Estradiol benzoate E 781 Vagifem (Novo Nordisk; RhBne-Poulenc Rorer) F: Estrofem (Novo Nordisk) Oestrogel (Besins- Iscovesco) Prkmarin (Wyeth-Ayerst)- comb. Trisequens (Novo Nordisk)-comb. Estradiol benzoate (Oestradiolbenzoat) GB: Cycloprogynova (ASTA USA: Medica) Hormonin (Shire) Trisequens (Nova)-comb. numerous generics I: Estraderm (Ciba-Geigy) Progynon (Schering) J: Ovahormon Pasta (Teikoku Zoki) Alora (Procter & Gamble) Climara (Berlex) Estraderm (Novartis) Estring (Pharmacia & Upjohn) Estro-Plus (Rocky Mtn.)- comb. FemPatch (Parke Davis) Vivelle (Novartis) ATC: G03CA Use: estrogen RN: 50-50-0 MF: C25H2,0, MW: 376.50 EINECS: 200-043-7 CN: (17P)-estra-1,3,5(10)-triene-3,17-diol 3-benzoate eatmdiol (9. v.) benzoyl chloride I Estradiol benzoate Referencefs): a US 2 054 271 (Schering Corp.; 1933; D-prior. 1932). GB 485 388 (Lab. Franq. de ChimiothCrapie; appl. 1936). b DRP 641 994 (Schering AG; appl. 1932). alternative synthesis: US 2 225 419 (Schering Corp.; 1940; D-prior. 1937). US 2 156 599 (Ciba; 1939; CH-prior. 1936). Formulation(s): amp. 2 mglml, 10 mglml, 50 mg12 ml; sol. 5 mg1100 ml Trade Namefs): D: Alpicort F (Wo1ff)-comb. . Jephagynon (Wo1ff)-comb. Ney Normin (vit0rgan)- comb. Syngynon (Jenapharm) I? Benzo-Gynoestryl (Roussel) Dermestril (Sanofi Winthrop) Estraderm (Novartis) Estreva (ThCramex) Estrofem (Specia) Menorest (Specia) Oesclim (Fournier) GB: Benztrone (Paines & Byrne); wfm I: Benztrone (Amsa) Duo-Ormogyn (Amsa)- comb. Menovis (Parke Davis)- comb. Progynon (Schering) J: Estradin Susp. (Santen- Yamanouchi) Femihormon (Tokyo Hosei) Follikelmon (Kyorin) Ovahormon Benzoat Susp. (Teikoku Zoki) Pelanin Inj. (Mochida) Profollior B (Schering) Progynon B (Nihon Schering) USA: Gynetone Inj. (Schering)- comb.; wfm Testradiol (Consolidated Midland)-comb.; wfm Testradiol (Truxton)-comb.; wfm Trimonal (Vitacine)-comb.; wfm numerous generics; wfm 782 E Estradiol cypionate Estradiol cypionate (Oestradiol- 17-cyclopentylpropionat) ATC: G03C Use: estrogen RN: 313-06-4 MF: C,,H,,O, MW: 396.57 EINECS: 206-237-8 LD,,: >I glkg (M, i.p.) CN: (17P)-estra- 1,3,5(IO)-triene-3,17-diol 17-cyclopentanepropanoate eslrodiol 3-benzoate 3-cyclopentyl- (9. v.1 propionic acid estrodiol (9. v.1 3-cyc~opentyl- propionyl chloride Reference(s): a FR 1 215 503 (Lab. Rolland; appl. 1955). h US 2 61 1 773 (Upjohn; 1952; prior. 195 1). For-mulation(s): amp. 10 mg (1 mglml), 25 mg (5 mglml), 50 mg (5 mglml) Trade Nume(s): D: Femovirin Amp. (Albert- I: Cicloestradiolo (Farmigea); Neoginon Depositum Rousse1)-comb.; wfm wfm (Lusofannaco); wfm F: Oestradiol-retard Rolland Estradiolo Depositum (L'Htpalrol); wfm (Orma): wfrn F Estradid valerate E 783 J: Depo-Estradiol (Upjohn- USA: Depo-Estradiol (Upjohn); Kodama) wfm Estradiol valerate ATC: G03CA Use: estrogen RN: 979-32-8 MF: C&& MW: 356.51 EINECS: 213-559-2 LD,,: 1224 mglkg (M, p.0.) CN: (17P)-estra- 1,3,5(IO)-triene-3,17-diol 17-pentanoate 17P-estradiol valeric anhydride (4. v.1 estrodiol divalerate (I) I &tradioI valerate Reference(s): US 2 205 627 (Ciba; 1940; CH-prior. 