U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H30O
Molecular Weight 310.473
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESOGESTREL

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]3([H])[C@@]4([H])CCCC=C4CC[C@@]23[H]

InChI

InChIKey=RPLCPCMSCLEKRS-BPIQYHPVSA-N
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

HIDE SMILES / InChI

Molecular Formula C22H30O
Molecular Weight 310.473
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Desogestrel is a prodrug of etonogestrel (3-keto-desogestrel) which was approved as oral contraceptove medicine. Desogestrel acts selectively binding to progesterone receptor and enchancing its activity.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
DESOGEN

Approved Use

Desogen (desogestrel and ethinyl estradiol) Tablets are indicated for the prevention of pregnancy in women who elect to use this product as a method of contraception.

Launch Date

1992
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.69 ng/mL
0.15 mg 1 times / day steady-state, oral
dose: 0.15 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ETONOGESTREL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
5840 pg/mL
0.15 mg 1 times / day steady-state, oral
dose: 0.15 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
ETONOGESTREL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: FEMALE
food status: UNKNOWN
2805 pg/mL
0.15 mg single, oral
dose: 0.15 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ETHINYL ESTRADIOL
ETONOGESTREL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
35.9 ng × h/mL
0.15 mg 1 times / day steady-state, oral
dose: 0.15 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ETONOGESTREL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
52299 pg × h/mL
0.15 mg 1 times / day steady-state, oral
dose: 0.15 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
ETONOGESTREL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: FEMALE
food status: UNKNOWN
33858 pg × h/mL
0.15 mg single, oral
dose: 0.15 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ETHINYL ESTRADIOL
ETONOGESTREL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
23.8 h
0.15 mg 1 times / day steady-state, oral
dose: 0.15 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ETONOGESTREL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
0.15 mg 1 times / day steady-state, oral
dose: 0.15 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
ETONOGESTREL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: FEMALE
food status: UNKNOWN
2%
0.15 mg single, oral
dose: 0.15 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ETHINYL ESTRADIOL
ETONOGESTREL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
150 ug 1 times / day steady, oral
Recommended
Dose: 150 ug, 1 times / day
Route: oral
Route: steady
Dose: 150 ug, 1 times / day
Co-administed with::
ethinylestradiol(20 mug)
Sources:
healthy, mean 24.6 years
n = 221
Health Status: healthy
Age Group: mean 24.6 years
Sex: F
Population Size: 221
Sources:
Disc. AE: Headache, Depression...
AEs leading to
discontinuation/dose reduction:
Headache (> 0.45)
Depression (> 0.45)
Menorrhagia (> 0.45)
Skin disorder (> 0.45)
Emotional lability (> 0.45)
Sources:
AEs

AEs

AESignificanceDosePopulation
Depression > 0.45
Disc. AE
150 ug 1 times / day steady, oral
Recommended
Dose: 150 ug, 1 times / day
Route: oral
Route: steady
Dose: 150 ug, 1 times / day
Co-administed with::
ethinylestradiol(20 mug)
Sources:
healthy, mean 24.6 years
n = 221
Health Status: healthy
Age Group: mean 24.6 years
Sex: F
Population Size: 221
Sources:
Emotional lability > 0.45
Disc. AE
150 ug 1 times / day steady, oral
Recommended
Dose: 150 ug, 1 times / day
Route: oral
Route: steady
Dose: 150 ug, 1 times / day
Co-administed with::
ethinylestradiol(20 mug)
Sources:
healthy, mean 24.6 years
n = 221
Health Status: healthy
Age Group: mean 24.6 years
Sex: F
Population Size: 221
Sources:
Headache > 0.45
Disc. AE
150 ug 1 times / day steady, oral
Recommended
Dose: 150 ug, 1 times / day
Route: oral
Route: steady
Dose: 150 ug, 1 times / day
Co-administed with::
ethinylestradiol(20 mug)
Sources:
healthy, mean 24.6 years
n = 221
Health Status: healthy
Age Group: mean 24.6 years
Sex: F
Population Size: 221
Sources:
Menorrhagia > 0.45
Disc. AE
150 ug 1 times / day steady, oral
Recommended
Dose: 150 ug, 1 times / day
Route: oral
Route: steady
Dose: 150 ug, 1 times / day
Co-administed with::
ethinylestradiol(20 mug)
Sources:
healthy, mean 24.6 years
n = 221
Health Status: healthy
Age Group: mean 24.6 years
Sex: F
Population Size: 221
Sources:
Skin disorder > 0.45
Disc. AE
150 ug 1 times / day steady, oral
Recommended
Dose: 150 ug, 1 times / day
Route: oral
Route: steady
Dose: 150 ug, 1 times / day
Co-administed with::
ethinylestradiol(20 mug)
Sources:
healthy, mean 24.6 years
n = 221
Health Status: healthy
Age Group: mean 24.6 years
Sex: F
Population Size: 221
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
yes
yes
yes (co-administration study)
Comment: Subjects received a 10-day pretreatment with an oral contraceptive, containing 30 microg ethinyl estradiol (INN, ethinylestradiol) and 150 microg desogestrel, and the bupropion dose was given 1 hour after the last hormone dose. The bupropion, hydroxybupropion, and hydrobupropion plasma concentrations were determined for up to 72 hours.
Drug as victim
PubMed

