Ethoheptazine E 801 Oophormin Luteum Ora-Lutin (Parke Davis); Progestoral (Organon); (Teikoku Zoki) wfm wfm USA: Duosterone (Rousse1)- Prodroxan (Dorsey); wfm Syngestrotabs (Pfizer); comb.; wfm Progestab (Beecham); wfm wfm Trosinone (Abbott); wfrn Ethohep tazine ATC: N02A Use: analgesic RN: 77-15-6 MF: C,6H23N02 MW: 261.37 EINECS: 201-007-3 LD,,: 65 mgkg (M, i. v.); 3 1 8 mglkg (M, p.0.); 34 mgkg (R, i.v.); 355 mglkg (R, p.0.) CN: hexahydro-l-methyl-4-phenyl-1H-azepine-4-carboxylic acid ethyl ester citrate (1:l) RN: 6700-56-7 MF: C16H2,N02 . C6H80, MW: 453.49 EINECS: 229-743-0 LDSo: 580 mgkg (R, p.0.) 1. NoNHZ VH3 H3C\ 2. clbN\ N-CH3 '. CH3 2. B/"%r bC 1. sodium ornide 1. 1.3-dibromo- phenyloceto- 2. 2-(dimeth~iorni- 4-dimethylomino- propone nitrile nO)eth~l 2-phenylbutyronitrile H3C\ p3 7H3 pH3 nitrobenzene. 100 Oc _____* CH3 . 4-cyono-1 -methyl- 4-phenylhexohydro- ozepine (11) I Ethoheptozine Reference(s): US 2 666 050 (American Home Products; 1954; prior. 1952). Formulation(s): tabl. 75 mg in comb. Trade Narnefsj: GB: Equagesic (Wyeth)-comb. combination preparations; USA: Equagesic (Wyeth); wfm I: Panalgin (Padil); wfm wfm Mepro (Schein); wfm J: Zactirin (Banyu)-comb. Zactane (Wyeth); wfm 802 E Ethosuximidc Zactirin (Wyeth); wfm Ethosuximide ATC: N03ADOl Use: antiepileptic, antiparkinsonian RN: 77-67-8 MP: C7H,,NO2 MW: 141.17 EINECS: 201-048-7 LDS,,: 780 mglkg (M, i.v.); 1530 mglkg (M, p.0.) CN: 3-ethyl-3-methyl-2,5-pyrrolidinedione NC NaCN 0 4 + oxcH3 ti3C / 0 '3'3 ethyl butanone cvonoocetote HOOC CH~, 0- NH: 2-ethyl-2-methyl- succinic acid Ethosuxirnide 2. Reference(s): US 2 993 835 (Parkc Davis; 25.7.1961; prior. 27.10.1958). Sahay, S.; Sircar, G.: J. Chem. Soc. (JCSOA9) 1927, 1252. Formulatinn(s): cps. 250 mg; sol. 50 gI100 g; syrup 250 mg/5 ml Trade Name(s): D: Petnidan (Desitin) Zarontin (Parke Davis) Zarontin (Parke Davis- Suxilep (Jenapharm) I: Zarontin (Parke Davis) Sankyo) Suxinutin (Parke Davis) J: Emeside (Technish- USA: Zarontin (Parke Davis) F: Zarontin (Parke Davis) Kodama) GB: Emeside (Labs. for Applied Epileo Petitmal (Eisai) Biology) Ethotoin (Aethotoin) ATC: N03ABO1 Use: antiepilcptic RN: 86-35] MF: C,,H,,N,O, MW: 204.23 EINECS: 201-665-1 LD,,,: 1750 mglkg (M, p.0.); 1500 mglkg (R, p.0.) CN: 3-ethyl-5-phenyl-2,4-imidazolidinedione ocHo + NoCN + QpH a H2N NH2 CN or NH,HCO, CN NH, benzaldehyde sodium mondela- (I) cyanide nitrile Ethoxzolamide