Carfecillin C 351 Carfecillin ATC: GOlAA08; JOlCA Use: antibiotic RN: 27025-49-6 MF: C23H22N206S MW: 454.50 EINECS: 248-1 71-2 LD,,: 728 mg/kg (M, i.v.); 3924 mglkg (M, p.0.) CN: [2S-(2a,5a,6~)1-6-[(1,3-dioxo-3-phenoxy-2-phenylpropyl)amino]-3,3-dimethyl-7-oxu-4-thia-1- azabicyclo[3.2.0]heptane-2-carboxylic acid u phenylrnalonic acid HOOC COOH X SOC12, DM., cl;)(;OO~ I' OOH, phenol NaHC03, rnonophenyl phenyl malonote (I) COOH .NaHCO, 6-ominapenicillanic acid Carfecillin 1 US 3 853 849 (Beecham; 10.12.1974; prior. 2.1 1 .I 967 and 29.5.1969). US 3 881 013 (Beecham; 29.4.1975; CB-prior. 5.1 1 .I966 and 27.1.1967) Formula~ion(s): tabl. 500 mg Trade Name(s): I: Uricillirla (IBI) J: Gripenin-0 (Fujisawa) Urocarf (SPA; as sodium Uticillin (SmithKline salt) Beecham) Carfenazine (Carphenazine) ATC: NO5AK Use: neuruleptic RN: 2622-30-2 MF: C2,H,,N3O2S MW: 425.60 EINECS: 220-072-9 CN: 1-[10-[3-[4-(2-hydroxyethyl)-l-piperazinyl]propy1]-1OH-phenothiazin-2-yl]-I-propanone dimaleate RN: 2975-34-0 MF: C2,H3,N302S 2C4H404 MW: 657.74 EINECS: 221-019-2 LD,,: 42 mgkg (M, i.v.); 156 rnglkg (M, p.0.); 162 mglkg (R, p.0.) 2-propionyl- chloropropane 10-(3-chloropropyl)-2- phenothiozine prapionylphenothiazine (1) 352 C Carindacillin Carfenazine Reference(s): US 2 985 654 (Schering Corp.; 1961; appl. 1956). US 3 023 146 (American Home; 27.2.1962; appl. 6.6.1960; prior. 3.6.1959). Formulation(s): tabl. 25 mg, 400 mg Trade Name(s): USA: Proketazine (Wyeth); wfm Carindacillin ATC: JOlCAO5 (Indanylcarbenicilline; Carbenicillin Indanyl Sodium) Use: antibiotic RN: 3553 1-88-5 MF: C2,H,,N20,S MW: 494.57 LD,,: 3600 mgkg (M, p.0.); 2 glkg (R, p.o.1; >500 mglkg (dog, p.0.) CN: [2S-(2a,5a,6P)]-6-[[3-[(2,3-dihydro- IH-inden-5-yl)oxy]- 1,3-dioxo-2-phenylpropyl]aminoJ-3,3-dimethyl- 7-oxo-4-thia-l-azabicyclo[3.2.0]heptane-2-carboxy1ic acid monosodium salt RN: 26605-69-6 MF: C26H,,N,Na06S MW: 5 16.55 EINECS: 247-845-3 LD,,,: 210mglkg(M, i.v.);4400mg/kg(M,p.o.); 295 mglkg (R, i.v.); 4450 mglkg (R, p.0.); >15.3 mglkg (dog, p.0.) PCI5 phosphoru? HOO:;'OOH pento;. 5-indanol ' chloride phenylmalonic phenyl(ch1ora- - phenylketene (I) COOH COOH Carindocillin US 3 557 090 (Pfizer; 19.1.1971; appl. 5.1.1968). US 3 574 189 (Pfizer; 6.4.1971 ; appl. 5.1.1968). US 3 679 801 (Pfizer; 25.7.1972; prior. 5.1.1968,4.6.1969, 19.5.1970). DAS 1 967 024 (Pfizer; appl. 3.1.1969; USA-prior. 5.1.1968). Carisoprodol C 353 allernative synthesis: DOS 1 959 569 (Pfizer; appl. 27.1 1.1969; USA-prior. 