Etamivan E 791 e Name(s): Longtussin duplex (Fink)- GB: comb.; wfrn Ultratussin (Fink-comb.; wfm : Camphophyline (Millot; as camphersulfonate); wfrn Iodaphyline (Millot; as I: iodomethylate); wfrn MilhCparine(Mil1ot)-comb. with heparin; wfm : Etamivan * (Ethamivan) Dechophyllinc (Millot- Solac)-comb.; wfm lodaphylline (Millot-Solac; as iodomethylate); wfm Millophyline (Dales; as camphersulfonate); wfm Aricodil (Malesci1)-comb.; wfm Benzofillina (Courtois; as p-aminobenzoate): wfm Convivial (Ma1escil)- comb.; wfm Decofillina (Malesci1)- comb.; wfm Jod-Melil-Fillina (Malcscil; as iodomethylate); wfm Spasmodil complex (ABC)-comb.; wfm ATC: R07AB04 Use: analeptic (central and respiratory stimulant) RN: 304-84-7 MF: CI2H,,NO, MW: 223.27 EINECS: 206-157-3 LDR: 15 mgkg (M, i.v.); 67 mgkg (M, p.0.); 28 mgkg (R, i.p.1; 17 mglkg (R, i.v.); 154 mglkg (R, p.0.); 30 mgkg (dog, i.v.); 300 mglkg (dog, p.0.) CN: N,N-dicthyl-4-hydroxy-3-methoxybenzamide 0 pH3 S N-CH, 0 N,CH3 (CH3 &#H3 a 0/CH3 + HNUCH3 ruifur 6 OH OH OH vanillln d~ethyl- "th~ovond~d" Etomivon omlne (I) Reference(s): US 2 641 612 (Oslerr. ~tickstoffwcrke AG; 1953; A-prior. 1949). Fomularion(s): drg. 10 mg in comb.; drops 20 mglml in comb. Trade Name(s): D: Normotin-R rapid (0TW)- GB: Clairvan (Sinclair); wfrn I: Corivanil (Sirt-BBP); wfm comb. Vandid (Riker); wfm Romecor (Benvegna); wfm Etamsylate (Ethamsylate) ATC: B02BXO1 Usc: hemostatic (capillary protective) RN: 88-46-0 MF: C6H,0sS MW: 190.18 EINECS: 201-833-4 CN: 2,5-dihydroxyhenzenesulfonic acid 792 E Ethacridine diaethylammonium salt (1:l) RN: 2624-44-4 MF: C6H60SS.C4111,N MW: 263.31 EINECS: 220-090-7 LD,,: 785 mgtkg (M, i.v.); 8300 mglkg (M, p.0.); 1350 mglkg (R, i.v.); 7500 mglkg (R, p.0.) p-benzoquinone diethylammonium hydrogen sulfiie Etamsylate u Reference(s): GB 895 709 (Lab. OM S.A.; appl. 31.12.1959; CH-prior. 28.1.1959). Fonmdation(s): amp. 250 mg12 ml; tabl. 250 mg, 500 mg Trade Narne(s): D: Altodor (Deutsche OM) I: Dicynone (Delalande Transil (Malexi)-comb. F: Dicynone (SynthClabo) Isnardi) J: Aglumirr (Eisai) GB: Dicynene (Delandale) Esclin (Ravizza) Dicynone (Torii) Ethacridine (Acrinol; Aethacridin) ATC: B05CA08; D08AAOI Use: wound antiseptic, intestinal disinfcctant RN: 442-16-0 MF: Cl,Hl,N,O MW: 253.31 EINECS: 207-130-9 CN: 7-ethoxy-3,9-acridinediamine lactate (1:l) RN: 1837-57-6 MF: C,,H,,N,O, C,H60, MW: 343.38 EINECS: 217-408-1 LD,,,: 42 mglkg (M, i.p.); 120 mglkg (M, s.c.) COOH + ~~"~~1 Cu, K2C0, 02N H2N 2-chloro-4-nitro- 4-ethoxyaniline benzoic acid 2-(4-ethoxy0nilino)-4 nitrobenzoic acid (1) CI POCI, 1 pJ3J0-~~3 .EL, &0"CH3 02N O2N Ethacridine Ethambutol E 793 Reference(s): DRP 360 421 (Hoechst; 1922). DRP 393 41 1 (Hoechst; 