E 803 F. f HCI 1 * C ethyl '-CH, 5-phenyl- hydantoin Ethotoin u I Reference(s): ) Rnner, A,: Chem. Ber (CHBEAM) 21,2325 (1888) ; US 2793 157 (Abbott; 1957; appl. 1954). Formulution(s): tabl. 250 mg, 500 mg Trade Narnets): GB. Peganone (Ahhott); wfm J: Accenon (Dainippon) USA: Peganone (Abbott) Ethoxzolamide (Ethoxy zolamide) ATC: C03BA Use: diuretic (carboanhydrase inhibitor) RN: 452-35-7 MF: C9H,,N2O3S2 MW: 258.32 EINECS: 207-199-5 CN: 6-ethoxy-2-benzothiazolesulfonamide 4-athoxyoniline corbon B-ethoxybenzo- disulfide thiozole-2-thiole S-ethaxybenzothiozole- 2-sulfenomide (I) Reference(s): US 2 868 800 (Upjohn, 1959; appl. 1954) Formulation(s): tabl. 125 rng Trade Nume(s): D: Redupresin (Thilo); wfm I: Glaucotensil (Farmila); wfn1 Ethyl biscoumacetate ATC: BOlAAO8 Use: anticoagulant, antithrombotic RN: 548-00-5 MF: C2,H,,08 MW: 408.36 EINECS: 208-940-5 LD,: 750 mgfkg (M, p.0.); 840 mglkg (R, p.o.1 CN: 4-hydroxy-a-(4-hydroxy-2-oxo-2H-l-benzopyran-3-yl)-2-oxo-2H-1-benzopyran-3-acetic acid ethyl ester 804 E Ethylestrenol 0 00 0 COOH 0 H OH OH COOH 4-hydroxy- glyoxylic Ethyl biscoumocetate coumorin acid Keference(s): US 2 482 510 (Sp6jene farmaceutickk Zovody; 1949). US 2 482 5 1 1 (Sp6jed farmaceutickk Zovody; 1949). US 2 482 512 (Spojenk farmaccutickk Zovody; 1949). Formr~lation(s): tabl. 300 mg Trade Name(s): D: Tromexan (Geigy); wfm GB: Tromexan (Geigy); wfm F: Tromexane (Geigy); wfrn I: Etilbis (Tanff. Intcgrativo) Ethylestrenol (~th~lestrenol; ~thyloestrenol) ATC: A14AB02 . Use: anabolic RN: 965-90-2 MF: C20H320 MW: 288.48 EINECS: 213-523-6 LD,,,: >666.7 mgkg (M, p.0.) CN: (l7a)- 19-norpregn-4-en-17-01 1. CH,OH, HCI NoBH,, CH30H 2. Li, NH3 b sodium borohydride Ethylestrenol 2. chromium(V1) oxide nandralone 1,2-ethane- (4. v.1 dithiol + ~rh4g-c~~ Ethylestrenol * / (1) ethylmagnesium bromide (cf. also lynestrol synthesis) Ethyl loflazepate E 805 Reference(s): a US 2 878 267 (Organon; 1959; N-prior. 1957). b Winter, M.S. de et al.: Chem. Ind. (London) (CHINAG) 1959,905. alternative synthesis: US 3 112 328 (Organon; 26.11.1963; NL-prior. 