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

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
The new pills: awaiting the next generation of oral contraceptives.	1992 Sep-Oct	1426186
Pro-inflammatory effects of oestrogens during use of oral contraceptives and hormone replacement treatment.	2002 Aug	12616983
Genetic polymorphisms modify the response of factor VII to oral contraceptive use: an example of gene-environment interaction.	2002 Aug	12616980
Determination of steroid hormones in oral contraceptives by high-performance liquid chromatography.	2002 Jul	12149967
Clinical risk factors for venous thromboembolus in users of the combined oral contraceptive pill.	2002 Jun	12047488
Can changes in sex hormone binding globulin predict the risk of venous thromboembolism with combined oral contraceptive pills?	2002 Jun	12047300
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
Changes in prescription patterns of oral contraceptives in a northern Italian province: relation with venous thromboembolism.	2003 Apr	12812381
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
Carpal tunnel syndrome and oral contraceptive drugs: risk or protective factor?	2003 Dec	14641645
Classification and pharmacology of progestins.	2003 Dec 10	14670641
Venous and arterial thrombosis during oral contraceptive use: risks and risk factors.	2003 Feb	15199494
Changes of hemostatic variables during oral contraceptive use.	2003 Feb	15199493
The effect of progesterone and synthetic progestins on serum- and estradiol-stimulated proliferation of human breast cancer cells.	2003 Feb	12734785
A randomized placebo-controlled study of the effect of transdermal vs. oral estradiol with or without gestodene on homocysteine levels.	2003 Feb	12568832
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
Thromboembolic disease and present oral contraception.	2003 Jan	12643323
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
Lack of difference among progestins on the anti-atherogenic effect of ethinyl estradiol: a rabbit study.	2003 Jul	12832362
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 effects of seven monophasic oral contraceptive regimens on hemostatic variables: conclusions from a large randomized multicenter study.	2003 Mar	12618251
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 May	12742559
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 May	12742557
The truth about oral contraceptives and venous thromboembolism.	2003 Nov	14686030
Effects of low-dose oral and transdermal estrogen replacement therapy on hemostatic factors in healthy postmenopausal women: a randomized placebo-controlled study.	2003 Nov	14634544
Oral, more than transdermal, estrogen therapy improves lipids and lipoprotein(a) in postmenopausal women: a randomized, placebo-controlled study.	2003 Nov-Dec	14627865
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
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 Apr	15306751
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 Apr	15033409
Pharmacological profile of progestins.	2004 Apr 15	15063480
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 Aug	15229206
Third generation oral contraceptive use and cardiovascular risk factors.	2004 Feb	15019538
Adrenal adenoma and normal androgen levels in a young woman with polycystic ovaries: a case of idiopathic hirsutism?	2004 Jan	15053246
Associated response in bone and lipids during hormone replacement therapy.	2004 Jan 20	14706764
A prospective open-label study to evaluate the effects of the oral contraceptive Harmonet (gestodene75/EE20) on body fat.	2004 Jul	15208055
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 Jun	15497494
The role of combined oral contraceptives in the management of acne and seborrhea.	2004 Jun	15449823
Comparative evaluation of androgen and progesterone receptor transcription selectivity indices of 19-nortestosterone-derived progestins.	2004 Jun	15261304
Serum resistin levels in women taking combined oral contraceptives containing desogestrel or gestodene.	2004 Jun	15157792
[Third-generation oral contraceptives--how big is the risk of venous thrombosis?].	2004 Jun 3	15195157
[The effectiveness and acceptability of oral contraceptives (Logest), containing 20 micrograms ethinylestradiol and 75 micrograms gestodene].	2004 Mar	15181879
Oral contraception does not alter single dose saquinavir pharmacokinetics in women.	2004 Mar	14998420
Sexual behavior of women taking low-dose oral contraceptive containing 15 microg ethinylestradiol/60 microg gestodene.	2004 Mar	14969672
Risk of venous thromboembolic disease associated with hormonal contraceptives and hormone replacement therapy: a clinical review.	2004 Oct 11	15477430

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

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