Ethinylestradiol/norelgestromin

Ethinylestradiol/norelgestromin
Combination of
Ethinylestradiol	Estrogen
Norelgestromin	Progestogen
Clinical data
Trade names	Ortho Evra, Xulane
MedlinePlus	a602006
Pregnancy category	US: X (Contraindicated)
Routes of administration	Transdermal (patch)
Legal status
Legal status	US: ℞-only
Identifiers
CAS Number	396715-57-4
PubChem CID	91758695
ChemSpider	None
KEGG	D10839^Y

Ethinylestradiol/norelgestromin (brand names Ortho Evra, Evra, Xulane) is a contraceptive patch containing the estrogen ethinylestradiol and the progestin norelgestromin which is marketed in the United States, Canada, Europe, and elsewhere in the world.^[1] As of December 2016, the Ortho Evra product has been discontinued in the U.S. while the Xulane product continues to be marketed in this country.^[1]

References

1 2 "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved 22 December 2016.

Birth control methods (G02B, G03A)

Comparison

Behavioral

Avoiding vaginal intercourse: Abstinence
Anal sex
Masturbation
Non-penetrative sex
Oral sex
Including vaginal intercourse: Breastfeeding infertility (LAM)
Calendar-based methods (rhythm, etc.)
Fertility awareness (Billings ovulation method
Creighton Model, etc.)
Withdrawal

Barrier and / or
spermicidal

Hormonal
(formulations)

Combined	Contraceptive patch Extended cycle Injectable NuvaRing Oral / 'the pill'
Progestogen-only	LARC (Depo-Provera Implanon/Nexplanon Norplant/Jadelle) Progestogen-only pill Progesterone vaginal ring

Anti-estrogen

Ormeloxifene (Centchroman)

Post-intercourse

Emergency contraception (pills or copper IUD) (Ulipristal acetate
Yuzpe regimen)

Intrauterine device

IUD with copper
- Paragard
IUD with progestogen (Mirena)

Abortion

Medical (RU-486/abortion pill)
Surgical

Sterilization

Female: Essure
Tubal ligation
Male: Vasectomy

Experimental

Reversible inhibition of sperm under guidance (Vasalgel)

Hormonal contraception (G02B, G03A)

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: 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

Estrogen receptor modulators

Agonists	Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodo-E2 16α-LE2 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17β-Dihydroequilenin 17β-Dihydroequilin Abiraterone Abiraterone acetate 17α-Estradiol (alfatradiol) Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate DHEA DHEA-S Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Estetrol Estradiol Estradiol esters Lipoidal estradiol Polyestradiol phosphate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol esters Estrofurate Estromustine Estrone Estrone esters Estropipate Etamestrol (eptamestrol) Ethinylestradiol Ethinylestradiol sulfonate Ethinylestriol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene Quinestradol Quinestrol Nonsteroidal: (R,R)-THC (S,S)-THC 2,8-DHHHC AC-186 Allenestrol Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol Dienestrol diacetate Diethylstilbestrol Diethylstilbestrol esters Dimestrol (dianisylhexene) Doisynoestrol (fenocycline) Doisynolic acid Efavirenz ERB-196 (WAY-202196) Erteberel (SERBA-1, LY-500307) Estrobin (DBE) Fenestrel FERb 033 Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol esters ICI-85966 (Stilbostat) Mestilbol Methallenestril Methestrol Methestrol dipropionate Paroxypropione Pentafluranol Phenestrol Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene (triphenylpropene) WAY-166818 WAY-200070 WAY-214156 Unknown/unsorted: ERB-26 ERA-45 ERB-79 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, 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) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Others (e.g., agnuside, rotundifuran)
Mixed (SERMs)	2-Phenylbenzofuran 2-Phenylbenzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Elacestrant Chlorotrianisene Clomifene Clomifenoxide Cyclofenil D-15413 Droloxifene Enclomifene Endoxifen Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW-7604 ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LN-1643 LN-2299 LY-117018 Menerba Miproxifene Miproxifene phosphate Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Pipendoxifene Raloxifene Spironolactone SS1010 Tamoxifen TAS-108 (SR-16234) Tibolone Toremifene Trioxifene TZE-5323 Y-134 Zindoxifene Zuclomifene
Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrol acetate Epitiostanol ERA-90 ERB-88 Fulvestrant (ICI-182780) Glyceollins (I, II, III, IV) ICI-164384 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-58668 SS1020 TAS-108 (SR-16234) ZB716 ZK-164015 ZK-191703