23.1.1969). Formulalion(s): tabl. 500 mg Trade Name(s): D: Carindapen (Pfizer; 1973); J: Geopen-U (Taito Pfizer; wfm 1976) 1: Geopen orale (Pfizcr; 1973) USA: Geocillin (Pfizer; 1972) Carisoprodol ATC: M03BA02 Use: muscle relaxant RN: 78-44-4 MF: C,,H,N,O, MW: 260.33 EINECS: 201-118-7 LDS{ 165 mglkg (M, i.v.); 1800 mglkg (M, p.0.); 450 mgkg (R, i.v.); 1320 mgkg (R, p.0.) CN: (1-methylethy1)carbamic acid 2-[[(aminocarbonyl)oxy]methyl]-2-methylpenty ester 0 CH, + isopropyl- H CH3 CI 0 arnine CH3 2-methyl-2- phosgene (1) propylpropane- 1,3-diol (cf. meprobamate synthesis) ethyl corbamate I Carisoprodol I Reference( s): US 2 937 119 (Carter Products; 17.5.1960; prior. 11.6.1959). Formulation(s): tabl. 350 mg Trade Name(s): D: Sanoma (Heilit) Flexartal (Clin-Midy); wfm numerous combination F: Flexagit (Clin-Midy)- GB: Carisoma (Pharmax) preparations comb.; wfm I: Flexidone (Pierrel)-comb. J: Myobutazolidin (Ciba- Flexalgit (Clin-Comar- Soma Complex Geigy-Fujisawa)-comb. Byla)-comb.; wfm (Teofarma)-comb. Somanil (Banyu) Flexartal (Clin-Comar- Teknadone (Teknofarma)- USA: Soma (Wallace) Byla); wfm comb. 354 C Carmofur Carmofur (HCFU) ATC: LOlBC04 Use: antineoplastic, orally active fluorouracil derivative RN: 61422-45-5 MF: C,,HI,FN303 MW: 257.27 LD,,: 1129 mgkg (M, p.0.); 268 mglkg (R, p.0.); 65 mgkg (dog, p.0.) CN: 5-fluoro-N-hexyl-3,4-dihydro-2,4-dioxo- l(2H)-pyrimidinecarboxamide 5-fluoro- phosgene uracil (I) (4. v.1 n-hexyl isocyanate Reference(s): a JP 531098 977 (Mitsui; appl. 2.8.1977). b DOS 2 639 135 (Mitsui; appl. 31.8.1976; USA-prior. 5.1 1 .l975). US 4 071 519 (Mitsui; 31.1.1978; prior. 5.11.1975). Formulation(s): tabl. 100 mg Trade Name(s): J: Mifurol (Mitsui; 1981) Yamaful (Yarnanouchi; 1981) Carmustine (BCNU) ATC: LOlADOl Use: antineoplastic RN: 1 54-93-8 MF: C5H9C12N302 MW: 2 14.05 EINECS: 205-838-2 LD,,,: 26 mgkg (M, i.p.); 45 mgkg (M, i.v.); 19 mg/kg (M, p.0.); 24 mgkg (M, s.c.); 13.8 mglkg (R, i.v.); 20 mg/kg (R, p.0.) CN: N,W-bis(2-ch1oroethyl)-N-nitrosourea I Carmustine I Rqference(s): DOS 2 528 365 (The Government of US; appl. 25.6.1975; USA-prior. 13.11.1974). Carnitine C 355 nitmation with NaNO,, Johnston, T.P. et al.: J. Med. Chem. (JMCMAR) 6, 669 (1963). synthesis of N,N1-bis-(2-chloroethy1)urea: Bastian, H.: Justus Liebigs Ann. Chem. (JLACBF) 566, 210 (1950). review: Carter, S.K. et al.: "Advances in Cancer Research" (Ed. G. Klein, S. Weinhouse) 16,273 (1972) Formulation(s): tabl. 7.7 mg Trade Name(s): D: Carmubris (Bristol-Myers GB: BICNU (Bristol-Myers USA: BICNU (Bristol-Myers Squibb) Squibb) Squibb) F: BICNU (Bristol-Myers I: Nitrumon (Astra-Simes) Gliadel (RhGne-Poulenc Squibb) Rorer) Carnitine (Levocarni tine) ATC: A12AX; Al4B; AIIJC Use: appetite stimulant, antiarrhythmic, cardiomyopathy therapeutic RN: 541-15-1 MF: C7HI5NO3 MW: 161.20 LD,,: 9 g/kg (M, s.c.); 