1936). US 2 233 025 (Ciba; 1941; CH-prior. 1936). use as antidepressant: DOS 2 758 549 (Schering AG; appl. 23.12.1977). Formulafion(s): amp. 5 mglml, 10 mglml; drg. 1 mg, 2 mg; drops 2 mg10.5 ml; f. c. tabl. 2 mg; tabl. 2 mg, 4 mg Trade Name(s): Gynokadin (Kade) Merimono (Novartis Pharma) - Progynon Depot (Schering) Progynova (Schering) numerous combination preparations Climkne (Schering)-comb. Divina (1nnothCra)-comb. Progynova (Schering) Cyclo-Progynova (ASTA Medica)-comb. Progynova (Schering) Gravibinan (Schering)- comb. Gynodian Depot (Schering)-comb. Progynon Depot (Schering) Progynova (Schering) J: Pelanin Depot (Mochida) Progynon Depot (Nihon Schering) USA: Ardefem (Burgin-Arden); wfm Atladiol (Atlas); wfm Delestrogen (Squibb); wfm Depogen (Hyrex); wfm Depogen (Sig); wfm Dioval (Keene); wfm Ditate DS (Savage); wfm Dura-Estate (Ries); wfm Dura-Estradiol (Myers- Carter); wfm Dura-Estradiol (Ruckstuhl); wfm Duratrad (Ascher); wfm Estate (Savage); wfm Estral-L (Pasadena Res.); wfm Estraval (Kay); wfm Estravel-P.A. (Tutag); wfm Feminate (Western Res.); wfm Femogen L.A. (Fellows); wfm Repo-Estra (Central); wfm Repo-Estro Med (Medics); wfm Reposo E (Canfield); wfrn Retestrin (Rocky Mtn.); wfm Span-Est (Scrip); wfm Testaval (Legere); wfm Valergen (Hyrex); wfm 784 E Estradiol undecylate numerous combination preparations; wfm Estradiol undecylate (Oestradiolundecanoat) ATC: G03CA Use: estrogen RN: 3571-53-7 MF: C2,H,03 MW: 440.67 EINECS: 222-677-3 CN: (1 7p)-estra- 1 ,3,S(IO)-triene-3,l'i'-diol 17-undecanoate 176-estrodiol undeconoyl estrodiol diundeconoote (1) US 2 990 414 (Syntex; 27.1.1 961; appl. 18.3.1948; MEX-prior. 26.3.1957). Fornzulation(s): amp. 100 rnglml Trade Name(s): F: Oestradiol-Retard J: Depogin (Shionogi) ThCramex (Thkramex) USA: Delestrec (Squibb); wfm Estramustine phosphate ATC: LOlAA Use: antineoplastic RN: 489 1- 15-0 MF: C2,H,2C12N0,P MW: 520.39 EINECS: 225-5 12-3 CN: (I7~)-estra-l,3,5(10)-tr1ene-3,17-diol 3-[bis(2-chloroethyl)carbamate] 17-(dihydrogen phosphate) disodium salt RN: 52205-73-9 MF: C2,H&I,NNa,O6P MW: 564.35 0 cLJ b 1 estradiol bis(2-chloro- N-chloroforrnyl- ethy1)omine bis(2-chloro- ethy1)arnine 1 Estriol E 785 Reference(s): GB 1 016 959 (Leo; appl. 9.4.1963; valid from 24.3.1964). US 3 299 104 (Leo; 17.1.1967; GB-prior. 9.4.1963). GB 1 523 035 (Leo; appl. 10.3.1976; valid from 8.3.1977). complex compounds with alcohols (for purification): US 4 115 414 (Leo; 19.9.1978; GB-prior. 10.3.1976). DE2710 293 (Leo; appl. 9.3.1977; GB-prior. 