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Estradiol benzoate/estradiol valerate/hydroxyprogesterone caproate

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Combination drug

Pharmaceutical compound

Estradiol benzoate /
estradiol valerate /
hydroxyprogesterone caproate
Combination of
Estradiol benzoate	Estrogen
Estradiol valerate	Estrogen
Hydroxyprogesterone caproate	Progestogen
Clinical data
Trade names	Sin-Ol
Other names	EB/EV/OHPC
Routes of administration	Intramuscular injection

Estradiol benzoate/estradiol valerate/hydroxyprogesterone caproate (EB/EV/OHPC), sold under the brand nameSin-Ol, is acombination medication ofestradiol benzoate (EB), anestrogen,estradiol valerate (EV), an estrogen, andhydroxyprogesterone caproate (OHPC), aprogestin, which was reportedly used as acombined injectable contraceptive in women in the early 1970s.^[1] It contained 1 mg EB, 10 mg EV, and 250 mg OHPC inoil solution, was provided in the form of 3 mLampoules, and was administered byintramuscular injection at regular intervals.^[1] The medication was manufactured by thepharmaceutical company Reuffer inMexico.^[1]

References

[edit]

^^a ^b ^cRudel HW, Kinel FA (September 1972). "Oral Contraceptives. Human Fertility Studies and Side Effects". In Tausk M (ed.).Pharmacology of the Endocrine System and Related Drugs: Progesterone, Progestational Drugs and Antifertility Agents. Vol. II. Pergamon Press. pp. 385–469.ISBN 978-0080168128.OCLC 278011135.

Estrogens andantiestrogens

Estrogens

ERTooltip Estrogen receptor agonists

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 Imlunestrant 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 andantiprogestogens

Progestogens
(andprogestins)

PRTooltip Progesterone receptoragonists

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 andesters,trenbolone andesters,ethylestrenol,norethandrolone, others)

Antiprogestogens

SPRMsTooltip Selective progesterone receptor modulators	Telapristone^§ Ulipristal acetate
PRTooltip Progesterone receptorantagonists	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

