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
Synonyms
  • 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol
  • Cerazette
  • Desogestrelum
External IDs
ORG 2969
Product Images
International/Other Brands
Cerazette (Organon) / Marvelon (Adcock Ingram Pharmaceuticals)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ApriDesogestrel + Ethinyl EstradiolKitA S Medication Solutions1999-10-222017-06-20Us
ApriDesogestrel + Ethinyl EstradiolKitPhysicians Total Care, Inc.2003-03-10Not applicableUs
Apri 21Desogestrel (0.15 mg) + Ethinyl Estradiol (0.03 mg)TabletOralTeva2008-09-29Not applicableCanada
Apri 28Desogestrel (0.15 mg) + Ethinyl Estradiol (0.03 mg)TabletOralTeva2008-09-29Not applicableCanada
Apri 28 DayDesogestrel + Ethinyl EstradiolKitTeva1999-10-22Not applicableUs00555 9043 58 nlmimage10 d5136aab
AzuretteDesogestrel (0.15 mg/1) + Ethinyl Estradiol (0.02 mg/1) + Ethinyl Estradiol (0.01 mg/1)KitMayne Pharma2016-11-14Not applicableUs
BekyreeDesogestrel (0.15 mg/1) + Ethinyl Estradiol (0.02 mg/1) + Ethinyl Estradiol (0.01 mg/1)KitLupin Pharmaceuticals2015-10-26Not applicableUs
BekyreeDesogestrel (0.15 mg/1) + Ethinyl Estradiol (0.02 mg/1) + Ethinyl Estradiol (0.01 mg/1)KitLupin Pharmaceuticals2015-10-26Not applicableUs
CaziantDesogestrel + Ethinyl EstradiolKitWatson Pharma, Inc.2005-05-012017-07-22Us52544 0959 28 nlmimage10 c53ae297
CaziantDesogestrel + Ethinyl EstradiolKitRemedy Repack2015-07-282017-04-18Us
Categories
UNII
81K9V7M3A3
CAS number
54024-22-5
Weight
Average: 310.473
Monoisotopic: 310.229665582
Chemical Formula
C22H30O
InChI Key
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

Pharmacology

Indication

For the prevention of pregnancy in women who elect to use this product as a method of contraception.

Structured Indications
Not Available
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.

