Codeine C 541 I" odeine ATC: R05DA04 Use: antitussive, narcotic, analgesic * W: 76-57-3 MF: Cl,H21N03 MW: 299.37 EINECS: 200-969-1 &DtDSO: 54 mgkg (M, i.v.); 250 mgkg (M, p.0.); 75 mgkg (R, i.v.); 427 mglkg (K, p.0.); 69 mgkg (dog, i.v.) CN: (5a,6a)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methy1morphinan-6-01 hydrobromide RN: 125-25-7 MF: C,,H2,N03. HBr MW: 380.28 EINECS: 204-730-2 LDm: 535 mg/kg (M, p.0.) hydriodide m, 125-26-8 MF: C,,H,,NO, . HI MW: 427.28 EINECS: 204-731-8 phosphate (1:l) RN: 52-28-8 MF: Cl,H,INO, . H,P04 MW: 397.36 EINECS: 200-137-8 LD,,: 62 mgkg (M, i.v.); 237 mglkg (M, p.0.); 54 mgkg (R, i.v.); 85 mglkg (R, p.0.); 97.8 mgkg (dog, i.v.) 1 H,C-N+CH, KOH. CH, + H3C-OH , trimethylphenyl- ammonium chloride momhine Codeine Referencefs): Ehrhart-Ruschig I, 117-1 18. DRP 247 180 (C. H. Boehringer; 1912). Ullrnanns Encykl. Tech. Chem., 3. AuH., Vol. 3, 232. Formulation(s): cps. 30 mg; drops 2.4 gI100 ml; suppos. 30 mg; syrup 0.1 17 g1100 g; tabl. 30 mg, 50 mg Trade Name($): D: Bronchicum (Nattermann) Codeinum phophoricum Compretten (Glaxo WellcomeICascan) Codicept (Sanol) Codipront (Mack, Illert.) Dolomo (Klinge; as phosphate)-comb. Dolviran (Bayer Vital)- comb. Gelonida (Godecke; as phosphate)-comb. Lonarid (Boehringer 1ng.)- comb. Optipyrin (Thiemann)- comb. Spasmo-Cibalgin Comp. (Novartis Pharma)-comb. Treupel (ASTA Medica AWD) Tricodein (Soleo) I: Tussipect (Beiersdorf- Lil1y)-comb. numerous combination preparations F: numerous combination preparations GB: Aspar (Hoechst)-comb. Codafen Continus (Napp; as phosphate)-comb. J: Migralere (Pfizer Consumer; as phosphate)- comb. USA: Solpadol (Sanofi Winthrop; as phosphate)-comb. Tylex (Schwarz; as phosphate)-comb. numerous combination preparations Bromocodeina (Menarini) Codeinol (Saba)-comb. Codipront (Bracco)-comb. Lactocol (0gna)-comb. Hedrix Plan (Saba)-comb. Senodin (Bristol-Myers Squibb)-comb. numerous combination preparations Codeine Phosphate (Dainippon; Sankyo; Shionogi; Takeda; Tanabe) Brontex (Procter & Gamble; as phosphate) Dimetane (Robins; as phosphate) 542 C Colecalciferol Nucofed (Monarch; as Robitussin (Robins; as numerous generics and phosphate) phosphate) combination preparations Colecalciferol (Cholecalciferol; Vitamin D3) ATC: A1 ICCOS Use: antirachitic RN: 67-97-0 MF: C,,H,O MW: 384.65 EINECS: 200-673-2 LD,,,: 42.5 mg/kg (M, p.0.); 42 rnglkg (R, p.0.); 80 mglkg (dog, p.0.) CN: (3~,5Z,7E)-9,1O-secocholesta-5,7,10(19)-trien-3-ol HO HO" 7-dehydrocholesterol precholecolciferal Colecolciferol Hqference(s): Kirk-Othmer, Encycl. Chem. Technol., Vol. 21,549 ff. Ullmanns Encykl. Tech. Chem., 3. Aufl., Vol. 18, 236 ff. (synthesis of 7-dehydrocholesterol as described). synthesis from 7-dehydrocholesterol ester: US 3 661 939 (Nisshin Flour Milling; 9.5.1972; J-prior. 