Aceglutamide aluminum A I1 Aceglutamide aluminum RN: 12607-92-0 MF: C35Hs9A13N,o024 MW: 1084.85 LD,,,: 460 mglkg (M, i.v.); 13.1 glkg (M, p.0.); 400mglkg (R,i.v.);>14.5 g/kg(R,p.o.) CN: pentakis(~-acetyl-~-glutaminato)tetral~ydroxyirialuminum ATC: A02AB; N06B Use: peptic ulcer therapeutic acetic anhydride L-glutamine I + AI(OCH(CH,),), + aluminum isopropylate Aceglutamide aluminum I DOS 2 127 176 (Kyowa Hakko; appl. 1.6.1971; J-prior. 5.6.1970). US 3 787 466 (Kyowa Hakko; 22.1.1974; J-prior. 5.6.1970). preparation oj'Nz-acetyl-L-glutamine: Reddy, A.V; Ravindranath, B.: Synth. Commun. (SYNCAV) 22 (2). 257 (1992). Synge: Biochem. J. (BIJOAK) 33,673 (1939). Fonnulation(s): gran. 700 mg Trade Nnme(s): J: Glumal (Ky owa Hakko) Acemetacin ATC: MO~AB~~ Use: non-steroidal anti-inflammatory RN: 53164-05-9 MF: C,lH,,CINO, MW: 415.83 EINECS: 258-403-4 LDs,,: 55 mglkg (Mm, p.0.); 18.42mglkg (Mf, p.0.); 24.2 mglkg (Rm, p.0.); 30.1 mglkg (Rf, p.0.) CN: 1 -(4-chlorobenzoyl)-5-methoxy-2-methyl-lH-indole-3-acetic acid carboxymethyl ester 4-methomyaniline 4-methoxyphenylhydrazine (I) 12 A Acemetacin 1. NaOC2H5 2. CI*O H3CpCOOH 0 0 - 2. benzyl chloroacetate 0 0 levulinic acid benzyl levulinoyloxyacetate benzyl 12-(4-methoxyphenylhydrozano)- '=?' benzyl (5-meVloxy-2-methyl-3-lndolyl- 4-chloro- benzoyl chloride benzyl [I -(4-chlorobenzoyl)-5-methoxy- 2-methyl-3-indolylocetoxy]acetate (IV) 07 COOH I Acemetocin indometacin (4. v.) benzyl bromo- acetate Reference(s): DOS 2 234 65 1 (Tropon; appl. 14.7.1972). FR 2 192 828 (Tropon; appl. 13.7.1973; D-prior. 14.7.1972). US 3 910 952 (Troponwerke Dinklage; 7.10.1975; appl. 28.6.1973; D-prior. 14.7.1972). Acenocoumarol A 13 preparation of 4-methoxyphenylhydrazine from 4-methoxyaniline b-anisidine): Lee, A R. et al.: J. Heterocycl. Chem. (JHTCAD) 32 (I), 1-12 (1995). Clade, D.W. et al.: J. Chem. Soc., Perkin Trans. 2 (JCPKBH) , 909-916 (1982). DE 70 459 (Riedel; 12.1 1.1891). Altschul: Ber. Dtsch. Chem. Ges. (BDCGAS) 25, 1849 (1892). preparation of benzyl levulinoyloxyacetate: Boltze, K H.; Brendler, 0.; Jacobi, H.; Opitz, W.; Raddatz, S. et al.: Arzneim Forsch. (ARZNAD) 30 @a), 1314- 1325 (1980). ~ormulati&(s): cps. 30 mg, 60 mg; s. r. cps. 90 mg Trade Name(s): D: Rantudil (Bayer; 1980) I: Acemix (Bioprogress) J: Rantudil (Kowa; 1984) GB: Emflex (Merck) Solar (Bioindustria) Acenocoumarol (Acenocumarin; Nicoumalone) ATC: BOlAA07 Use: anticoagulant RN: 152-72-7 MF: C,9H,5N06 MW: 353.33 EINECS: 205-807-3 LD,,: 115 mg/kg(M,i.p.); 1470mg/kg(M,p.o.); 513 mglkg (R, p.0.) CN: 4-hydroxy-3-[l-(4-nitrophenyl)-3-oxobutyl]-2H-l-benzopyran-2-one methyl acetic anhydride salicylote (wintergreen oil) methyl ocetyl- solicylote OH 4-hydroxy- coumorin (I) , + pN02 - C", 0 4-nitro- benzolocetone Acenocournorol US 2 648 862 (Geigy; 1953; CH-prior. 