Butylscopolammonium bromide B 3 1 1 Butylscopolammonium bromide ATC: A03BBOI (Butylscopolamine bromide; Scopolamine butyl bromide; antispasmodic Hyoscin butyl bromide) RN: 149-64-4 MF: C,,H30BrN04 MW: 440.38 EINECS: 205-744-1 LD,,: 10.3 mg/kg(M,i.v.); 1170mglkg(M,p.o.); 24 mglkg (R, i.v.); 1040 mglkg (R, p.0.) CN: [7(S)-(la,2~,4~,5a,7P)1-9-butyl-7-(3-hydroxy-1-oxo-2-phenylpropoxy)-9-methyl-3-oxa-9- azoniatricyclo[3.3.1 .02"]nonane bromide butyl bromide (-)-scopolamine I Butylscopolommonium bromide Reference(s): DE 856 890 (Boehringer Ing.; appl. 1950). Formulation(s): amp. 20 mglml; drg. 10 mg; f. c. tabl. 10 mg; suppos. 7.5 mg, 10 mg; tabl. 20 mg; vial 200 mg/lO ml Trade Name(s): D: Buscopan (Boehringer 1ng.)-comb. F: GCnoscopolamine (Amino) Scopoderm (Novartis) GB: Buscopan (Boehringer Ing.) I: Buscopan (Boehringer Ing.) Buscopan compost0 (Boehringer 1ng.)-comb. Tranquo-Buscopan (Boehringer 1ng.)-comb. J: Antispasmin (Green Cross) Bubusco-S (Sawai) Buscopan (Boehringer- Tanabe) Buscoridin (Kanebo) Buscote (Kotani) Buspon (Toyo Pharmar) Butibol (Towa) Butylpan (Hokuriku) Butymide (Ohta) Butysco (Kobayashi) Diaste-M (Fukuchi- Fujizoki) Hyoscomin (Vitacain) Hyospan (Toiyo) Moryspan (Beppu) Reladan (Isei) Scobro (Ono) Scobron (Mohan) Scobutylamin (Horii) Scordin-B (Ono) Scorpan (Kanto) Sparicon (Yamanouchi) Spasmopan (Nichiiko) Stibron (Iwaki) 312 C Cabergoline Cabergoline ATC: GO~CBO~ Use: doparnine D, receptor antagonist, prolactin inhibitor for prevention or suppression of puerperal lactation RN: 81409-90-7 MF: C,,H,,N,O, MW: 451.62 CN: (8~)-N-[3-(Dirnethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)ergoline-8-carboxamide 1. K2C03, DMF 2. NaOH. CH30H 8p-methoxycarbonyl- ergoline (cf. pergolide synthesis) ally1 bromide THF d N-ethyl-Na-[3-(dirnethyl- amino)propyl]corbo- diirnide 6-allyl-88-ergoline- carboxylic acid (I) Cabergoline 0CNvCH3, toluene or '33 H3CbN=c=Nq CH3 @ CH2CIZ. CuCl (cot.), PPh3 H3C 1- 3-dimethylamino- ethyl isocyanate propylarnine. diisopropylcarbo- diimide H N~ 6-allyl-N-[3-(dimethyl- amino)propyl]-8p- ergolinecorboxarnide Reference(s): a GB 2 074 566 (Farmitalia Carlo Erba S.p.A.; appl. 31.3.1981; GB-prior. 3.4.1980). b US 4 526 892 (Farrnitalia Carlo Erba S.p.A.; 2.7.1985; USA-prior. 3.3.1981). BE 894 060 (Farmitalia Carlo Erba S.p.A.; appl. 9.8.1982; GB-prior. 11.8.1981). b,c WO 9 31 8 034 (Farmitalia Carlo Erba S.p.A.; appl. 15.2.1993; GB-prior. 