Ethinylestradiol/gestodene - Misplaced Pages

Combination drug Pharmaceutical compound

Ethinylestradiol/gestodene
Combination of
Ethinylestradiol
Gestodene
Ethinylestradiol	Estrogen
Gestodene	Progestogen; Progestin
Clinical data
Trade names	Femodene, Gynera, Harmonet, Lindynette, Logest, Meliane, Minesse, Minulet, Mirelle, others
Other names	EE/GSD
Routes of administration	By mouth
Drug class	Estrogen; Progestin; Progestogen
Legal status
Legal status	US: ℞-only
Identifiers
CAS Number	109852-02-0

Ethinylestradiol/gestodene (EE/GSD), sold under the brand names Femodene and Minulet among others, is a combination of ethinylestradiol (EE), an estrogen, and gestodene (GSD), a progestin, which is used as a birth control pill to prevent pregnancy in women. It is taken by mouth and contains 20 or 30 μg EE and 0.075 mg GSD per tablet. EE/GSD is marketed widely throughout the world.

References

^ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 440–. ISBN 978-92-832-1291-1.
^ Bartke A, Constanti A (9 July 2003). Basic Endocrinology. Taylor & Francis. pp. 128–. ISBN 978-1-135-29850-0.
"Gestodene". drugs.com.

Medical uses

Birth control methods

Sterilization

Tubal ligation (female)
Vasectomy (male)

Hormonal contraception

Combined estrogen–progestogen	Oral pill Extended cycle Pill Contraceptive patch Monthly injections Vaginal ring
Progestogen-only	Multi-month injections Progestogen-only pill Vaginal ring
SERMs	Ormeloxifene

Barrier Methods

Emergency Contraception
(Post-intercourse)

Spermicides

Behavioral

Including vaginal intercourse	Breastfeeding method Calendar (rhythm) methods Fertility awareness methods Withdrawal
Avoiding vaginal intercourse	Non-penetrative sex Abstinence

Experimental

Male contraceptives in development

Active molecules in hormonal contraceptives

Androgens

Estrogens

Progestogens

First generation (estranes)	Ethisterone Etynodiol diacetate Lynestrenol Norethisterone (norethindrone) Norethisterone acetate Norethisterone enanthate Noretynodrel Quingestanol
Second generation	Estranes: Norethisterone enanthate Norgestrienone Gonanes: Levonorgestrel Norelgestromin Norgestrel
Third generation (gonanes)	Desogestrel Etonogestrel Gestodene Norgestimate
Fourth generation	Estranes: Dienogest Norpregnanes: Segesterone acetate Demegestone Nomegestrol acetate Promegestone Trimegestone Spironolactone derivatives: Drospirenone
Pregnanes	Chlormadinone acetate Medrogestone Medroxyprogesterone acetate Megestrol acetate
Miscellaneous	Mifepristone Ulipristal acetate Algestone acetophenide Dydrogesterone Gestrinone Progesterone Proligestone

Estrogens and antiestrogens

Estrogens

ERTooltip Estrogen receptor agonists

Steroidal: Alfatradiol
Certain androgens/anabolic steroids (e.g., testosterone, testosterone esters, methyltestosterone, metandienone, nandrolone esters) (via estrogenic metabolites)
Certain progestins (e.g., norethisterone, noretynodrel, etynodiol diacetate, tibolone)
Clomestrone
Cloxestradiol acetate
Conjugated estriol
Conjugated estrogens
Epiestriol
Epimestrol
Esterified estrogens
Estetrol
Estradiol
Estradiol esters (e.g., estradiol acetate, estradiol benzoate, estradiol cypionate, estradiol enanthate, estradiol undecylate, estradiol valerate, polyestradiol phosphate, estradiol ester mixtures (Climacteron))
Estramustine phosphate
Estriol
Estriol esters (e.g., estriol succinate, polyestriol phosphate)
Estrogenic substances
Estrone
Estrone esters
- Estrone sulfate
- Estropipate (piperazine estrone sulfate)
Ethinylestradiol
- Ethinylestradiol sulfonate
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Prasterone (dehydroepiandrosterone; DHEA)
- Prasterone enanthate
- Prasterone sulfate
Promestriene
Quinestradol
Quinestrol