1950). Formulation(s): tabl. 1 mg, 4 mg Trade Name(s): D: Sintrom (Geigy); wfm GB: Sinthrome (Geigy) J: Sintrom (Ciba-Geigy) F: Sintrom (Novartis) I: Sintrom (Novartis) USA: Sintrom (Geigy); wfm 14 A Acepromazine Acepromazine ATC: N05AA04 Use: neuroleptic, anti-emetic, tranquilizer RN: 61-00-7 MF: C,,H22N20S MW. 326.46 EINECS: 200-496-0 LD,,,: 59 mgkg (M, i.v.) CN: 1-[I0-[3-(dimethylamino)propyl]-I0H-phenothiazin-2-yl]ethanone maleate (1:l) RN: 3598-37-6 MF: CLyHZ2N2OS , C,H,O, MW: 442.54 EINECS: 222-748-9 LD,,,: 65 mgkg (M, i.v.); 95 mglkg (R, i.v.); 400 mgtkg (R, p.0.) 2-ocetylphenothiazine 3-dimethylomino- Acepromozine prapyl chloride Reference(s): DE 1 049 865 (Bayer; appl. 7.9.1955). Schmitt, J. et al.: Bull. Soc. Chim. Fr. (BSCFAS) 1957,938, 1474. Formulation(s): drops 1 mg/lO drops; syrup 2.5 mg; tabl. 10 mg (as maleate) Trade Narne(s): F: Noctran (Menarini)-comb. J: Plebal (Fujinaga-Sankyo)- comb. Aceprometazine ATC: NOSAA Use: neuroleptic, antitussive RN: 13461-01-3 MF: C,yH22N20S MW: 326.46 EINECS: 236-661-9 LD,,: 517 mgkg (M, p.0.) CN: 1-[l0-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl]ethanone maleate RN: 7455-18-7 MF: C,,H,N,OS. C,H,O, MW: 442.54 2-a~et~lphenothiozine 2-dimethylomino- Aceprometozine propyl chloride Reference(s): DE 1 049 865 (Bayer; appl. 7.9.1955). Formulation(s): tabl. 13.55 mg (as maleate in combination with 400 mg meprobramate) Acetarsol A 15 Trade Nume(s): D: Clindorm (Midy)-comb. Noctran (Menarini)-comb. F: MCpronizine (Sanofi)- J: Noctran (Clin-Midy- comb. Sanofi); wfm Acetarsol (Acetarsone) ATC: A07AX02; GO 1ABOI; POlCD02 Use: antiprotozoal (trichomonas) RN: 97-44-9 MF: C,H,,,AsNO, MW: 275.09 EINECS: 202-582-3 LD,,,: 180 mglkg (M, i.v.); 4 mglkg (M, p.0.) CN: [3-(acety1amino)-4-hydroxyphenyl]arsonic acid monosodium salt RN: 5892-48-8 MF: C,H,AsNNaO, MW: 297.07 EINECS: 227-573-1 sodium CI CI orsenite 4-chloro- 4-chlorobenzene- 4-chlorophenyl- 4-chloro-3-nitro- aniline diazonium chloride arsonic acid phenylarsonic acid (I) R 0 I I ~oOH(33%), 100°C HO-As-OH No,S,04 or Fe-NaOH HO-As-OH 1 + 8- sodium