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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26O2
Molecular Weight 310.4299
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GESTODENE

SMILES

CC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1C=C[C@@]2(O)C#C

InChI

InChIKey=SIGSPDASOTUPFS-XUDSTZEESA-N
InChI=1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

HIDE SMILES / InChI
Molecular Formula C21H26O2
Molecular Weight 310.4299
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/2548807

Gestodene (17alpa-ethynyl-13beta-ethyl-17beta-hydroxy-4,15-gonadien-3-one) is the most potent synthetic progestin currently available and it is widely used as a fertility regulating agent in a number of contraceptive formulations because of its high effectiveness, safety and acceptability. Products containing gestoden include Meliane, which contains 20 ug of ethinylestradiol and 75 ug of gestodene; and Gynera, which contains 30 ug of ethinylestradiol and 75 ug of gestodene. Gestodene is androgenically neutral, meaning that contraceptive pills containing gestodene do not exhibit the androgenic side effects (e.g. acne, hirsutism, weight gain) often associated with second-generation contraceptive pills. Gestodene displays a high binding affinity to the progesterone receptor, also binds to adrogen and glucocorticoid receptors but no measurable affinity for the estrogen receptor.

Approval Year

2018
425
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1076
Binding Agent
1076
Binding Agent
1076
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Phase III
665
MELODEN 21

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.07 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8222659/
0.1 mg single, oral
dose: 0.1 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 GESTODENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
0.11 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8222659/
0.1 mg 1 times / day multiple, oral
dose: 0.1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 GESTODENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
0.1 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8222659/
0.1 mg 1 times / day multiple, oral
dose: 0.1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 GESTODENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.3 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8222659/
0.1 mg single, oral
dose: 0.1 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 GESTODENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
1.03 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8222659/
0.1 mg 1 times / day multiple, oral
dose: 0.1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 GESTODENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
0.98 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8222659/
0.1 mg 1 times / day multiple, oral
dose: 0.1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 GESTODENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
18 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8222659/
0.1 mg single, oral
dose: 0.1 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 GESTODENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
20 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8222659/
0.1 mg 1 times / day multiple, oral
dose: 0.1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 GESTODENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
21.9 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8222659/
0.1 mg 1 times / day multiple, oral
dose: 0.1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 GESTODENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1.3%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8222659/
0.1 mg single, oral
dose: 0.1 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 GESTODENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
0.6%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8222659/
0.1 mg 1 times / day multiple, oral
dose: 0.1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 GESTODENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
75 ug 1 times / day multiple, oral
Studied dose
Dose: 75 ug, 1 times / day
Route: oral
Route: multiple
Dose: 75 ug, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
Other AEs: Breast tension, Headache...
Other AEs:
Breast tension (12.4%)
Headache (13.1%)
Nausea (6%)
Nervousness (8.4%)
Dizziness (2.9%)
Depression (3.9%)
Acne (5.8%)
Oedema (1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
AEs

AEs

AESignificanceDosePopulation
Oedema 1%
75 ug 1 times / day multiple, oral
Studied dose
Dose: 75 ug, 1 times / day
Route: oral
Route: multiple
Dose: 75 ug, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
Breast tension 12.4%
75 ug 1 times / day multiple, oral
Studied dose
Dose: 75 ug, 1 times / day
Route: oral
Route: multiple
Dose: 75 ug, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
Headache 13.1%
75 ug 1 times / day multiple, oral
Studied dose
Dose: 75 ug, 1 times / day
Route: oral
Route: multiple
Dose: 75 ug, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
Dizziness 2.9%
75 ug 1 times / day multiple, oral
Studied dose
Dose: 75 ug, 1 times / day
Route: oral
Route: multiple
Dose: 75 ug, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
Depression 3.9%
75 ug 1 times / day multiple, oral
Studied dose
Dose: 75 ug, 1 times / day
Route: oral
Route: multiple
Dose: 75 ug, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
Acne 5.8%
75 ug 1 times / day multiple, oral
Studied dose
Dose: 75 ug, 1 times / day
Route: oral
Route: multiple
Dose: 75 ug, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
Nausea 6%
75 ug 1 times / day multiple, oral
Studied dose
Dose: 75 ug, 1 times / day
Route: oral
Route: multiple
Dose: 75 ug, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
Nervousness 8.4%
75 ug 1 times / day multiple, oral
Studied dose
Dose: 75 ug, 1 times / day
Route: oral
Route: multiple
Dose: 75 ug, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8521763/
PubMed