1923). improved method for 9-amino-2-ethoxy-6-nitroacridine: DAS 1 952 086 (Hoechst; appl. 16.10.1969). Formulation(s): drg. 200 mg; eye drops 1 mglg (as free base); gargle tabl. 25 mg (as hydrochloride); ointment 2 mglg; sol. 0.1 %; tabl. 0.1 g Trade Name(s): D: Biseptol (Winzer) numerous combination I: Rivanolo (Tariff. Metifex (Cassella-med) preparations Integrativo) Rivanol (Chinosolfabrik) F: Dentinox (Pharmastra)- J: Hectalin (Daiichi) Uroseptol (Fresenius- comb. Rimaon (Takeda) Praxis; as acetate) Pyorex (Bail1y)-comb. Ethambutol ATC: J04AK02 Use: tuberculostatic RN: 74-55-5 MF: CI,,H,N2O2 MW: 204.31 EINECS: 200-810-6 LD,o: 240 mgkg (M, i.v.); 8700 mgkg (M, p.0.) CN: [S-(R*,R*)]-2,2'-(1,2-ethanediyldiimino)bis[l-butanol] dihydrochloride RN: 1070-1 1-7 MF: C,,H,N202. 2HCl MW: 277.24 I-nitropropane form- 2-nitro- aldehyde 1 -butan01 (+)-2-amino- 1 -butand (I) racemate resolution with H3C L(+)-tartoric acid 1- 1.2-dichloro- (+)-2-amino- ethane 1-butanol (11) H Ethambutol 0 HCI NH2 NH2 L-2-amino- butyric acid L-ethyl 2-ominobutyrate hydrochloride (N) HZ, Raney-Ni or PtO 111 NaOH [V + 11 , HCI H3C-xCHI + H3C-CN + HN CH, 'f 0 1-butene aceto- N-[l -(chlorornethyl)- nitrile propyl]ocetamide (V) rocemate resolution with HCI L(+)-tartaric acid Ill . NaOH -+ I -, -, FI Reference(s): a Wilkinson, R.G. et al.: J. Am. Chem. Soc. (JACSAT) 83,2212 (1961). Wilkinson, R.G. et a].: J. Med. Pharm. Chcm. (JMPCAS) 5, 835 (1962). US 3 I76 040 (American Cyanamid; 30.3.1965; prior. 2.6.1960). BE 600 640 (American Cyanamid; appl. 24.2.1961 ; USA-prior. 2.6.1960, 20.12.1960). BE 6 13 545 (American Cyanamid; appl. 6.2.1962; USA-prior. 23.1.1962). racemate resolution of (+)-2-aminobutanol with tartaric acid: US 3 553 257 (Amcrican Cyanamid; 5.1.1971; prior. 16.9.1966). reaction with 1.2-dichloroethane: US 3 769 347 (American Cyanamid; 30.10.1973; prior. 11.2.1971). DOS 2 205 269 (American Cyanamid; appl. 4.2.1972; USA-prior. 11.2.1971). US 3 944 616 (American Cyanamid; 16.3.1976; prior. 29.10.1974). FR 2 351 090 (Soc. Chim. Grande Paroisse; appl. 11.5.1976). b DAS 2 446 320 (Denki Kagaku Kogyo; appl. 27.9.1974; J-pnor. 28.9.1973). GB 1 469 014 (Denkl Kagaku Kogyo; appl. 30.9.1974, J-prior. 28.9.1973). reduction with sodium diethylalum~num hydride: JP-appl. 780 06-127 (Crc co di Rlcerca; appl. 22.5.1973; CH-prior. 1.3.1973). c US 3 944 617 (American Cyanamid; 16.3.1976; prior. 1.8.1974). US 3 944 618 (American Cyanamid; 16.3.1976; pr~or. 1.8.1974). US 3 944 619 (American Cyanamid; 16.3.1976; prior. 1.8.1974). GB 1 541 290 (American Cyanamid; appl. 9.2.1976). alternative syntheses: from I ,2-epoxybutane: US 3 953 513 (Gruppo Lepetlt; 27.4.1976; GB-prior. 