NO2 dithionite OH @ OH NH2 4-hydroxy-3-nitro- 3-amino-4-hydroxy- phenylarsonic acid phenylarsanic acid (11) Refermce(s): Raiziss, G.W.; Gavron, J.L.: J. Am. Chem. Soc. (JACSAT) 43, 583 (1921). Raiziss, G.W.; Fisher, B.C.: J. Am. Chem. Soc. (JACSAT) 48, 1323 (1926). DRP 250 264 (H. Bart; appl. 1910). DRP 245 536 (Hoechst; appl. 191 1). DRP 224 953 (Hoechst; appl. 1909). Formulution(s): collutorium (mouth wash) 0.5 mg1100 g Trade Name(s): F: Arpha collutoire Gynoplix (Doms-Adrian); Humcx collutoire (Fournier)-comb.; wfm wfm (Fournier)-comb.; wfm Collargent ac6tarsol Gynoplix (ThCrap1ix)- Humex Fournier collutoire (Sarbach)-comb.; wfm comb.; wfm (Fournier)-comb.; wfm 16 A Acetazolamide Polygynax (1nnothCra)- Sanogyl (Pharmascience)- I: Gynoplix (Vaillant) comb.; wfm comb.; wfm J: Neo Osvarsan (Banyu) Polygynax Virgo Sanogyl (Vilette); wfm Osvarsan (Banyu) (1nnothCra)-comb.; wfm GB: Pyorex (Bengue)-comb.; Pyorex (Bailly-Speab)- wfm comb.; wfm S. V. C. (May & Baker) Acetazolamide (Acetazoleamide) ATC: SOlECOl Use: diuretic RN: 59-66-5 MF: C4H6N,03S2 MW: 222.25 EINECS: 200-440-5 LD,,: 1175 mgkg (M, i.p.1; >3000 mglkg (M, i.v.1; 4300 mgkg (M, p.0.); >3000 mg/kg (M, s.c.); 2750 mgkg (R, i.p.); >I 500mg/kg (g. p., LC.) >2000 mglkg (dog, i.v.); CN: N-[5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamide ommonium hydrozine hydrozine- 1,2-bis- 2-amino-5-mercopto- rhodanide (thiacorboxamide) 1,3,4-thiodiozole (1) H H o o H,C~N~S~SO,-CI I + -+ H~CYN-C~Y~H c& H3C 0 CH3 0 N-N 0 N-N acetic anhydride 2-acetylornino-5- 2-ocetylomino-1,3,4- mercapta-1.3.4- thiadiozole-5-sulfonyl thiadiazole chloride (11) I Acetazolamide I Reference(s): US 2 554 816 (American Cyanamid; 1951; prior. 1950). Roblin, R.O.; Clapp, J.W.: J. Am. Chem. Soc. (JACSAT) 72,4890 (1 950). similar process: US 2 980 679 (Omikron-Gagliardi; 18.4.1961; I-prior. 4.4.1957). Formularion(s): amp. 500 mg; cream 10 9%; lyo. 500 mg; powder 500 mg; s. r. cps. 500 mg; tabl. 125 mg, 250 mg Trade Name(s): D: Diamox (Lederle) Diamox Sustets (Lederle); Diamox S. R. (Lederle- Diuramid (medpharm) wfm Takeda) Glaupax (CIBA Vision) I: Diamox (Cyanamid) Didoc (Sawai) F: DCfiltran (Labs. Jumer) J: Acetamox (Santen) Donmox (Hotta) Diamox (ThCraplix) Atenezol (Tsuruhara) Zohnox (Konto) GB: Diamox (Storz) Diamox (Lederle-Takeda) USA: Diamox (Lederle) Acetiamine A 17 Acetiamine ATC: All Use: vithin B,-derivative, neurotropic analgesic RN: 299-89-8 MF: C,,H2,N404S MW: 366.44 CN: ethanethioic acid S-[l-[2-(acetyloxy)ethyll-2-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]- 1-propenyl] ester thiamine (1) (9. v.) Acetiamine I Reference (s): US 2 752 348 (Takeda; 1956; J-prior. 