7 glkg (dog, route unreported) CN: (R)-3-carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium hydroxide inner salt L-hydrochloride RN: 6645-46-1 MF: C7H15N03 . HCl MW: 197.66 EINECS: 229-663-6 DL-carnitine RN: 406-76-8 MF: C7H15N03 MW: 161.20 EINECS: 206-976-6 DL-hydrochloride RN: 461-05-2 MF: C7H15N03 . HCI MW: 197.66 EINECS: 207-309- 1 LD,,: 6 glkg (M, s.c.); 10 gkg (R, s.c.) epichloro- hydn'n (I) 4-chloro-3- hydroxy- butyronitrile cornitinenitrile chloride (IV) I DL-Cornitine hydrochloride I 356 C Carnitine (2.3-epoxypropy1)- trimethylornmonium chloride ethyl 4-chloro ocetoocetote I DL-Carnitii hydrochloride - I cornitine ethyl ester chloride (V) DL-carnitinomide chloride H,C COOH &CH, isopropanol VI + CH3 COOH DL-cornitinomide hydroxide (VI) microbiologicolly 044 K74 H3C 1. H20, A H3C\ / OH 0 CI- 2. oxolic acid NU - NH2 H~C/ L-cornitinomide chloride (VII) DL-cornitine crotonobetaine (WI) 1 L-Cornitine H C H3C\ 3 OH CI- ,N&~~~~ H3C L-Cornitine hydrochloride 0 rn~crob~olog~colly e.g. with Acinetobocter lwoffi (ATCC 9036) or Proteus mirobilis (ATCCF 15290) VIll Reference(s): la US 3 135 788 (Nihon Zoki Seiyaku; 2.6.1964; J-prior. 28.9.1959). hydrolysis of carnitinenitrile chloride with conc. HCI: DAS 1 090 676 (Labaz; appl. 24.10.1958). b US 4 070 394 (Ethyl Corp.; 24.1.1978; appl. 11.3.1977; prior. 23.1.1976). c CH 588 433 (Lonza; appl. 25.9.1974). similar process from y-chloroacetanilide: CH 589 604 (Lonza; appl. 26.4.1974). 241 DOS 2 927 672 (C. Cavazza; appl. 9.7.1979; I-prior. 10.7.1978). US 4 254 053 (C. Cavazza; 3.3.1981; I-prior. 10.7.1978). electrolytic methods for release of base: DOS 3 342 713 (Sigma-Tau; appl. 25.11.1983; I-prior. 25.1 1.1982). US 4 521 285 (Sigma-Tau; 4.6.1985; I-prior. 25.1 1.1982). b EP 148 132 (Sigma-Tau; appl. 31.10.1984; DDR-prior. 3.1 1.1983). c EP 122 794 (Ajinomoto; appl. 13.4.1984; J-prior. 13.4.1983). enzymatic methods from y-butyrobetaine and 2-ketoglutaric acid with y-butyrobetaine hydroxylase from Neurospora crassa: GB 2 078 742 (Sigma-Tau; appl. 23.6.1981; I-prior. 24.6.1980). synthesis from ~-mannitol: US 4 413 142 (Anic; 1.1 1.1983; I-prior. 18.3.1981). use as antiarrhythmic: US 3 830 931 (S. L. De Felice; 20.8.1974; appl. 6.1 1.1972). US 3 968 241 (S. L. De Felice; 6.7.1976; prior. 6.1 1.1972, 2.7.1974). paren feral use for improvement of myocard function: US 4075 352 (S. L. De Felice; 21.2.1978; appl. 28.4.1976). use for reduction of cardiotoxicity of cytostatics, e. g. daunomycin: US 4 320 110 (S. L. De Felice; 16.3.1982; appl. 4.10.1979). US 4400 371 (S. L. De Felice; 23.8.1983; appl. 12.5.1981). use as appetite stimulant: US 3 810 994 (Ethyl Corp.; 14.5.1974; appl. 1.6.1972). additive to parenteral feeding: DOS 3 032 300 (A. Lohninger, Wien; appl. 27.8.1980). US 4 320 145 (C. Cavazza; 16.3.1982; I-prior. 