29.1 1.1973). DOS 2 454 950 (Gruppo Lepetit; appl. 20.1 1.1974; GB-prior. 29.1 1.1973). DAS 2 410 988 (Polska Akad. Nauk Inst. Chem. Organ.; appl. 7.3.1974; PLprior. 20.3.1973). @om 3,4-epoxybutene (butadiene monoxide): . DAS 2 263 7 15 (Soc. Farmaceutici Italia; appl. 28.12.1972; I-prior. 30.12.1971). from 1 -hydroxy-2-butanone: DOS 2 547 654 (BASF; appl. 24.lO.1975). asymmetric hydrogenation of 2-acylamino-crotonic acid derivatives: BE 862 627 (American Cyanamid; appl. 4.1.1978; USA-prior. 7.1.1977). DOS 2 800 461 (American Cyanamid; appl. 5.1 .l978; USA-prior. 7.1.1977). racemate resolution of (+)-2-aminobutanol with (+)-N-benzoyl-trans-2-aminocyclohexanecarboxylic acid: GB 1 471 838 (Nippon Soda; appl. 26.3.1975; J-prior. 4.4.1974). Formulation(s): amp. 400 mg14 ml, 1000 mg/lO ml; f. c. tabl. 100 mg, 250 mg, 400 mg, 500 mg (as dihydrochloride); vial I g Trade Narne(s): D: EMB-Fatol (Fatol) Myambutol (Lederle) F: Dexambutol(1,'Arguenon) Ethaverine E 795 Dexambutol-INH I: Etambu (Formulario Naz.) Esanbutol (Lederle) (L'Arguenon)-comb. with Etambu (Lifepharma) Ethambutol (Lederle- isoniazid Etanicozid (Piam)-comb. Takeda) Myambutol (Wyeth- Etapiam (Piam) USA: Myambutol (Lederle Labs.; Lederle) Etibi (Zoja) as hydrochloride) GB: Myambutol (Lederle); wfm Miambutol (Cyanamid) Mynak (Leder1e)-comb. Miazide (Cyanamid)-comb. with isoniazid; wfm J: Ebutol (Kaken) Ethaverine ATC: AO~ Use: antispasmodic RN: 486-47-5 MF: Cz4HzyN04 MW: 395.50 EINECS: 207-633-3 LDso: 45600 ~g/kg (M, i.v.) CN: l-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxyisoquinoline hydrochloride RN: 985-13-7 MF: C,H,,NO,. HCI MW: 431.96 EINECS: 213-573-9 LD,: 86 mglkg (M, i.v.) 1-(3,4-diethoxypheny1)- 3,4-diethoxyphenyl- 2-aminoethanol acetyl chloride Referencels): US 1 962 224 (E. Wolf; 1934; D-prior. 1930). Formulafion(s): suppos. 30 mg in comb. (as hydrochloride) Fade Nnmels): D: Migdne-Kranit (Krewel Meuselbach) F: Etadil (Charpentier); wfrn Plaquiverine (Monal); wfm Surparine (Licardy)-comb.; wfm 1: Azimol ITA (1TA)-comb.; wfrn Ceracin (Panthox & Isovex (U.S. Buck)-comb.; wfm Pharmaceutical); wfm Etaverina (Biologici Italia); Laverin (Lemmon); wfm wfm Pasmol (RAM Labor); wfm Predem (Biologici 1talia)- Tensodin (Knoll)-comb.; comb.; wfm wfm USA: Ethaquin (Ascher); wfrn Ethatab (Meyer); wfm 796 E Ethchlorvynol Ethchlorvynol RN: 113-18-8 MF: C,HyCIO MW: 144.60 LDso: 290 mg/kg (M, p.0.); 55 mgkg (dog, i.v.) CN: 1-chloro-3-ethyl-1-penten-4-yn-3-01 Li, liq. NH3 + HCECH -b C I 1 -chloro- acetylene 1 -penten-3-one ATC: N05CM08 Use: hypnotic, sedative CI Ethchlorvynol Reference(s): US 2 746 900 (Pfizer; 1956; prior. 