1952). Matsukawa, T.; Kawasaki, H.: Yakugaku Zasshi (YKKZAJ) 23, 705 (1953). Gauthier, B. et al.: Ann. Pharm. Fr. (APFRAD) 21,655 (1963). Formulation(s): drg. 50 mg Trade Name(s): D: Thianeurone (RhBne- F: Algo-Ntvriton (Pharmuka); Poulenc); wfm wfm Acetohexamide (Cyclamide) ATC: AlOBB31 Use: antidiabetic RN: 968-81-0 MF: C,,H20N204S MW: 324.40 EINECS: 213-530-4 LD,,,: >2500 mglkg (M, p.o.); Wkg (R, p.0.) CN: 4-acetyl-N-[(cyclohexylamino)carbonyl]benzenesulfonamide 4-amino- acetaphenone 4-acetylphenyl- 4-acetylbenzene- sulfonyl chloride sulfonomide (1) 18 A Acetophenazine 1. K,CO,, ocetone 3. aq. HCI I _____* 2. cyclohexyl isocyanate 0 Acetohexamide Reference(s): US 3 320 312 (Lilly; 16.5.1967; prior. 28.4.1960). DE 1 177 631 (Lilly; appl. 21.4.1961; USA-prior. 28.4.1960). DE 1 135 891 (Hoechst; appl. 30.6.1960). Forrnulation(s): tabl. 250 mg, 500 mg Trade Name(s): GB: Dimelor (Lilly); wfm J: Dimelin (Shionogi) I: Dimelor (Lilly); wfm USA: Dymelor (Lilly) Acetophenazine ATC: N05AB07 Use: neuroleptic, antipsychotic RN: 2751-68-0 MF: C,,H,,N,O,S MW: 411.57 CN: 1-[10-[3-[4-(2-hydroxyethyl)-l-piperaziny1]propyl]-l0H-phenothiazin-2-yl]ethanone maleate (1:2) RN: 5714-00-1 MF: C,,H,9N,0,S. 2C4H404 MW: 643.71 EINECS: 227-202-3 LD,o: 71 mglkg (M, i.v.); 60 mgkg (R, i.p.); 39 mglkg (R, i.v.); 415 mglkg (R, p.0.) chloropropane 2-acetylphenothiazine 2-acetyl-10-(3-chloro- propyl)phenothiozine (I) 1 -(2-hydroxyethy1)- piperazine Acetophenazine I Reference(s): US 2 985 654 (Schering Corp.; 23.5.1961; prior. 21.9.1956). Formularion(s): tabl. 20 mg (as dimaleate) Trade Name(s): USA: Tindal (Schering); wfm Acetorphan A 19 Acetorphan (Racecadotril) ATC: A07XA04 Use: antisecretory, enkephalinaseinhibitor RN: 81 110-73-8 MF: C2,H,,NO4S MW: 385.48 CN: (f)-N-[2-[(Acetylthio)methyl]-1-oxo-3-phenylpropyl]glycine phenylmethyl ester 0 . AcO, 0 0 OHCyJ + 0 0 toluene ___, H3CfiOIU10nCH3 piperidine benzaldehyde diethyl rnalanate diethyl benzylidenernalonate (1) 1. HZ, Pd-C HOOC COOH Y H2C COOH 2. NoOH. H20 (CH20), . Et,NH Y' I - - poraforrnoldehyde, diethylornine benzylrnolonic acid 2-benzylacrylic acid (11) thioocetic ocid (+)-2-acetylthiornethyl- 3-phenylpropionic acid (111) TEA, DCC, HOBt, 0a TOS-OH TYI/CHCI~ 111 + H~N- A 0 glycine benzyl ester tosylate Acetorphan EP 38 758 (Roques, B. et al.; appl. 17.4.1981; F-prior. 