16.12.1969). synthesis from 25-~uorocholestero1 ester: JP-appl. 540 46-768 (Teijin; appl. 19.9.1977). crystalline vitamin D,: US 3 665 020 (Hoffmann-La Roche; 23.5.1972; CH-prior. 25.2.1969). total synthesis: Inhoffen, H.H.: Angew. Chem. (ANCEAD) 72,875 (1960). Formulation(s): amp. 1.25 mg/ml, 2.5 mglml; cps. 0.5 mg; drops 0.5 mglml; emulsion 6 mg/ml; tabl. 0.01 mg, 0.25 mg, 5 mg Trade Narne(s): D: Dekristol (Jenapharm) D-Mulsin (Mucos) D-Tracetten (Albert- Roussel, Hoechst) D,-Vicotrat (Heyl) Ospur D, (Henning) Provitina D, (Promonta) Vigantol (Merck) Vigantoletten (Merck) Vigorsan (Albert-Roussel, Hoechst) numerous combination preparations Alvityl (So1vay)-comb. CernCvit (Baxter)-comb. Quotivit (Mayoly- Spindler)-comb. Survitine (Roche Nicholas)-comb. numerous combination preparations Octovit (Smith Kline & French)-comb.; wfm 1: Adiboran (Eurospital)- comb. Antilinf (Delalande 1snardi)-comb. Calciozim (Pierrel)-comb. Calisvit (Menarini)-comb. Haliborange (Eurospita1)- comb. Iper D, (Zambon Italia) Tridelta (Ceccarelli) J: Vitasol AD, + E (Tiger)- comb. USA: Al-Vite (Drug Industries)- Ultra "A" & "DM (Nature's Ultra "D"-Tabl. (Nature's comb.; wfm Bounty), wfm Bounty); wfm Colfosceril palmitate 1 i ATC: R07AAOI Use: synthetic lung surfactant, prophylactic treatment of respiratory distress syndrome RN: 99732-49-7 MF: C40H80NOHP. C,6H340 . [C,4H220 . C2H40 . CH20]x MW: unspecified CN: (R)-N,N,N-trimethyl-IO-oxo-7-[(l-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-I-amln1um-4 oxide inner salt, mixt. with formaldehyde polymer with oxirane and 4-(I, 1,3,3-tetramethylbutyl)phenol and 1-hexadecanol 0 Colfosceril palmitate Lyophilization of 1,2-dipalmitoyl-sn-3-glycerophosphorylcholine, n-hexadecan-1-01, tyloxapol solution in 0. I n NaC1. Reference(s): US 4 826 821 (The Regents of the Univ. of California; 2.5.1 989; appl. 5.11.1986; prior. 26.6.1 985, 17.10.1983). EP 50 793 (The Regents of the Univ. of California; appl. 14.10.1981 ; USA-prior. 24.10.1980). Formulation(s): vial 108 mg (lyo.) Trade Name(& D: Exosurf (Glaxo Wellcome) I: Exosurf Neonatate (Glaxo USA: Exosurf (Glaxo Wellcome; GB: Exosurf Neonatal (Glaxo Wellcome) 1991) Wellcome; 1 99 1) Colistin (Colistin A + B; Polymyxin E) ATC: A07AA10; JOI XBOI Use: antibiotic (macrocyclic peptide) RN: 1066-17-7 MF: unspecified MW: unspecified EINECS: 213-907-3 CN: colistin suIfate . RN: 1264-72-8 MF: H204S . x unspecified MW: unspecified EINECS: 215-034-3 LD,,: 6 mglkg (M, i.v.); 793 mglkg (M, p.0.) pentasodium mesylate RN: 8068-28-8 MF: unspecified MW: unspecified EINECS: 232-516-9 LD,& 222 mg (M, i.v.); >767 mg (M, p.0.); 5450 mgkg (R, p.0.) Cyclopolypeptide antibiotic from Aerobacillus colistinns. 