Clorprenaline C 531 : Reference(s): ! DOS 2 846 083 (Fidia; appl. 23.10.1978; I-prior. 17.11.1977). US 4 296 039 (Fidia; 2O.lO.lY8 I; I-prior. 17.1 1 .l977). , synthesis of ethyl 2-(2-diethy1aminoethyl)acetoacetate: Weizmann, Ch.; Bergmann, E.; Sulzbacher, M.: J. Org. Chem. (JOCEAH) 15, 918 (1950). synthesis of 2-chlororesorcinol: Schamp, N.: Bull. Soc. Chim. Belg. (BSCBAG) 73,35 (1946). Wauzlick, H.V.; Mohrmann, S.: Chem. Ber. (CHBEAM) 96, 2257 (1963). Fonnulation(s): amp. 30 mg15 ml; cps. 100 mg; vial 30 mg Trade Name(s): I: Assogen (Metapharma) Proendotel (Fidia; 199 1) Clorprenaline ATC: R03 Use: bronchodilator RN: 3811-25-4 MF: CIIHl,CINO MW: 213.71 EINECS: 223-291-8 CN: 2-~hloro-a-[[(l-methylethyl)amino]methyl]benzenemethanol hydrochIoride monohydrate RN: 5588-22-7 MF: C,lH16C1N0 . HC1. H,O MW:. 268.18 LD,: 54 mg/kg (M, i.v.); 298 mglkg (M, pa.); 68 mgkg (R, i.v.); 450 mglkg (R, p.0.); >400 rn@g (dog, p.0.) Br2, peroxide NaBH Br A Br 0 0 OH 2'-chloro- acetophenone P-bromo- 2'-chloro- acetophenone isopropylamine I ~lorprenoline 1 Reference(s): US 2 816 059 (Lilly; 1957; appl. 1956). Formulation(s): sol. 2 % (inhalation) Trade Name(s): J: Aremans (Zensei) Conselt (San-a) Neoasutoma (Nihon Asthone (Eisai) Cosmoline (Chemiphar) Yaku hin) Bronocon (Wakamoto) Fusca (Hoei) Pentadoll (Showa) Clopinerin (Nippon Shoji) Kalutein (Tatsumi) Propran (Kobayashi Kako) Clorprenalin HC1 (Kongo) ir 532 C Clortermine Clortermine RN: 10389-73-8 MF: Cl,HI4ClN MW: 183.68 CN: 2-chloro-a,a-dimethylbenzeneethanamine hydrochloride RN: 10389-72-7 MF: Cl,H14ClN . HCI MW: 220.14 LD,,,: 332 mgkg (R, p.0.) ATC: NO7 Use: appetite depressant 15; / M9* (c2H5)20, d' H3c acetone \ 2-chlaro- 2-chlorobenzyl- 1 -(2-chloro- benzyl magnesium phenyl)-2-me- chloride chloride thyl-2-propanol Reference(s): US 3 415 937 (Ciba; 10.12.1968; appl. 1.12.1966; prior. 31.8.1964). Formulation(s): tabl. 50 mg Trade Namefs): USA: Voranil (USV); wfm Clostebol acetate ATC: DllAE Use: anabolic RN: 855-19-6 MF: C,,H&10, MW: 364.91 EINECS: 212-720-4 CN: (1 7P)- 17-(acetyloxy)-4-chloroandrost-4-en-3-one clostebol RN: 1093-58-9 MF: Cl,H,7C10, MW: 322.88 EINECS: 214-133-9 0 0 O H20Z, NaOH HCI, CHC13 ____, hydrogen peroxide 0 0 CI Clostebol acetote Reference(s): US 2 953 582 (Soc. Farmaceutici Italia; 20.9.1960; appl. 26.10.1M6; I-prior. 23.4.1956). US 2 933 510 (Julian Labs.; 19.4.1960, Prior. 3.2.1955). Formulation(s): cream 0.5 %; sugar coated tabl. 15 mg; vial 10 mgl1.5 ml Trade Name(s): D: Megagrisevit (Pharmacia & Megagrisevit N (Pharmacia F: Trofoseptine (Boehringer Upjohn) & Upjohn)-comb. 1ng.)