Sulfoxone sodium S 1941 Trade Name(s): D: Inofal (Sandoz); wfm Sulfoxone sodium (Aldesulfon Natrium) ATC: DO8 Use: chemotherapeutic (leprosy) RN: 144-75-2 MF: CI,Hj4N,Na206S3 MW: 448.45 LD,,: 10 g/kg (M, p.0.) CN: [sulfonylbis(4,1-phenyleneimino)]bis[methanesulfinic acid] disodium salt free acid RN: 144-76-3 MF: Cl4HlhN2OhSR MW: 404.49 dopsone sodium form- (9. 4 oldehydesulfoxylote Sulfoxone sodium US 2 234 981 (US-Secretary of the Treasury; 1941; appl. 1938). Formulation(s): tabl. 330 mg Trade Name(sJ: J: Diazon (Joshitomi) USA: Diasone Sodium (Abbott); wfm Sulindac ATC: M01AB02 Use: anti-inflammatory, analgesic, antipyretic RN: 38194-50-2 MF: C2,H1,FO,S MW: 356.42 EINECS: 253-819-2 LD,,,: 507 mglkg (M, p.0.); 264 mg/kg (R, p 0.) CN: (~-5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-1H-indene-3-acetic acid 4-fluarobenz- propionic oldehyde anhydride 4-fluoro-a-methyl. cinnomic acid 1942 S Sulmetozin polyphosphoric ocid 2. KOH + I1 t- 0 1. cyonoacetic ocid 4-fluoro-a-methyl- dihydrocinnomic acid (I) 5-fluoro-2-methyl- indene-Facetic acid (11) 4-methylthio. benzaldehyde 5-fluoro-2-methyl-l- (4-methylthiobenzy1idene)- indene-3-ocetic ocid (111) Sulindoc DE 2 039 426 (Merck & Co.; appl. 7.8.1970; USA-prior. 8.8.1969, 1.5.1970). US 3 654 349 (Merck & Co.; 4.4.1972; prior. 8.8.1969, 1 S.1970). US 3 647 858 (Mcrck & Co.; 7.3.1972; prior. 19.1 1.1969, 1.5.1970). US 3 725 548 (Merck & Co.; 3.4.1973; prior. 6.10.1971). US 3 882 239 (Merck & Co.; 651975; prior. 21.1.1971,6.9.1972, 13.6.1974). Fortmdation(s): tabl. 150 mg, 200 mg Trade Name(s): D: Imbaral (Merck Sharp & Citereuma (CT) Sulinol (In) Dohme; 1977); wfm Clinoril (Neopharmed) J: Chinoril (Merck-Banyu) F: Arthrocine (Merck Sharp & Lyndac (Eurofarmaco) USA: Clinoril (Merck Sharp & Dohme-Chibret; 1977) Sulartrene (NGSN) Dohme; 1978) GB: Clinoril (Merck Sharp & Sulen (Farmacologico Dohme; 1977) Milanese) I: Algocetil (Francia Farm.) Sulic (Crosara) Sulmetozin (Trithiozine) ATC: A02BX Use: gastric acid secretion inhibitor, peptic ulcer therapeutic RN: 35619-65-9 MF: C,,JII9NO,S MW: 297.38 EINECS: 252-645-4 LD,,,: 3 g/kg (M, p.0.); 670 mg/kg (R, p.0.) CN: 4-[th1oxo(3,4,5-trimethoxyphenyl)methyl]morpholine 3,4,5-trimethoxy- morpholine benzoldehyde Sulmetozin u Reference(s): DOS 2 102 246 (ISF; appl. 19.1.1971; I-prior. 31.7.1970) Banfi, S. et al.: Chim. Thcr. (CHTPBA) 4,462 (1973). Trade Name(s): I: Tresanil (Italseber); wh Suloctidil ATC: COlDX Use: vasodilator RN: 54767-75-8 MF: C,,,H,,NOS MW: 337.57 EINECS: 259-332-1 CN: (R*,S*)-4-[(1-methylethyl)thio]-a-[1-(octylamino)ethyl]benzenemethanol 2-bromo-4'-isopropyl- octylomine thiopropiophenone Reference(s): DOS 2 334 404 (Continental Pharma; appl. 6.7.1973; GB-prior. 9.4.1973). US 4 228 187 (Continental Pharma; 14.10.1980; appl. 30.8.1976; GB-prior. 