Progonadotropins

Antiandrogens (e.g., bicalutamide)
GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
Gonadotropins (e.g., FSHTooltip follicle-stimulating hormone, LHTooltip luteinizing hormone)

Antiestrogens

ERTooltip Estrogen receptor antagonists (incl. SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)	Acolbifene Anordrin Bazedoxifene Broparestrol Clomifene Cyclofenil Enclomifene Epitiostanol Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen Toremifene Exclusively antagonistic: Elacestrant Fulvestrant Noncompetitive inhibitors: Trilostane
Aromatase inhibitors	First-generation: Aminoglutethimide Testolactone Second-generation: Fadrozole Formestane Third-generation: Anastrozole Exemestane Letrozole
Antigonadotropins	Androgens/anabolic steroids (e.g., testosterone, testosterone esters, nandrolone esters, oxandrolone, fluoxymesterone) D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride) GnRH agonists (e.g., leuprorelin, goserelin) GnRH antagonists (e.g., cetrorelix, elagolix) Progestogens (e.g., chlormadinone acetate, cyproterone acetate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone acetate, megestrol acetate)
Others	Mixed mechanism of action: Danazol Gestrinone Androstenedione immunogens: Androvax (androstenedione albumin) Ovandrotone albumin (Fecundin)

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

See also: Estrogen receptor modulators; Androgens and antiandrogens; Progestogens and antiprogestogens; List of estrogens

Progestogens and antiprogestogens

Progestogens
(and progestins)

PRTooltip Progesterone receptor agonists

Progesterone derivatives: Progesterone
Quingestrone

Retroprogesterone derivatives: Dydrogesterone
Trengestone

17α-Hydroxyprogesterone (and closely related) derivatives: 17α-Hydroxylated: Acetomepregenol (mepregenol diacetate)
Algestone acetophenide (dihydroxyprogesterone acetophenide)
Anagestone acetate
Chlormadinone acetate
Chlormethenmadinone acetate
Cyproterone acetate
Delmadinone acetate
Flugestone acetate (flurogestone acetate)
Flumedroxone acetate
Hydroxyprogesterone acetate
Hydroxyprogesterone caproate
Hydroxyprogesterone heptanoate
Medroxyprogesterone acetate
Megestrol acetate
Melengestrol acetate
Methenmadinone acetate
Osaterone acetate
Pentagestrone acetate
Proligestone; 17α-Methylated: Medrogestone; Others: Haloprogesterone

19-Norprogesterone derivatives: 17α-Hydroxylated: Gestonorone caproate (gestronol hexanoate)
Nomegestrol acetate
Norgestomet
Segesterone acetate (nestorone, elcometrine); 17α-Methylated: Demegestone
Promegestone
Trimegestone

Testosterone derivatives: Estranes: Danazol
Dimethisterone
Ethisterone

19-Nortestosterone derivatives: Estranes: Allylestrenol
Altrenogest
Dienogest
Etynodiol diacetate
Lynestrenol
Norethisterone (norethindrone)
Norethisterone acetate
Norethisterone enanthate
Noretynodrel
Norgesterone
Norgestrienone
Normethandrone (methylestrenolone)
Norvinisterone
Oxendolone
Quingestanol acetate
Tibolone; Gonanes: Desogestrel
Etonogestrel
Gestodene
Gestrinone
Levonorgestrel
Norelgestromin
Norgestimate
Norgestrel

Spirolactone derivatives: Drospirenone

Others: Anabolic–androgenic steroids (e.g., nandrolone and esters, trenbolone and esters, ethylestrenol, norethandrolone, others)

Antiprogestogens

SPRMsTooltip Selective progesterone receptor modulators	Telapristone Ulipristal acetate
PRTooltip Progesterone receptor antagonists	Aglepristone Mifepristone

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

See also: Progesterone receptor modulators; Androgens and antiandrogens; Estrogens and antiestrogens; List of progestogens

Androgens and antiandrogens

Androgens
(incl. AASTooltip anabolic–androgenic steroid)

ARTooltip Androgen receptor agonists

Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT)
Androstanolone esters
Bolazine capronate
Drostanolone propionate (dromostanolone propionate)
Epitiostanol
Mepitiostane
Mesterolone
Metenolone acetate (methenolone acetate)
Metenolone enanthate (methenolone enanthate)
Stenbolone acetate