10.3.1976) Formulation(s): cps. 151.8 mg, 303.6 rng (as disodiurn salt); vial 621 rng (as meglumine salt) Trade Name(s): D: Cellmustin (cell pharm) F: Estracyt (Pharmacia & J: Estracyt (Nippon Shinyaku) Estracyt (Pharmacia & Upjohn). USA: Erncyt (Pharmacia & Upjohn) GB: Estracyt (Pharmacia & Upjohn; as sodium salt) Multosin (Takeda) Upjohn) Prostamustin (Azupharma) I: Estracyt (Farmitalia) 1 Estriol ATC: G03CA04 Use: estrogen RN: 50-27-1 MF: C,,HUO3 MW: 288.39 EINECS: 200-022-2 LD,,: >2 gkg (R, p.0.) CN: (16a,l7~)-estra-l,3,5(10)-triene-3,16,17-triol isopropenyl 3-rnethoxyestra-1,3.5(10).16-tetra- acetate en-1 7-01 acetate (I) I - perbenzoic acid olonote 16a.17~-epoxy-3-rnethoxy- Estriol estro-1,3.5(10)-trien-17-01 acetate Reference(s): Gallagher, T.F.: J. Am. Chem. Soc. (JACSAT) 76, 2943 (1954). a 786 E Estriol succinate alternative syntheses: Butenandt, A.;. Schaffler, E.L.: Z. Naturforsch. (ZNTFA2) 1, 82 (1946). Huffmann, M.N. et al.: Science (Washington, D.C.) (SCIEAS) 100,312 (1944). Huffmann, M.N.; Lott, M.H.: J. Am. Chem. Soc. (JACSAT) 69, 1835 (1947). US 1 967 351 (Pres. and Board of Trustees of St. Louis; 1934; appl. 1930). The Merck Index. 12th Ed., 63 1 (Rahway 1996). Formulnrion(s): cream 0.5 mg/g; drg. 1 mg; f. c. tabl. 2 mg; ovula 0.03 mg, 0.5 mg; tabl. I mg, 2 mg Trade Name(s): D: Cordes (Ichthyol) Estiol (Jenapharm) Gynasan (Bastian-Werk)- comb. Oekolp (Kade) Ortho-Gynest (Janssen- Cilag) Ovestin (Organon) Ovo-Vinces 200 (Wolff) Synapause (Nourypharma) Xapro (Jenapharm) numerous combination preparations F: Gydrelle (Iprad) Physiogine (Organon) Trophicrkme (Sanofi J: Winthrop) Trophigil (Sanofi Winthrop)-comb. GB: Hormonin (Shire)-comb. Ortho-Gynest (Janssen- USA:. Cilag) Ovestin (Organon) Trisequens (Novo Nordisk)-comb. I: Colpogyn (Angelini) Ortho Gynest Depot (Cilag) Ovestin (Organon Italia) Climatol (Santen) Estriel (Mochida) Molin (Teikoku Zoki) Ovapause (Organon) Season (Teikoku Zoki) Estro Plus Tab. (Rocky Mtn.)-comb.; wfm Hormonin (Camrick)- comb.; wfm Estriol succinate ATC: G03C Use: estrogen RN: 514-68-1 MF: C2,H3,0, MW: 488.53 EINECS: 208-185-1 CN: (1 6a, 17P)-estra- 1,3,5(10)-triene-3,16,17-trio1 16,17-bis(hydrogen butanedioate) disodium salt RN: 113-22-4 MF: C,,H,,,Na,O, MW: 532.50 Rejerence(s): GB 879 014 (Organon; appl. 26.5.1960; NL-prior. 29.5.1959). estriol succinic Formulation(s): tabl. 2 mg, 4 mg (as disodium salt); vial 20 mg (as disodium salt) Estriol succinate Trade Natne(s): D: Orgastyptin (Organon Synapause (Nourypharma); F: Synapause (Organon); wfm Teknika); wfm wfm I: Ovestin (Organon Italia) (4. v.) anhydride Estrone E 787 Estrone (Oestron) ATC: G03CA07; G03CC04 Use: estrogen RN: 53-16-7 MF: Cl,HzzOz MW: 270.37 EINECS: 200-164-5 CN: 3-hydroxyestra-1,3,5(10)-trien-17-one oxide androatenolone 3.17-dioxo-1.4- ondrostadiene (n) $17-dioxo-1.4.6- ondrostatnene (from 3,17-dioxo- 1,4-androstadiene) 3-ocetoxy-19-hydroxycholesterol (from cholesterol) microarganism CSD-I 0 . Estrone El H,C~SO,H 1 + Ho-oH - -, Estrone lithium, biphenyl. diphenylmethane n ethylene glycol Reference(s): a,b Ehrhart, Ruschig, 111, 3 15. c Sih, Ch. et al.: J. Am. Chem. Soc. (JACSAT) 87, 2765 (1965). 