Citrulline C 491 Hepasteril B. compositum, Reducdyn (Nordmark)- F: Thioncycline (Merrel1)- forte (Fresenius)-comb.; comb.; wfm comb.; wfm wfm Sterofundin-CH (Braun ThioxidrCne (Boltu); wfm Mederma (Merz)-comb.; Melsungen); wfm I: Citiolase (Roussel) wfm Tutofusin LC (Pfrimmer); wfrn Citrulline ATC: V03AB99 Use: liver therapeutic RN: 372-75-8 MF: C6H,,N303 MW: 175.19 EINECS: 206-759-6 CN: fl-(aminocarbony1)-L-ornithine malate (1:l) RN: 70796-17-7 MF: C6H,,N303. C,H,O, MW: 291.26 @ by fermentation o from Socchorornyces genus L-arginine hydrochloride b from orniihine Citrulline c from Arthrobaciel Referencefs): 1 Fox, S.W.: J. Biol. Chem. (JBCHA3) 123,687 (1938). 2a JP 52 143 288 (Kyowa; appl. 20.5.1976). 2b JP 50 148 588 (Miura; appl. 23.5.1974). 2c JP 53 075 387 (~yowa; appl. 13.12.1976). alternative syntheses: JP 122 48/67 (Ajinomoto; appl. 1 1.9.1965). JP 117 58/68 (Kyowa; appl. 15.1 1.1965). Fox, S.W. et al.: J. Org. Chem. (JOCEAH) 6, 410 (1 941). crystallization: JP 7 100 174 (Ajinomoto; appl. 20.1 1.1968). isolation from Citrullus vulgaris Schrad.: Wada, M.: Biochem. Z. (BIZEA2) 224,420 (1930). use as liver therapeutic: FR-M 4 182 (Inst. de Recherche Sci.; appl. 9.3.1965). FR-M 5 594 (Dimaphar; appl. 1.7.1966). FR-M 5 703 (Lab. Carriere Carron; appl. 30.8.1965). FR-M 6 305 (Dimaphar; appl. 15.12.1966). use as digestant: FR-M 5 695 (Lab. Carriere Carron; appl. 29.8.1966). citrulline fumarate: FR-M 6 306 (Dimaphar; appl. 15.12.1966). 492 C Cladribine citrulline maleate: FR-M 6 443 (Dimaphar; appl. 21 A.1967). Formulation(s): amp. 60 mg/15 ml; drg. 25 mg, 100 mg Trade Name(s): D: Polilevo (Taurus Pharma)- Perifago (Pharmacia & Citruplexina (Synthe1abo)- comb. Upjohn) comb. F: Azonutril (Pharmacia & Stimol (Biocodex; as Ipoazotal (SIT)-comb. Upjohn)-comb. malate) Epurarn (Pharmafarm)- I: Biotassina (UCM)-comb. comb. Cladribine (NSC- 105014-F; RWJ-2625 1 ; 2-CdA) RN: 4291-63-8 MF: C,,H,,CIN,O, MW: 285.69 CN: 2-chloro-2'-deoxyadenosine ATC: LOlBB04 Use: antineoplastic CH, 2.6-dichloro- 2-deoxy-3.5-di-O-p- purine toluayl-a-D-erythro- pentofuronosyl chloride 1. NH3, CH,OH. 100 OC 2. chrornatogrophy . Clodribine I purine (I) Cladribine C 493 guanosine 1. pyridine. OMF k 1. pentyl nitrite, K2C03, CH2C12. (C,H,),CCI 2. NH,OH, THF n F OH OH Z-chloro- odenosine pyridine 111 1.3-dichloro- 1 .l.3,3-tetro- DMAP, ocetonitrile + c'rO~ +. 0-phenyi chloro- thioformote 1 Bu3SnH. AIBN, benzene, A 2. Bu,N+F THF Clodribine 1. tributyltin hydride 2. tetrobutvlommonium fluoride .El 2-chloro-2'-0-phenoxy- thiocorbonyl-3'.5'-0- (tetroisopropyldisiioxonylene)- adenosine (N) 494 C Clavulanic acid Refc?rence(s): a Kazimierczuk, Z. et al.: J. Am. Chem. Soc. (JACSAT) 106,6379-6382 (1984). EP 173 059 (Univ. Brigham Young; appl. 17.7.1985; USA-prior. 