-comb. Clotiazepam C 533 I: Alfa-Trofodermine Trofodermin (Farmitalia)- J: Steranabol (Sumitomo) (Farmitalia) comb. with neomycine Ciotiazepam ATC: NOSBA~I Use: anxiolytlc, benzodiazepine analog RN: 33671-46-4 MF: C,,H,,ClN,OS MW: 318.83 EINECS: 251-627-3 LD,,: 440 mglkg (M, i.p.); 636 mglkg (M, p.0.) CN: 5-(2-chlorophenyl)-7-ethyl-1,3-dihydro-l-methyl-2H-thieno[2,3-e]-1,4-diazep~n-2-one 3-(2-chloro- ethyl glycinote benzoyl)-5-ethyl- hydrochloride (11) 2-methylomino- thiophene (I) 40; CH3 - Clotiazepom N-benzyloxy- corbonylglycyl chloride NH, dimethyl zulfote sodium methylate 534 C Clotrimazole Reference(s): DOS 2 107 356 (Yoshitomi; appl. 16.2.1971; J-prior. 17.2.1970, 23.2.1970, 7.3.1970, 25.6.1970, 31.7.1970). US 3 849 405 (Yoshitomi; 19.1 1.1974; J-prior. 17.2.1970, 23.2.1970,7.3.1970, 25.6.1970, 31.7.1970). Formulntion(s): drops 1 %; tabl. 5 mg, 10 mg, 20 mg Trade Name(s): D: Trecalmo (Bayer Vital; Tienor (Farmaka) 1979) J: Emolex (Nichiiko) F: VCratran (Murat; 1984) Isocline (Sawai) I: Rizen (Puropharma; 1984) Lieze (Yoshitomi) Reilyfter (Maruko) Rize (Yoshitomi) Clotrimazole ATC: AOlAB18; DOlACOl; G01AF02 Use: antifungal RN: 23593-75-1 MF: C,,H,,ClN, MW: 344.85 EINECS: 245-764-8 LD,,: 76 1 mg/kg (M, p.0.); 708 mglkg (R, p.0.); >2 g/kg (dog, p.0.) CN: I -[(2-chlorophenyl)diphenylmethyl]- IH-imidazole 2-chloro- 2-chlorobenzo- toluene trichloride 2-chlorotriphenyl- methyl chloride (11) 2-chloro- phenylrnognesiurn 2-chlorotriphenyl- benzophenone (In) bromide corbinol CI arnine Clotrimazole Reference(s): DE 1 617 481 (Bayer; appl. 15.9.1967). DAS 1 670 976 (Bayer; appl. 29.1.1968). DE 1 670 977 (Bayer; D-prior. 29.1.1968). US 3 660 577 (Bayer; 2.5.1972; D-prior. 15.9.1967). US 3 705 172 (Bayer; 5.12.1972; D-prior. 15.9.1967). mode of mechanism: Berg, D. et a].: Arzneim Forsch. (ARZNAD) 34 (I), 139 (1984). Cloxacillin C 535 ! medical use at Herpes labialis: $ US 4 438 129 (Pennwalt; 20.3.1984; appl. 27.9.1982). special formulations: DOS 3 321 043 (Bayer; appl. 10.6.1983). EP 128 459 (Bayer; appl. 30.5.1984; D-prior. 10.6.1983). EP 112 485 (Bayer; appl. 17.1 1.1983; D-pr~or. 25.1 1.1982) combination wirh corticosteroids: EP49 468 (Schering Corp.; appl. 30.9.1981; USA-prior. 6.10.1980) &rmulation(s): pessaries 100 mg, 200 mg, powder 10 mglg (1 %); 500 mg; sol. I %, 10 mg; spray 10 mglml (1 %); topical cream 1 %, 10 mg; vaginal cream 10 mg, 20 mglml (2 %, 10 %); vaginal tabl. 100 mg, 200 mg, 500 mg Trade Name(s): D: Antifungal (Hexal) Apocanda (esparma) ARU Spray (Chauvin ankerpharm) Azutrimazol (Azupharma) Benzoderm (Athenstaedt) Candazol (Apogepha) Canesten (Bayer; 1973) Canifug (Wolff) Cloderm (Dermapharm) Cutistad (Stada) Durafungol (durachemie) Gilt (Solvay