1 544 C Convallatoxin I Colistin Colistin A Colistin B Refer-ence(s): Vogler, K.; Studer, R.O.: Experientia (EXPEAM) 22, 345 (1966). Formulation(s): tabl. 24 mg, 95 mg; vial 33.3 mg Trade ATame(s): D: Diaront (Chephasaar) Colimycine (Bellon) Methacolimycin (Kaken) F: Bacicoline (~erck Sharp 9r GB: Colomycin (Pharmax) USA: Coly-Mycin (Parke Davis; Dohme-Chibret)-comb. I: Colbiocin (SIF1)-comb. as sulfate) Colicort (Merck Sharp & Colimicina (UCB) Dohme-Chibret)-comb. J: Colimycin-S (Kaken) Convallatoxin ATC: COlAA Use: cardiac glycoside, cardiotonic RN: 508-75-8 MF: C,H,,O,,, MW: 550.65 EINECS: 208-086-3 LD,,,: 1 mglkg (M, i.v.); >2 glkg (M, p.0.); 15.2 mg/kg (R, i.v.) CN: (3~,5~)-3-[(6-deoxy-a-~-mannopyranosyl)oxy]-5,l4-dihydroxy-l9-oxocard-2O(22)-enolide From Convallaria majalis. Cortisone C 545 Reference(s): DRP 490 648 (Hoffmann-La Roche; appl. 1928; CH-prior. 1928). Karrer, P.: Helv. Chim. Acta (HCACAV) 12,506 (1929). SU 64 447 (F. D. Zilbert; appl. 1945). PL51 371 (Inst. Farmaceutyczny; appl. 17.5.1965). partial synthesis: Reichstein, T. et al.: Helv. Chim. Acta (HCACAV) 33, 1541 (1950). DD 19 239 (E. Liidde; appl. 18.7.1960). SU 198 319 (Kharkov Scientific Research Chemical-Pharmaceutical Institut; appl. 9.8.1965). alternative syntheses: The Merck Index, 2505 (Rahway 1990). DOS 1 933 090 (Hoechst; appl. 30.6.1969). Trade Name(s): D: Cor-Eusedon (Krewel); several combination I: several combination wfm products containing products containing standardized Convallariu standardized Convallaria rnajalis extract. majalis extract. Cortisone ATC: H02AB 10; SOlBA03 Use: glucocorticoid RN: 53-06-5 MF: C2,H2,0s MW: 360.45 EINECS: 200-162-4 LD,,; 230 mgkg (M, i.p.) CN: l7,2l -dihydroxypregn-4-ene-3,11,20-trione acetate RN: 50-04-4 MF: C,,H,,O, MW: 402.49 EINECS: 200-006-5 bromine sernicarbazide ii ii O H dihydrocortisone 21 -acetate (from deoxycholic acid) 546 C Cortisone Cortisone microbiological hydroxylation [Rhizopus arrhizus Fischer (ATCC- 11 145)] progesterone (~1) cro3 111 chromium(VI) oxide 1. Br2 2. Na0-CH, IV * 1. bromine 1. HiO/H+ LiAIH, v _____, lithium olanate 0 chromium(VI) oxide 1. osmium(VII1) oxide 2. manganese dioxide or N-methylmorpholine/ hydragen peroxide Cortivazol C 547 Reference(s): a Applezweig, N.: Steroid Drugs, Vol. 1, 14,61 (New York, Toronto, London 1962). Kendall, E.C. et al.: J. Biol. Chem. (JBCHA3) 166,345 (1946), 173,271 (1948). synthesis of dihydrocortisone acetate: Applezweig, N.: Steroid Drugs, Vol. 1, 62 (New York, Toronto, London 1962). The Merck Index, 2862 (Rahway 1976). b US 2 602 769 (Upjohn; 1952; prior. 1950). US 2 769 823 (Upjohn; 1956; appl. 1954). Applezweig, N.: Steroid Drugs, Vol. 1,59 (New York, Toronto, London 1962). alternative syntheses: FR 1 091 734 (Upjohn; appl. 1953; USA-prior. 