Atropine A 1.51 acryloyl pentane chloride 1.5-did methyl benzene- sulfonate Atracurium besilate - Atracurium besilate Reference(s): DOS 2 655 883 (Wellcome; appl. 9.12.1976;~R-prior. 10.12.1975,29.10.1976). US 4 179 507 (Wellcome; 18.12.1979, GB-prior. 10.12.1975, 29.10.1976). Stenkale, J.B. et al.: Eur. J. Med. Chem. (EJMCA5) 16, 515 (1981). Formulation(s): amp. 25 mgl2.5 ml, 50 mg/5 ml Trade Name(s): + D: Tracrium (Glaxo F: Tracrium (Glaxo I: Tracrium (Wellcome) Wellcome; 1987) Wellcome) USA: Tracrium (Glaxo GB: Tracrium (Wellcome; 1982) Wellcome; 1983) Atropine (DL-Hyoscy amine) ATC: A03BAOl; SOlFAOl Use: anticholinergic, mydriatic, antispasmodic RN: 51-55-8 MF: C,,H,N03 MW: 289.38 EINECS: 200-104-8 LD,,: 30 mgkg (M, i.v.); 75 mg/kg (M, p.0.); 73 mgkg (R, i.v.); 500 mglkg (R, p.0.) CN: endo-(?)-a-(hydroxymethyl)benzeneacetic acid 8-melhyl-8-azabicyclo[3.2.1]oct-3-y1 ester 152 A Atropine methonitrate borate (1:l) RN: 51460-78-7 MF: C,,H,,NO,. H,BO, MW: 351.21 sulfate (2:l) RN: 55-48-1 MF: C17H23N03 1/2H2S04 MW: 676.83 EINECS: 200-235-0 LD,,,: 3 1 mglkg (M, i.v.); 468 mgkg (M, p.0.); 37 mgkg (R, i.v.); 600 mg/kg (R, p.0.); 60 mglkg (dog, i.v.) By extraction of Solanacean drugs, especially Atropa belladonna, Hyoscyamus niger or other species. On careful extraction L-hyoscyamine is obtained first, which can be racemized to atropine by addition of alkali in ethanolic solution. Reference(s): Ullmanns Encykl. Tech. Chem., 3. Aufl., Vol. 3,201 f. Ullmanns Encykl. Tech. Chem., 4. Aufl., Vol. 7, 151. Formulation(s): amp. for inj. 100 mg; eye drops 10 mg; inj. sol. 0.25 mg, 0.5 mg, 1 mg, 2 mg; tabl. 0.5 mg Trade Name(s): D: Angiocardyl (Rhenomed) Atropin in der Ophtiole (Mann) Atropinol Augentropfen (Winzer) Atropin POS (Ursapharm) Borotropin Augentropfen (Winzer) Cansat (Sanofi Winthrop) generics and combination preparations F: Atropine Aguettant (Aguettant) Atropine Lavoisier (Caix et du Marais) Atropine Martinet (CIBA Vision Ophthalmics) Chibro-Atropine (Merck Sharp & Dohme-Chibret) genen'cs and numerous combination preparations GB: Lomotil (Sear1e)-comb. I: Atropina Aolfato (Scfm) Atropina Lux (Allergan; as sulfate) Atropi S (Formulario Naz.; Tariff. Nazionale; Bieffe Medital; Bioindustria; Collalto; Farge; Galenica (Senese); Jacobo Monicol; Ogna; Salf) Atrop S (Sifra) Atro S (Farge) Liotropina (SIFI; as sulfate) generics (Farmigea; Scfm) and combination preparations J: generics USA: Arco-Lase Plus (Arco) Atrohist Plus (Medeva) Bellatal (Richwood) Donnatal (Robins) Enlon-Plus (Ohmeda) Larox (Geneva) Lomotil (Searle) Motofen (Carnrick) ProsedIDS (Star) Urised (PolyMedica) Atropine methonitrate ATC: AO~BBO~ (Atropinmethylnitrat; Methylatropine Nitrate; Use: anticholinergic, mydriatic, antispasmodic Methonitrate d'atropine) RN: 52-88-0 MF: Cl,H,,N,O, MW: 366.41 EINECS: 200-156-1 LD,,: 9300 pglkg (M, i.v.); 1320 mglkg (M, p.0.); 1902 