Arzneimittel) Gyno Canesten (Bayer Vital) Holfungin (Holborn) Jenamazol (Jenapharm) Lobalacid (Kade) Mono Baycuten (Bayropharm) M ycofug (Hermal) Myko Cordes (Ichthyol) Mykofungin (Wyeth) Mykohaug (betapharm) Ovis (Warner-Lambert) Pedisafe (BASF Generics) Radical (Maurer) Uromycol (Hayer) F: Trimysten (Roger Bellon; 1978); wfm GB: Canesten (Bayer; 1973) Canesten HC (Bayer)- comb. Lotriderm (Dominion)- comb. Masnoderm (Dominion) I: Antimicotico Same (Savoma) Canesten (Bayropharm; 1973) Desamix Effe (Savoma)- comb. Gy no-Canesten (Bayropharm) Meclon (Farmigea) J: Empecid (Bayer-Takeda; 1976) Tao (Toko-Fujisawa) USA: Fungoid (Pedinol) Lotrimin (Schering; 1976) Lotrisone (Schering) Mycelex (Bayer) Cloxacillin ATC: JOlCFO2 Use: antibiotic RN: 61-72-3 MF: C,yH18ClN30SS MW: 435.89 EINECS: 200-5 14-7 CN: [2S-(2a,5a,6~)~-6-[[[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4- thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid monosodium salt RN: 642-78-4 MF: Cl,H,7ClN,NaOSS MW: 457.87 EINECS: 21 1-390-9 LDS,: 916 mglkg (M, i.v.); 5 glkg (M, p.0.); 1660 mgkg (R, i.v.); 5 glkg (R, p.0.) monosodium salt monohydrate RN: 7081-44-9 MF: ClyH,7C1N3NaOSS . H,O MW: 475.89 LD,,: ll00mg/kg(M,i.v.);5g/kg(M,p.o.); 1660 mgkg (R, i.v.); 5 glkg (R, p.0.) 536 C Cloxazolam 7 - r. CHO hydroxyl- - \=N-OH )=N-OH ethyl acetoacetate ornine CI 2-chloro- Z-chlorobenz- benzaldehyde aldehyde oxirne 3-(2-chlorapheny1)- 5-methylisaxazale- 4-carboxylic acid COOH CH3 US 2 996 501 (Beecham; 15.8.1961; GB-prior. 3 1.3.1960). GB 905 778 (Beecham; appl. 31.3.1960; valid from 14.3.1961). GB 958 478 (Beecham; appl. 28.2.1963; USA-prior. 13.3.1962). Formulation(s): amp. 250 mg, 500 mg; cps. 250 mg, 500 mg; tabl. 250 mg, 500 mg (as sodium salt) Trade Name(s): D: Ampiclox (Beecham)- comb. with ampicillin; wfm Pyoclox (Beecham)-comb. with carbenicillin; wfm Pyolox (Beecham)-comb. with carbenicillin; wfm F: Orbenine (SmithKline Beecham) GB: Ampiclox (SmithKline Beecham)-comb. with ampicillin Orbenin (Beecham); wfm I: Amplium (Sigma-Tau)- comb. Cloxac (Formulario Naz.) J: Acucillin (Fuji)-comb. Methocillin-S (Meiji Seik Orbenin (Beecham- Fujisawa) Prostaphlin (Bristre-Bany Solcillin C (Takeda)-coml Totaclox (Beecham)-com USA: Cloxapen (Beecham); wfi Tegopen (Bristol); wfm Cloxazolam ATC: N05BA22 Use: tranquilizer RN: 24166-13-0 MF: C1,H,,C12N202 MW: 349.22 LD,,,: 2630 mglkg (M, p.0.); 1780 mglkg (R, p.0.) CN: 1 0-chloro- 1 1 b-(2-chloropheny1)-2,3,7,11 b-tetrahydrooxazolo[3,2-d][l,4]benzodiazepin-6(5H)-one Clozapine C 537 3 + '12. - cl$ir HOrvNH2 , cH,cooN~ CI - / ethonolornine N"2 N 0 H 2-amino-2'3- bromoocetyl dlchlorobenzo- chloride heno one Referencefs): DOS 1 812 252 (Sankyo; appl. 26.11.1968; J-prior. 