12.3.1982). Candiani; Cabri, W.; Zarini, F.; Bedeschi, A,: Synlett (SYNLES) 1995 (6), 605. Cadexomer iodine C 3 13 synthesis and nidation inhibitory activity of a new class of ergoline derivatrves: Brambillh, E.; Dlsalle, E.; Briatlco, G.; Mantegani, S.; temper ill^, A.: Eur. J. Med. Chem. (EJMCAS) 24, 421 (1989) ' Formulution(s): tabl. 0.5 mg, 1 mg, 2 mg, 4 mg Tmde Namefs): : D: CABASERIL (Pharmacia GB: Cabaser (Pharmacla & & Upjohn) Upjohn) Dostinex (Pharmacia & Dostinex (Pharmacia & Upjohn) Upjohn) Cadexomer iodine ATC: Use: RN: 94820-09-4 MF: unspecified MW: unspecified LD50: >2 glkg (R, i.p.); >2 glkg (R, LC.) CN: cadexomer iodine 12, acetone drxtrin + Cl> epichloro- hydrin I: Dostinex (Pharmacia & Upjohn) USA: Dostinex (Pharmacia & Upjohn) D03AXO 1 ; D08AG antiseptic for treatment of decubitus and venous leg ulcers Cadexorner iodine I Referencefs): DE 2 533 159 (A. 0. Johannson; appl. 24.7.1975). US4010 259 (A. 0. Johannson; 1.3.1977; appl. 17.7.1975). FR 2 320 112 (A. 0. Johannson; appl. 5.8.1975). Formulation(s): dry sterile powder, micropellets, sachet 3 g, 1 % bioavailable iodine Trade Namefs): D: Iodosorb (Strathmann) F: Iodosorb (Millot; 1984); wfm 3 14 C Cadralazine 7 GB: Iodoflex (Perstorp) Iodosorb (Perstorp; 1983) I: Iodosorb (Valeas; 1989) Cadralazine ATC: CO~DBO~ Use: antihypertensive, vasodilator RN: 64241-34-5 MF: Cl,H,,N,O, MW: 283.33 LD,,,: 700 mg/kg (M, i.p.); 269 mg/kg (R, i.v.); 2060 mg/kg (R, p.0.) CN: 2-[6-[ethyl(2-hydroxypropyl)amino]-3-pyndazinyl]hydrazinecarboxylic acid ethyl ester cCH3 - Wc, & + OH fCH3 -, I NH2 3.6-dichloro- H3C pyridozine propylene ethylamine N-eth~i-2-h~droxY- (cf. azintarnide) oxide propylornine OH cCH3 H + CI 0 ethyl carbazate (1) Cadralazine Reference(s): US 4 002 753 (I.S.F.; 11.1.1977; I-prior. 7.3.1973). alternative syntheses: US 4 575 552 (I.S.F.; 11.3.1986; I-prior. 28.4.1983). US 4 632 982 (I.S.F.; 30.12.1986; I-prior. 28.4.1983). US 4 757 142 (I.S.F.; 12.7.1988; I-prior. 13.5.1985). cf. also synthesis of pildralazine Formulation(s): cps. 10 mg, 15 mg, 29 mg Trade Name(s): I: Cadraten (SmithKline Cadrilan (Novartis) Beecham) J: Cadral (Novartis) Cafaminol (Mecoffaminum; Methylcoffanolamine) Use: rhinological therapeutic RN: 30924-3 1-3 MF: C,,H,,N,O, MW: 267.29 EINECS: 250-390-3 LD,,,: 700 mg/kg (M, s.c.) CN: 3,7-dihydro-8-[(2-hydroxyethyl)methylamino]-l,3,7-trimethyl-1H-purine-2,6-dione Cafedrine C 315 caffeine 8-chlorocaffeine Cofaminol (4. v.1 Reference(s): DE 1 085 530 (J. Klosa; appl. 15.8.1958). US 3 094 531 (Delmar Chemicals; appl. 30.4.1959). Formulation(s): drg. 50 mg Trade Nanie(s): D: Rhinoptil (Promonta); wfm I: Katasma balsamic0 (Bruschettini) Cafedrine ATC: COlCA21 