19-Nortestosterone derivatives: Bolandiol dipropionate
Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)
Norclostebol
Norclostebol acetate
Oxabolone cipionate (oxabolone cypionate)
Trenbolone acetate
Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)

17α-Alkylated testosterone derivatives: Bolasterone
Calusterone
Chlorodehydromethyltestosterone (CDMT)
Fluoxymesterone
Formebolone
Metandienone (methandienone, methandrostenolone)
Methandriol (methylandrostenediol)
Methandriol bisenanthoyl acetate
Methandriol dipropionate
Methandriol propionate
Methyltestosterone
Methyltestosterone 3-hexyl ether
Oxymesterone
Penmesterol
Tiomesterone (thiomesterone)

17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
Furazabol
Mebolazine (dimethazine)
Mestanolone
Oxandrolone
Oxymetholone
Stanozolol

17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol
Mibolerone
Norethandrolone
Normethandrone (methylestrenolone, normethisterone)
Propetandrol (propethandrol)

17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)

17α-Ethynyltestosterone derivatives: Danazol
Gestrinone
Progestins (e.g., ethisterone (ethynyltestosterone), levonorgestrel, norgestrel, norethisterone (norethindrone), lynestrenol, norgestrienone)
Tibolone

Progesterone derivatives: Medroxyprogesterone acetate

Progonadotropins

Antiestrogens (e.g., tamoxifen, clomifene)
GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
Gonadotropins (e.g., LHTooltip luteinizing hormone, hCGTooltip human chorionic gonadotropin)

Antiandrogens

ARTooltip Androgen receptor antagonists

Steroidogenesis
inhibitors

5α-Reductase	Alfatradiol Dutasteride Epristeride Finasteride Saw palmetto extract
Others	Abiraterone acetate +niraparib Aminoglutethimide Bifluranol Cyproterone acetate Flutamide Ketoconazole Nilutamide Seviteronel Spironolactone

Antigonadotropins

D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
Estrogens (e.g., bifluranol, diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
GnRH agonists (e.g., leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Progestogens (incl., chlormadinone acetate, cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, medroxyprogesterone acetate, megestrol acetate)

Others

Androstenedione immunogens: Androvax (androstenedione albumin)
Ovandrotone albumin (Fecundin)

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

See also: Androgen receptor modulators; Estrogens and antiestrogens; Progestogens and antiprogestogens; List of androgens/anabolic steroids

Pharmacodynamics

Androgen receptor modulators

ARTooltip Androgen receptor

Agonists

5α-Dihydro-19-nortestosterone derivatives: 5α-Dihydronandrolone
5α-Dihydrotrestolone
19-Norandrosterone

17α-Alkylated 5α-dihydrotestosterone derivatives: Androisoxazole
Desoxymethyltestosterone
Furazabol
Mebolazine (dimethazine)
Mestanolone
Metenolone
- Metenolone acetate
- Metenolone enanthate
Methasterone
Methyl-1-testosterone
Methylepitiostanol
Methylstenbolone
Oxandrolone
Oxymetholone
Stanozolol

17α-Alkylated 19-nortestosterone derivatives: Bolenol
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol
Methyldienolone
Methylhydroxynandrolone (MOHN, MHN)
Metribolone
Mibolerone
Norboletone
Norethandrolone
Propetandrol
RU-2309
Tetrahydrogestrinone

17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: 5α-Dihydronorethandrolone
5α-Dihydronormethandrone

17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)

17α-Vinyl-19-nortestosterone derivatives: Vinyltestosterone

17α-Ethynyltestosterone derivatives: Danazol
Ethinylandrostenediol
- Ethandrostate
Ethisterone (ethynyltestosterone)

5α-Dihydro-17α-ethynyltestosterone derivatives: 17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
Dihydroethisterone

17α-Ethynyl-19-nortestosterone derivatives: Δ-Tibolone
Desogestrel
Etonogestrel
Etynodiol
- Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate)
Lynestrenol
- Lynestrenol phenylpropionate
Norethisterone
Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)
Norgestrel
Norgestrienone
Quingestanol
- Quingestanol acetate
Tibolone

5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
5α-Dihydronorethisterone

Progesterone derivatives: 6α-Methylprogesterone
Medroxyprogesterone acetate
Megestrol acetate