9.4.1973). (0 alternative syndmes: ES 460 766 (Lab. F. Bonet; appl. 14.7.1977). JP 54 005 928 (Mitsubish~; appl. 15.6.1977). JP 54 005 929 (Mitsuh~shi; appl. 15.6.1977). JP 54 005 930 (Mitsubishi; appl. 15.6.1977). JP 54 019 927 (Zambeletti; appl. 11.7.1977). Suloctidil use as vasodilator: JP 54 005 930 (Mitsubishi; appl. 1979). Formulation(s): cps. 100 mg, tabl. 100 mg 1944 S Sulpiride z Trade Name(s): E D: Fluversin (Searle; 1980); Euvasal (Selvi); wfm ~olivasol (~oli); wfm wfm Llangene (Farmochimica i GB: Duloctil (Searle); wfm Ital.); wfm i 1: Cerebro (Sidus); wfm Locton (Lepetit); wfm 1 Sulpiride ATC: NOSALOI Use: psychotropic drug, antispasmodic, antl-emetic, antidepressant, antipsychotic RN: 15676- 16-1 MF: C,,H2,N304S MW: 341.43 EINECS: 239-753-7 LD,,,: 48 mglkg (M, i.v.); 1700 mglkg (M, p.0.); 40 mglkg (R, i.v.); 9800 mglkg (R, p.0.); 137 mglkg (dog, i.v.); 2 glkg (dog, p.0.) CN: 5-(aminosulfonyl)-N-[(1-ethyl-2-pyrrolidiny1)methyl]-2-methoxybenzamide 0 COOH II FH3 p-s-0 I I d H3C 0 O\\ S ,5f0\CH3 H~N' \\O 5-ominosulfonyl salicylic acid 1. 1 .l'-carbonylbis- imidazole dimethyl sulfate 5-aminosulfo~yl-2- methoxybenzoic acid (I) ethylpyrrolidine Sulpiride Reference(s): DOS I 595 9 15 (Soc. d'Etudes Scientif. et Ind. de 1'Ile-de-France; appl. 8.1.1965; USA-prior. 13.1.1964). DOS 1 795 723 (Soc. d'Etudes Scientif. et Ind. de 1'Ile-de-France; appl. 8.1.1965; USA-prior. 13.1.1964). US 3 342 826 (Soc. &Etudes Scientif. et Ind. de l'lle-de-France; 19.9.1967; appl. 13.1.1964). alternative synthesis via the enamine from 2-aminomethyl-1 -ethylpyrrolidine and acetylacetic acid methyl ester: US 4 077 976 (Soc. d'Etudes Scientif. et Ind. de 1'Ile-de-France; 7.3.1978; F-prior. 12.6.1975). alternative synthesis: GB I 492 166 (Alkaloids Vegyeszetigyar; appl. 26.3.1976; H-prior. 28.3.1975). preparation of2-aminomethyl-1-ethylpyrrolidine from I-ethyl- resp. I-vinyl-2-pyrrolidinonc via l-ethyl-2- nitromethylpyrrolidine: DAS 1 941 536 (Soc. &Etudes Scientif. et lnd. de 1'Ile-de-France; appl. 14.8.1969; J-prior. 19.8.1968,20.5.1969, 9.6.1969). DAS 1 966 195 (Soc. d'Etudes Scientif. et Ind. de 1'Ile-de-Francc; appl. 14.8.1969; J-prior. 19.8.1968,20.5.1969, 9.6.1969). optically active "Leva"-sulpiridu: DOS 2 903 89 1 (Ravtzza; appl. 1.2.1979; I-prior. 16.2.1978) Fornrularion(s): amp. 100 mg12 ml, 100 mgl3 ml; cps. 50 mg; tabl. 50 mg, 200 mg k Sultamicillin S 1945 Trade hlame(s): D: Arminol (Krcwcl Meuselbach) Desulpid (Desitin) Dogmatil (Synthelabo; 1972) Meresa (Dolorgiet) Neogama (Hormosan) Sulp (Neuro Hexal) Sulpirid-ratiopharm (ratiopharm) Sulpivert (Hennig) vertigo-neogama (Hormosan) F: Aiglonyl (Fumouze) Dogmatil (Synthklabo; 1969) S ynCdil (Yamanouchi Pharma) GB: Dolmatil (Delalande; 1983) Sulparex (Bristol-Myers Squibb) Sulpitil (Pharmacia & Upjohn) I: Championyl (Synthelabo) Dobren (Ravizza) Equilid (Bruno Farmaceutici) J: Abilit (Sumitorno) Coolspan (Hishiyama) Dogmatyl (Fujisawa) Miradol (Mitsui) Omperan (Taiho) ' Sultamicillin (CP-49952; VD- 1827) ATC: JOlCR04 Use: antibacterial, semisynthetic p-lactam antibiotic (double ester of ampicillin and sulbactam) RN: 