Cetylpyridinium chloride C 421 k 2 1 Trade Name(s): 1 D: Cetrotide (ASTA Medica GB: Cetrotide (ASTA Medlca) k I AWD; 1999) ! f Cetylpyridinium chloride i ATC: BO5CAO1; D08AJ03; D09AA07; R02AA06 Use: dls~nfectant, antisept~c ! RN: 123-03-5 MF: C,,H,,ClN MW: 340.00 EINECS: 204-593-9 i LD,,: 10 mglkg (M, i.v.); 108 rnglkg (M, p.o.), E 200 mgkg (R, p.o.1 CN. 1-hexadecylpyridinium chloride pyridine cetyl chloride Cetylpyridinium chloride Reference(s): Budesinsky-Protiva, 53 1-532. Formulation(s): eff. tabl. 1.5 mg, 3 mg; lozenge 1.4 mg; sol. 5 mg/lO rnl (0.01 %, 0.05 %); tabl. 2 mg Trade Name(s): D: Dobendan (Cassella-med) Merocame (Seton)-comb. Pcnaten (Johnson & Formamint N (Beecham- Merocet (Seton) Johnson) W~ilfing) I: Borocaina (Schiapparelli Ragaden (Ganassini) Tyrosolvetten (Byk Gulden; Salute) Vidermina (Ganassini) Roland)-comb. numerous combination preparations F: Alodont (Warner-Lambert)- comb. Broncorinol (Roche Nicholas)-comb. CCtylyre (Oberlin) GB: Calgel (Warner-Lambert) Fluprim (Roche) Gola (Sella) Golagamma (Avantgarde) J: Neocepacol (Lepetit) Neocoricidin (Schering- Plough) USA: Neoformitrol (Sandoz) Neogola (Sella) Noalcool (Sella) numerous combination preparations Colgen 123 (Kowa)-comb. Pabron Troche (Taisho) Suprol (Iwaki) Cepacol (Lakeside)-comb.; wfm Cobrex (Reid-Rowell)- comb.; wfrn Chenodeoxycholic acid (Chenodiol; Acide chenodtoxycholique; Chenodesoxycholsaure) ATC: AOSAAOI Use: choleretic, anticholethithogenic dissolution of cholesterol gallstones RN: 474-25-9 MF: C24H4004 MW: 392.58 EINECS: 207-481-8 LD,: 100 mgkg (M, i.v.); 3 glkg (M, p.0.); 106 mdkg (R, i.v.); 4 glkg (R, p.0.); >I dkg (dog, PO.) CN: (3a,5P,7a)-3,7-dihydroxycholan-24-oic acid 422 C Chenodeoxycholic acid 0 0 0/CH3 H~cAo"XH, 'zS04 pyr~dine + HO-CH, + E Me ,,\+ -1 Me H '"OH H O."' H H "'OH cholic acid methyl cholote methyl 3a,7a-diacetoxy- methyl 3a.7~-diocetoxy 12a-hydroxycholonote (I) 12-oxocholonote (11) 1. H2N-NH2 .H20. HO~OH , 200 OC 2. HCI II b 1. hydrozine hydrote I Chenodeoxycholic ocid ~ieser, L.F.; Rajagopalan, S.: J. Am. Chem. Soc. (JACSAT) 72,5530 (1950). Hauser, E. et a].: Helv. Chim. Acta (HCACAV) 43, 1595 (1960). Hofmann, A.F.: Acta Chem. Scand. (ACHSE7) 17, 173 (1963). Sato, Y.; Ikekawa, N.: J. Org. Chem. (JOCEAH) 24, 1367 (1959). purification: DOS 2 302 744 (Union International; appl. 20.1.1973; GB-prior. 20.1.1972). DE 2 404 102 (Schering AG; appl. 25.1.1974). DOS 2 613 346 (Diamalt; appl. 29.3.1976). US 4 163 017 (Diamalt; 31.7.1979; D-prior. 29.3.1976). JP-appl. 52 153 955 (Tokyo Tanabe; appl. 18.6.1976). isolation from animal bile: US 3 919 266 (Intellectual Property Dev. Corp.; 11.1 1.1975; prior. 21.9.1972, 19. - 1973). US 4 014 908 (Intellectual property Dev. ~orp.; 29.3.1977; prior. 21.9.1972, 19.1 1.1973,7.5.1974, 30.5.1974, 20.2.1976). US 4 072 695 (Intellectual Property Dev. Corp.; 7.2.1978; prior. 