Use: circulatory analeptic RN: 58166-83-9 MF: C,,H,,N,O, MW: 357.41 CN: 3,7-dihydro-7-[2-[(2-hydroxy-l-methyl-2-phenylethyl)amino]ethyl]-1,3-dimethy-1 H-purine-2,6-dione [R-(R*,S*)]-cafedrine RN: 78396-34-6 MF: C,,H,,N,O, MW: 357.41 [R-(R*,S*)]-monohydrochloride RN: 3039-97-2 MF: C,,H,N,O,. HCl MW: 393.88 EINECS: 221-243-0 LD,,: 525 mgkg (M, i.p.) theophylline 1,2-dibramo- 7-(2 bramaethyl)- ethane theophylline (I) L-norephedrine I Cafedrine Reference(s): DE 1 095 285 (Degussa; appl. 25.9.1956). US 3 029 239 (Degussa; 10.4.1962; D-prior. 17.4.1954). Formulation(s): amp. 200 mg; f. c. tabl. 100 mg 316 C Caffeine Trade Name(s): D: Akrinor (Homburg)-comb. F: Praxinor (Lipha SantC)- I: Akrinor (ASTA Medica; as with theodrenaline comb. with thCodrCnaline hydrochloride) Caffeine (Cafkine; Coffein) ATC: N06BCOl Use: analeptic. diuretic RN: 58-08-2 MF: CUH,,N4O2 MW: 194.19 EINECS: 200-362-1 LD,,,: 62 mglkg (M, i.v.); 127 mglkg (M, p.0.); 105 mglkg (R, i.v.); 192 mglkg (R, p.0.); 140 mglkg (dog, p.0.) CN: 3,7-dihydro-1,3,7-trimethyl-lH-purine-2,6-dione O\\ 0 - + H,C,~,S~ \CH, OYN 0 CH3 theophylline dirnethyl sulfate Caffeine (9. v.) Reference(s): DE 834 105 (Boehringer Ing.; appl. 1949). Formulation(s): tabl. 200 mg Trade Name(s): D: Coffeinum (Merck) GB: Cefergot.(Novartis)-comb. J: Percoffedrinol N (Passauer) Doloxene (Lil1y)-comb. numerous generics and combination preparations numerous combination Migril (Glaxo Wellcome)- USA: Darvon (Lilly) preparations comb. DHCplus (Purdue F: Cafkine Aguettant I: . Caffeina (Tariff. Nazionale; Frederick) (Aguettant) as citrate) Esgic-plus (Forest)-comb. PercutafCine (Fabre) numerous combination numerous combination generics and combination preparations preparations preparations Caffeine acetyltryptophanate (A 50; Coftrinum) ATC: N06BCOl Use: psychotonic RN: 60364-24-1 MF: Cl,H14N203. CuHloN402 MW: 440.46 CN: 1-acetyl-L-tryptophan compd. with 3,7-dihydro-1,3,7-trimethyl-lH-purine-2,6-dione (1: 1) " 8" '' HN CH, CH3 K 0 HN CH, K 0 N-acetyl- L-tryptophan I Caffeine acetyltryptaphanate Calcifediol C 317 Reference(s): FR-M 1 759 (A. E. C.; appl. 22.2.1962). Trade Name(s): F: Adrifane (Adrian, Paris); wfm Calcifediol ATC: A1 1CC06 Use: calcium regulator RN: 19356-17-3 MF: C,,H,O, MW: 400.65 EINECS: 242-990-9 CN: (3~,5Z,7E)-9,l0-secocholesta-5,7,10(19)-triene-3,25-diol 25-hydroxycholesterol 3-ocetote acetic anhydride dimethylhydantoin 2. trirnethyl phosphite 3. lithium aluminum hydride dirnethylhydontoin 2. trimethyl phosphite 3. rnethylmognesium iodide Reference(s): a,bBlunt, J.W.; DeLuca, H.F.: Biochemistry (BICHAW) 8,671 (1969). DeLuca, H.F.: Am. J. Clin. Nutr. (AJCNAC) 22,412 (1969). Halkes, S.J.; Vliet, N.P. van: Recl. Trav. Chim. Pays-Bas (RTCPA3) 88, 1080 (1969). alternative svntheses: Sodano, Ch. S.: Vitamins, Synthesis, Product~on and Use, p. 131, 159 (New Jersey 1979). US 4 001 096 (Upjohn; 4.1.1977; prior. 21.2.1975). US 3 833 622 (Upjohn; 3.9.1974; prior. 17.3.1969). structure and isolation: DeLuca, H.F.: Am. J. Clin. Nutr. (AJCNAC) 22,412 (1 969). Formulation(s): drops 0.15 mglml, 0.45 mglml Trade Nameis): D: Dedrogyl (Albert-Roussel, F: DCdrogyl (Roussel) I: Didrogyl (Roussel) Hoechst) Un-Alfa (Lb) USA: Calderol (Organon) Calcipotriol ATC: A1 1CC; D05AX02 Use: antipsoriatic, topical vitamin D,- analog RN: 112828-00-9 MF: C,,H,,O, MW: 412.61 CN: (la,3~,5Z,7E,22E,24S)-24-cyclopropyl-9,1O-secochola-5,7,10(19),2~-tetraene-1,3,24-triol '?3 CH3 CH3 - I1 tert-butyld~methyl- sflyl chlor~de (I) vitamin D2 CH, CH, Me ,NH % CH3 CH3 CH3 CH, CH3 CH, CH, CH, triphenylphosphine propane NaOH VI d 1. V, A 2. chrornotography CH3 CH3 CH, CH, (cyclapropylcarbo- nylrnethy1ene)tri- phenylphasphorane 320 C Calcitriol 2. chromotagraphy m1 - C H cH cH Li~o-&o-jiTcH3 'CH cH I CH3 CH3 CH, CH3 (W Bu4N+F- b tetrobutyl- ammonium fluoride I Calcipotriol Reference(s): EP 227 826 (Leo; appl. 14.7.1986; GB-prior. 2.8.1985). WO 8 700 834 (Leo; appl. 14.7.1986; GB-prior. 2.8.1985). Calverley, M.J.: Tetrahedron (TETRAB) 43,4609 (1987). Fonmdation(s): ointment 50 pglg D: Daivonex (Leo) F: Daivonex (LCo) I: Daivonex (Formenti) Psorcutan (Schering AG) GB: Daivonex (Leo; 1991) Psorcutan (Schering) Calcitriol (la,25-Dihydroxy-vitamin D,) ATC: A 1 ICC04; DOSAX03 Use: calcium regulator RN: 32222-06-3 MF: C,,H,O, MW: 416.65 EINECS: 250-963-8 LDS,,: 1350 pglkg (M, p.0.); I05 pglkg (R, i.v.); 620 pgkg (R, p.0.) CN: (la,3~,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-l,3,25-triol 1 a.25-dihydroxycholesterol acetic anhydride . RN: 5816 6-8 3-9 MF: C,,H,,N,O, MW: 357.41 CN: 3,7-dihydro- 7-[ 2-[ (2-hydroxy-l-methyl-2-phenylethyl)amino]ethyl ]-1 ,3-dimethy-1 H-purine-2,6-dione [R-(R*,S*)]-cafedrine RN: 7839 6-3 4-6 MF: C,,H,,N,O,. therapeutic RN: 3092 4-3 1-3 MF: C,,H,,N,O, MW: 267.29 EINECS: 25 0-3 9 0-3 LD,,,: 700 mg/kg (M, s.c.) CN: 3,7-dihydro- 8-[ (2-hydroxyethyl)methylamino]-l,3,7-trimethyl-1H-purine-2,6-dione Cafedrine. 8140 9-9 0-7 MF: C,,H,,N,O, MW: 451.62 CN: (8~)-N-[ 3-( Dirnethylamino)propyl]-N-[(ethylamino)carbonyl ]-6 -( 2-propenyl)ergoline-8-carboxamide 1. K2C03, DMF 2. NaOH. CH30H 8p-methoxycarbonyl-