PubMed

TitleDatePubMed
Risk of venous thromboembolism from oral contraceptives containing gestodene and desogestrel versus levonorgestrel: a meta-analysis and formal sensitivity analysis.
2001 Aug
Third-generation progestogen type influences hemostatic changes caused by oral contraceptives in Brazilian women.
2001 Dec
Contraceptive vaginal rings.
2001 Dec
Transdermal contraception.
2001 Dec
Oral contraceptives and the risk of myocardial infarction.
2001 Dec 20
Sex steroids used in hormonal treatment increase vascular procoagulant activity by inducing thrombin receptor (PAR-1) expression: role of the glucocorticoid receptor.
2001 Dec 4
Nonpalpable ultrasonographically not detectable Implanon rods can be localized by magnetic resonance imaging.
2001 Jun
Effect of second and third generation oral contraceptives on lipid metabolism in the absence or presence of the factor V Leiden mutation.
2001 Nov
The effects of two progestogen-only pills containing either desogestrel (75 microg/day) or levonorgestrel (30 microg/day) on lipid metabolism.
2001 Nov
Excretion and metabolism of desogestrel in healthy postmenopausal women.
2001 Nov
A novel male contraceptive pill-patch combination: oral desogestrel and transdermal testosterone in the suppression of spermatogenesis in normal men.
2001 Nov
Medical management of dysfunctional uterine bleeding.
2001 Nov
A prospective study evidencing rhinomanometric and olfactometric outcomes in women taking oral contraceptives.
2001 Nov
The effect of hormone replacement therapy on serum homocysteine levels in perimenopausal women: a randomized controlled trial.
2001 Oct
A prospective, controlled study of the effects of hormonal contraception on bone mineral density.
2001 Oct
[Hormonal contraception and thromboembolic disease--pathophysiologic findings and practical recommendations].
2001 Sep
[New gestagens--advantages and disadvantages].
2001 Sep
Suppression of spermatogenesis by etonogestrel implants with depot testosterone: potential for long-acting male contraception.
2002 Aug
Editor's reply.
2002 Dec
Implanon.
2002 Dec
Randomized controlled study of the influence of two low estrogen dose oral contraceptives containing gestodene or desogestrel on carbohydrate metabolism.
2002 Dec
Primary dysmenorrhea treatment with a desogestrel-containing low-dose oral contraceptive.
2002 Dec
Serum concentrations of markers of type I collagen metabolism in women taking monophasic oral contraceptives.
2002 Feb
Effects of second and third generation oral contraceptives and their respective progestagens on the coagulation system in the absence or presence of the factor V Leiden mutation.
2002 Feb
Reduction of aromatic steroidal A rings by lithium in ethyl amine.
2002 Feb
Base promoted air oxidation of 13beta-ethyl-11-methylenegon-4-en-17-one.
2002 Feb
Female hormones and thrombosis.
2002 Feb 1
Implantable contraceptives for women.
2002 Jan
Different effects of oral contraceptives containing levonorgestrel or desogestrel on plasma lipoproteins and coagulation factor VII.
2002 Jan
Cyproterone acetate versus a continuous monophasic oral contraceptive in the treatment of recurrent pelvic pain after conservative surgery for symptomatic endometriosis.
2002 Jan
Triphasic oral contraceptives: review and comparison of various regimens.
2002 Jan
[Changed routines in connection with first prescription of oral contraceptives. Lower risk of venous thromboembolism with levonorgestrel preparations].
2002 Jan 10
[Third generation oral contraceptives and risk of venous thrombosis].
2002 Jan 14
Effect of desogestrel on blood-lipid in relation to its biological activities.
2002 Jan-Feb
Clinical risk factors for venous thromboembolus in users of the combined oral contraceptive pill.
2002 Jun
Can changes in sex hormone binding globulin predict the risk of venous thromboembolism with combined oral contraceptive pills?
2002 Jun
Oral desogestrel with testosterone pellets induces consistent suppression of spermatogenesis to azoospermia in both Caucasian and Chinese men.
2002 Jun
Contraceptives and cerebral thrombosis: a five-year national case-control study.
2002 Mar
Long-acting progestogen contraceptives.
2002 May
Androgen and lipid profiles in adolescents with polycystic ovary syndrome who were treated with two forms of combined oral contraceptives.
2002 May
Investigation of hormonal male contraception in African men: suppression of spermatogenesis by oral desogestrel with depot testosterone.
2002 Nov
Persistent vaginal bleeding in a patient with a broken Implanon.
2002 Oct
An assessment of the use of Implanon in three community services.
2002 Oct
Bleeding problems and progestogen-only contraception.
2002 Oct
Contraception failure and wrongful birth claims.
2002 Oct
Implanon. The new alternative.
2002 Oct
Ultrasonographic features of the endometrium and the ovaries in women on etonogestrel implant.
2002 Oct
Sonographic imaging in progestin users and future directions.
2002 Oct
Improving cycle control in progestogen-only contraceptive pill users by intermittent treatment with a new anti-progestogen.
2002 Oct
Auditory brainstem response in premenopausal women taking oral contraceptives.
2003 Jan
Patents