788 E Etacrvnic acid starting material: Kalvoda, J. et al.: Helv. Chim. Acta (HCACAV) 46, 1361 (1963). d Dryden, H.L. et al.: J. Am. Chem. Soc. (JACSAT) 86,742 (1964). production of conjugated estrogens: US 2 565 115 (Squibb; 1951; prior. 1948). US 2 720 483 (Oh Mathieson; 1955; prior. 1951). US 4 154 820 (Akzona; 15.5.1979; prior. 26.9.1977, 23.2.1976). toral syntheses: EP 37 973 (Hoechst; appl. 2.4.1981; D-prior. 12.4.1980). Morand, P.; Lyall, J.: Chem. Rev. (Washington, D. C.) (CHREAY) 68, 85 (1968). Veliuz, L. et al.: Angew. Chem. (ANCEAD) 72,725 (1960). Velluz, L. et al.: Angew. Chem. (ANCEAD) 77, 185 (1965). Smith, 13. et al.: J. Chem. Soc. (JCSOA9)1963,5072. Smith, H. et al.: Experientia (EXPEAM) 19, 177 (1963). Anachenko, S.N.; Torgov, J.V.: Tetrahedron Lett. (TELEAY) 1963, 1553; 1964, 171. Blickenstaff, R.T.; Ghosh, A.C.; Wolf, G.C.: Total Synthesis of Steroids (Organic Chemistry Vol. 30) p. 58-63, 142-145, Academic Press, New York, London 1974. Formulation(s): e. g. 1.4 mg in comb.; amp. 20 mg; drg. 0.625 mg, 1.25 mg, 2.5 mg; vial 20 mg Trade Narne(s): D: Coniugen (K1inge)-comb.; wfrn GT 50 B (Gewo)-comb.; wfm J: Menrium (Roche)-comb.; USA: wfrn Oestro-Feminal (Mack, Illert.; as estrogen conjugate)-comb.; wfm Ovaribran (Thomae; as estrogen conjugate)-comb.; wfrn Ovowop (Hor-Fer-Vit)- comb.; wfrn F: Colpormon (Lipha SantC) PrCmarin (Wyeth-Lederle) Synergon (Lipha Sant6)- comb. GB: Hormonin (Shire)-comb. I: Emopremarin (Wyeth; as estrogen conjugate) Premarin (Wyeth; as estrogen conjugate) Prempak (Wyeth)-comb. Estropan (Mochida)-comb. Di-Genik (Savage)-comb.; wfrn Di-Met (0rganon)-comb.; wfrn Duogen (Smith, Miller & Patch)-comb.; wfrn Estro-V (Webcon); wfrn Estrus01 (Smith, Miller & Patch); wfrn FolleStrol (Blue Line); wfrn Foygen (Foy); wfm Hormestrin (Smith, Miller & Patch)-comb.; wfrn Mal-0-Fem (Fellows)- comb.; wfm Menagen (Parke Davis); wfrn Menformon (Organon); wfm Natural Estrogenic Substance (Legere); wfm Nestronaq (Noyes); wfm Ogen (Abbott; as estropipate); wfrn Prinn (Scirp); wfrn Propagon-S (Spanner); wfrn Spanestrin (Savage)-comb.; wfrn Theelin (Parke Davis); wfm Wynastron (Wyeth); wfm further combination preparations and generic; wfrn Etacrynic acid (~thacrynsaure; Acide etacrynique) ATC: CO3CCO1 Use: diuretic RN: 58-54-8 MF: C,,HI2Cl2O4 MW: 303.14 EINECS: 200-384-1 LD,,,: 176 mglkg (M, i.v.); 600 mglkg (M, p.0.); 1 glkg (R, p.0.) CN: [2,3-dichloro-4-(2-methylene- 1-oxobutyl)phenoxy]acetic acid sodium salt RN: 6500-81-8 MF: C,,H,,CI,NaO, MW: 325.12 Etafenone E 789 1 hutyry chloride 2.3-dichlorophen- t oxyacet~c acld 4-butyryl-2,3-dichloro- phenoxyacetic acid (I) form- dimethyl- aldehyde amine I Etocrynic ocid BE 612 755 (Merck & Co. appl. 17.1.1962;USA-prior. 19.1.1961). US 3 255 241 (Merck & Co.; 7.6.1966; prior. 