1953). McLamore, W.M. et al.: J. Org. Chem. (JOCEAH) 20, 109 (1955). Formulation(s): cps. 200 mg, 500 mg, 750 mg Trade Name(s): GB: Arvynol (Pfizer); wfm J: Arvynol (Taito Pfizer) USA: Placidyl (Abbott) Serenesil (Abbott); wfm Nostel (Dainippon) Ethenzamide (Ethoxy benzamide) ATC: N02BA07 Use: analgesic RN: 938-73-8 MF: CyH,,N02 MW: 165.19 EINECS: 213-346-4 LD,,,: 700 mg/kg (M, p.0.); 2630 mgkg (R, p.0.) CN: 2-ethoxy benzamide solicylornide diethyl sulfote Ethenzornide Reference(s): GB 656 746 (Lundbeck; appl. 1948; DK-prior. 1947). Formulation(s): drg. 150 mg in comb.; tabl. 100 mg in comb. Trade Narne(s): D: Antifohnon (Siidmedica)- F: CCphil (Boiron)-comb. comb. I: Etocil (Biomedica Glutisal (Ravensberg)- Foscama)-comb. comb. Etocil Pirina (Biomedica Kolton grippale N (Byk Foscama)-comb. Gulden)-comb. J: Amisal (Daiichi)-comb. Ethoxybenzamide (Juzen Kagaku) Grelan High S (Gre1an)- comb. Grelan Shin A (Grelan) Konjisui Soft (Tanpai) Ethiazide E 797 Pyr~pan A (Tanabe)-comb. Sedes A (Shionog~) Synpyrin F (Sumitomo) Ethiazide (Aethiazidum) ATC: C03BA Use: diuretic RN: 1824-58-4 MF: CyH12ClN304S2 MW: 325.80 EINECS: 217-358-0 LD,: >310mg/kg (M, i.v.); >2gkg (M, p.0.); >10 gkg (R, p.0.) CN: 6-chloro-3-ethyl-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide I, I -dioxide 5-chloro-2,4-di- propionoldehyde sulfornoylaniline Referencefs): GB 861 367 (Ciba; appl. 1959; USA-prior. 1958). Trade Name(s): J: Ethiazide (Tokyo Tanabe); wfm / Ethiazide Ethinamate ATC: NOSC Use: hypnotic, sedative RN: 126-52-3 MF: CyH,,N02 MW: 167.21 EINECS: 204-789-4 LD,: 108 mgkg (M, i.v.); 490 mglkg (M, p.0.); 157 mgtkg (R, i.v.); 331 mglkg (R, p.0.); 144 mglkg (dog, i.v.); 190 mglkg (dog, p.0.) CN: 1-ethynylcyclohexanol carbamate CH 0 C H 1. C0Cl2 No, liq. NH3 + HCECH cyclo- acetylene hexanone l-ethynyl- cyclohexonol Reference(s): US 2 816 910 (Schering; 1957; D-prior. 1953). DE 1 021 843 (Rheinpreussen; appl. 1953). Formulation(s): cps. 500 mg Trade Name(s): D: Valarnin (Asche); wfm J: Valamin (Schering) USA: Valamid (Dista); wfm 798 E Ethinylestradiol Ethinylestradiol ATC: GO~CAOI ; L02~~03 (Aethinylostradiol; Ethinyloestradiol) Use: estrogen (in combination with progestogen as oral contraceptive) RN: 57-63-6 MF: C,,,H240, MW: 296.41 EINECS: 200-342-2 LD,,,: 1737 mglkg (M, p.0.); 1200 mglkp (R, p.0.) CN: (1 7a)-19-norpregna- 1,3,5(10)-trien-20-yne-3.17-diol K or Na,liq. NH3 & + HC=CH - &OH HO estrone ri Ethlnylestrodiol (9. v.1 Rcference(s): Inhoffen, H.H. et al.: Ber. Dtsch. Chem. Ges. (BDCGAS) 71, 1024 (1938). DRP 702 063 (Ciba; appl. 1938; CH-prior. 