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists	Steroidal:2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g.,testosterone andesters,methyltestosterone,metandienone (methandrostenolone),nandrolone andesters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent-Estradiol Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estradiol esters Lipoidal estradiol Polyestradiol phosphate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol esters Polyestriol phosphate Estrofurate Estrogenic substances Estromustine Estrone Estrone esters Estrone methyl ether Estropipate Etamestrol (eptamestrol) Ethinylandrostenediol Ethandrostate Ethinylestradiol Ethinylestradiol 3-benzoate Ethinylestradiol sulfonate Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Nonsteroidal:(R,R)-THC (S,S)-THC 2,8-DHHHC β-LGND1 β-LGND2 (GTx-878) AC-186 Allenestrol Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Butestrol Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol Dienestrol diacetate Diethylstilbestrol Diethylstilbestrol esters Dimestrol (dianisylhexene) Dimethylstilbestrol Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Elacestrant 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) M2613 meso-Butestrol meso-Hexestrol Mestilbol Methallenestril Methestrol Methestrol dipropionate Paroxypropione Pentafluranol Phenestrol Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-3296 SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene (triphenylpropene) WAY-166818 WAY-169916 WAY-200070 WAY-204688 (SIM-688) WAY-214156 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)	2-Phenylbenzofuran 2-Phenyl-1-benzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Camizestrant Chlorotrianisene Clomifene Clomifenoxide CN-55945-27 Cyclofenil D-15413 Desmethylchlorotrianisene 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 MRL-37 Nafoxidine Nitromifene NNC 45-0095 NNC 45-0320 NNC 45-0781 NNC 45-1506 Ormeloxifene Ospemifene Panomifene Pipendoxifene Promensil Raloxifene Rimostil (P-081) Spironolactone SS1010 Tamoxifen TAS-108 (SR-16234) Toremifene Trioxifene TZE-5323 U-11555A U-11634 Y-134 Zindoxifene Zuclomifene
Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrol acetate EM-800 (SCH-57050) Epitiostanol ERA-90 ERB-88 Fulvestrant (ICI-182780) Glyceollins (I,II,III,IV) ICI-164384 MDL-101906 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-39411 RU-58668 SS1020 TAS-108 (SR-16234) ZB716 ZK-164015 ZK-191703 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	Progesterone derivatives:3β-Dihydroprogesterone 5α-Dihydroprogesterone 6α-Methylprogesterone 9α-Bromo-11-ketoprogesterone 11-Dehydroprogesterone 11-Deoxycorticosterone 16α-Hydroxyprogesterone 17α-Methyl-11-deoxycorticosterone acetate 20α-Dihydroprogesterone 20β-Dihydroprogesterone Dimepregnen Diosgenin P1-185 Progesterone Progesterone 3-acetyl enol ether Quingestrone Retroprogesterone derivatives:20α-Dihydrodydrogesterone 20α-Dihydrotrengestone DU-41164 DU-41165 Dydrogesterone Retroprogesterone Ro 6-3129 Trengestone 17α-Substituted progesterone derivatives:6α-Methyl-17α-bromoprogesterone 15β-Hydroxycyproterone acetate 16-Methylene-17α-hydroxyprogesterone acetate 17α-Bromoprogesterone 17α-Hydroxyprogesterone (hydroxyprogesterone) 17α-Methylprogesterone Acetomepregenol (mepregenol diacetate) Algestone Algestone acetonide Algestone acetophenide Anagestone Anagestone acetate Bromethenmadinone Bromethenmadinone acetate Butagest (buterol) Chlormadinone Chlormadinone acetate Chlormadinone caproate Chlormethenmadinone Chlormethenmadinone acetate Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clomegestone acetate Cymegesolate Cyproterone acetate Delmadinone Delmadinone acetate Edogestrone Flugestone Flugestone acetate Fluorometholone Fluorometholone acetate Flumedroxone Flumedroxone acetate Fluoromedroxyprogesterone acetate Gestaclone Gestobutanoyl Haloprogesterone Hydromadinone Hydromadinone acetate Hydroxyprogesterone acetate Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate) Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate) Hydroxyprogesterone heptanoate benzilic acid hydrazone Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Medroxyprogesterone caproate Megestrol Megestrol acetate Megestrol caproate Melengestrol Melengestrol acetate Methenmadinone Methenmadinone acetate Methenmadinone caproate Mometasone Mometasone furoate Osaterone Osaterone acetate Pentagestrone Pentagestrone acetate Pentarane A Proligestone Triamcinolone acetonide 19-Norprogesterone derivatives:17α-Methyl-19-norprogesterone 18-Methylsegesterone acetate 19-Norprogesterone Amadinone Amadinone acetate Demegestone Fluoro ethyl norprogesterone Fluoro furanyl norprogesterone Gestadienol Gestadienol acetate Gestonorone acetate (gestronol 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 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)	Steroidal:Dihydroethisterone 5α-Dihydrolevonorgestrel 5α-Dihydronorethisterone Asoprisnil Asoprisnil ecamate Guggulsterone J1042 LG-120838 Metapristone (RU-42633) Mifepristone (RU-486) ORF-9371 ORF-9326 ORG-31710 ORG-33628 RMI-12936 Telapristone Ulipristal acetate Vilaprisan ZK-137316 Nonsteroidal:Apigenin Kaempferol LG-120920 Naringenin PRA-910 Syringic acid
Antagonists	Steroidal:Aglepristone Lilopristone Lonaprisan Onapristone ORG-31710 ORG-31806 ORG-33628 RTI 3021–022 Toripristone Zanoterone Nonsteroidal:Darolutamide LG-001447 LG-100127 LG-100128 LG-120830 LG-121046 Valproic acid ZM-150271 ZM-172406

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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