GPER

Agonists

Antagonists

CCL18
Estriol
G-15
G-36
MIBE

See also: Receptor/signaling modulators; Androgenics; Glucocorticoidics; Mineralocorticoidics; Progestogenics; Steroid metabolism modulators; List of estrogens

Progesterone receptor modulators

Agonists	Progesterone derivatives: 5α-Dihydroprogesterone 9α-Bromo-11-ketoprogesterone 11-Dehydroprogesterone 11-Deoxycorticosterone 16α-Hydroxyprogesterone 20α-Dihydroprogesterone Dimepregnen Diosgenin P1-185 Progesterone Quingestrone Retroprogesterone derivatives: Dydrogesterone Retroprogesterone Ro 6-3129 Trengestone 17α-Substituted progesterone derivatives: 6α-Methyl-17α-bromoprogesterone 15β-Hydroxycyproterone acetate 17α-Hydroxyprogesterone (hydroxyprogesterone) 17α-Methylprogesterone Acetomepregenol (mepregenol diacetate) Algestone Algestone acetonide Algestone acetophenide Anagestone Anagestone acetate Butagest (buterol) Chlormadinone Chlormadinone acetate Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clomegestone acetate Cyproterone acetate Delmadinone Delmadinone acetate Edogestrone Flugestone Flugestone acetate Flumedroxone Flumedroxone acetate Gestaclone Haloprogesterone Hydromadinone Hydromadinone acetate Hydroxyprogesterone acetate Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate) Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate) Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Megestrol Megestrol acetate Melengestrol Melengestrol acetate Mometasone Mometasone furoate Osaterone Osaterone acetate Pentagestrone Pentagestrone acetate Pentarane A Proligestone 19-Norprogesterone derivatives: 19-Norprogesterone Amadinone Amadinone acetate Demegestone Gestadienol Gestadienol acetate Gestonorone caproate (gestronol hexanoate) Gestronol (gestonorone) Nomegestrol Nomegestrol acetate Norgestomet ORG-2058 Oxogestone Oxogestone phenpropionate (xinogestone) Promegestone Segesterone Segesterone acetate (nestorone) Trimegestone Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone 6,6-Difluoronorethisterone acetate Allylestrenol Altrenogest Chloroethynylnorgestrel Cingestol Danazol Desogestrel Dienogest Ethisterone Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel butanoate Lynestrenol Metynodiol Metynodiol diacetate Norelgestromin Norethisterone (norethindrone) Norethisterone acetate Norethisterone acetate oxime 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 Bolandiol Bolandiol dipropionate Bolandione Dimethisterone Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate 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) Tetrahydrogestrinone Trenbolone (trienolone) Trestolone Trestolone acetate Spirolactone derivatives: Canrenoic acid Canrenone Drospirenone Mespirenone Potassium canrenoate SC-5233 (spirolactone) SC-8109 Spironolactone Spirorenone Nonsteroidal: 3,8-Dihydrodiligustilide LG-100128 Riligustilide RWJ-26819 RWJ-49853 RWJ-60130 Tanaproget ZM-182345
Mixed (SPRMs)	Steroidal: Asoprisnil Asoprisnil ecamate Guggulsterone J1042 LG-120838 Mifepristone ORG-31710 ORG-33628 Telapristone Ulipristal acetate Vilaprisan ZK-137316 Nonsteroidal: Apigenin Kaempferol LG-120920 Naringenin PRA-910 Syringic acid
Antagonists	Steroidal: Aglepristone Lilopristone Lonaprisan Onapristone RTI 3021–022 Toripristone Zanoterone Nonsteroidal: LG001447 LG-100127 LG-100128 LG-120830 LG-121046 Valproic acid ZM-150271 ZM-172406

mPR
(PAQR)

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; Androgenics; Estrogenics; Glucocorticoidics; Mineralocorticoidics; Steroid metabolism modulators; List of steroidal progestogens

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Ethinylestradiol/norelgestromin

See also

References