6.8.1984, 15.1.1987). Christensen, L.F. el al.: J. Med. Chem. (JMCMAR) 15,735 (1972). b US 5 208 327 (Ortho Pharm. Corp.; appl. 16.4.1992; USA-prior. 18.12.1991). compositions for treatment of rheumatoid arthritis: US 5 310 732 (Scripps Res. Inst.; appl. 19.2.1992; USA-prior. 3.2.1986). Formulatiort(s): inj. sol. 10 mg/lO ml Trade Name( s): D: Leustatin (Janssen-Cilag) GB: Leustat (Janssen-Cilag) F: Leustatine (Janssen-Cilag) USA: Leustatin (Ortho Biotech) Clavulanic acid ATC: JOICRO2 Use: P-lactamase inhibitor RN: 58001 -44-8 MF: C,H,NO, MW: 199. I6 EINECS: 261-069-2 LDS,,: 4 g/kg (M, i.v.); 4526 mg/kg (M, p.0.); 7936 rnglkg (R, p.0.) CN: [2R-(2a,3Z,5a)]-3-(2-hydroxyethylidene)-7-oxo-4-oxa-l-azabicyclo[3.2.0]heptane-2-carboxylic acid monosodium salt RN: 57943-81-4 MF: C,H,NNa05 MW: 221.14 EINECS: 261-032-0 LD,,,: 4 glkg (M, i.p.); 4500 rnglkg (M, LC.) From cultures of Streptornyces clavuligerns. Reference(s); US 4 529 720 (Beecham; 16.7.1985; GB-prior. 2.4.1974). US 4 367 175 (Glaxo; 4.1.1983; GR-prior. 7.2.1975). GB 1 508 977 (Beecham; appl. 11.4.1975; GB-prior. 2O.4.l974,2l.6.l974.9.lO.l974, 1 I. 12.1974). DOS 2 517 316 (Beecham; appl. 18.4.1975; GB-prior. 20.4.1974, 21.6.1974,9.10.1974, 11.12.1974) DE 2 560 074 (Beecham; appl. 18.4.1975; GB-prior. 20.4.1974, 21.6.1974.9.10.1974, 1 1.12.1974). pure salts (e. g. Nu-, Li- and other salts); US 4 490 294 (Beecham; 25.12.1984; GB-prior. 7.2.1975, 17.3.1975). US 4 490 295 (Beecham; 25.12.1984; GB-prior. 7.2.1975, 17.3.1975). GB 1 543 563 (Glaxo; appl. 7.2.1975, 17.3.1975; Compl. Spect. 6.2.1976). tert-bu~lamine salt: EP 26 044 (Beecham; appl. 15.8.1980; GB-prior. 24.8.1979). US 4 454 069 (Beecham; 12.6.1984; GR-prior. 24.8.1979). various salts: US 4 367 175 (Glaxo; 4.1.1983; GB-prior. 7.2.1975, 17.3.1975) esters: Clebopride C 495 formularion with amoxicillin: EP 8 905 (Beecham; appl. 21.8.1979; GB-prior. 6.9.1978). US 4 301 149 (Beecham; 17.1 1.1981; GB-prior. 11 .lO.I977). EP 49 061 (Beecham; appl. 6.9.198 1 ; GB-prior. 27.9.1980). EP 52 962 (Beecham; appl. 2.1 1.1981; GB-prior. 20.1 1.1980). GB 2 084 016 (Beecham; GB-prior. 27.9.1980). formulation with penicillins and cephalosporins: DOS 2 559 41 1 (Beecham; appl. 18.4.1975; GB-prior. 