1952). cj hydrocortisone from dehydropregnenolone acetate: Ehrhart, Ruschig, 111, 399. from ergosterol and stigmasterol: Rosenkranz, G.: Fortschr. Chem. Org. Naturst. (FCONAA) 10,274 (1953). from hecogenin: Applezweig, N.: Steroid Drugs, Vol. 1,66 (New York, Toronto, London 1962). from sitosterol: US 4 041 055 (Upjohn; 9.8.1977; appl. 17.11.1975). total synthesis: Fieser, L.F.; Fieser, M.: Steroide, 779 (Weinheim 1961). review: Fieser. L.F.; Fieser, M.: Steroide, 679 (Weinheim 1961). Ullmanns Encykl. Tech. Chem., 4. Aufl., Vol. 13, 50. Formldation(s): ointment 0.5 %, 1 %; tabl. 25 mg, 5 mg, 50 mg; vial 25 mg (2.5 mglml), 500 rng (50 mglml) (as acetate) Trade Narne(s): D: Cortison Augensalbe Dr. I: Cortone Acetato (Merck J: Winzer (Dr. Winzer) Sharp & Dohme) Cortison Ciba (Novartis Dutimelan (Hoechst)- Pharma) comb. F: Cortisme Roussel (Roussel) generics USA: GB: Cortisyl (Hoechst) Cortisone Acetat Sup. (Upjohn) Cortone (Banyu) Scheroson (Schering) Cortisone Acetate (Merck) Cortone Acetat (Merck) Cortivazol ATC: H02AB17 Use: glucocorticoid RN: 11 10-40-3 MF: C3,H3,N20s MW: 530.67 EINECS: 214-175-8 CN: (11~,16a)-21-(acetyloxy)-ll,17-dihydroxy-6,16-dimethyl-2'-phenyl-2'H-pregna-2,4,6-trieno[3,2- clpyrazol-20-one 548 C Creatinolfosfate CH3 6.1 6a-dimethyl-3,20- forrn- dioxo-1 l@.l7.21-tri- oldehyde hydroxy-4.6-pregnodiene triethyl orthoformote CH3 Q "3 phenyl- (11) hydrozine 1. formic ocid Cartivazol Reference(s): US 3 067 194 (Merck & Co.: 4.12.1962: orior. 1.12.1961.4.11.1960). US 3 300 483 (~erck & CO.; 24.1.1967; prior. 4.12.1962, 2.7.1962,1.12.1961,4.11.1960). Fried, J.H. et al.: J. Am. Chern. Soc. (JACSAT) 85,236 (1963). Formulation(s): syringe 3.75 mg Trade Name(s): F: Altim (Roussel) Creatinolfosfate (Creatinol phosphate) ATC: COIEBOS Use: cardiac preparation, cardiac stimulant RN: 6903-79-3 MF: C4H,,N,04P MW: 197.13 EINECS: 230-011-8 LD,,,: 1200 mglkg (M, i.v.); >S glkg (M, p.0.); 1300 rngkg (R, i.v.); >5 glkg (R, p.0.) CN: N-methyl-N-[2-(phosphonooxy)etl~yl]guanidine disodium salt RN: 6903-80-6 MF: C4H,,N,Na,04P MW: 241.10 Croconazole C 549 NH palyphosphoric ac~d, 160 OC yNAN+~~ H~PO., d I CH3 N-methyl-N-(2-hydroxy- Creat~nolfosfote 8thyl)guanidine phosphate 6 1 Reference(s): : DOS 2 550 430 (E. Allievi; appl. 13.1 1.1974; I-prior. 13.1 1.1974). : alternative syntheses: FR-M 6 401 (Siphar; appl. 14.1 1.1966). Ferrari, G.; Casagrande, C.: Farmaco, Ed. Sci. (FRPSAX) 20, 879 (1965). medical use as cardiac preparation: DOS 2 144 584 (Siphar; appl. 6.9.1971; B-prior. 