5.10.1979). EP59 775 (Leopold & Co.; appl. 1.6.1981; YU-prior. 9.6.1980). use as antihyperlipidemic: US4 315 944 (Sigma-Tau; 16.2.1982; I-prior. 21.9.1979). use as geriatric for improvement of mental ability: US 4 474 812 (Sigma-Tau; 2.10.1984; I-prior. 29.10.1982). treatment of lung diseases: DE 2 360 332 (Otsuka; appl. 4.12.1973; J-prior. 7.12.1972). Formulation(s): drinking sol. 1 g/10 ml; inj. sol. lg15 ml; syrup 1 g13.3 ml Trade Name(s): D: Biocarn (Medice) L-Carn (Sigma-Tau) F: Uvoearnil (Sigma-Tau) 1: Anetin (Ibirn) Biocarnil (Gentili) Briocor (Farge) Cardimet (Errekappa Euroter.) Cardiogen (Chemil) Carnitene (Sigma-Tau) Carnitolo (Recordati Farma) Carnitop (Virginia Farmac.) Carnovis (Duncan) Carnum (Firma) Carrier (Chiesi) Carvit (AGIPS) Eucar (Salus Research) Eucarnil (Pulitzer) Kernit (CT) L-Carnitina Coli (Coli) Lefcar (Glaxo) Levocarvit (Mitim) Medocarnitin (Medosan) 358 C Caroxazone Metina (Pierrel) Transfert (Piam) USA: L-Carnitine (Tyson) Miocardin (Magis) J: Abedine (Nippon Zoki) Carnitor (Sigma-Tau) Miocor (Ecobi) Entomin (Maruko) Miotonal (Caber) Monocamin (Tanabe) Caroxazone ATC: N06A Use: antidepressant RN: 18464-39-6 MF: C1,Hl0N2O3 MW: 206.20 EINECS: 242-345-1 LD,,,: 728 mglkg (M. p.0.) CN: 2-oxo-2H-1,3-benzoxazine-3(4H)-acetamide NaHC03, HZO. CH2C12 NH3, H20 COCI, ' adNH2 phosgene b ethyl (2-hydroxy- benzyl0mino)acetate NH2 Caroxazone Reference(s): CH 586 687 (Farmitalia; appl. 26.4.1974). ZA 742 435 (Farmitalia; appl. 17.4.1974). alternative synthesis: US 3 427 3 13 (Farmitalia; 11.2.1969; I-prior. 23.12.1965, 14.9.1966). Bernardi, L. et al.: Experientia (EXPEAM) 24,774 (1968). Trade Narne(s): I: Timostenil (Carlo Erba); Timostenil (Farmi talia); w fm w fm Carpipramine (Carbadipimidine) ATC: N06B Use: antidepressant RN: 5942-95-0 MF: C2,H3,N,0 MW: 446.64 EINECS: 227-700-0 LD,,,: 28 mglkg (M, i.v.); 2180 mglkg (M, p.0.); 37 mgkg (R, i.v.); 1025 mglkg (R, p.0.) CN: 1'-[3-(10,11 -dihydro-SH-dibenz[b~azepin-5-yl)propyl][l,4'-bipiperidine]-4'-carboxamide dihydrochloride monohydrate RN: 7075-03-8 MF: C,,H,,N,O. 2HC1 . H,O MW: 537.58 EINECS: 230-372-1 LD,,,: 136 mglkg (M, i.p.); 28 mglkg (M, i.v.); 2180 mglkg (M, p.0.); 76 mglkg (R, i.p.); 37 mglkg (R, i.v.); 1025 mgkg (R, p.0.); 18 mgkg (rabbit, i.v.) maleate (1:l) RN: 100482-23-3 MF: C2,H3,N,O . C,H,O, MW: 562.71 LDSo: 147 mglkg (M, i.p.); 2055 mglkg (M, p.0.); 169 mglkg (R, i.p.) Carprofen C 359 iminodibenzyl 1,3-dibrarna- propane b~ r 3-(10.11 -dihydra- 5H-dibenz[b.f]ozepin- 5-yl)propyl bromide (I) Reference(s): JP 66 006 572 (Yoshitomi; appl. 29.6.1963). Nakanishi, M. eta].: J. Med. Chem. (JMCMAR) 13, 644 (1970). (1 ,4'-bipiperidine)- medical use as anxiolytic, hypnotic: Carpipromine EP 374 042 (~h6ne-~oulenc; appl. 13.12.1989; F-prior. 