PubMed

TitleDatePubMed
Risk of venous thromboembolic disease associated with hormonal contraceptives and hormone replacement therapy: a clinical review.
2004-10-11
Flutamide-metformin plus an oral contraceptive (OC) for young women with polycystic ovary syndrome: switch from third- to fourth-generation OC reduces body adiposity.
2004-08
A prospective open-label study to evaluate the effects of the oral contraceptive Harmonet (gestodene75/EE20) on body fat.
2004-07
[Third-generation oral contraceptives--how big is the risk of venous thrombosis?].
2004-06-03
Plasma concentrations of endogenous hormones during one regular treatment cycle with a low-dose oral contraceptive and during two cycles with deliberate omission of two tablets.
2004-06
The role of combined oral contraceptives in the management of acne and seborrhea.
2004-06
Comparative evaluation of androgen and progesterone receptor transcription selectivity indices of 19-nortestosterone-derived progestins.
2004-06
Serum resistin levels in women taking combined oral contraceptives containing desogestrel or gestodene.
2004-06
Pharmacological profile of progestins.
2004-04-15
Long term use of oral contraceptives without thrombosis in patients with FV Leiden polymorphism: a study of 37 patients (2 homozygous and 35 heterozygous).
2004-04
Effect of a low-dose ethinylestradiol and gestodene in combination on the frequency of micronuclei in human peripheral blood lymphocytes of healthy women in vivo.
2004-04
[The effectiveness and acceptability of oral contraceptives (Logest), containing 20 micrograms ethinylestradiol and 75 micrograms gestodene].
2004-03
Oral contraception does not alter single dose saquinavir pharmacokinetics in women.
2004-03
Sexual behavior of women taking low-dose oral contraceptive containing 15 microg ethinylestradiol/60 microg gestodene.
2004-03
Third generation oral contraceptive use and cardiovascular risk factors.
2004-02
Associated response in bone and lipids during hormone replacement therapy.
2004-01-20
Adrenal adenoma and normal androgen levels in a young woman with polycystic ovaries: a case of idiopathic hirsutism?
2004-01
Classification and pharmacology of progestins.
2003-12-10
Carpal tunnel syndrome and oral contraceptive drugs: risk or protective factor?
2003-12
Oral, more than transdermal, estrogen therapy improves lipids and lipoprotein(a) in postmenopausal women: a randomized, placebo-controlled study.
2003-11-25
The truth about oral contraceptives and venous thromboembolism.
2003-11
Effects of low-dose oral and transdermal estrogen replacement therapy on hemostatic factors in healthy postmenopausal women: a randomized placebo-controlled study.
2003-11
Gateways to clinical trials.
2003-10
Gateways to clinical trials.
2003-09-02
Effects of oral and transdermal low-dose estrogen therapy on echocardiographic parameters of cardiac function.
2003-09
A screening study on the liability of eight different female sex steroids to inhibit CYP2C9, 2C19 and 3A4 activities in human liver microsomes.
2003-08
Lack of difference among progestins on the anti-atherogenic effect of ethinyl estradiol: a rabbit study.
2003-07
Effect of oral and transdermal estrogen replacement therapy on hemostatic variables associated with venous thrombosis: a randomized, placebo-controlled study in postmenopausal women.
2003-06-01
A 13-month multicenter clinical experience of a low-dose monophasic oral contraceptive containing 20 microg ethinylestradiol and 75 microg gestodene in Latin American women.
2003-05
Effects of a low-dose and ultra-low-dose combined oral contraceptive use on bone turnover and bone mineral density in young fertile women: a prospective controlled randomized study.
2003-05
Changes in prescription patterns of oral contraceptives in a northern Italian province: relation with venous thromboembolism.
2003-04
Do oral contraceptives improve vocal quality? Limited trial on low-dose formulations.
2003-04
The effects of seven monophasic oral contraceptive regimens on hemostatic variables: conclusions from a large randomized multicenter study.
2003-03
Roles of human liver cytochrome P450 3A4 and 1A2 enzymes in the oxidation of myristicin.
2003-02-03
Influence of the third generation pill controversy on prescriptions for oral contraceptives among first time users: population based study.
2003-02-01
Venous and arterial thrombosis during oral contraceptive use: risks and risk factors.
2003-02
Changes of hemostatic variables during oral contraceptive use.
2003-02
The effect of progesterone and synthetic progestins on serum- and estradiol-stimulated proliferation of human breast cancer cells.
2003-02
A randomized placebo-controlled study of the effect of transdermal vs. oral estradiol with or without gestodene on homocysteine levels.
2003-02
Thromboembolic disease and present oral contraception.
2003-01
Auditory brainstem response in premenopausal women taking oral contraceptives.
2003-01
Low-dose combination of flutamide, metformin and an oral contraceptive for non-obese, young women with polycystic ovary syndrome.
2003-01
[Effect and control of oral contraceptive Minesse (15 mkg EE/60 mkg Gestoden) on menstrual cycle and body weight].
2003
Randomized controlled study of the influence of two low estrogen dose oral contraceptives containing gestodene or desogestrel on carbohydrate metabolism.
2002-12
A comparison of cycle control, efficacy, and side effects among healthy Thai women between two low-dose oral contraceptives containing 20 microg ethinylestradio1/75 microg gestodene (Meliane) and 30 microg ethinylestradio1/75 microg gestodene (Gynera).
2002-12
The effect of 17beta-estradiol on endothelial and inflammatory markers in postmenopausal women: a randomized, controlled trial.
2002-12
Effects of low-dose OCs on weight in women with Central European nutritional habits and lifestyle.
2002-09
Pro-inflammatory effects of oestrogens during use of oral contraceptives and hormone replacement treatment.
2002-08
Genetic polymorphisms modify the response of factor VII to oral contraceptive use: an example of gene-environment interaction.
2002-08
The new pills: awaiting the next generation of oral contraceptives.
1992-09-01
Patents

