Sulfadicramide S 1921 Sterinor (Heumann)-comb. with textroprim Sulfadiazin (Heyl) Urospasmon (Heumannl- comb. Adiazine (Doms-Adrian) Antrima (Doms-Adrian)- comb. Flamenacerium (Solvay Pharma; as silver salt)- comb. Flammazine (Solvay Pharma; as silver salt) Sicazine (Smith & Nephew; as silver salt) Flamazine (Smith & Nephew; as silver salt); wfrn Streptotriad (M. & B.)- comb.; wfm I: Connettivina (Fidia; as silver salt) Kombinax (Bracco)-comb. Oxosint (Medivis)-comb. Sofargen (Sofar; as silver salt) Sterinor (ABC Farmaceutici)-comb. Sulfadiazina (Ecobi; IFI) Sulfadiazina Sodica (Salf; as sodium salt) J: Theradia (Daiichi) Theradiazine (Daiichi) USA: Coco-Diazine (Lilly); wfm Neotrizine (Lilly)-comb.; wfm Silvadene (Marion Labs.; as silver salt); wfm Sodium Sulfadiazine (City Chem.); wfm Sodium Sulfadiazine (Lederle); wfrn Sulfonamides Duplex (Lilly); wfrn Sulfose (Wyeth)-comb.; wfm Terfonyl (Squibb)-comb.; wfm Triple Sulfas (Leder1e)- comb.; wfrn Trisem (Beecham)-comb.; wfrn further combination preparations; wfrn Sulfadicramide ATC: SOlAB03 Use: chemotherapeutic RN: 115-68-4 MF: C, ,H14N20,S MW: 254.3 1 EINECS: 204-099-3 CN: N-[(4-aminophenyl)sulfonyl]-3-methyl-2-butenamide L 3-methyl- amide crotonamide j 4-acetomidobenzene- sulfonyl chloride Sulfadicramide Reference(s): US 2 417 005 (Geigy; 1947; CH-prior. 1943). Forrnulation(s): ophthalmic ointment 150 mg/g Trade Narne(s): D: Irgamid Augensalbe (Dispersa); wfrn Irgamid Augensalbe (Zyma-Blaes); wfrn 71 1922 S Sulfadimethoxine Sulfadimethoxine ATC: JOIEDO~ Use: chemotherapeutic RN: 122-1 1-2 MF: Cl2Hl4N4O,S MW: 310.33 EINECS: 204-523-7 LD,,,: 844 mdkg (M, i.v.1; ~3200 mglkg (dog, p.0.) CN: 4-amino-N-(2,6-dimethoxy-4-pyrimidinyl)henzenesulfonamide 4-ominobenrenesulfon- 2.4-dimethoxy-6-tri- ornide sodium salt methylommonio- pyrimidine chloride Sulfadimethoxine urea ethyl 6-om1no-2.4-d1- 6-amino-2.4-di- cyonoocetote iydroxypyrimidine chloropyrimidine (I) 0, 1. 4-acetomidobenzene- 1 I CH3 sulfonyl chloride 6-omino-2.4-di- methoxypyrimidine Reference(s): a US 2 703 800 (Osterr. Stickstoffwerke; 1955; A-prior. 1951). b Bretschneider, H. et al.: Monatsh. Chem. (MOCMB7) 87. 136 (1956); 92,75 (1961); 92. 128 (1961). Formulrition(s): drops 200 mglml; syrup 250 mg15 ml; tabl. 250 mg, 500 mg Trade Name(s): D: Madribon (Koche); wfm Dimexin (Fuso) Sulmethon (Mohan) F: Madribon (Roche); wfm Hachimetoxin (Toyo S Sulmetoxyn (Nichiiko) GB: Madr~bon (Koche); wfm Ono) Sulxin (Chugai) I: Sulfadimetossina (IFI) Melfa (Tanabe) Sumetamin (Samva) J: Abcid (Daiichi) Mition-D (Taisho) USA: Albon (Roche); wfm Asthoxin (Kobay ashi) Omunibon (Yamanouchi) Dimetoxin (Nissin) Sulfalon (Sumitomo) Sulfadoxine S 1923 Sulfadoxine ATC: POIBDSI (Sulforrnetoxinum; Sulforlhomidine; Sulformethoxine) Use: (su'fonamide) RN: 2447-57-6 MF: C,2H,4N,04S MW: 310.33 EINECS: 219-504-9 LD5,,: 5200 mglkg (M, p.0.) CN: 4-amino-N-(5,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide methyl meth- dirnethyl oxyacetote oxalate OHC-NH2 0JH3 NoOC,H, 0/CH3 POCI, b Ir forrnamide NH2NH2 NbN dimethyl rnethoxy- methoxy- malonate (I) rnolonomide 4,6-dichloro- 4-arnino-6- 5-methoxy- chloro-5- pyrimidine (11) methoxy- pyrimidine 4-amino-5,6- dirnethoxy- pyrimidine (111) 4-acetomidobenzene- sulfonyl chloride Sulfodoxine US 3 132 139 (Roche; 1964; CH-prior. 