Sample Use Guides

Take 1 tablet (0.15 mg desogestrel and 0.03 mg ethinyl estradiol) at the same time every day, and at intervals not exceeding 24 hours.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:46:54 GMT 2023
Edited
by admin
on Fri Dec 15 15:46:54 GMT 2023
Record UNII
81K9V7M3A3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DESOGESTREL
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
VIORELE COMPONENT DESOGESTREL
Brand Name English
DESOGESTREL [EP MONOGRAPH]
Common Name English
desogestrel [INN]
Common Name English
CERAZETTE
Brand Name English
DESOGESTREL [USP-RS]
Common Name English
DESOGESTREL COMPONENT OF CYCLESSA
Common Name English
ORTHO-CEPT COMPONENT DESOGESTREL
Common Name English
ISIBLOOM COMPONENT DESOGESTREL
Brand Name English
VELIVET COMPONENT DESOGESTREL
Common Name English
DESOGESTREL [USAN]
Common Name English
DESOGESTREL COMPONENT OF ORTHO-CEPT
Common Name English
DESOGESTREL [USP MONOGRAPH]
Common Name English
CYCLESSA COMPONENT DESOGESTREL
Common Name English
18,19-DINORPREGN-4-EN-20-YN-17-OL, 13-ETHYL-11-METHYLENE-, (17.ALPHA.)-
Common Name English
DESOGESTREL [MART.]
Common Name English
DESOGESTREL COMPONENT OF DESOGEN
Common Name English
DESOGESTREL [JAN]
Common Name English
BEKYREE COMPONENT DESOGESTREL
Brand Name English
DESOGESTREL [ORANGE BOOK]
Common Name English
ORG 2969
Code English
DESOGESTREL COMPONENT OF MIRCETTE
Common Name English
ENSKYCE COMPONENT DESOGESTREL
Brand Name English
VOLNEA COMPONENT DESOGESTREL
Brand Name English
PIMTREA COMPONENT DESOGESTREL
Brand Name English
KARIVA COMPONENT DESOGESTREL
Common Name English
DESOGEN COMPONENT DESOGESTREL
Common Name English
13-ETHYL-11-METHYLENE-18,19-DINOR-17A-PREGN-4-EN-20-YN-17-OL
Common Name English
DESOGESTREL COMPONENT OF KARIVA
Common Name English
MIRCETTE
Brand Name English
DESOGESTREL [HSDB]
Common Name English
DESOGESTREL [VANDF]
Common Name English
ORG-2969
Code English
MIRCETTE COMPONENT DESOGESTREL
Common Name English
DESOGESTREL [MI]
Common Name English
DESOGESTREL COMPONENT OF VELIVET
Common Name English
Desogestrel [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC G03AA09
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
NDF-RT N0000011301
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
NDF-RT N0000175602
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
WHO-VATC QG03FB10
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
WHO-VATC QG03AC09
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
LIVERTOX 285
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
WHO-VATC QG03AB05
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
WHO-ATC G03FB10
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
WHO-ATC G03AC09
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
WHO-ATC G03AB05
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
NCI_THESAURUS C776
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
WHO-VATC QG03AA09
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
Code System Code Type Description
MERCK INDEX
m4198
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1173235
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
LACTMED
Desogestrel
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
HSDB
3593
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
IUPHAR
7065
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
INN
4384
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
CAS
54024-22-5
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
WIKIPEDIA
DESOGESTREL
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
DRUG CENTRAL
818
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
DAILYMED
81K9V7M3A3
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL1533
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
NCI_THESAURUS
C47476
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
MESH
D017135
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
DRUG BANK
DB00304
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
ECHA (EC/EINECS)
258-929-4
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
FDA UNII
81K9V7M3A3
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022898
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
CHEBI
4453
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
RXCUI
22656
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY RxNorm
SMS_ID
100000083191
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
EVMPD
SUB07003MIG
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
USAN
CC-14
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
PUBCHEM
40973
Created by admin on Fri Dec 15 15:46:54 GMT 2023 , Edited by admin on Fri Dec 15 15:46:54 GMT 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
METABOLITE INACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.8
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY