrelDetails
Desogestrel
3b-hydroxydesogestrelDetails
Desogestrel
Not Available
6-alpha-hydroxydesogestrelDetails
Desogestrel
Not Available
6-beta-hydroxydesogestrelDetails
Desogestrel
Not Available
16-hydroxy-desogestrelDetails
Desogestrel
Not Available
13-ethyl-hydroxy desogestrelDetails
Desogestrel
Not Available
Desogestrel sulfateDetails
3a-hydroxydesogestrel
3-KetodesogestrelDetails
Desogestrel
Not Available
15-alpha-hydroxydesogestrelDetails
15-alpha-hydroxydesogestrel
Glucuronic acidDetails
Route of eliminationNot Available
Half life27.8±7.2 hours
ClearanceNot Available
ToxicitySymptoms of overdose include nausea and vaginal bleeding.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9941
Blood Brain Barrier+0.9619
Caco-2 permeable+0.774
P-glycoprotein substrateSubstrate0.6665
P-glycoprotein inhibitor IInhibitor0.6013
P-glycoprotein inhibitor IINon-inhibitor0.8924
Renal organic cation transporterNon-inhibitor0.7478
CYP450 2C9 substrateNon-substrate0.8183
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.6794
CYP450 1A2 substrateNon-inhibitor0.8353
CYP450 2C9 inhibitorNon-inhibitor0.7484
CYP450 2D6 inhibitorNon-inhibitor0.9132
CYP450 2C19 inhibitorInhibitor0.8537
CYP450 3A4 inhibitorNon-inhibitor0.764
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6204
Ames testNon AMES toxic0.923
CarcinogenicityNon-carcinogens0.9213
BiodegradationNot ready biodegradable0.9935
Rat acute toxicity2.3315 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7135
hERG inhibition (predictor II)Non-inhibitor0.7626
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Kit
Tabletoral
Prices
Unit descriptionCostUnit
Mircette 28 0.15-0.02/0.01 mg (21/5) tablet Disp Pack79.99USD disp
Kariva 28 0.15-0.02/0.01 mg (21/5) tablet Disp Pack62.38USD disp
Cyclessa 28 tablet Disp Pack56.39USD disp
Desogen 28 day tablet1.86USD tablet
Cyclessa 28 day tablet1.82USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point109-110Van den Broek, A.J.; US. Patent 3,927,046; December 16, 1975; assigned to Akzona, Inc.
logP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00301 mg/mLALOGPS
logP4.3ALOGPS
logP4.42ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)17.99ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity95.73 m3·mol-1ChemAxon
Polarizability37.54 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Klaus Nickisch, “METHODS FOR THE PREPARATION OF ETONOGESTREL AND DESOGESTREL.” U.S. Patent US20130123523, issued May 16, 2013.

US20130123523
General References
  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:15963096 ]
  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:9864282 ]
External Links
ATC CodesG03AC09G03AB05G03AA09G03FB10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabDesogestrel may decrease the anticoagulant activities of Abciximab.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Desogestrel.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Desogestrel.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Desogestrel.
Anthrax immune globulin humanDesogestrel may increase the thrombogenic activities of Anthrax immune globulin.
ApixabanThe therapeutic efficacy of Apixaban can be decreased when used in combination with Desogestrel.
ArgatrobanThe therapeutic efficacy of Argatroban can be decreased when used in combination with Desogestrel.
BatimastatThe serum concentration of Desogestrel can be decreased when it is combined with Batimastat.
BexaroteneThe serum concentration of Desogestrel can be decreased when it is combined with Bexarotene.
BivalirudinThe therapeutic efficacy of Bivalirudin can be decreased when used in combination with Desogestrel.
BortezomibThe metabolism of Bortezomib can be decreased when combined with Desogestrel.
ButabarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Butabarbital.
ButethalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Butethal.
C1 Esterase Inhibitor (Human)Desogestrel may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Desogestrel.