21.9.1972, 19.1 1.1973, 7.5.1974, 30.5.1974, 20.2.1976, 17.9.1976). combination with hymecromone: DOS 2 700 085 (Lipha; appl. 4.1.1977; F-prior. 13.7.1976) Formulation(s): cps. 250 mg; tabl. 250 mg Trade Nante(s): D: Chenofalk (Falk) Hekbilin (Strathmann)- GB: Chendol (CP Pharrn.) Cholit-Ursan (Fresenius- comb. Chenofalk (Tharnes) Praxis) Ursofalk (Fa1k)-comb. I: Chenofalk (Interfalk) F: ChCnodex (Hoechst HoudC) Chenossil (Midy) Chloral hvdrate C 423 Fluibil (Zambon Italia) Cholasa ('Tokyo Tanabe) USA: Chcnix (Reid-Rowell); I: Chenochol (Yamanouchi) wfm Chloral hydrate ATC: NO~CCOI Use: hypnotic, scdative RN: 302-17-0 MF: C,H,CI,O, MW: 165.40 EINECS: 206-1 17-5 LD56 530 mglkg (M, i.v.); 1100 mglkg (M, p.o.1; 479 mag (R, p.0.) CN: 2,2,2-trichloro-1 ,l -ethanediol ethanol trichloro- 1 Chlarol hydrate acetaldehyde (1) Reference(s1: UUmanns Encykl. Tech. Chem., 4. Aufl., Vol. 9, 377. Formulation(s): cps. 250 mg, 500 mg Trade Nume(s): D: Chloraldurat (Pohl) GB: Welldorm elixir (S & N) USA: Noctec (Squibb); wrm F: numerous combination I: Cloral (Tariff. Nazionale) generica preparations J: Escre (SS) Chloralodol (Chlorhexadol) ATC: N05CC02 Use: hypnotic RN: 3563-58-4 MF: C,HI,C1303 MW: 265.56 EINECS: 222-634-9 CN: 2-methyl-4-(2,2,2-trichloro-1-hydroxyethoxy)-2-pentanol 2-methylpentane- chloral hydrate 2,4-diol Reference(s): US 2 931 838 (Det Danske Med & Kern Komp.; 5.4.1960; DK-prior. 8.12.1956). Fonnulation(s): tabl. 400 mg, 800 mg 424 C Chlorambucil Trade Narne(s): GB: Medodorm (Medo); wfm Chlorambucil ATC: LOlAA02 Use: antineoplastic RN: 305-03-3 MF: C,,H,,C12N02 MW: 304.22 EINECS: 206-162-0 LD,,,: 80 mgkg (M, p.0.); 76 mgkg (R, p.0.) CN: 4-[bis(2-chloroethyl)amino]benzenebutanoic acid ocetanilide succinic 4-(4-ocetamidophenyl)- anhydride 4-oxobutanoic ocid oxide 4-(4-ominopheny1)- butonoic ocid (U) Reference(s): US 3 046 301 (Borroughs Wellcome; 24.7.1962; prior. 29.10.1959). 1. POCI, 2. H20 b CkPN 1. phosphorus ~ld Formulation(s): drg. 2 mg; tabl. 2 mg, 5 mg oxychlaride Trade Narne(s): D: Leukeran (Glaxo GB: Leukeran (Glaxo Linfolysin (Nuovo ISM) Wellcome) Wellcome) USA: Leukeran (Glaxo F: Chloraminophtne (Techni- I: Leukeran (Glaxo Wellcome) Pharma) Wellcome) Chlorambucil Chloramphenicol ATC: D06AX02; D 1OAF03; GO1 AAOS; JOlBAOl; SOlAAOl; S02AAO1; S03AA08 Use: antibiotic RN: 56-75-7 MF: C, ,H12C12N20, MW: 323.13 EINECS: 200-287-4 LD,,,: 110 mgkg (M, i.v.); 1500 mglkg (M, p.0.); 171 mg/kg (R, i.v.); 2500 mg/kg (R, p.0.) CN: [R-(R*,R*)]-2,2-dichloro-N-[2-hydroxy-l-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]aceta~de Chloramphenicol C 425 0 (CH2)6N4 2. HCI 1. hexamethylene- "."-"a OH.[ tetramine NO, 4'-nitro- acetophenone 2-bromo-4'-nitro- ocetophenone 2-amino-4'-nitroaceto- phenone hydrochloride (I) acetic anhydride 2-acetamido-4'-nitro- acetophenone D-camphorsulfonic ocid 1u - 1 Chloramphenicol I H C CH, OH OH 3oxo cinnarnyl alcohol 2-bromo-l- phenyl-12- proponediol 5-bromo-2.2- dimethyl-4- phenyl-l,3- dioxane (IV) DL-threo-5- omino-2.2- dirnethyl-4- phenyl- 1.3-dioxone D(-)-threo-5- amino-2,2- dirnethyl-4- phenyl-1,3- dioxane D(-)-threo-5-di- chloroacetarnido- 2.2-dimethyl-4- phenyl-1.3-dioxane (V) 426 C Chloramphenicol phenyl) 1,3-propane- dial dinitrate Rqference(s): Ehrhart-Ruschig IV, 398 ff. a Long, L.M.; Troutman, H.D.: J. Am. Chem. Soc. (JACSAT) 71,2469,2473 (1949). US 2 483 871 (Parke Davis; 1949; appl. 1948). US 2 483 884 (Parke Davis; 1949; appl. 1948). US 2 483 885 (Parke Davis; 1949; appl. 1949). US 2 483 892 (Parke Davis; 1949; appl. 1948). US 2 687 434 (Parke Davis; 1954; appl. 1953). US 2 651 661 (Monsanto; 1953; appl. 1950). US 2 786 870 (Parke Davis; 1957; appl. 1954). Rebstock, M.C. et al.: J. Am. Chem. Soc. (JACSAT) 71,2458-2468 (1949). b BE 539 991 (Boehringer Mannh.; appl. 1955; D-prior. 1954). DE 1 01 6 718 (Boehringer Mannh.; appl. 1953). BE 558 378 (Boehringer Mannh.; appl. 14.6.1957; D-prior. 27.6.1956,22.12.1956). alternative synthesis (from benzaldehyde and nitromethane or 0-nitroethanolvia 2-n~tro-1-phenyl- l,3- propanediol): DE 862 302 (Parke Dam; appl. 1949; USA-prior. 1948). DE I 064 937 (Roehringer Mannh.; appl. 1957). DOS 2 708 301 (Egyt; appl. 25.2.1977; H-pnor. 25.2.1976). 0-3-monophosphate: DAS 1 668 96 1 (Roussel-Uclaf; appl. 20.2.1968; I-prior. 20.2.1967, 18.5.1967). Formulation(s): amp. 1 g (as hydrogen succinate sodium salt); cps. 250 mg, 500 mg; ear drops 5 g/100 ml, 50 mglg; eye drops 5 mg, 10 mg; ointment 1 % (10 mglg) Trade Name(s): D: Aquamycetin (Winzer) Chloramphenicol-PW (Pharma Wernigerode) Chloramsaar (Chephasaar) Oleomycetin (Winzcr) Paraxin (Boehringer Mannh.) Thilocanfol C (Alcon) numerous combination preparations F: CCbtdexacol (Chauvin)- comb. CCbCnicol (Chauvin) numerous combination preparations GB: Chloromycetin (Goldshield) Kemicetine Succinate (Pharmacia & Upjohn) Minims Chloramphenicol (Chauvin) SNO Phenicol (Chauvin) I: Chemicetina (Carlo Erba) Chloromycetin (Parke Davis) Cloram (Formulario Naz.) Minims (Smith & Nephew) Mycetin (Farmigea) Sificetina (SIFI) Vitamfenicolo (Allergan) numerous salts and combination preparations J: Antacin (Sumitorno) Chloromycetin (Sankyo) Kemicetine (Fujisawa) Myclocin (Takeda) Paraxin (Yamanouchi) Synthomycetine (Otsuka) numerous gcncrics and combination preparations USA: Elase-Chloromycetin (Fujisawa) Chlorazanil C 427 Chlorazanil ATC: C03 Use: diuretic RN: 500-42-5 MF: C9HRC1N5 MW: 221.65 EINECS: 207-904-6 LD,,: 300 mglkg (M, p.0.); 16 mglkg (R, i.v.) CN: N-(4-chloropheny1)- 1,3,5-triazine-2,4-diamine monohydrochloride RN: 2019-25-2 MF: C,HRC1N5 . HC1 MW: 258.1 1 EINECS: 21 7-962-4 1-(4-chlaropheny1)- formic I C~orazanil biguonide hydrochloride acid Reference(s): DE 1 008 303 (Heumann & Co.; appl. 1955). Formulation(s): tabl. 150 mg Trade Name(s): D: Orpidan-150 (Heumann); wfm Chlorbenzoxamine ATC: A03AX03 Use: anticholinergic RN: 522-18-9 MF: C,,H,,ClN,O MW: 435.01 EINECS: 208-323-0 CN: I-[2-[(2-chlorophenyI)phenylmethoxy]ethyl]-4-[(2-methylphenyl)methyl]piperazine dihydrochloride RN: 5576-62-5 MF: C,,H,,ClN,O. 2HCl MW: 507.93 EINECS: 226-951-3 LD,,: 1400 mglkg (M, p.0.); 66 mgkg (R, i.v.); 3350 mglkg (R, p.0.) Reference(s): BE 549 420 (H. Morren; appl. 10.7.1956), 2-chlarobenz- 1 -(2-hydroxyethyl)- Formulation(s): tabl. 30 mg (as dihydrochloride) Chlorbenzoxamine hydlyl chloride 4-(2-methylbenzy1)- piperazine 1 428 C Chlorcyclizine nade Name(s): D: Libratar (UCB); wfm Gastomax (Brocchieri); Libratar (UCB-Smith). I: Antiulcera Master (Cali); wfm comb.; wfm wfm J: Anratal (Tobishi) Chlorcy clizine (Histachlorazine) ATC: R06AE04 Use: antihistaminic RN: 82-93-9 MF: ClxH2,CIN2 MW: 300.83 EINECS: 201-446-0 CN: 1-[(4-chlorphenyl)phenylmethyl]-4-methylpiperazine monohydrochloride RN: 14362-3 1-3 MF: C,,H2,CIN2. HCI MW: 337.29 dihydrochloride RN: 129-71-5 MF: ClxH2~C1N2 2HCI MW: 373.76 4-chlorobenz- 1 -methyl- / Chlorcyclizine 1 hydryl chlaride piperazine Reference(s): US 2 630 435 (Burroughs Wellcome; 1953; prior. 1948). Formulation(s): tabl. 50 mg (as hydrochloride) Trade Name(s): F: Di-ParalCne (Abbott); wfm I: Clorciclizina (Tariff. USA: Mantadil (Burroughs GB: Histofax (Wellcome); wfm Integrativo) Wellcome)-comb. with Di-Paralene (Abbott); wfm hydrocortisone; wfm Chlordiazepoxide ATC: N05BA02 Use: tranquilizer RN: 58-25-3 MF: C,,H,,ClN,O MW: 299.76 EINECS: 200-371-0 LD,,,: 95 mgkg (M, i.v.); 200 mgkg (M, p.0.); 165 mg/kg (R, i.v.); 392 mglkg (R, p.0.) CN: 7-chloro-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-amine 4-oxide CI 3 hydroxyl- NH20H - cH3c00H , amine \ 2-arnino-5- chlorobenzo- phenone 6-chloro-2-chloromethyl 4-phenylquinazoline 3-oxide (I) Chlorhexidine C 429 g Chlordiazepoxide f :: Referencefs): US 2 893 992 (Hoffmann-La Roche; 7.7.1959; prior. 15.5.1958). 1 ,DE 1096 363 (Hoffmann-La Roche; appl. 24.4.1959; USA-prior. 15.5.1958) P Stembach, L.H. et al.: J. Org. Chem. (JOCEAH) 26, 11 11 (196 1). 1 ? Formulation(s): drg. 10 mg; f. c. tabl. 5 mg; tabl. 5 mg, 10 mg, 25 mg Tmde Name(s): D: Limbatril (Roche)-comb. Multum (Rosen Pharma) Radepur (ASTA Medica AWD) F: Librax (Roche)-comb. GB: Librium (Roche) 1: Diapatol (Teofarma)-comb. Librium (Roche) Limbitryl (Roche)-comb. Psicofar (Terapeutico) USA: Librax (Roche Products; as Reliberan (Geymonat) hydrochloride) Sedans (Ganassini)-comb. Librium (Roche Products; Seren Vita (Synthelabo) . as hydrochloride) J: Balance (Yamanouchi) Limbitrol (Roche Products) Contol (Takeda) generics Sophiamin (Kyowa Yakuhin) Trakipearl (Hishiyama) Chlorhexidine ATC: AOlAB03; B05CA02; D08AC02; D09AA12; R02AA05; SO1 AX09; S02AA09; S03AA04 Use: antiseptic RN: 55-56-1 MF: C22H,oC12Nlo MW: 505.46 EINECS: 200-238-7 LD,: 24 mgkg (M, i.v.); 25 15 nig/kg (M, p.0.); 21 mgkg (R, i.v.); 9200 pL/kg (R, p.0.) CN: N,N'-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide diacetate RN: 56-95-1 MF: C22H30C12Nlo . 