196 1 ). Griissner, A. et al.: Monatsh. Chem. (MOCMB7) 96, 1676 (1965). Bretschneider, H. et a].: Monatsh. Chem. (MOCMB7) 96, 1661 (1965) Formulation(s): amp. 400 mg; tabl. 500 mg (in comb. with 25 mg pyrimethamine) 1924 S Sulfaethidole Trade Name(s): D: Fansidar (Roche)-comb.; GB: Fansidar (Roche)-comb. USA: Fansidar (Roche) wfm I: Fanasil (Roche); wfm F: Fansidar (Roche)-comb. J: Fansidar (Roche)-comb. Sulfaethidole ATC: G04A Usr: chemotherapeutic RN: 94-19-9 MF: C,oHi,N,02S2 MW: 284.36 EINECS: 202-312-4 LD,,,: 1300 mglkg (R, i.v.) CN: 4-amino-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide 4-nitrobenzene- 5-amino-2-ethyl- sulfonyl chloride 1 J.4-thiadiazole 4-acetomidobenzene- propionaldehyde sulfonyl chloride thiosemicarbazone I potossium hexo- cyanoferrote(li1) . . a US 2 358 03 1 (American Cyanamid; 1944; prior. 1940). DE 957 841 (Schering AG; appl. 1940). b US 2 447 702 (Lundbeck; 1948; DK-prior. 1942). Fonnulation(s): drg. 150 mg (in comb. with 350 mg sulfamethiozole) Trade Narne(sj: D: Harnosal (TAD)-comb. Sulfafurazole (Sulfisoxazole; Sulphafurazole) ATC: JOlEBO5; SOlAB02 Use: chemotherapeutic RN: 127-69-5 MF: CIiH13N30,S MW: 267.3 1 EINECS: 204-858-9 LD,,,: 2500 mglkg (M, i.v.); 6800 mglkg (M, p.0.); I0 glkg (R, p.0.) CN: 4-amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide Sulfaguanidine S 1925 "J- , CH3 hydroxyl- H,C' 7 arnine CH3 sufonyl chloride 2-methylaceta- acetonitrile Reference(s): US 2430 094 (Hoffmann-La Roche; 1947; prior. 1944). DE 819 855 (Hoffmann-La Roche; USA-prior. 1944). Fonnulation(s): amp. 4 rngfml; eye drops 4 %; tabl. 500 mg Trade Name(s): D: Gzntrisin (Roche); wfm F: Gantrisine (Roche); wfm USA: PMiazole (Abbott)-comb. with erythromycine GB: Gantrisin (Roche); wfm 1: Fultrexin (Zambon)-comb.; wfm Pancid (Lister); wfm 1: lsoxamin (Fuso) Sulfazin (Shionogi) Thiasin (Yamanouchi) Azo-Gantrisin (Roche)- comb.; wfm Dow-Sulfisoxazolc (Dow); w fm Erythromycin Ethylsuccinate / Sulfisoxazole Acetate (Warner Chilcott) Gantrisin (Roche): wfm Koro-Sulf (Holland- Rantos); wfm SK-Soxazole (Smith Kline & French); wfm Sosol (McKesson); wfm Soxomide (Upjohn); wfm Sulfalar (Parke Davis); w fm combination preparations and generics Sulfaguanidine (Sulphaguanidine) ATC: A07AB03 Use: chemotherapeutic RN: 57-67-0 MF: C7H,,N402S MW: 214.25 EINECS: 200-345-9 CN: 4-amino-N-(arninoiminornethyl)benzenesulfonamide Reference(s): US 2 218 490 (American Cyanamid; 1940; appl. 1940). US 2 229 784 (American Cyanamid; 1941; appl. 1940). 