19.1.1961, 6.12.1961). alternative synthesis: DE 1 276 030 (Merck & Co.; appl. 18.12.1964; USA-prior. 23.12.1963). Formulation(sJ: tabl. 25 rng, 50 mg (as free acid); vial 53.6 mg (as sodium salt) Trade Name(s): D: Hydromedin (Merck Sharp GB: Edecrin (Merck Sharp & Reomax (Bioindustria) & Dohme) Dohme) J: Edecril (Merck-Banyu) F: Edecrine (Merck Sharp & I: Ac Etacr (Formulario Naz.) USA: Edecrin (Merck Sharp & Dohme); wfm Edecrin (Merck Sharp & Dohme) Dohme) Etafenone ATC: COIDX07 Use: coronary vasodilator RN: 90-54-0- MF: C2,H2,N02 MW: 325.45 EINECS: 202-002-9 CN: l-[2-[2-(diethylamino)ethoxy]phenyl]-3-phenyl-l-propanone hydrochloride RN: 2192-21-4 MF: C2,H2,NO2 . HCl MW: 361.91 EINECS: 218-587-9 LD,,: 28 mgkg (M, i.v.); 352 mglkg (M, p.0.); 20.8 mgkg (R, i.v.); 71 6 mgkg (R. p.0.); 50 mgkg (dog, p.0.) 790 E Etamiphylline 2'-hydroxy-3- 2-diethylomino- phenylpropio- ethyl chloride phenone I Etofenone I R<ference(s): DAS 1 265 758 (S. p. A. Lab. Guidotti; appl. 25.5.1960). Formulation(s): amp. 25 mg; drg. 75 mg; s. r. cps. 50 mg (as hydrochloride) Trade Name(s): D: Baxacor (Helopharm); wfrn Baxacor (Mack, Illert.); wfrn Digi-Baxacor (Mack, 1llert.)-comb.; wfrn Iso Baxacor (Helopharm)- comb.; wfrn Pagano-Cor (Helopharm); wfrn Seda-Baxacor (Helopharm)-comb.; wfm Seda-Baxacor (Mack. 1llert.)-comb.; wfm I: Dialicor (Guidotti) J: Asamedel (Maruko) Cardilicor (Uji) Corodilan (Meiji) Dialicor (Kissei) Esanthin-S (Kyoritsu Yakuhin) Etafenarin (Taiyo) Korofenon (Nissin) Etamiphylline (Dietamiphylline) ATC: R03DA06 Use: cardiotonic, diuretic RN: 314-35-2 MF: C13H2,N,02 MW: 279.34 EINECS: 206-244-6 LD,,,: 1237 mgkg (M, p.0.) CN: 7-[2-(diethylamino)ethyl]-3,7-dihydro- 1,3-dimethyl-1 H-purine-2,6-dione monohydrochloride RN: 17140-68-0 MF: CI3H2,N,O2, HCI MW: 315.81 EINECS: 241-204-1 LD,,,: 127 mglkg (M, i.v.1 camphersulfonate (1 : 1) RN: 19326-29-5 MF: C13H?IN50? . C10Hlh04S MW: 51 1.64 EINECS: 242-962-6 LD,,,: 604 mglkg (M, s.c.) 1. NoOH 2. rCH3 CI~N-CH, "'\N%- , A O Y 2. 2-diethylomino- CH3 ethyl chloride CH3 theophylline I Etomiphylline Reference(s): GB 669 070 (A. J M. Moussalli et al.; appl. 1949; F-prior. 1948). Klosa, J.: Arch. Pharm. Ber. Dtsch. Pharm. Ges. (APBDAJ) 288160, 301 (1955). Formulation(s): 75 mg in comb.; suppos. 200 mg, 500 mg; tabl. 100 mg (as camphersulfonate) . estrogen RN: 5 3-1 6-7 MF: Cl,HzzOz MW: 270.37 EINECS: 20 0-1 6 4-5 CN: 3-hydroxyestra-1,3,5(10)-trien-17-one oxide androatenolone 3.17-dioxo-1. 4- ondrostadiene (n) $17-dioxo-1.4. 6- ondrostatnene. 9 0-5 4-0 - MF: C2,H2,N02 MW: 325.45 EINECS: 20 2-0 0 2-9 CN: l-[ 2-[ 2-( diethylamino)ethoxy]phenyl ]-3 -phenyl-l-propanone hydrochloride RN: 219 2-2 1-4 MF: C2,H2,NO2 . HCl MW: 361.91 EINECS: 21 8-5 8 7-9 . 20 6-2 4 4-6 LD,,,: 1237 mgkg (M, p.0.) CN: 7-[ 2-( diethylamino)ethyl ]-3 ,7-dihydro- 1,3-dimethyl-1 H-purine-2,6-dione monohydrochloride RN: 1714 0-6 8-0 MF: CI3H2,N,O2, HCI MW: 315.81 EINECS: 24 1-2 0 4-1