17.4.1980). EP 729 936 (Soc. Civile Bioprojet; appl. 1.3.1996; F-prior. 3.3.1995). synthesis of Ill: Mannich, C.; Ritsert, K.: Ber. Dtsch. Chem. Ges. (BDCGAS) 57, 11 16 (1924). Formidation(s): cps. 100 mg Trade Name(s): F: Tiorfan (Bioprojet; 1993) 20 A Acetrizoic acid Acetrizoic acid ATC: V08AA07 Use: X-ray contrast medium RN: 85-36-9 MF: CyH613N03 MW: 556.86 EINECS: 201-600-7 LD,,,: 8000 mgkg (M, i.v.); 20 g/kg (M, p.0.) CN: 3-(acety1amino)-2,4,6-triiodobenzoic acid meglumine salt (1:l) RN: 22154-43-4 MF: CyH,13N03. C,H,,NO, MW: 752.08 LD,: 10.1 g/kg (M, i.v.) sodium salt RN: 129-63-5 MF: CyH,13NNa0, MW: 578.85 EINECS: 204-956-1 LD,,: 12156 mg/kg (M, i.m.); 7800 mgkg (M, i.v.); 6400 mgkg (R, i.v.); 5200 mgkg (rabbit, i.v.); 5600 mgkg (cat, i.v.); 6300 mgkg (dog, i.v) COOH HN03.H2S04 Fe, CH3COOH ICI ZH .a NH2 chloride 1 benzoic 3-nitrobenzoic 3-ominobenzoic ocid acid ocid 3-omino-2,4.6- triiadobenzoic ocid (I) I Acetrizoic acid US 2 61 1 786 (Mallinckrodt; 1952; appl. 1950; prior. 21.7.1948). Wallingford et al.: J. Am. Chem. Soc. (JACSAT) 74,4365 (1952). 3-amino-2,4,6-triiodobenzoic acid: Kretzer: Ber. Dtsch. Chem. Ges: (BDCGAS) 30, 1944 (1 897). Formulation(s): vial. 250 mglml, 500 mglml Trade Name(s): F: Vasurix (Guerbet); wfm J: Diaginol (Banyu); wfm Py elokon-R GB: Diaginol (May & Baker); USA: Cystocon (Mallinckrodt); (Mallinckrodt); wfm wfm wfm Salpix (Ortho); wfm Acetylcholine chloride ATC: SOlEB09 Use: parasympathomimetic, miotic, vasodilator (peripheral) RN: 60-31-1 MF: C7H,,C1N0, MW: 181.66 EINECS: 200-468-8 LD,,,: lOmg/kg(M,i.v.);3gkg(M,p.o.); 22 mgkg (R, i.v.); 2500 mglkg (R, p.0.) CN: 2-(acety1oxy)-N,N,N-trimethylethanaminium chloride . levulinoyloxyacetate benzyl 1 2- ( 4-methoxyphenylhydrozano )- '=?' benzyl (5-meVloxy -2 - methyl-3-lndolyl- 4-chloro- benzoyl chloride benzyl [I -( 4-chlorobenzoyl )-5 -methoxy- 2- methyl-3-indolylocetoxy]acetate. RN: 15 2- 7 2- 7 MF: C,9H,5N06 MW: 353.33 EINECS: 20 5-8 0 7-3 LD,,: 115 mg/kg(M,i.p.); 1470mg/kg(M,p.o.); 513 mglkg (R, p.0.) CN: 4-hydroxy- 3-[ l-(4-nitrophenyl )-3 -oxobutyl ] -2 H-l-benzopyran -2 - one. C,yH22N20S MW: 326 .46 EINECS: 23 6-6 6 1-9 LD,,: 517 mgkg (M, p.0.) CN: 1-[ l 0-[ 2- ( dimethylamino)propyl ]-1 0H-phenothiazin -2 - yl]ethanone maleate RN: 745 5-1 8-7 MF: C,,H,N,OS. C,H,O, MW: 4 42. 54 2- a~et~lphenothiozine