20.4.1974,21.6.1974,9.10.1974, 11.12.1974). Fonnulution(s): drops 12.5 mglml; f. c. tabl. 125 mg; tabl. 125 mg; vial 0.1 g, 0.2 g, 0.275 g, 0.6 g, 1.2 g, 2.2 g (as potassium salt)-comb. with amoxicillin Trade Name(s): D: Augmentan (SmithKline Beecham; 1982)-comb. with amoxicillin Betabactyl (SmithKline Beecham)-comb, with t~carcillin F: Augmentin (Sm~thKline Beecham; 1984) I Ciblor (Inava) Claventin (SmithKline Beecham) GB: Augmentin (SmithKline Beecham; 1984)-comb. with amoxicillin Timentin (SmithKline Beecham)-comb. I: Augmentin (SmithKLine B. Farm.)-comb. Clavucar (Smith Kline & French)-comb. with ticarcilline Clavulin (Carlo Erba)- comb. Neoduplamox (Smith Kline & French)-comb: Timentin (SmithKline Beecham)-comb. with ticarcilline all combination preparations with amoxicillin J: Augmentin (Beecham- Meiji)-comb. with amoxicillin USA: Augmentin (SmithKline Beecham: 1984)-comb. with amoxicillin Timentin (SmithKline Beecham) Clebopride AT: A03FA06; A04AD Use: anti-emetic, specific antagonist of peripheral and central dopamine receptors, reversible MAO-inhibitor RN: 55905-53-8 MF: CzoHz4CIN,02 MW. 373.88 EINECS: 259-885-9 LD,,: 260 mg/kg (M, i.m.); 40 mglkg (M, i.p.); 51 mglkg (M, i.v.); 490 mglkg (M, p.0.): 350 mglkg (M, s.c.): 1450 mg/kg (R, i.m.); 155 mglkg (R, i.p.); 39 mglkg (R, i.v.); 2540 mglkg (R, p.0.); 4850 mglkg (R, s.c.) CN: 4-amino-5-chloro-2-methoxy-N-[l-(phenylmethyl)-4-piperidinyl]benzamide monohydrochloride RN: 57645-39-3 MF: C2,H2,C1N30, . HCI MW: 410.35 LD,,: >I @kg (M, pa) malate (1:l) RN: 57645-91-7 MF: C,,Hz4CIN,0z . C4H,0S MW: 507.97 EINECS: 260-874-6 LD,: 51 mgtkg (M, i.v.); 490 mglkg (M, p.0.); 39 mgkg (R, i.v.); 2540 mglkg (R, p.0.); >800 mg/kg (dog, p.0.) 2. CI2, FeCI, b 1 1, dimethyl sulfote HN CH, I' 2. chlorine 0 4-amino- salicylic acid 4-acetomido salicylic acid 496 C Clemastine F73 CI CH3 HN CH3 K 0 methyl 2-methoxy- 4-aceiamido-5- chlorobenzoate (I) COOH 2-methoxy-4- amino-5-chloro- benzaic acid (11) 2. 111 NH2 Clebopride 1-benzyl-4-amino- piperidine (In) . . DE 2 513 136 (Anphar; appl. 21.3.1975; GB-prior. 21.3.1974). US 4 138 492 (Anphar; 6.2.1979; appl. 17.3.1975; GB-prior. 21.3.1974). Prieto, J. et al.: J. Pharm. Pharmacol. (JPPMAB) 29, 147 (1977). alternative synthesis: JP 63 295 558 (Asahi; appl. 26.5.1987). JP 63 295 557 (Asahi; appl. 26.5.1987). synthesis of intermediates: JP 63 295 559 (Asahi; appl. 26.5.1987). transdermal patch: EP 303 445 (Fordonal; appl. 9.8.1988; J-prior. 13.8.1987). Formulation(s): amp. 1 mg; sol. 0.5 mg; syrup 0.5 mg; tabl. 0.25 mg, 0.5 mg (as hydrogen maleate) Trade Name(s): I: Cleprid (Recordati; 1987) J: Amicos (Banyu; 1985) Motilex (Guidotti) Clast (Meiji) Clemastine (Meclastine) ATC: D04AA 14; R06AA04 Use: antiallergic, antihistaminic RN: 15686-51-8 MF: CzIH,,CINO MW: 343.90 CN: [R-(R*,R*)]-2-[2-[1-(4-chlorophenyl)-l-phenylethoxy]ethyl]-l-methylpyrrolidine hydrogen fumarate (1:l) RN: 14976-57-9 MF: C2,H2,C1N0 . C4H404 MW: 459.97 EINECS: 239-055-2 LD,,: 43 mgkg (M, i.v.); 730 mglkg (M, p.0.); 82 mgkg (R, i.v.); 3550 mgkg (R, p.0.) Clemastine C 497 d CI 4-chloro- methylmagnesium (1) benzophenone chloride 4'-chloro- phenylmognesium OcetoDhenone bromide 1. NaH, aylene I + CI a \ 2. chromatogr. with silica gel H$j, CH3 / \ - CH3 (+)-2-(2-chloro- ethyl)-1 -methyl- pyrrolidine 1. froctionol crystollizotion of rnoleotes 2. resolution with (-)-dibenzoyl-L-tllrtoric acid 11 b c'l mixture of 4 isomers (U) Clemostine 1 Reference(s): Ebnijther, A.; Weber, H P.: Helv. Chim. Acta (HCACAV) 59, 2462 (1976). GB 942 152 (Sandoz; appl. 14.12.1960; CH-prior. 19. I .l96O, 3.8.1 960, 27.9.1960). FR-M 1 313 (Sandoz; appl. 13.7.1961). preparation of 2-(2-chloroethy1)- 1-methylpyrrolidine enantiomers: Vemier, J.M. et al.: I. Med. Chern. (JMCMAR) 42 (10). 1684 (1999). Formul~ion(s): amp. 2 rngl5 ml; gel 300 mglg (as hydrogen furnarate); syrup 0.5 mg/lO ml; tabl. 1 mg Trade Namr(s): Corto-Tavegil (Novartis Pharma)-comb. Tavegil (Novartis Consumer Health) Tavkgil (Sandoz); wfm Tavegil (Nnvartis; as hydrogen furnarate) Tavegil (Sandoz) J: Alagyl (Sawai) Clemanyl (Kyoritsu Alusas (Fuso) Yamagata) Anhistan (Nippon Zoki) Fulurninol (Tatsumi) Antriptin (Nippon Yakuhin) Fumalestine (Hishiyama) Batomu (Zensei) Fumartin (Torii) Benanzyl (Isei) Histamedine (Mohan) Chlonaryl (Ohta) Inbestan (Maruko) Kinotomin (Toa Eiyo) 498 C Clemizole Lacretin (Tokyo Tanabe) Natarilan (Nippon Telgin G (Takata) Lecasol (Kaken) Chemiphar) Trabest (Hoei) Maikohis (Nihon Yakuhin) Piloral (Nippon Kayaku) Xolamin (Sanko) Mallermin-F (Taiyo Raseltin (Mamishi) generics and combination Yakuko) Reconin (Toy ama) preparations Marsthine (Towa) Romien (Fuji Zoki) USA: Tavist (Dorsey); wfm Masletenc (Shioe) Tavegyl (Sandoz-Sankyo) Travist (Sandoz); wfrn Clemizole ATC: R06A Use: antihistaminic, antiallergic RN: 442-52-4 MF: C,,H,,CIN, MW: 325.84 EINECS: 207-133-5 CN: l-[(4-chlorophenyl)methyl]-2-(l-pyrrolidinylmethyl)-1H-benzi~dazole monohydrochloride RN: 1163-36-6 MF: C19H2,CIN, . HCI MW: 362.30 EINECS: 214-605-4 LDso: 75 mgkg (M, i.v.); 837 mgkg (M, p.0.); 74 mgkg (R, i.v.); 1950 mgfkg (R, p.0.) 1 -chloro- 4-chloro- 2-nitro- benzylamine benzene (1) pyrralidine Clernizole Reference(s): US 2 689 853 (Schering AG; 1954; D-prior. 1950). alternative syntheses: DE 980 644 (Schering AG; appl. 1950). DE 901 649 (Schering AG; appl. 1951). Formulation(s): cream 10 mgl40 g; suppos. 