27.1 1.1967). DOS 1 817 923 (Sankyo; appl. 26.1 1.1968; J-prior. 27.1 1.1967). alternative synthesis: DOS 1 954 065 (Sankyo; appl. 23.10.1969; J-prior. 24.10.1968, 17.4.1969). US 3 696 094 (Sankyo; 3.10.1972; J-prior. 24.10.1968,25.10.1968). US 3 772 371 (Sankyo; 13.1 1.1973; J-prior. 27.1 1.1967). review: Schulte, E.: Dtsch. Apoth. Ztg. (DAZEA2) 115, 1253, 1828 (1975). Formulation(s): tabl. 1 mg, 2 mg Trade Namefs): J: Enadel (Taito Pfizer) Sepazon (Sankyo) cl% H 0 Cloxozolorn Clozapine ATC: N05AH02 Use: neuroleptic RN: 5786-21-0 MF: Cl,H19C1N, MW: 326.83 EINECS: 227-313-7 LD,,: 36.5 mglkg (M, i.v.); 150 mgkg (M, p.0.); 41.6 mag (R, i.v.); 251 mgkg (R, p.0.); 145 mag (dog, p.0.) CN: 8-chloro-1144-methyl- 1 -piperazinyl)-5H-dibenzo[b,cJ[ 1,4]diazepine "q 2 4-chloro-2- nitrooniline H3C\ 05 methyl 2-chloro- benzoate FH3 8 b I -methyl- piperozine (1) cleOib \ H , I" clffO:h H oxychloride phosphorus b 538 C Cobamamide 1. KO-C(CH3)3 2. CI -NO, I Ciozopine 1. potossium tert-butylote H H 2. 4-nitrobenzyl chloride 8-chloro-ll -thioxo 10.1 1 -dihydro-5H- dibenzo[b.e][l.4]- diozepine Reference(s): CH 404 677 (Dr. A. Wander; appl. 2.12.1960). CH 398 620 (Dr. A. Wander; appl. 16.8.1960). GB 980 853 (Dr. A. Wander; appl. 16.8.1961; CH-prior. 16.8.1960,2.12.1960). NL 147 426 (Dr. A. Wander; appl. 24.5.1963; CH-prior. 25.5.1962, 8.6.1962, 5.12.1962, 15.2.1963). DE 1 280 879 (Wander; appl. 7.8.1961; CH-prior. 16.8.1960,2.12.1960). US 3 539 573 (Wander; 10.11.1970; CH-prior. 16.8.1060,2.12.1960,20.7.1961,25.5.1962,5.12.1962,15.2.1963, 22.3.1967, 11.7.1967, 3.11.1967). Hunziker, F. et al.: Helv. Chim. Acta (HCACAV) 50, 1588 (1967). Formulation(s): inj. sol. 50 mgl2 ml; tabl. 25 mg, 100 mg Trade Name(s): D: Clozaril (Novartis) F: Leponex (Novartis) Leponex (Novartis Pharma) USA: Clozaril (Novartis) Cobamamide ATC: B03BA04 (Adenosylcobalamin; Coenzym B,,; Djbencozide) Use: anabolic RN: 13870-90-1 MF: C7,Hl,C~N,RO17P MW: 1579.61 EINECS: 237-627-6 LDSo: 1 g/kg (M, i.v.) CN: cobinamide Co-(5'-deoxyadenosine-5') deriv. hydroxide dihydrogen phosphate (ester) inner salt 3'-ester with 5,6-dimethyl-l-a-~-ribofuranosyl-1H-benzimidazole Zn/HCI or Zn/CH3COOH or NoBH4 [under exclusion of 02] b I1 hydroxocobolomin (I) (9, v.1 Cobamamide C 539 hydridocobolornin (11) aq. HCI II f 1 Cobornomide 3. K2C03 or NoOH 1 2. 5'-deoxy-5'-iodoodenosin Reference(s): a Bemhauer, K. et al.: Angew. Chem. (ANCEAD) 75, 1145 (1963). US 3 213 082 (Glaxo; 19.10.1965; GB-prior. 11.12.1961). b US 3 461 114 (Yamanouchi; 12.8.1969; J-prior. 