76497-13-7 MF: C,,H,,N40,S, MW: 594.67 CN: [2S-[2a(2R*,5S*),Sa,6~(S*)]]-6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-l- azabicyclo[3.2.0]heptane-2-carboxylic acid [[(3,3-dimethyl-7-0x0-4-thia- I-azabicyclo[3.2.0]hcpt-2- yl)carbonyl]oxy~methyl ester S,S-dioxide monotosylate RN; 83105-70-8 MF: C,SH30N40,S,. C,H,O,S MW: 766.87 Nal, acetone I + iodornethyl penicillanote S,S-dioxide (11) 1946, S Sultiame COOH Oh N $~~3 H,C o K~CO,, DMF k, CH3 + - N' H &O - NH,H 0, CH3 0'CH3 ampicillin methyl Dane salt (4. v.) acetoacetate of ampicillin (HI) Reference(s): Baltzer, B. et al.: J. Antibiot. (JANTAJ) 33, 1183 (1980). US 4 342 772 (Leo; 3.8.1982; UK-prior. 13.2.1979, 19.6.1979,9.8.1979, 14.1 1.1979). US 4 407 751 (Lco; 4.10.1983; UK-prior. 13.2.1979, 19.6.1979,9.8.1979, 14.1 1.1979,25.1.1980). DOS 3 005 164 (Leo; appl. 12.2.1980; UK-prior. 13.2.1979, 19.6.1979,9.8.1979, 14.11 .I 979). Formulation(s): f. c. tabl. 375 mg (as tosylate); vial 375 mg Trade Name(s): D: Unacid P Doral (Pfizer) J: Unasyn (Pfizer Taito; 1987) USA: Unasyn (Pfizer); wfm Sultiame ATC: ~03~x03 (Sulthiame) Use: anticonvulsant, antiepileptic RN: 61-56-3 MF: CloH,4N204S2 MW: 290.36 EINECS: 200-51 1-0 LD,,,: 4852 mgkg (M, p.o.1; >5 g/kg (R, p.0.) CN: 4-(tetrahydro-2H-l,2-thiazin-2-yl)benzenesulfonamide SJdioxide - pyridine 0 ___+ C I CI butanesulfonyl sulfonamide chloride Sultopride S 1947 Reference(s): DE 1 111 191 (Bayer; appl. 28.3.1959). Formulatiort(s): f. c. tabl. 50 mg, 200 mg Trade Name(s): D: Ospolot/mite (Bayer) I: Ospolot (Bayer); wfm J: Ospolot (Bayer) F: Elisal (Special; wfm Ospolot (Bayropharm); USA: Conadil (Riker); wfm GB: Ospolot (Bayer): wfm wfm Trolone (Riker); wfm Sultopride ATC: N05AL02 Use: anti-emetic, psychotropic drug, antidepressant RN: 53583-79-2 MF: C,,H2,N204S MW: 354.47 EINECS: 258-641-9 LD,,: 665 mgtkg (M, pa.) CN: ~-[(l-eth~l-2-~~rrolidin~l)meth~l]-5-(eth~lsulfon~l)-2-methox~benzamide hydrochloride RN: 23694-17-9 MF: C,,H2,N204S . HCl MW: 390.93 N(C2H5)3. dioxane b 1. isobutyl chlaroformote 0 2. 2-ominomethyl-1 -ethyl- 5-ethylsulfonyl-2- pyrralidine methoxybenzoic acid Sultopride I DOS 2 327 192 (Soc. dlEtudes Scientifique et Industrielles de I'Ile-de-France; appl. 28.5.1973; F-pr~or. 1.6.1972, 12.6.1972, 3.4.1973). DOS 2 327 193 (Soc. dlEtudes Scientifique et Jndustrielles de l'lle-de-France; appl. 28.5.1973; F-prior. 1.6.1972, a 2.6.1972). FR 2 187 309 (Soc. cl'Etudes Scientifiquc et Industrielles de 1'Ile-de-France; appl. 1.6.1972). Fomlulation(s): amp. 200 mg12 ml; tabl. 400 mg (as hydrochloride) 1948 S Sultroponium Trade Name(s): F: BarnCtil (SynthClabo; as Sultopride Panpharma I: Barnotil (Vita; as hydrochloride) (Panpharma; as hydrochloride) hydrochloride) J: Barnetil (Mitsui) Sultroponium ATC: A03 Use: anticholinergic, antispasmodic RN: 15 130-9 1-3 MF: C2,,H2,N0,S MW: 41 1 .S2 CN: er~do-(+)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(3-sulfopropyl)-8- azoniabicyclo[3.2. lloctane hydroxide inner salt atropine propane 1 Sultmponium 1 . (4. v.) sultone Rejcrence(s): GB 1 082 445 (J. P. M. Raudnitz, H. Wahl; appl. 2.12.1965; F-prior. 