7.9.1970). effervescent tablet: BE 755 826 (Siphar; appl. 7.9.1970). Formulation(s): amp. 510 mgl4 ml; eff. gran. 500 mg/6 g; tabl. 250 mg Trade Name(s): I: Aplodan (Astra-Simes) Croconazole (Cloconazole) ATC: Use: RN: 77175-51-0 MF: C,,H,5CIN20 MW: 310.78 CN: 1-[I -[2-[(3-chlorophenyl)methoxy]phenyl]ethenyl]-1 H-imidazole monohydrochloride RN: 77174-66-4 MF: ClnH,,C1N2O . HCl MW: 347.25 LD,,: 1150 mgkg (M, p.0.); 2 gk (R, P.o ) o-hydmxy- N.NZ-thionyl acetophenone diirnidazole 3-chlorobenzyl bromide Croconazole 1 DOlA topical antifungal (for treatment of candidiasis) 4 550 C Cromoglicic acid R<ference(s): DOS 3 021 467 (Shionogi; appl. 6.6.1980; J-prior. 7.6.1979, 7.9.1979). US 4 328 348 (Shionogi; 4.5.1982; J-prior. 7.6.1979, 7.9.1979). US 4 463 01 1 (Shionogi; 3 1.7.1 984; J-prior. 7.6.1979,7.9.1979). US 4 483 866 (Shionogi; 20.11.1984; J-prior. 7.6.1979,7.9.1979). Formulatior~(s): cream 1 %; sol. 10 mglg (1 %) (as hydrochloride) Trade Nanze(s): D: Pilzcin (Merz & Co.) J: Pilzcin (Shionogi) Cromoglicic acid (Acidum cromoglicicum) ATC: A07EBOI ; ROI ACO1; ROSBCOI; SOIGXOI Use: antiallergic RN: 161 10-51-3 MF: C,,H,,O,, MW: 468.37 EINECS: 240-279-8 LD,,,: >2.15 g/kg(R,p.o.) CN: 5,5'-[(2-hydroxy-1,3-propanediyl)bis(oxy)]bis[4-oxo-4H- 1-benzopyran-2-carboxylic acid] disodium salt RN: 15826-37-6 MF: C,,H,,Na20,, MW: 512.33 EINECS: 239-926-7 , LD,,,: 3300mg/kg(M,i.v.);>11 g/kg(M,p.o.); 24 glkg (R, i.v.); >11 dkg (R, p.0.); >1.6 glkg (dog, i.v.); >4 glkg (dog, p.0.) 2'.6'-dihydroxy- epichloro- ocetophenone hydrin R<ference(s): DAS 1 543 579 (Fisons; appl. 23.3.1966; GB-prior. 25.3.1965,9.12.1965, 17.12.1965). GB 1 144 905 (Fisons; valid from 3.3.1966; prior. 25.3.1965, 9.12.1965, 17.12.1965). US 3 419 578 (Fisons; 31.12.1968; GB-prior. 25.3.1965,9.12.1965). Barker, G. et al.: J. Med. Chem. (JMCMAR) 16, 87 (1973). US 3 671 625 (Fisons; 20.6.1972; GB-prior. 25.3.1965). US 3 686 412 (Fitzmonrice et al.; 22.8.1972; GB-prior. 25.3.1965). US 3 777 033 (Fisons; 4.12.1973; GB-prior. 25.3.1965). (1) disodium cromoglycate with particular mass density: DOS 2 741 202 (Fisons; appl. 13.9.1977; GB-prior. 23.9.1976, 16.10.1976). Crornoglicic acid combination with anti-inJICImmatories: US 4 066 756 (Fisons; 3.1.1978; GB-prior. 28.11.1975). US 4 15 1 292 (Fisons; 24.4.1979; GB-prior. 25.1.1977). . RN: 11 1 0-4 0-3 MF: C3,H3,N20s MW: 530.67 EINECS: 21 4-1 7 5-8 CN: (11~,16a )-2 1-( acetyloxy)-ll,17-dihydroxy-6,16-dimethyl-2'-phenyl-2'H-pregna-2,4,6-trieno[3, 2- clpyrazol-20-one 548. 9973 2-4 9-7 MF: C40H80NOHP. C,6H340 . [C,4H220 . C2H40 . CH20]x MW: unspecified CN: (R)-N,N,N-trimethyl-IO-oxo- 7-[ (l-oxohexadecyl)oxy ]-3 ,5,9-trioxa-4-phosphapentacosan-I-amln1um-4 oxide. 50 8-7 5-8 MF: C,H,,O,,, MW: 550 .65 EINECS: 20 8-0 8 6-3 LD,,,: 1 mglkg (M, i.v.); >2 glkg (M, p.0.); 15.2 mg/kg (R, i.v.) CN: (3~,5~ )-3 -[ (6-deoxy-a-~-mannopyranosyl)oxy ]-5 ,l4-dihydroxy-l9-oxocard-2O(22)-enolide