24.8.1956). Formulation(s): sol. 2 mg/5 ml; tabl. 2 mg Trade Namefs): F: Orgaboline (Organon); GB: Orabolin (Organon); wfm J: Orgabolin (Organon- w fm I: Orgabolin (Ravasini Sankyo) Orgaboline infantile Organon); wfm USA: Maxibolin (Organon); wfm (Organon); wfm Ethyl loflazepate ATC: NOSBAI~ Use: tranquilizer RN: 29177-84-2 MF: Cl,H14CIFN20, MW. 360.77 EINECS: 249-489-4 LDs0: 5506 mgkg (M, p.0.); >10 gkg (R, p.0.) CN: 7-cNoro-5-(2-fluorophenyl)-2,3-dihydro-2-oxo-lH-1,4-benzodiazepine-3-carboxylic acid ethyl ester 2-amino-5-chloro- diethyl rnethoxy- 2'-fluorobenzo- corbonylomino- phenone rnclonote (cf. flunitrazepam synthesis) c,% CH COOH. CH COONo HBr F \ (1) BE 854 249 (Clin-Midy; appl. 5.5.1977; GB-prior. 5.5.1976). DOS 2 719 608 (Clin-Midy; appl. 2.5.1977; GB-prior. 5.5.1976). GB 1 538 165 (Clin-Midy; appl. 5.5.1977; prior. 5.5.1976). alternative synthesis: EP 22 710 (Clin-Midy; appl. 8.7.1980; F-prior. 12.7.1979). Formulation(s): tabl. 2 mg 806 E Ethylmorphine Trade Nrrmc>(s): F: Victan (Sanofi Winthrop); I: Victan (Midy); wfm w fm J: Meilax (Meiji Seika) Ethylmorphine (CodCthyline) ATC: ROSDAO 1 ; SO1 XAO6 Use: antitussive, analgesic RN: 76-58-4 MF: C,,H,,NO, MW: 313.40 EINECS: 200-970-7 LD,,,: 120 mgkg (M, i.p.); 520 mdkg (M, p.0.); 136 mglkg (M, s.c.); l I0 mglkg (R, i.p.); 62 mglkg (R, i.v.); 810 mgkg (R, p.0.); 200 mgkg (R, s.c.) CN: (5a,6a)-7,8-didehydro-3,5-epoxy-3-ethoxy- 1 7-methylmorphinan-6-01 hydrochloride RN: 125-30-4 MF: C,,H,,NO,. HCI MW: 349.86 EINECS: 204-734-4 LD,,,: 77 1 mglkg (M, p.0.); 265 mglkg (M, s.c.); 200 mglkg (R, s.c.) hydrochloride dihydrate RN: 6746-59-4 MF: C,,H,NO,. HCI . 2H20 MW: 385.89 LD,,,: 200 mglkg (M, s.c.) morphine ethyl benzenesulfonote I Ethylmorphine I Referencr(s): Ehrhart, Ruschig I, 1 18 DRP 13 1 980 (E. Merck AG; 1902). Formulation(s): drg. 5 mg; tabl. 5 mg, 15 mg (as hydrochloride dihydrate) Trade Nume(s): D: Frubiapect (Dieckmann). comb.; wfm Nedolon (Merck)-comb.; wfm Noviform- Aethylmorphin Dispersa Augensalbe (Dispersa Baeschlin)- comb.; wfm Theralene pectoral Sirup (Rh8ne-Poulenc Pharma)- comb.; wfm Tussedat Pastillen (Sagitta)-comb.; wfm F: Bronpax pates (Biocodexj- comb. CodCthyline Houdt (Hoechst Houdt) Ephydion (ACrocid)-comb. Poky (Veyron et Froment)-comb. Pulmosodyl (Bridoux). comb. Stdophon pectoral (Mayoly-Spindler)-comb. Trachyl (Novartis) Tussipax (Th6rica)-comb. VCgktos6mrn (Jurner)- comb. I: Codetilina Eucaliptolo HoudC (Teofarma)-comb. Dionina (Tariff. Integrativo; as hydrochloride) Etilm (Tariff. Integrativo; as hydrochloride) Mindol Merck (Bracco). comb. r Etidocaine E 807 Etidocaine ATC: NOIBB07 Use: local anesthetic RN: 36637-18-0 MF: C17H2xN20 MW: 276.42 EINECS: 253-143-8 LD,,: 47.5 mglkg (M, i.p.) CN: (?)