Patents

04081537
1
04719054
3
05858394
1
JP1070410A
6
JP2002529493A
1
JP2002543119A
4
JP2002543154A
5
JP2002543155A
8
JP2002543156A
35
JP2002543157A
8
JP2002543158A
5
JP2002543159A
33
JP2003518006A
6
JP2005500299A
34
JP2006096775A
34
JP2007506797A
3
JP2007508287A
7
JP2007512291A
11
JP2007535519A
3
JP2010248270A
3
JP2011526609A
9
JPH00386826A
1
JPH0386826A
1
JPH08231436A
1
JPS6470410A
6

Sample Use Guides

In Vivo Use Guide
Minimum daily dose required to inhibit ovulation is 40 ug of gestodene. Daily doses were given orally for 21 days.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 07:04:38 GMT 2025
Edited
by admin
on Wed Apr 02 07:04:38 GMT 2025
Record UNII
1664P6E6MI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GESTODENE
BAN   USAN  
Official Name English
SH B 331
Preferred Name English
SH-B-331
Code English
Gestodene [WHO-DD]
Common Name English
GESTODENE [MART.]
Common Name English
GESTODENE [MI]
Common Name English
13-Ethyl-17-hydroxy-18,19-dinor-17?-pregna-4,15-dien-20-yn-3-one
Common Name English
PREGNA-4,15-DIEN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-18,19-DINOR-, (17.ALPHA.)-
Common Name English
GESTODENE [USAN]
Common Name English
GESTODENE [EP IMPURITY]
Common Name English
gestodene [INN]
Common Name English
GESTODENE [EP MONOGRAPH]
Common Name English
GESTODENE [HSDB]
Common Name English
Classification Tree Code System Code
WHO-ATC G03AB06
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
WHO-ATC G03AA10
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
WHO-VATC QG03AA10
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
NCI_THESAURUS C776
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
WHO-VATC QG03AB06
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
Code System Code Type Description
PUBCHEM
3033968
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
DRUG CENTRAL
1291
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
INN
4244
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
FDA UNII
1664P6E6MI
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
DAILYMED
1664P6E6MI
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
MESH
C033273
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
EVMPD
SUB07901MIG
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID6046478
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
SMS_ID
100000092348
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
MERCK INDEX
m5717
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY Merck Index
RXCUI
25734
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY RxNorm
CAS
60282-87-3
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
ChEMBL
CHEMBL1213583
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
WIKIPEDIA
Gestodene
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
DRUG BANK
DB06730
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
NCI_THESAURUS
C87240
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
ECHA (EC/EINECS)
262-145-8
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
HSDB
3594
Created by admin on Wed Apr 02 07:04:38 GMT 2025 , Edited by admin on Wed Apr 02 07:04:38 GMT 2025
PRIMARY
Related Record Type Details
Structure of 15?-Acetoxy-gestodene
IMPURITY -> PARENT
Structure of 6?-Hydroxy-gestodene
IMPURITY -> PARENT
Structure of 6-Keto-gestodene
IMPURITY -> PARENT
Structure of Gestodene ketal
IMPURITY -> PARENT
Structure of Diethynyl-gestodene
IMPURITY -> PARENT
Structure of A-aromatic-gestodene
IMPURITY -> PARENT
Related Record Type Details
Structure of GESTODENE
ACTIVE MOIETY
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