16.12.1 988). 4'-corboxomide (cf. piparnperone synthesis) Formulation(s): powder 10 %; tabl. 25 mg, 50 mg Trade Nante(s): F: Prazinil (Pierre Fabre) J: Defekton (Yoshitomi) Carprofen ATC: MOlAE Use: non-steroidal anti-inflammatory RN: 53716-49-7 MF: C,SHI,C1N02 MW: 273.72 EINECS: 258-712-4 LD,,: 400 mglkg (M, p.0.) CN: (?)-6-chloro-a-methyl-9H-carbazole-2-ace acid 1. HCI H H,C- 0 CH3 + H~c-o~,,cH~ s, 03:) 3. C2H,0H, HCI b I 0 0 sad~um 2. 4-chloraphenyl- ethylate LCH3 hydrazine 2-cyclo- diethyl methyl- hexen- malonate 1 -one diethyl methyl- (3-oxocyclohexyl) rnalonote 360 C Carteolol H 2. NaOH CI MoLcH3 , ethyl B-chloro-a-methyl- 1.2.3.4-tetrahydro-9H- carbazole-2-acetate (I) Carprofen Rej'erence(s): US 3 896 145 (Hoffrnann-La Roche; 22.7.1975; prior. 17.5.1973, 24.7.1972). Formulution(s): tabl. 150 rng Trade Name(s): USA: Rirnadyl (Roche); wfrn Carteolol ATC: C07AA15; S01ED05 Use: beta blocking agent RN: 51781-06-7 MF: C,,H,N,O, MW: 292.38 LD,,: 810 rnglkg (M, p.0.); 830 rnglkg (dog, p.0.) CN: 5-[3-[(1,1-dirnethylethyl)arnino]-2-hydroxypropoxy]-3,4-dihydro-2(1~-quino1inone monohydrochloride RN: 51781-21-6 MF: C,6H,,N,0, . HC1 MW: 328.84 EINECS: 257-415-7 LD,,: 54.5rng/kg(M,i.v.);810n1g/kg(M,p.o.); 153 rnglkg (R, i.v.); 1330 rnglkg (R, p.0.); 830 rnglkg (dog, p.0.) HOOC~CH~ Pd-C, 195 "C, 140 OC, 3h ~O Ng aNH2 - decaline.3h -1 acrylic acid 0 0 0 cyclohexane- 3-amino-2- 1.3-dione cyclohexenone 5-hydroxy- epichloro- 5-(2.3-epoxypropoxy)- Corteolol 1,2.3.4- hydrin 1.2.3.4-tetra- tetrohydro- hydroquinolin-2-one quinolin- 2-one (I) Rej'erence(s): Winkler, W.: Arzneirn Forsch. (ARZNAD) 33,279 (1983). DOS 2 302 027 (Otsuka; appl. 16.1.1973; J-prior. 13.4.1972). US 3 910 924 (Otsuka; 7.10.1975; appl. 19.1.1973; J-prior. 13.4.1972). . EINECS: 22 0-0 7 2-9 CN: 1-[ 1 0-[ 3-[ 4-( 2-hydroxyethyl)-l-piperazinyl]propy1 ]-1 OH-phenothiazin-2-yl]-I-propanone dimaleate RN: 297 5-3 4-0 MF: C2,H3,N302S 2C4H404 MW: 657.74 EINECS: 22 1-0 1 9-2 LD,,:. 2702 5-4 9-6 MF: C23H22N206S MW: 454.50 EINECS: 24 8-1 7 1-2 LD,,: 728 mg/kg (M, i.v.); 3924 mglkg (M, p.0.) CN: [2S-(2a,5a,6~) 1-6 -[ (1,3-dioxo-3-phenoxy-2-phenylpropyl)amino ]-3 ,3-dimethyl-7-oxu-4-thia- 1-. 3553 1-8 8-5 MF: C2,H,,N20,S MW: 494.57 LD,,: 360 0 mgkg (M, p.0.); 2 glkg (R, p.o.1; >500 mglkg (dog, p.0.) CN: [2S-(2a,5a,6P) ]-6 -[ [ 3-[ (2,3-dihydro- IH-inden-5-yl)oxy ]- 1,3-dioxo-2-phenylpropyl]aminoJ-3,3-dimethyl-