CapromabDesogestrel may decrease effectiveness of Capromab as a diagnostic agent.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Desogestrel.
Citric AcidDesogestrel may decrease the anticoagulant activities of Citric Acid.
ColesevelamThe serum concentration of Desogestrel can be decreased when it is combined with Colesevelam.
Dabigatran etexilateThe therapeutic efficacy of Dabigatran etexilate can be decreased when used in combination with Desogestrel.
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Desogestrel.
DanaparoidThe therapeutic efficacy of Danaparoid can be decreased when used in combination with Desogestrel.
DesirudinThe therapeutic efficacy of Desirudin can be decreased when used in combination with Desogestrel.
DicoumarolDesogestrel may decrease the anticoagulant activities of Dicoumarol.
Edetic AcidDesogestrel may decrease the anticoagulant activities of Edetic Acid.
EdoxabanThe therapeutic efficacy of Edoxaban can be decreased when used in combination with Desogestrel.
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Desogestrel.
Eslicarbazepine acetateThe serum concentration of Desogestrel can be decreased when it is combined with Eslicarbazepine acetate.
Ethyl biscoumacetateDesogestrel may decrease the anticoagulant activities of Ethyl biscoumacetate.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Desogestrel.
FluvoxamineThe metabolism of Fluvoxamine can be decreased when combined with Desogestrel.
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Desogestrel.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Desogestrel.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Desogestrel.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Desogestrel.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Desogestrel.
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Desogestrel.
HeptabarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Heptabarbital.
HexobarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Hexobarbital.
IcosapentIcosapent may increase the thrombogenic activities of Desogestrel.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Desogestrel.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Desogestrel.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Desogestrel.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Desogestrel.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Desogestrel.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Desogestrel.
IsoflurophateThe serum concentration of Desogestrel can be decreased when it is combined with Isoflurophate.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Desogestrel.
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Desogestrel.
LumacaftorThe serum concentration of Desogestrel can be decreased when it is combined with Lumacaftor.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Desogestrel.
MethohexitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Methohexital.
NadroparinThe therapeutic efficacy of Nadroparin can be decreased when used in combination with Desogestrel.
PentobarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Pentobarbital.
PhenindioneDesogestrel may decrease the anticoagulant activities of Phenindione.
PhenprocoumonDesogestrel may decrease the anticoagulant activities of Phenprocoumon.
PhenytoinThe metabolism of Desogestrel can be increased when combined with Phenytoin.
PrimidoneThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Primidone.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Desogestrel.
RifabutinThe serum concentration of Desogestrel can be decreased when it is combined with Rifabutin.
RivaroxabanThe therapeutic efficacy of Rivaroxaban can be decreased when used in combination with Desogestrel.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Desogestrel.
SecobarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Secobarbital.
SimeprevirThe serum concentration of Desogestrel can be decreased when it is combined with Simeprevir.
St. John's WortThe therapeutic efficacy of Desogestrel can be decreased when used in combination with St. John's Wort.
SulodexideDesogestrel may decrease the anticoagulant activities of Sulodexide.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Desogestrel.
TinzaparinThe therapeutic efficacy of Tinzaparin can be decreased when used in combination with Desogestrel.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Desogestrel.
TreprostinilDesogestrel may decrease the anticoagulant activities of Treprostinil.
UlipristalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Ulipristal.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Desogestrel.
Vitamin CThe serum concentration of Desogestrel can be increased when it is combined with Vitamin C.
WarfarinThe therapeutic efficacy of Warfarin can be decreased when used in combination with Desogestrel.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial ...
Gene Name:
PGR
Uniprot ID:
P06401
Molecular Weight:
98979.96 Da
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:6645495 ]
  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:7750284 ]
  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:3139361 ]
  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:10601100 ]
  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:11041225 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
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 tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
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:7750284 ]
  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:10836199 ]
  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:2175153 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23