Others/unsorted: 3-Keto-5α-abiraterone
5α-Androstane
Alternariol
Cl-4AS-1
Drupanol
Trilostane
ZM-182345

SARMsTooltip Selective androgen receptor modulator

Nonsteroidal: 198RL26
ACP-105
AC-262,536
Acetothiolutamide
Acetoxolutamide
Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
BMS-564,929
DTIB
Enobosarm (ostarine, MK-2866, GTx-024, S-22)
FTBU-1
GLPG-0492
GSK2881078
GSK-4336A
GSK-8698
LG121071 (LGD-121071)
LGD-2226
LGD-2941 (LGD-122941)
LGD-3303
LGD-4033
LY305
JNJ-26146900
JNJ-28330835
JNJ-37654032
OPK-88004 (LY-2452473, TT-701)
ORM-11984
PF-06260414
R-1
RU-59063
S-1
S-23
S-40503
S-101479
Vosilasarm

Steroidal: EM-9017
MK-0773
TFM-4AS-1
YK-11

Antagonists

Nonsteroidal: 5N-Bicalutamide
AA560
Antarlides
Arabilin
Apalutamide
Atraric acid
AZD-3514
Bakuchiol
Bavdegalutamide
BAY-1024767
Bicalutamide
Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S)
BMS-501949
BMS-570511
BMS-641988
CH5137291
Cimetidine
Cioteronel
Cyanonilutamide
Darolutamide
DDT (via metabolite p,p’-DDE)
Dieldrin
DIMP
Endosulfan
Enzalutamide
EPI-001
Fenarimol
Flutamide
Hydroxyflutamide
Inocoterone
Inocoterone acetate
Ketoconazole
Ketodarolutamide
Lavender oil
LG-105
LG-120907
LGD-1331
Linuron
Masofaniten
Methiocarb
N-Butylbenzenesulfonamide
N-Desmethylapalutamide
N-Desmethylenzalutamide
Nilutamide
ONC1-13B
Pentomone
PF-998425
Phenothrin
Prochloraz
Procymidone
Proxalutamide
Pyrilutamide
Ralaniten (EPI-002)
Ralaniten acetate (EPI-506)
RD-162
Rezvilutamide
Ro 2-7239
Ro 5-2537
RU-22930
RU-56187
RU-57073
RU-58642
RU-58841
Seviteronel
Thalidomide
Topilutamide (fluridil)
Valproic acid
Vinclozolin
YM-580
YM-92088
YM-175735

GPRC6A

Agonists	Cations (incl. aluminium, calcium, gadolinium, magnesium, strontium, zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin SHBGTooltip Sex hormone-binding globulin Testosterone

See also: Receptor/signaling modulators; Androgens and antiandrogens; Estrogen receptor modulators; Progesterone receptor modulators; List of androgens and anabolic steroids

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

Progesterone receptor modulators

PRTooltip Progesterone receptor

Agonists

Retroprogesterone derivatives: 20α-Dihydrodydrogesterone
20α-Dihydrotrengestone
DU-41164
DU-41165
Dydrogesterone
Retroprogesterone
Ro 6-3129
Trengestone

Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
- Ethandrostate
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate)
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g., trenbolone acetate, trenbolone enanthate)
Trendione
Trestolone
Trestolone acetate

Spirolactone derivatives: Canrenoic acid
Canrenone
Drospirenone
Mespirenone
Potassium canrenoate
Prorenone
SC-5233 (spirolactone)
SC-8109
Spironolactone
Spirorenone

Nonsteroidal: 3,8-Dihydrodiligustilide
LG-2527
LG-100128
Riligustilide
RWJ-26819
RWJ-49853
RWJ-60130
Tanaproget
ZM-182345

Unknown: ORG-47241
ORG-201745

Mixed
(SPRMsTooltip Selective progesterone receptor modulators)

Antagonists

mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)

Agonists	5α-Dihydroprogesterone 5β-Dihydroprogesterone 11-Deoxycortisone (21-hydroxyprogesterone) 11-Deoxycortisol (17α,21-dihydroxyprogesterone) 17α-Hydroxyprogesterone Allopregnanolone Mifepristone Pregnenolone Progesterone
Antagonists	Mifepristone

See also: Receptor/signaling modulators; Progestogens and antiprogestogens; Androgen receptor modulators; Estrogen receptor modulators; List of progestogens

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References