5 mg Trade Name(s): D: Megacillin (Grunentha1)- F. Deliproct (Schering)- Ultraproct (&hering)- comb. wlth penicillin; wfm comb.; wfm comb.; wfm Scheriproct (Scherax)- Ultralan (Schering); wfm I: Ultraproct (Schenng)- comb.; wfm Ultraproct (Schering)- comb. Ultraproct (Scherax)- comb.; wfm J: Histacur (Nichidoku) comb.; wfm GB: - Scheriproct (Schering)- comb.: wfm Clenbuterol C 499 Clenbuterol ATC: R03AC14;R03CC13 IJse: bronchodilator RN: 37148-27-9 MF: C,2H,8C12N20 MW: 277.20 EINECS: 253-366-0 LD5,: 27.6 mgkg (M, i.v.) CN: 4-amino-3,5-dichloro-a-[[(1,1-dimethylethyl)amino)methyl]benzenemethanol hydrochloride RN: 21898-19-1 ME C,2H,8C12N20. HCI MW: 313.66 4'-nitro- 2-brorno-4'-nitro- acetophenone acetophenone Hz, Raney-Ni 0 H 0 CI I Clenbuterol 1 500 C Clidanac Reference(s): Keck, J. et al.: Arzneim Forsch. (ARZNAD) 22, 861 (1972). a DOS 1 793 416 (Thornae; appl. 5.9.1967). BE 704 213 (Thornae; appl. 22.9.1967; D-prior. 22.9.1966, 15.2.1967, 2.6.1967). US 3 536 7 12 (Boehringer Ing.; 27.10.1970; D-prior. 22.9.1966, 15.2.1967, 2.6.1967). b DOS 2 157 040 (Thornae; appl. 17.1 1.1971). DE 1 543 928 (Thornae; appl. 22.9.1966). alternative syntheses: DAS 2 354 959 (Thomae; appl. 2.1 1.1973). Fort?zulation(s): drops 0.059 mg/ml, 15 mg12 ml; syrup 0.005 rnd5 ml; tabl. 0.01 mg, 0.02 rng (as hydrochloride) Trade Name(s): D: Contraspasrnin (ASTA I: Broncodil (Leben's) Prontovent (Salus Medica AWD) Clenasma (Biomedica Research) Spiropent (Boehringer Ing.) Foscarna) Spiropent (Boehringer Ing, Spasrno-Mucosolvan Contrasrnina (Falqui) J: Spiropent (Teijin-Kissei) (Boehringer 1ng.)-comb. Monores (Valeas) Clidanac ATC: MOlAB Use: non-steroidal anti-inflammatory, antipyretic RN: 34148-01-1 MF: Cl,Hl,CI02 MW: 278.78 LD,,,: 41 mglkg (R, p.0.) CN: 6-chloro-5-cyclohexyl-2,3-dihydro-1H-indene-l-carboxylic acid 1. Li, ?I 1. AICI, & ~.H~c-&~H 2. H,SO, 3. HCI. CH ,COOH * 11 CI 1. lithium, 1.3-dithiane phenylcyclo- J-chloro- hexone (I) propionyl chloride 5-cyclohexyl-l- indonane F' ___* N-chloro- succinimide 5-cyclohexyl- 1 -indon- corboxylic acid (11) Clidonoc L TiCI, CI 0, 1 + Y CH, + A c I titonium diethyl tetrochloride molonate dichloromethyl 4-cyclohexyl- (1~) methyl ether benzoldehyde . I6 EINECS: 26 1-0 6 9-2 LDS,,: 4 g/kg (M, i.v.); 4526 mg/kg (M, p.0.); 7936 rnglkg (R, p.0.) CN: [2R-(2a,3Z,5a) ]-3 -( 2-hydroxyethylidene )-7 -oxo-4-oxa-l-azabicyclo[3.2.0]heptane-2-carboxylic. antihistaminic RN: 1568 6-5 1-8 MF: CzIH,,CINO MW: 343.90 CN: [R-(R*,R*) ]-2 -[ 2-[ 1-( 4-chlorophenyl)-l-phenylethoxy]ethyl]-l-methylpyrrolidine hydrogen fumarate (1:l) RN: 1497 6-5 7-9 MF: C2,H2,C1N0. CN: 4-amino-3,5-dichloro-a-[[(1,1-dimethylethyl)amino)methyl]benzenemethanol hydrochloride RN: 2189 8-1 9-1 ME C,2H,8C12N20. HCI MW: 313.66 4'-nitro- 2-brorno-4'-nitro- acetophenone