-N-(2,6-dlmethylphenyl)-2-(ethylpropylamino)butanar1lide monohydrochloride RN: 36637-19-1 MF: C17H2,N20 , HCl MW: 3 12.89 EINECS: 253-144-3 LD,: 6700 yglkg (M, i.v.) acid chloride KI, CH OH IL H3C I H,c-NHz ___, propylamine Etidocoine I diethyi suifate Reference(s): US 3 812 147 (Astra; 21.5.1974; prior. 22.12.1970, 19.7.1971). US 3 862 321 (Astra; 21.1.1975; prior. 22.12.1970, 19.7.1971,4.3.1974). DOS 2 162 744 (Astra; appl. 17.12.1971; USA-prior. 22.12.1970, 19.7.1971). Formulation(s): amp. 5 mg12 ml, 10 mglml, 12.5 mg15 ml (as hydrochloride) Trade Name(s): D: Dur-Anest (Astra) F: Duranest (Aslra) Duranest Adrhaline (Astra) USA: Duranest (Astra) Etidronic acid ATC: MOSBAOI Use: calcium regulator RN: 2809-21-4 MF: C,Hx07P2 MW: 206.03 EINECS: 220-552-8 LD,,,: 1800 mglkg (M, p.0.) CN: (1-hydroxyethylidene)bis[phosphonic acid] 808 E Etifelmine disodium salt RN: 7414-83-7 MF: C2H,Na207P2 MW: 249.99 EINECS: 23 1-025-7 LD,,,: 49 mglkg (M, i.v.); 2050 mglkg (M, p.0.); 73 mglkg (R, i.v.); 1340 mglkg (R, p.0.) 1 Etidronic ocid 1. H,C-COOH. 120 OC CO, A 2. H 0, 140 "C p4 + 0, - PO Reference(s): FR 1 53 1 9 13 (Procter & Gamble; appl. 19.7.1967; USA-prior. 20.7.1966). alternative synlheses: US 3 366 675 (Procter & Gamble; 30.1.1968; prior. 30.3.1965). NL 6 606 548 (Procter & Gamble; appl. 12.5.1966; USA-prior. 13.5.1965). OH H,O,P+PO,H, CH3 NL 6 610 762 (Procter & Gamble; appl. 29.7.1966; USA-prior. 29.7.1965, 31.5.1966). Formulation(s): amp. 300 mg16 ml; tabl. 200 mg, 400 mg (as disodium salt) Trade Name(s): D: Diphos (Procter & Gamble) GB: Didronel (Procter & USA: Didronel (MGI) F: Didronel (Procter & Gamble; 1992) Didronel (Procter & Gamble) I: Etidron (Gentili) Gamble; as disodium salt) Etifelmine Use: antihypotensive RN: 341-00-4 MF: C17Hl,N MW: 237.35 CN: 2-(diphenylmethy1ene)-1-butanamine gluconate (1: 1) RN: 28599-37-3 MF: C,,H,,N . C,H1207 MW: 433.50 hydrochloride RN: 1146-95-8 MF: C17H,,N. HC1 MW: 273.81 LD,,,: 28.6 mgkg (M, i.v.); 115 mglkg (M, p.0.); 17.4 mgkg (R, i.v.); 148 mglkg (R, p.0.) nicotinate (1:l) RN: 31 149-45-8 MF: C17H1,N . C,H,NO, MW: 360.46 benzophenone butyronitrile amide HCI. CH,-COOH - (1) Etitelrnine Etilefrine E 809 Reference(s): DE 1 122 514 (Giulini: appl. 8.9.1959). Formulation(s): drg. 1 1 mg in comb. Trade Narne(s): D: Gilute~lsin (Giu1ini)-comb.; Orthoheptamin (Giulini)- J: Tensinase-D (Nippon wfm comb.; wfm