1937). Formulation(s): tabl. 0.02 mg, 0.025 mg, 0.05 mg; drg. 1 mg Trade Name(s): D: Riviol (Nourypharma)- Neorlest (Parke-Davis)- Synphasec (Griinentha1)- comb. comb. comb. Cilest (Janssen-Cilag)- Neo-Stedirile (Wyeth)- Tetragynon (Schering)- comb. comb. comb. Concephan (Griinentha1)- Non-Ovlon (Jenapharm)- Triette (Brenner-Efeka)- comb. comb. comb. Cyclosan (Nourypharma)- Nuriphasic Trigoa (LAW)-comb. comb. (Nourypharma)-comb. Triguilar (%hering)-comb. Diane 35 (Schering)-comb. 0slrv-~rimolut (Schcring)- Trinordiol (Wyeth)-comb. EVE (Griinentha1)-comb. . comb. TriNoum (Janssen-Ci1ag)- Femigoa (LAW)-comb. Ovanon (Nourypharma)- comb. Femovan (Schering)-comb. comb. Trisiston (Jenapharm)- Femranetle rnikro Ovanon (Nourypharma)- comb. (Brenner-Efeka)-comb. comb. TriStep (Asche)-comb. Gravistat (Jenapharm). Oviol (Nourypharma)- Turis teron (Jcnapharm) comb. comb. Valette (Jenapharm)-comb. Leios (Wyeth)-comb. Ovoresta (Organon)-comb. Yermonil (Novartis Lovelle (Organon)-comb. Ovysmen (Wyeth)-comb. Pharma)-comb. Lyndiol (Organon)-comb. Perikursal (Wyeth)-comb. numerous combination Marvelon (Organon)-comb. Pramino (Janssen-Ci1ag)- preparations Microgynon (Schering)- comb. F: Adepal (Wyeth-Lederle) comb. Pregnon (%hering)-comb. Cilest (Janssen-Cilag) Minisiston (Jenapham- Progynon C (Schering) Cycleane (Monsanto) comb. Promisiston (&hering)- Diane 35 (Schering) Minulet (Wyeth)-comb. comb. Effiprcv (Effik) Miranova (Schering)-comb. Prosiston (Schering)-comb. Ethinyl-Estradiol Roussel MonoStep (Asche)-comb. Sequilar (Schering)-comb. (Roussel) Neo-Eunomin Sequostat (Jenapharm). Harmonet (Wyeth-Lcderle) (Griinentha1)-comb. comb. Mkliane (Schering) Neogynon (Schering)- Sinovula (Asche)-comb. Minidril (Wyeth-Lederle) comb. Stediril (Wyeth)-comb. Minulet (Wyeth-Lederle) Ethionamide E 799 Tri-Minulet (Wyeth- Lederle) generic and numerous combination preparations GB: Marvelon (Schering) numerous combination preparations I: Binordiol (Wyeth)-comb. Bivlar (Schering)-comb. Diane (Schering)-comb. Egogyn (Schering)-comb. J: Etinilestradiolo (Amsa) Eugynon (Schering)-comb. Evanor (Wyeth)-comb. USA: Ginoden (Schering)-comb. Mercilon (Organon 1talia)- comb. Microgynon (%hering)- comb. Milvane (Schering)-comb. Minulet (Wyeth)-comb. Novogyn (Schering)-comb. Ovranet (Wyeth)-comb. Planum (Menarini)-comb. Practil (Organon 1talia)- comb. Securgin (Menarini)-comb. Trigynon (Schering)-comb. Triminulet (Wyeth)-comb. Trinordiol (Wyeth)-comb. Trinovum (Ci1ag)-comb. Estrogen (Nichinan Kogyo) Ovahormon Strong (Teikoku Zoki) Alesse (Wyeth-Ayerst) Brevicon (Searle) Demulen (Searle) Desogen (Organon) Estrostep (Parke Davis) Ethynodiol Diacetate and Ethinyl Estradiol (Watson) Levlen (Berlex) Lo/Ovral (Wyeth-Ayerst) Modicon (Ortho-McNeil Pharmaceutical) Nelova (Warner Chilcott) Nordette (Wyeth-Ayerst) Norethin (Roberts) Norethindrone and Ethinyl Estradiol (Watson) Norinyl (Searle) Ortho-Cept (Ortho-McNeil