TargetActionsOrganism
AProgesterone receptor
agonist
Human
AEstrogen receptor alpha
agonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Desogestrel.Investigational
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Desogestrel.Approved
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Desogestrel.Approved, Investigational
AcenocoumarolDesogestrel may decrease the anticoagulant activities of Acenocoumarol.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Desogestrel.Investigational, Withdrawn
AcitretinThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Acitretin.Approved
AdapaleneThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Adapalene.Approved
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be decreased when used in combination with Desogestrel.Experimental, Investigational
AlitretinoinThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Alitretinoin.Approved, Investigational
AllicinThe therapeutic efficacy of Allicin can be decreased when used in combination with Desogestrel.Investigational
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Desogestrel.Approved
AmobarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Amobarbital.Approved, Illicit
AncrodThe therapeutic efficacy of Ancrod can be decreased when used in combination with Desogestrel.Investigational
Antithrombin III humanThe therapeutic efficacy of Antithrombin III human can be decreased when used in combination with Desogestrel.Approved
ApixabanThe therapeutic efficacy of Apixaban can be decreased when used in combination with Desogestrel.Approved
AprepitantThe serum concentration of Desogestrel can be decreased when it is combined with Aprepitant.Approved, Investigational
ArdeparinThe therapeutic efficacy of Ardeparin can be decreased when used in combination with Desogestrel.Approved, Investigational, Withdrawn
ArgatrobanThe therapeutic efficacy of Argatroban can be decreased when used in combination with Desogestrel.Approved, Investigational
ArtemetherThe serum concentration of Desogestrel can be decreased when it is combined with Artemether.Approved
AtazanavirThe serum concentration of Desogestrel can be increased when it is combined with Atazanavir.Approved, Investigational
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Desogestrel.Investigational
BarbexacloneThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Barbexaclone.Experimental
BarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Barbital.Illicit
BecaplerminThe therapeutic efficacy of Becaplermin can be decreased when used in combination with Desogestrel.Approved, Investigational
Bempedoic acidThe therapeutic efficacy of Bempedoic acid can be decreased when used in combination with Desogestrel.Investigational
BexaroteneThe serum concentration of Desogestrel can be decreased when it is combined with Bexarotene.Approved, Investigational
BivalirudinThe therapeutic efficacy of Bivalirudin can be decreased when used in combination with Desogestrel.Approved, Investigational
BoceprevirThe serum concentration of Desogestrel can be increased when it is combined with Boceprevir.Approved, Withdrawn
BosentanThe serum concentration of Desogestrel can be decreased when it is combined with Bosentan.Approved, Investigational
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Desogestrel.Investigational, Withdrawn
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Desogestrel.Approved
CarbamazepineThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Carbamazepine.Approved, Investigational
CarbutamideThe therapeutic efficacy of Carbutamide can be decreased when used in combination with Desogestrel.Experimental
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Desogestrel.Experimental
CertoparinThe therapeutic efficacy of Certoparin can be decreased when used in combination with Desogestrel.Approved, Investigational
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Desogestrel.Approved
CholestyramineThe serum concentration of Desogestrel can be decreased when it is combined with Cholestyramine.Approved
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Desogestrel.Experimental
Citric AcidThe therapeutic efficacy of Citric Acid can be decreased when used in combination with Desogestrel.Approved, Nutraceutical, Vet Approved
ClobazamThe serum concentration of Desogestrel can be decreased when it is combined with Clobazam.Approved, Illicit
ClorindioneDesogestrel may decrease the anticoagulant activities of Clorindione.Experimental
CobicistatThe serum concentration of Desogestrel can be increased when it is combined with Cobicistat.Approved
ColesevelamThe serum concentration of Desogestrel can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Desogestrel can be decreased when it is combined with Colestipol.Approved
Conestat alfaDesogestrel may increase the thrombogenic activities of Conestat alfa.Approved
Dabigatran etexilateThe therapeutic efficacy of Dabigatran etexilate can be decreased when used in combination with Desogestrel.Approved
DabrafenibThe serum concentration of Desogestrel can be decreased when it is combined with Dabrafenib.Approved
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Desogestrel.Approved
DanaparoidThe therapeutic efficacy of Danaparoid can be decreased when used in combination with Desogestrel.Approved, Withdrawn
DarexabanThe therapeutic efficacy of Darexaban can be decreased when used in combination with Desogestrel.Investigational
DarunavirThe serum concentration of Desogestrel can be decreased when it is combined with Darunavir.Approved
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Desogestrel.Investigational
DesirudinThe therapeutic efficacy of Desirudin can be decreased when used in combination with Desogestrel.Approved
DextranThe therapeutic efficacy of Dextran can be decreased when used in combination with Desogestrel.Approved, Vet Approved
Dextran 40The therapeutic efficacy of Dextran 40 can be decreased when used in combination with Desogestrel.Approved
Dextran 70The therapeutic efficacy of Dextran 70 can be decreased when used in combination with Desogestrel.Approved
Dextran 75The therapeutic efficacy of Dextran 75 can be decreased when used in combination with Desogestrel.Approved
DicoumarolDesogestrel may decrease the anticoagulant activities of Dicoumarol.Approved
DiphenadioneDesogestrel may decrease the anticoagulant activities of Diphenadione.Experimental
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Desogestrel.Approved
Edetic AcidThe therapeutic efficacy of Edetic Acid can be decreased when used in combination with Desogestrel.Approved, Vet Approved
EdoxabanThe therapeutic efficacy of Edoxaban can be decreased when used in combination with Desogestrel.Approved
EfavirenzThe serum concentration of Desogestrel can be decreased when it is combined with Efavirenz.Approved, Investigational
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Desogestrel.Approved
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Desogestrel.Approved
Eslicarbazepine acetateThe serum concentration of Desogestrel can be decreased when it is combined with Eslicarbazepine acetate.Approved
Ethyl biscoumacetateDesogestrel may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
ExenatideThe serum concentration of Desogestrel can be decreased when it is combined with Exenatide.Approved, Investigational
FelbamateThe serum concentration of Desogestrel can be decreased when it is combined with Felbamate.Approved
Ferulic acidThe therapeutic efficacy of Ferulic acid can be decreased when used in combination with Desogestrel.Experimental
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Desogestrel.Approved
FluindioneDesogestrel may decrease the anticoagulant activities of Fluindione.Investigational
FondaparinuxThe therapeutic efficacy of Fondaparinux can be decreased when used in combination with Desogestrel.Investigational
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Desogestrel.Approved, Investigational
FosamprenavirThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Desogestrel resulting in a loss in efficacy.Approved
FosaprepitantThe serum concentration of Desogestrel can be decreased when it is combined with Fosaprepitant.Approved
FosphenytoinThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Fosphenytoin.Approved
GabexateThe therapeutic efficacy of Gabexate can be decreased when used in combination with Desogestrel.Investigational
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Desogestrel.Investigational, Withdrawn
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Desogestrel.Approved
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Desogestrel.Approved
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Desogestrel.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Desogestrel.Approved, Investigational
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Desogestrel.Approved
GriseofulvinThe serum concentration of Desogestrel can be decreased when it is combined with Griseofulvin.Approved, Vet Approved
GusperimusThe therapeutic efficacy of Gusperimus can be decreased when used in combination with Desogestrel.Investigational
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Desogestrel.Approved, Investigational
HexobarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Hexobarbital.Approved