2C2H,02 MW: 625.56 EINECS: 200-302-4 LD,: 25 mgkg (M, i.v.); 2 g/kg (M, p.0.) dihydrochloride RN: 3697-42-5 MF: C22H~oC12N~o~2HCI MW: 578.38 EINECS: 223-026-6 LD,,: >5 g/kg (M, s.c.) di-~.glW~nate RN: 18472-51-0 MF: C22H30C12NLo. 2C6H1207 MW: 897.77 EINECS: 242-354-0 LD,: 12.9 mg/kg (M, i.v.); 1260 mglkg (M, p.0.); 24.2 mglkg (R, i.v.); 2 @kg (R, p.0.) 430 C Chlorhexidine hexornethylenebis- 4-chlorooniline (dicyonodiornide) hydrochloride HHH HHH I Chlorhexidine I hexornethylenediornine (4-chlorophenyl)- dihydrochloride dicyonodiomide Reference(s): GB 705 838 (ICI; appl. 1951; valid from 1952). 1 $ I Formlclation(s): gel 1 g1100 g; powder 1 g1100 g; sol. 0.1 g/100 g, 0.2 g1100 g, 1 g/50 ml (as digluconate) ! Trade Nume(s): D: Chlorhexamed (Blend-a- Hibidil (Zeneca; as Hibidil (Zeneca) med ) digluconate) Hibiscrup (Zeneca) C hlorhexidindigluconat Hibiscrub (Zeneca; as Hibitane (Zeneca) (Engelhard) Corsodyl (SmithKline Beecham OTC Medicines) Frubilurgyl (Boehringer Mannh.) Hansamed (Beiersdorf) numerous combination preparations F: Antalyre (Boehringer Ing.; as g1uconate)-comb. Collunovar (Dexo; as gluconate) Collupressine (SynthClabo; as g1uconate)-comb. Collustan (Oberlin; as dig1uconate)-comb. Corsadyl (SmithKline Beecham; as digluconate) CytCal (Sinbio; as g1uconate)-comb. Dacryne (Johnson & Johnson) Diseptine (Nicholas; as g1uconate)-comb. Eludril (Inava; as digluconate) Hibitane (Zeneca; as gluconate) Merfene (Novartis; as - gluconate) Plurexid (Evans; as gluconate) Prexidine (Pred; as gluconate) SepCal (Sinbio; as digluconate) Thiovalone (Eurorga; as diacetate)-comb. GB: Bactigras (Smith & Nephew) Chlorhexitulle (Hoechst) Corsodyl (SmithKline Beecham) numerous preparations I: Clorex (Formulario Naz.) Contact (Vaas; as Lenixil (Eurospital) Neomercurocromo (SIT) Neoxene (Ecobi) Odontoxina (Ipfi) Oramil (Ganassini) Plak Out (Byk Gulden) Sanoral (Kemiprogress) Savlodil (Zeneca)-comb. Savlol (Zeneca)-comb. Vaxidina (Vaas) Vidermina (Ganassini) J: Hexad01 (Green Cross) Hibiscrub (ICI) Hibitane Digluconate (Sumitorno) Maskin (Maruishi) Pabron (Taisho Seiyaku) White Go1 (Tamagawa Eizai) White Rive (Eisai) USA: Betasept (Purdue hydrochloride) Frederick; as gluconate) Corsodyl (SmithKline Hibiclens (Zeneca; as Beecham) gluconate) Effetre (Farma3 Medicalex) Hibistat (Zeneca; as dig1uconate)-comb. Hansarned (Beiersdoro gluconate) . dimethyl- 4- phenyl-l, 3- dioxane (IV) DL-threo- 5- omino-2. 2- dirnethyl- 4- phenyl- 1.3-dioxone D (-) -threo- 5- amino-2, 2- dirnethyl- 4- phenyl-1, 3- dioxane D (-) -threo-5-di- chloroacetarnido-. Use: hypnotic RN: 356 3-5 8-4 MF: C,HI,C1303 MW: 265.56 EINECS: 22 2-6 3 4-9 CN: 2-methyl- 4-( 2,2,2-trichloro-1-hydroxyethoxy )-2 -pentanol 2-methylpentane- chloral hydrate 2,4-diol Reference(s):. anhydride 2-acetamido-4'-nitro- acetophenone D-camphorsulfonic ocid 1u - 1 Chloramphenicol I H C CH, OH OH 3oxo cinnarnyl alcohol 2-bromo-l- phenyl-1 2- proponediol 5-bromo-2. 2- dimethyl-4-