Chemiphar) Etilefrine ATC: COlCAOl Use: sympathomimetic, circulatory analeptic RN: 709-55-7 MF: C,,HI5NO, MW: 181.24 EINECS: 21 1-91 0-4 LD,o: 770 mg/kg (M, p.o.1; 114 mgkg (R, p.0.) CN: a-[(ethylam~no)methyl]-3-hydroxybenzenemethanol hydrochloride RN: 943-17-9 MF: C,,,H,,NO, .HC1 MW: 217.70 EINECS: 213-398-8 LD,: 860 mglkg (M, s.c.); 920 mglkg (R, s.c.) 0 CH3 0 CH3 4,, + - 6.,% Br2 / J'-hydroxy- benroyl 3'-benzoyloxy- (1) occtophenonc chloride acetophenone ethylornine -( 3'-hydroxy-2- ethylomino-aceto- Dhenone Etilefrine - Reference(s): DRP 520 079 (H. Legerlotz; 1926). DRP 522 790 (H. Legerlotz; 1929). Formularion(s): amp. I0 mglml; drops 5 mglml, 7.5 mglml; sol. 7.5 mg/ml; s. r. cps. 20 mg, 25 mg; tabl. 5 mg, 25 mg (as hydrochloride) Trade Naine(s1: D: Adrenam (NAM Circuvit (Pharma Kreislauf Katovit Neukonigsforder) Wernigerode) (Boehringer Ing.) Bioflutin (Siidmedica) Confidol (Medopharm) Thomasin (Apogepha) Cardanat (Temmler) Effortil Depot (Boehringer numerous combination Cardialgine (MIP Pharma) Ing.1 preparations and generics Circupon RR-Kapseln Etilefrin (Chephasaar) F: Effortil (Boehringer Ing.) (gegepharm) Eti-Puren (Isis Puren) I: Effortil (Boehringer Ing.) 810 E Etiroxate J: Effortil (Boehringer- Tanabe) Etiroxate ATC: ClOA Use: antiarteriosclerotic (cholestcrol depressant and antihyperlipidemic) RN: 17365-01-4 MF: C,8H,714N0, MW: 818.95 CN: O-(4-hydroxy-3,5-diiodophcnyl)-3,5-diiodo-a-methyl-~~-Iyrosine ethyl ester hydrochloride RN: 55327-22-5 MF: C,xH,71,N04. HCl MW: 855.41 EINECS: 259-593-1 4-methoxybenzyl methyl ketone NO2 OH, Tos-OH. pyridina '0 / 02N NH hydroquinone NH 0 0 monornethyl 5-(4-hydroxybenzyl)- ether 5-nethylhydontoin (I) NU2 H2, Raney-Ni HA. 0 OzN NH + H C nowyo H2N NH 0 0 1. CHJCOOH, H2SO4. NoN02 2. KI. l2 III NH 0 HI. CH3COOH 2N NaOH 140 'C IV v HO NH 0 . 54 8-0 0-5 MF: C2,H,,08 MW: 408.36 EINECS: 20 8-9 4 0-5 LD,: 750 mgfkg (M, p.0.); 840 mglkg (R, p.o.1 CN: 4-hydroxy-a-(4-hydroxy-2-oxo-2H-l-benzopyran-3-yl )-2 -oxo-2H-1-benzopyran-3-acetic. 2917 7-8 4-2 MF: Cl,H14CIFN20, MW. 360.77 EINECS: 24 9-4 8 9-4 LDs0: 5506 mgkg (M, p.0.); >10 gkg (R, p.0.) CN: 7-cNoro- 5-( 2-fluorophenyl )-2 ,3-dihydro-2-oxo-lH-1,4-benzodiazepine-3-carboxylic. 45 2-3 5-7 MF: C9H,,N2O3S2 MW: 258.32 EINECS: 20 7-1 9 9-5 CN: 6-ethoxy-2-benzothiazolesulfonamide 4-athoxyoniline corbon B-ethoxybenzo- disulfide thiozole-2-thiole S-ethaxybenzothiozole- 2-sulfenomide