Pharmaceutical) Ortho-Cyclen (Ortho- McNeil Pharmaceutical) Ortho Novum (Ortho- McNeil Pharmaceutical) Ortho-Tri-Cyclen (Ortho- McNeil Pharmaceutical) Ovral (Wyeth-Ayerst) Tri-Levlen (Berlex) Tri-Norinyl (Searle) Triphasil (Wyeth-Ayerst) Ethionamide ATC: J04AD03 (Etionamide) Use: tuberculostatic RN: 536-33-4 MF: C,H,,N,S MW: 166.25 EINECS: 208-628-9 LDs,,: 1 g/kg (M, p.0.); 1320 mgkg (R, p.0.) CN: 2-ethyl-4-pyridinecarbothioamide diethyl butanone oxalote ethyl 2,4-dioxo hexonoate 1. POC13, Pel5 o i4 2 HO-CH, vcH3 , c'ycH3 COOH 0 or'cti3 6-ethyl-1.2- dihydra-2-oxo- 4-pyridine- carboxylic acid ethyl 2-chlaro- 6-ethyl-iso- nicotinote (11) A 0 or'cH3 C N ethyl 2- 2-ethyl- Ethionamide ethyliso- isonicotino- nicotrnate nitrile 800 E Ethisterone Referenceis): GB 800 250 (Chimic et Atomistique; appl. 1957; F-prior. 1956). Libermann, S. et al.: C. R. Hebd. Seances Acad. Sci. (COREAF) 242,2409,2412 (1956). Formulation(s): s. c. tabl. 250 mg; tabl. 100 mg Trade Name(s): D: Trecator (ThCraplix); wfm J: Ethimide (Tanabe) Thioniden (Kaken) F: TrCcator (ThCraplix); wfm Ethinamin (Takeda) Tuberrnin (Meiji) GB: Trescatyl (May & Baker); Itiocide (Kyowa) Tuberoid (Sankyo) wfm Scrtinon (Daiichi) Tuberoson (Shionogi) Trescazide (May & Baker)- Teberus (Dainippon) USA: Trecator-SC (Wyeth- comb.; wfrn Thiornid (Nikken) Ayerst) Ethisterone ATC: G03DC04 Use: progestogen RN: 434-03-7 MF: Cp,H,,O, MW: 312.45 EINECS: 207-096-5 CN: (17a)-17-hydroxypregn-4-en-20-yn-3-one potassium tert-pentylate + HCECH b 1 androstenolone acetylene aluminum HO tri-tert-butylate Ethisterone I Reference(s): US 2 272 131 (Ciba; 1942: CH-prior. 1937). Ehrhart, Ruschig 111, 343. alternative synthesis: US 4 041 055 (Upjohn; 9.8.1977; appl. 17.11.1975). review: Ullrnanns Encykl. Tech. Chem., 4. Aufl., Vol. 13,30 Formulation(s): cps. 50 rng, 100 rng, 250 rng; tabl. 25 mg Trade Name(s): D: Cycloestrol-A.H. Lutogynestryl (Rousse1)- ProgestCrone (Bruneau); comb.; wfm wfm GB: Amenoren (Rousse1)- I: F: Cycloestrol-A.H. comb.; wfm ProgestCrone (Bruneau)- Menstrogcn (Organon)- J: comb.; wfm comb.; wfm Orastxron (Schering Chemicals); wfm Pre Ciclo (Ibis)-comb.; wfm Estormon (Hokunku)- comb. . 6-ethyl-1. 2- dihydra-2-oxo- 4-pyridine- carboxylic acid ethyl 2-chlaro- 6-ethyl-iso- nicotinote (11) A 0 or'cH3 C N ethyl 2- 2-ethyl- Ethionamide ethyliso- isonicotino-. 6-chloro-3-ethyl-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide I, I -dioxide 5-chloro-2,4-di- propionoldehyde sulfornoylaniline Referencefs): GB 861 367 (Ciba; appl. 1959; USA-prior mg/kg (M, p.0.); 55 mgkg (dog, i.v.) CN: 1-chloro-3-ethyl-1-penten-4-yn- 3-0 1 Li, liq. NH3 + HCECH -b C I 1 -chloro- acetylene 1 -penten-3-one ATC: N05CM08 Use: hypnotic, sedative