GESTODENE

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 Search

SMILES

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

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
Sources: http://www.medicatione.com/?c=drug&s=meloden%2021
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

Targets

Primary Target	Pharmacology	Condition	Potency
Progesterone receptor 61 Target ID: CHEMBL208 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2548807	Binding Agent 1064
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2548807	Binding Agent 1064
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2548807	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pregnancy 65 Sources: http://www.medicatione.com/?c=drug&s=meloden%2021	Preventing		Phase III 656	MELODEN 21 Approved Use Unknown

PubMed

Title	Date	PubMed
Non-protein bound dienogest in serum and salivary dienogest in women taking the oral contraceptives Certostat and Valette.	2001 Apr	11338674
In vitro metabolism of gestodene in target organs: formation of A-ring reduced derivatives with oestrogenic activity.	2001 Apr 13	11334857
Oral contraceptives and the risk of myocardial infarction.	2001 Dec 20	11752354
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	11219554
A prospective study evidencing rhinomanometric and olfactometric outcomes in women taking oral contraceptives.	2001 Nov	11679506
Dose finding in a low-dose 21-day combined oral contraceptive containing gestodene.	2001 Oct	11747874
Blood pressure stability in a normotensive population during intake of a monophasic oral contraceptive containing 20 microg ethinylestradiol and 75 g gestodene.	2001 Sep	11763980
Oral contraceptives and venous thromboembolism: which are the safest preparations available?	2002 Apr	12121057
Pro-inflammatory effects of oestrogens during use of oral contraceptives and hormone replacement treatment.	2002 Aug	12616983
Randomized controlled study of the influence of two low estrogen dose oral contraceptives containing gestodene or desogestrel on carbohydrate metabolism.	2002 Dec	12499033
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 Dec	12499032
The effect of 17beta-estradiol on endothelial and inflammatory markers in postmenopausal women: a randomized, controlled trial.	2002 Dec	12417281
Triphasic oral contraceptives: review and comparison of various regimens.	2002 Jan	11779584
Long-term effects of combined oral contraceptives on markers of endothelial function and lipids in healthy premenopausal women.	2002 Mar	11929645
Contraceptives and cerebral thrombosis: a five-year national case-control study.	2002 Mar	11929641
Effects of transdermal and oral oestrogen replacement therapy on C-reactive protein levels in postmenopausal women: a randomised, placebo-controlled trial.	2002 Oct	12362231
Effects of low-dose OCs on weight in women with Central European nutritional habits and lifestyle.	2002 Sep	12384203
Effects of two oral contraceptives on plasma levels of nitric oxide, homocysteine, and lipid metabolism.	2002 Sep	12200770
[Effect and control of oral contraceptive Minesse (15 mkg EE/60 mkg Gestoden) on menstrual cycle and body weight].	2003	14682015
Do oral contraceptives improve vocal quality? Limited trial on low-dose formulations.	2003 Apr	12681885
A screening study on the liability of eight different female sex steroids to inhibit CYP2C9, 2C19 and 3A4 activities in human liver microsomes.	2003 Aug	12899669
Influence of the third generation pill controversy on prescriptions for oral contraceptives among first time users: population based study.	2003 Feb 1	12560275
Roles of human liver cytochrome P450 3A4 and 1A2 enzymes in the oxidation of myristicin.	2003 Feb 3	12523956
Auditory brainstem response in premenopausal women taking oral contraceptives.	2003 Jan	12525445
Low-dose combination of flutamide, metformin and an oral contraceptive for non-obese, young women with polycystic ovary syndrome.	2003 Jan	12525441
Gateways to clinical trials.	2003 Jul-Aug	12949633
Effect of oral and transdermal estrogen replacement therapy on hemostatic variables associated with venous thrombosis: a randomized, placebo-controlled study in postmenopausal women.	2003 Jun 1	12730085
The truth about oral contraceptives and venous thromboembolism.	2003 Nov	14686030
Gateways to clinical trials.	2003 Oct	14671684
Effects of oral and transdermal low-dose estrogen therapy on echocardiographic parameters of cardiac function.	2003 Sep	12969696
Associated response in bone and lipids during hormone replacement therapy.	2004 Jan 20	14706764
Comparative evaluation of androgen and progesterone receptor transcription selectivity indices of 19-nortestosterone-derived progestins.	2004 Jun	15261304
[Third-generation oral contraceptives--how big is the risk of venous thrombosis?].	2004 Jun 3	15195157

Patents

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 `Sat Dec 16 16:02:59 GMT 2023` Edited by `admin` on `Sat Dec 16 16:02:59 GMT 2023`
Record UNII	1664P6E6MI
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

GESTODENE

Official Name

English

SH-B-331

Code

English

Gestodene [WHO-DD]

Common Name

English

GESTODENE [MART.]

Common Name

English

SH B 331

Code

English

GESTODENE [MI]

Common Name

English

13-Ethyl-17-hydroxy-18,19-dinor-17α-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