1.10.1966). Formulation(s): cps. 0.25 mg, 1 mg; drops 30 mg; tabl. 0.25 mg, I mg, 2.5 mg Trade Name(s): D: Xobaline (Albert-Roussel); wfm 540 C Cocarboxvlase F: Vibalgan (Doms-Adrian)- comb. I: Amico (SIT)-comb. Aminozim (Pierrel)-comb. J: Anabasi (Zilliken) Calciozim (Pierrel)-comb. Calisvit (Menarini)-comb. Cobaforte (Roussel) Cocametina B 12 (Sigma- Tau)-comb. Glutacomplex (Chemi1)- comb. Hepafactor Complex (Sigma-Tau)-comb. Indusil (Recordati) Actavix (Nippon Kayaku) Actimide (Tobishi) Ademide (Toyo Jozo) Cabarol (Daiko) Calomide (Yamanouchi) Cobaforte (Roussel- Chugai) Cobalan (Daiichi) Cobaltamin-S (Wakamoto) Cobamyde (Shiu Nihon Jitsugyo) Funacomide (Funai) Hokurarnide (Hokuriku) Hycobal (Eisai) Hyrasedon (Sawai) Lasedmeide (Choseido) Metamide (Nakataki) Sabalamin (Sato-Santen) Satomid (Shinshin) generics and combination preparations Cocarboxylase ATC: A~~DA Use: enzyme against metabolic disturbance RN: 154-87-0 MF: CI,H,,CIN,O,P,S MW: 460.77 EINECS: 205-836-1 LD,,,: >I g/kg (M, i.m.); >500 mglkg (R, i.m.) CN: 3-[(4-amino-2-methyl-5-pyrimidinyl)methy1]-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6- diphosphahex-1-y1)thiazolium chloride H2N Cacarboxylase Work up of the reaction mixtures on ion-exchangers. Reference(s): US 2 991 284 (E. Merck AG; 4.7.1961; D-prior. 28.9.1957). Formulation(s): vial 5.8 mgIlO mg, 20 mg, 50 mg, 100 mg Trade Name(s): D: Cernevit (Baxter)-comb. F: CernCnit (Baxter)-comb. Plenyl (0berlin)-comb. generics and combination preparations I: Adenobeta (Salus Research)-comb. Adenoplex (Lepetit)-comb. Adenovit (Nuovo Cons. Sanit. Naz.)-comb. Benexol (Roche)-comb. Bivitasi (ISI) Firmavit (Firma)-comb. Fosforilasi (Po1ifarma)- comb. Neogeynevral (Geymonat)- comb. Piruvasi (Delalande 1snardi)-comb. salts and combination preparations J: Bicholase (Fuso) Cocalbose (Fuji Zoki) Cocalox (Maruko) Co-Carten (Sanken) Coxylase (Funai) Carboxin (Toa Eiyo- Yamanouchi) Hiactose (Ohno) Metabolase (Takeda) Neo Alinachiol (Kanto) Nutrase (Kyorin) Paraboramin (Hoei) Proffit (Isei) Pyrolase (Chugai) Reborase (Kanto) Thiamilase (Hokuriku) . MW: 435.89 EINECS: 20 0-5 1 4-7 CN: [2S-(2a,5a,6~) ~-6 -[ [[ 3-( 2-chlorophenyl )-5 -methyl-4-isoxazolyl]carbonyl]amino ]-3 ,3-dimethyl-7-oxo- 4- thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid monosodium. EINECS: 20 5-8 3 6-1 LD,,,: >I g/kg (M, i.m.); >500 mglkg (R, i.m.) CN: 3-[ (4-amino-2-methyl-5-pyrimidinyl)methy1 ]-4 -methyl- 5-( 4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4, 6- diphosphahex-1-y1)thiazolium. 3367 1-4 6-4 MF: C,,H,,ClN,OS MW: 318.83 EINECS: 25 1-6 2 7-3 LD,,: 440 mglkg (M, i.p.); 636 mglkg (M, p.0.) CN: 5-( 2-chlorophenyl )-7 -ethyl-1,3-dihydro-l-methyl-2H-thieno[2,3-e ]-1 ,4-diazep~n-2-one