Human C1-esterase inhibitorDesogestrel may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
IdraparinuxThe therapeutic efficacy of Idraparinux can be decreased when used in combination with Desogestrel.Investigational
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Desogestrel.Approved
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Desogestrel.Approved
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Desogestrel.Approved
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Desogestrel.Approved
Insulin HumanThe therapeutic efficacy of Insulin Human can be decreased when used in combination with Desogestrel.Approved, Investigational
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Desogestrel.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Desogestrel.Approved
IsotretinoinThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Isotretinoin.Approved
LamotrigineThe serum concentration of Desogestrel can be decreased when it is combined with Lamotrigine.Approved, Investigational
LepirudinThe therapeutic efficacy of Lepirudin can be decreased when used in combination with Desogestrel.Approved
LetaxabanThe therapeutic efficacy of Letaxaban can be decreased when used in combination with Desogestrel.Investigational
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Desogestrel.Approved
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Desogestrel.Approved
LopinavirThe serum concentration of Desogestrel can be decreased when it is combined with Lopinavir.Approved
LumacaftorThe serum concentration of Desogestrel can be decreased when it is combined with Lumacaftor.Approved
MelagatranThe therapeutic efficacy of Melagatran can be decreased when used in combination with Desogestrel.Experimental
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Desogestrel.Approved
MethohexitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Methohexital.Approved
MethylphenobarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Methylphenobarbital.Approved
MetreleptinThe serum concentration of Desogestrel can be decreased when it is combined with Metreleptin.Approved
MifepristoneThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Mifepristone.Approved, Investigational
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Desogestrel.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Desogestrel.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Desogestrel.Approved, Investigational
Mycophenolic acidThe serum concentration of Desogestrel can be decreased when it is combined with Mycophenolic acid.Approved
NadroparinThe therapeutic efficacy of Nadroparin can be decreased when used in combination with Desogestrel.Approved
NafamostatThe therapeutic efficacy of Nafamostat can be decreased when used in combination with Desogestrel.Approved, Investigational
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Desogestrel.Approved, Investigational
NelfinavirThe serum concentration of Desogestrel can be decreased when it is combined with Nelfinavir.Approved
NevirapineThe serum concentration of Desogestrel can be decreased when it is combined with Nevirapine.Approved
OtamixabanThe therapeutic efficacy of Otamixaban can be decreased when used in combination with Desogestrel.Investigational
OxcarbazepineThe serum concentration of Desogestrel can be decreased when it is combined with Oxcarbazepine.Approved
Pentaerythritol TetranitrateThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Desogestrel.Approved
PentobarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateThe therapeutic efficacy of Pentosan Polysulfate can be decreased when used in combination with Desogestrel.Approved
PerampanelThe serum concentration of Desogestrel can be decreased when it is combined with Perampanel.Approved
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Desogestrel.Approved, Investigational, Withdrawn
PhenindioneDesogestrel may decrease the anticoagulant activities of Phenindione.Approved, Investigational
PhenobarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Phenobarbital.Approved
PhenprocoumonDesogestrel may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenytoinThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Phenytoin.Approved, Vet Approved
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Desogestrel.Approved, Investigational
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Desogestrel.Approved, Investigational
PrimidoneThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Primidone.Approved, Vet Approved
Protein CThe therapeutic efficacy of Protein C can be decreased when used in combination with Desogestrel.Approved
Protein S humanThe therapeutic efficacy of Protein S human can be decreased when used in combination with Desogestrel.Approved
ProtocatechualdehydeThe therapeutic efficacy of Protocatechualdehyde can be decreased when used in combination with Desogestrel.Approved
PrucaloprideThe serum concentration of Desogestrel can be decreased when it is combined with Prucalopride.Approved
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Desogestrel.Approved, Investigational
ReviparinThe therapeutic efficacy of Reviparin can be decreased when used in combination with Desogestrel.Approved, Investigational
RifabutinThe serum concentration of Desogestrel can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Desogestrel can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Desogestrel can be decreased when it is combined with Rifapentine.Approved
RifaximinThe serum concentration of Desogestrel can be decreased when it is combined with Rifaximin.Approved, Investigational
RivaroxabanThe therapeutic efficacy of Rivaroxaban can be decreased when used in combination with Desogestrel.Approved
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Desogestrel.Approved, Investigational
SaquinavirThe serum concentration of Desogestrel can be decreased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Desogestrel.Approved
SecobarbitalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Secobarbital.Approved, Vet Approved
SelegilineThe serum concentration of Selegiline can be increased when it is combined with Desogestrel.Approved, Investigational, Vet Approved
SitagliptinThe therapeutic efficacy of Sitagliptin can be decreased when used in combination with Desogestrel.Approved, Investigational
SotagliflozinThe therapeutic efficacy of Sotagliflozin can be decreased when used in combination with Desogestrel.Investigational
St. John's WortThe therapeutic efficacy of Desogestrel can be decreased when used in combination with St. John's Wort.Investigational, Nutraceutical
SugammadexThe serum concentration of Desogestrel can be decreased when it is combined with Sugammadex.Approved
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Desogestrel.Approved, Investigational
TelaprevirThe serum concentration of Desogestrel can be decreased when it is combined with Telaprevir.Approved, Withdrawn
ThalidomideDesogestrel may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
ThiamylalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Thiamylal.Approved, Vet Approved
ThiopentalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Thiopental.Approved, Vet Approved
TioclomarolDesogestrel may decrease the anticoagulant activities of Tioclomarol.Experimental
TipiracilThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Tipiracil.Approved
TipranavirThe serum concentration of Desogestrel can be increased when it is combined with Tipranavir.Approved, Investigational
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Desogestrel.Approved
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Desogestrel.Approved
TopiramateThe serum concentration of Desogestrel can be decreased when it is combined with Topiramate.Approved
Tranexamic AcidTranexamic Acid may increase the thrombogenic activities of Desogestrel.Approved
TretinoinThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Tretinoin.Approved, Investigational, Nutraceutical
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Desogestrel.Investigational, Withdrawn
TroxerutinThe therapeutic efficacy of Troxerutin can be decreased when used in combination with Desogestrel.Investigational
UlipristalThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Ulipristal.Approved
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Desogestrel.Approved, Investigational
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Desogestrel.Approved, Investigational
VoriconazoleThe serum concentration of Desogestrel can be increased when it is combined with Voriconazole.Approved, Investigational
WarfarinDesogestrel may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Desogestrel.Approved, Investigational, Withdrawn
Food Interactions
Not 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
Human Metabolome Database
HMDB14449
KEGG Drug
D02367
KEGG Compound
C07629
PubChem Compound
40973
PubChem Substance
46505739
ChemSpider
37400
BindingDB
50423510
ChEBI
4453
ChEMBL
CHEMBL1533
Therapeutic Targets Database
DAP001209
PharmGKB
PA449238
RxList
RxList Drug Page
Wikipedia
Desogestrel
ATC Codes
G03AC09 — DesogestrelG03AB05 — Desogestrel and ethinylestradiolG03AA09 — Desogestrel and ethinylestradiolG03FB10 — Desogestrel and estrogen

