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

7.2394559E11
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
Department of health changes advice on third generation pills.
1999 Apr 17
Induction of estrogen receptor-alpha and -beta activities by synthetic progestins.
2000 Apr
Influence of two low-dose oral contraceptives on pulsatile gonadotropin secretion.
2001 Aug
Contraceptive vaginal rings.
2001 Dec
Transdermal contraception.
2001 Dec
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
What is the risk of venous thromboembolism (VTE) among women taking third-generation oral contraceptives (OCs) in comparison with those taking contraceptives containing levonorgestrel?
2001 Feb
Suppression of spermatogenesis with desogestrel and testosterone pellets is not enhanced by addition of finasteride.
2001 Jan-Feb
Implanon: when is the ideal time to insert?
2001 Jul
Nonpalpable ultrasonographically not detectable Implanon rods can be localized by magnetic resonance imaging.
2001 Jun
Protein S levels are lower in women receiving desogestrel-containing combined oral contraceptives (COCs) than in women receiving levonorgestrel-containing COCs at steady state and on cross-over.
2001 Jun
Implanon contraceptive implants: effects on carbohydrate metabolism.
2001 Mar
The effects of two progestogen-only pills containing either desogestrel (75 microg/day) or levonorgestrel (30 microg/day) on lipid metabolism.
2001 Nov
A prospective study evidencing rhinomanometric and olfactometric outcomes in women taking oral contraceptives.
2001 Nov
[Hormonal contraception and thromboembolic disease--pathophysiologic findings and practical recommendations].
2001 Sep
Effect of conjugated estrogens on free IGF-I?
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
Reduction of aromatic steroidal A rings by lithium in ethyl amine.
2002 Feb
Prothrombotic effects and clinical implications of third-generation oral contraceptives use.
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
New developments in contraception.
2002 Jun
[Low-dose combination oral contraceptives use in women with uterine leiomyomas].
2002 Jun
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
FDA approves NuvaRing contraceptive implant.
2002 Mar-Apr
Long-acting progestogen contraceptives.
2002 May
Risk of Arterial Thrombosis in Relation to Oral Contraceptives (RATIO) study: oral contraceptives and the risk of ischemic stroke.
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
Contraception failure and wrongful birth claims.
2002 Oct
Efficacy, cycle control, and user acceptability of a novel combined contraceptive vaginal ring.
2002 Sep
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 Wed Jul 05 23:15:23 UTC 2023
Edited
by admin
on Wed Jul 05 23:15:23 UTC 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 Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
NDF-RT N0000011301
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
NDF-RT N0000175602
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
WHO-VATC QG03FB10
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
WHO-VATC QG03AC09
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
LIVERTOX 285
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
WHO-VATC QG03AB05
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
WHO-ATC G03FB10
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
WHO-ATC G03AC09
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
WHO-ATC G03AB05
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
NCI_THESAURUS C776
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
WHO-VATC QG03AA09
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
Code System Code Type Description
MERCK INDEX
M4198
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1173235
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
LACTMED
Desogestrel
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
HSDB
3593
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
IUPHAR
7065
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
INN
4384
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
CAS
54024-22-5
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
WIKIPEDIA
DESOGESTREL
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
DRUG CENTRAL
818
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
DAILYMED
81K9V7M3A3
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL1533
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
NCI_THESAURUS
C47476
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
MESH
D017135
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
DRUG BANK
DB00304
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
ECHA (EC/EINECS)
258-929-4
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
FDA UNII
81K9V7M3A3
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID6022898
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
CHEBI
4453
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
RXCUI
22656
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY RxNorm
SMS_ID
100000083191
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
EVMPD
SUB07003MIG
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
USAN
CC-14
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 2023
PRIMARY
PUBCHEM
40973
Created by admin on Wed Jul 05 23:15:24 UTC 2023 , Edited by admin on Wed Jul 05 23:15:24 UTC 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