4-arninobenzene- guanidine carbonate US 2 233 569 (American Cyanamid; 194 1 ; appl. 1940). Sulfaguanidine sulfonarnide 1926 S Sulfaguanole Fonnulation(s): tabl. 0.5 g (as hydrate) Trade Name(s): D: Diaront (Chephasaar)- comb.; wfm Enterastrept (Hey1)-comb.; F: wfrn Guabeta (OTW); wfm I: Jacosulfon (Giu1ini)-comb.; wfrn Sulfaguanole Resulfon-S (Nordmark); Streptoguanidin w Cm (Lisapharma)-comb.; wfm Litoxol (SmithKline combination preparations; Beecham) wfm Aseptil-Guanidina J: Aterian (Takeda) (Wassermann); wfrn Kin01 (Lafare)-comb.; wfrn ATC: DO8 Use: chemotherapeutic (depot sulfonamide) RN: 27031-08-9 MF: C,,H,,N,O,S MW: 309.35 EINECS: 248-175-4 CN: 4-ami1~o-N-[[(4,5-dimethyl-2-oxazolyl)amino]iminomethyl]benzenesulfonamide N'-(4-aminophenylsulf0nyl)- acetoin ~'-c~ano~uanidine Sulfaguanole I Reference(s): US 3 562 258 (Nordmark; 9.2.1971; prior. 10.2.1969). GB 1 185 139 (Nordmark; appl. 13.2.1969). Formulation(s): drg. 400 mg Trade Name(s): D: Enterocura (Nordmark); I: Asorec (Radiumfarma); Enterocura (De Angeli); wfm wfm wfm Sulfalene (Sulfametopyrazine) ATC: JOlBD02 Use: chemotherapeutic (depot sulfonamidc) RN: 152-47-6 MF: C,,H,,N,O,S MW: 280.31 EINECS: 205-804-7 LD,,,: 893 mglkg (M, i.v.); 1292 mglkg (M, p.0.); 1790 mglkg (R, i.v.); 2739 mglkg (R, p.o ) CN: 4-amino-N-(3-methoxypyrazinyl)benzenesulfonamide Sulfaloxic acid S 1927 starting product: 0 Br2 ti$-ONa (I) CtI&ooti H2NXNX + H2NXNX pd-c, H2N N, Br N Br 9 N Br 0 1 N 1 1-amino- pyrozine 3-chloro-2- cyonopyrozine fi~l product: 3-amino-2- methoxy- pyrazine (D) NC N X 4 0 N . I CH3 2-cyono-3- methoxy- pyrozine (Ill) 4-acetomidobenzene- sulfonyl chloride Reference(s): US 3 098 069 (Carlo Erba; 16.7.1963; GB-prior. 14.7.1959). Formulation(s): tabl. 2 g Trade Name(s): D: Longum (Pharmacia & I: Kclfiprim (Pharmacia & Upjohn) Upjohn)-comb. GB: Kelfizine-W (Pharmacia & Kelfizina (Pharmacia & Upjohn) Upjohn) Sulfaloxic acid (Sulphaloxate; Sulphaloxic Acid) ATC: DO8 Use: chemotherapeutic (sulfonamide), antibacterial RN: 14376-16-0 MF: C,,H,,N,O,S MW: 393.38 EINECS: 238-348-2 CN: 2-[[[4-[[[[(hydroxymethyl)amino]carhonyl]am~no]sulfonyI]phcnyl]amino]carhonyl~benzoic acld 1928 S Sulfamerazine calcium salt RN: 97259-91-1 MF: C,2H28CaN,014S, MW: 824.81 phthalic sulfacarbamide anhydride (4. v.) Referertce(s): DE 960 190 (Cheni. Fabrik von Heyden; appl. 1954). DAS 1 002 3 19 (Chem. Fabrik von Heyden; appl. 15.6.1954). farm- Formulationjs): tabl. 0.55 g (as calcium salt) Sulfalaxic acid Trade Narne(s): r D: Intestin-Euvernil (Heyden) Sulfa-Adsorgan GB: Enteromide (Consolidated; Myacine (Schur)-comb.; (Combustin); wfm as calcium salt); wfm wfm aldehyde 1 Sulfamerazine (Methylsulfadiazine) ATC: JOlED07 Usc: chemotherapeutic, antibacterial RN: 127-79-7 MF: C,,H,,N,O,S MW: 264.31 EINECS: 204-866-2 LD,,,: 25 glkg (M, p.0.); I100 mglkg (R, Lv.) CN: 4-amino-N-(4-methyl-2-pyrimld~nyl)benzenesulfonamlde sodium salt RN: 127-58-2 MF: C,,H,,N4Na02S MW: 286.29 0 CH, H N N CH, H N N CH, HzNx:H2 + H,c-oJ - ". ' 0 0 CI guanidlne ethyl ocetoocetate 2-omino-4- methyl- pyrimidine (I) Sulfamethizole S 1929 Reference(s): US 2 407 966 (Sharp & Dohme; 1946; appl. 1940). Formulation(s): susp. 60 mg1.5 ml; tabl. 120 mg (as sodium salt) Trade Name(s). D: Dosulfin (Gcigy)-comb.; F: Dosulfine (Gomenol). I: Polagin (De Angeli)-comb.; wfm comb.; wfm w fm Solumedine (Spccia); wfm J: Romezin (Tanabe) Sulfamethizole (Sulphamethizole) ATC: B05CA04; D06BA04; J01 EB02; SOlABO1 Use: chemotherapeutic, antibacterial RN: 144-82-1 MF: C9HI,,N,02S, MW: 270.34 E!NECS: 205-64 1- 1 LD,,: 1820 mgkg (M, i.v.); >I0 glkg (M, p.0.); 2710 mglkg (R, i.v.); 3500 mglkg (R, p.0.) CN: 4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide 4-nitrobenzene- 5-amino-2-methyl- sulfonyl chloride 1.3.4-thiodiozole H SH + H,N~\ //rCH3 d 1 N-N N-N H3C N H 4-ocetomidobenzene- acetaldehyde sulfanyl chloride thiosemicarbozone 1930 S Sulfamethoxazole potossiurn hexocyona- ferrote(ii1) Rgf?rence(s): a US 2 358 03 1 (American Cyanamid; 1944; prior. 1940). b US 2 447 702 (Lundbeck & Co.; 1948; DK-prior. 1942). Fo~~nzulahn(s): cps. 250 mg in comb. with oxytetracycline.HCI(250 mg) and phenazopyridine.HC1 (SO mg); drg. 350 mg in comb. with sulfaethidiole Trade Name(s): D: Harnosal (TAD)-comb. Thiosulfil (Ayerst); wfm Urosol (Kanto) F: Rufol (Dtbat) J: Harnway (Nichiiko) Urosul (Mohan) GB: Urolucosil (Warner); wfm Salimol (Maruishi-Kanebo) USA: Urobiotic-250 (Pfizer)- I: Rufol (Roussel-Maestretti); Urokinon (Chugai) comb. wfm Urokizol (Chugai) Sulfamethoxazole (S ulphamethoxazole) ATC: JOlECOl Use: antipneumocystis, chemotherapeutic (urogenital tract infections) RN: 723-46-6 MF: C,,H,,N,O,S MW: 253 28 EINECS: 211-963-3 LD,,,: 1460 mgkg (M, i.v.). 2300 mglkg (M, p.0.); 6200 mgkg (R, p.0.) CN: 4-amino-N-(5-methyl-3-1soxazolyl)benzenesulfonamide 4-ocetornidobenzene- 3-omino-5- sulfonyl chloride rnethylisoxozole Rejerence(s): US 2 888 455 (Shionogi; 26.5.1959; J-prior. 4.9.1956) Formulation(s): amp. 400 mg1.5 ml, 800 mg13 ml; susp. 200 mgf5 ml; syrup 200 mgf5 ml, 400 mg15 ml; tabl. 100 mg, 400 mg, 800 mg, 960 mg Trade Name(s): D: Bactoreduct (Azupharma)- Bactrimlforte (Roche)- Berlocid (Bcrlin-C11emie)- comb. with rimet tho prim comb. with trimethoprim comb. with trimethoprim . RN: 9 4-1 9-9 MF: C,oHi,N,02S2 MW: 284.36 EINECS: 20 2-3 1 2-4 LD,,,: 1300 mglkg (R, i.v.) CN: 4-amino-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide 4-nitrobenzene- 5-amino-2-ethyl- sulfonyl. 4-amino-N-(2,6-dimethoxy-4-pyrimidinyl)henzenesulfonamide 4-ominobenrenesulfon- 2.4-dimethoxy-6-tri- ornide sodium salt methylommonio- pyrimidine chloride Sulfadimethoxine urea ethyl 6-om1no-2.4-d 1- 6-amino-2.4-di- cyonoocetote iydroxypyrimidine. chemotherapeutic RN: 11 5-6 8-4 MF: C, ,H14N20,S MW: 254.3 1 EINECS: 20 4-0 9 9-3 CN: N-[(4-aminophenyl)sulfonyl ]-3 -methyl-2-butenamide L 3-methyl- amide crotonamide j 4-acetomidobenzene- sulfonyl chloride