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingOtherBiological Availability1
1, 2CompletedTreatmentOvarian Stimulation1
2CompletedBasic ScienceHemostasis / Oral Contraceptives (OC)1
2CompletedTreatmentHealthy Volunteers1
2Unknown StatusTreatmentWomen With PMS1
2, 3CompletedTreatmentOndine Syndrome1
3CompletedPreventionContraception1
3Not Yet RecruitingTreatmentInfertility, Female / Polycystic Ovaries Syndrome1
3RecruitingTreatmentDysfunctional Uterine Bleeding1
3RecruitingTreatmentExercise-related Amenorrhea1
4CompletedTreatmentInfertilities1
4RecruitingBasic ScienceBone; Disorder, Development and Growth1
4RecruitingBasic ScienceOther Disorders of Bone Development and Growth1
4SuspendedTreatmentInfertilities1
4TerminatedNot AvailableInfertilities1
4Unknown StatusDiagnosticHaemorrhage1
4Unknown StatusTreatmentMenstrual Problem1
4Unknown StatusTreatmentUterine Leiomyomas1
4WithdrawnTreatmentInfertilities1
Not AvailableCompletedNot AvailableContraception1
Not AvailableCompletedNot AvailableContraceptive Usage / Vaginal Epithelial Disruption1
Not AvailableCompletedNot AvailableControlled Ovaria Stimulation1
Not AvailableCompletedHealth Services ResearchOvarian Follicle1
Not AvailableCompletedTreatmentEndometriosis1
Not AvailableRecruitingNot AvailableFemale Sexual Function1
Not AvailableTerminatedTreatmentIn-Vitro Fertilization / Infertilities1
Not AvailableUnknown StatusTreatmentCongenital Central Hypoventilation Syndrome1

Pharmacoeconomics

Manufacturers
Not 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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)109-110Van 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 RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrane steroids
Alternative Parents
17-hydroxysteroids / Delta-4-steroids / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / Hydroxysteroid / Estrane-skeleton / Delta-4-steroid / Ynone / Tertiary alcohol / Cyclic alcohol / Acetylide / Organic oxygen compound / Hydrocarbon derivative
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, 17beta-hydroxy steroid (CHEBI:4453) / C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C07629) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030104)

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 ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
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 tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
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]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:35