3.12.1964). Formulation(s): amp. 5 mg; suppos. 25 mg; tabl. 15 mg Trade Nanle(s): F: Sultroponium B (BiothCrax); wfm Sumatriptan ATC: NO~CCOI Use: antimigraine agent, selective 5-HT,- receptor agonist RN: 103628-46-2 MF: C,,H21N302S MW: 295.41 CN: 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide succinate (1:l) RN: 103628-48-4 MF: CI4H2,N,O,S. C,H,04 MW: 413.50 LD,,,: 43.112 mglkg (R, i.v.); >2.939 glkg (R, p.0.) methonesuMonomide methonesulfonornide (I) Sumatriptan S 1949 H [,,&fJN.N c' polyphosphoric acid - H3C H,C/ // 0 dimethylomine (IV) N-CH, Sumatriptan 1. HCI H~C/O~'-"-'?/~~~ 2. polyphosphoric ocid ru- _ 4-(dimethylomino)butonal dimethyl acetol u 1. HCI (phenylthio). N-methyl-4-[2-[2-(phenylthia). acetaldehyde ethylidene]hydrazino]benzene- methonesulfanamide N-methyl-1 H-indale- oxolyl 5-methanesulfon- chloride omide (V) Reference (s): a DOS 3 320 521 (Glaxo; appl. 6.7.1983; GB-prior. 6.7.1982). GB 2 124 210 (Glaxo; appl. 7-6-1982). b,c DOS 3 527 648 (Glaxo; appl. 8.1.1985; GB-prior. 8.1.1984). GB 2 162 522 (Glaxo; appl. 8.1.1984). Formulation(s): f. c. tabl. 50 mg, 100 mg; nasal spray 10 mg1O.l ml, 20 mg1O.l ml; suppos. 25 mg; syringe 6 mg; tabl. 25 mg, 50 mg; vial 6 mg10.5 ml (as succinate) 1950 S Suplatast tosilate Trade Name(s): D: Imigran (Glaxo Wellcomel Imijekt (Glaxo Wellcome) USA: Imitrex (Glaxo Wellcome) Cascan) GB: Imigran (Glaxo Wellcome; F: Imigrane (Glaxo 1991) Wellcome) I: Imigran (Glaxo Wellcome) Suplatast tosilate (IPD-11SlT) ATC: R03 Use: antiallergic, antiasthmatic RN: 94055-76-2 MF: C,,H,NO,S . C7H70, MW: 467.58 LD,,,: 81 mglkg(M,i.v.);>12.5gkg(M,p.o.); 93 mgkg (R, i.v.); > 10 glkg (R, p.0.); 21 24 mgkg (dog, p.0.) CN: [3-[[4-(3-ethoxy-2-hydroxypropoxy)phenyl]amino]-3-oxopropyl]dimethylsulfonium p-toluenesulfonate 4-(3-ethoxy-2-hydroxy- 3-(methylthb- propoxy)aniline propionyl chloride Reference(s): DE 3 408 708 (Taiho Pharm.; 13.9.1984; J-prior. 11.3.1983). methyl 4-toluene- resolution: JP 07 252 213 (Taiho Pharm. 3.1.1995; J-prior. 27.1.1994). Suplatast tosilate topical application: EP 624 367 (SenjuITaiho Pharm.; 17.11 .l994; J-prior. 14.5.1993). sulfonate Formulation(s): cps. 50 mg, 100 mg Trade Namr(s): J: IPD (Taiho) MPD (Taiho) . [2S-[2a(2R*,5S*),Sa,6~(S*)] ]-6 -[ (aminophenylacetyl)amino ]-3 ,3-dimethyl-7-oxo-4-thia-l- azabicyclo[3.2.0]heptane-2-carboxylic acid [[(3,3-dimethyl- 7-0 x 0-4 -thia- I-azabicyclo[3.2.0]hcpt- 2- yl)carbonyl]oxy~methyl. ocid 4-fluoro-a-methyl- dihydrocinnomic acid (I) 5-fluoro-2-methyl- indene-Facetic acid (11) 4-methylthio. benzaldehyde 5-fluoro-2-methyl-l- (4-methylthiobenzy1idene )- indene-3-ocetic. anticholinergic, antispasmodic RN: 15 13 0-9 1-3 MF: C2,,H2,N0,S MW: 41 1 .S2 CN: er~do-(+ )-3 -( 3-hydroxy-1-oxo-2-phenylpropoxy )-8 -methyl- 8-( 3-sulfopropyl )-8 - azoniabicyclo[3.2. lloctane hydroxide