mgkg (R, p.0.) CN: endo-(f)-3-(3-hydroxy-l-oxo-2-phenylpropoxy)-8,8-dimethyl-8-azoniabicyclo[3.2.l]octane nitrate Auranofin A 153 atropine (I) methyl nitrate 1 Atropine methanitrate I methyl chloride N-methylatropine chloride (11) N-methylatropine sulfate Reference(s): DRP 137 622 (Bayer; 1901). DRP 138 443 (Bayer; 1901). Fomulation(s): drops Trade Narne(s): D: Afdosa (Hefa-Frenon)- Bronchovydrin Perphyllon (Homburg)- comb.; wfm Inhalationslosung (Searle- comb.; wfm Afpred (Hefa-Frenon)- Endopharm)-comb.; wfm Tonaton (Luitpo1d)-comb.; comb.; wfm Brox (Redel)-comb.; wfm wfm Ansudoral (Basotherm) Myocardetten (Byk USA: Festalan (Hoechst- comb.; wfm Gulden)-comb.; wfm Rousse1)-comb. Myocardon (Byk Gulden)- comb.; wfrn Auranofin ATC: MOlCB03 Use: rheumatoid arthrosis therapeutic RN: 34031-32-8 MF: C,,H,,AuO,PS MW: 678.52 EINECS: 251-801-9 LD,: 310 mgkg (M, p.0.); 265 mglkg (R, p.0.) CN: (2,3,4,6-tetra-O-acetyl-l-thio-~-~-glucopyranosato-S)(triethylphosphine)gold 154 A Azacitidine 2. HBr. CH,COOH HO 3. NH, b 3. thioureo S-(2.3.4,6-tetra-0-ocetyl- ~-~-~luco~~ronos~l)- thiuronium bromide (I) triethylphosphine- gold chloride Auranofin US 3 635 945 (Smith Kline & French; 18.1.1972; prior. 28.10.1969). DE 2 051 495 (Smith Kline & French; appl. 20.10.1970; USA-prior. 28.10.1969). US 3 708 579 (Smith Kline & French; 2.1.1973; prior. 28.10.1969, 1 .lO.l97l). Sutton, B.M. et al.: J. Med. Chem. (JMCMAR) 15, 1095 (1972). synthesis of S-(2,3,4,6-tetra-O-acetyl-P-~-glucopyranosyl)thiuronium bromide: Bommer, W.A.; Kahn, J.R.: J. Am. Chem. Soc. (JACSAT) 73,2241 (1951). DOS 2 215 653 (Konishiroku; appl. 30.3.1972). Horton, D.: Methods Carbohydr. Chem. (MCACAL) 3,435 (1963). Formulation(s): f. c. tabl. 3 mg Trade Name(s): D: Ridaura (Yamanouchi; GB: Ridaura (Yamanouchi; J: Ridaura (Fujisawa; 1986) 1982) 1987) USA: Ridaura (SmithKline F: Ridauran (Robapharm) I: Ridaura (Smith Kline & Beecham; 1985) French; 1984) Azacitidine ATC: LOIBc Use: antineoplastic RN: 320-67-2 MF: C,HI,N,O, MW: 244.21 EINECS: 206-280-2 LD,,: 1159 mgkg (M, i.v.); 572.3 mglkg (M, p.0.) CN: 4-amino- 1-P-D-ribofuranosyl-1 ,3,5-triazin-2(1 H)-one Azacosterol A 155 HCI AgNCO d H C 0 0 CH, K H C 0 0 CH3 0 0 3K K 0 0 1,2.3,5-tetra-0-ocetyl- O-rnethyl- isoureo H C 6 0 CH, K 0 0 0/CH3 - b H C 0 0 CH3 orthafarrnote 3K K 0 0 Azacitidine u Reference(s): Piskala, A.; Sorm, F.: Collect. Czech. Chem. Commun. (CCCCAK) 29,2060 (1964). US 3 350 388 (F. Sorm, A. Piskala; 1967; prior. 1965). formalion from Streptoverticillium ladrrkanus: Hanka, L.J. et al.: Antimicrob. Agents Chemother. (AACHAX) 1966, 619. isolation and structure elucidation: Rergy, M.E.; Herr, R.R.: Antimicrob. Agents Chemother. (AACHAX) 1966, 625. Trade Name(s): USA: Mylosar (Upjohn); wfm Azacosterol (Diazasterol) Use: cholesterol depressant RN: 313-05-3 MF: C,,H,N,O MW: 388.64 LD,: 90 mgkg (M, p.0.) CN: (3~,17~)-17-[[3-(dimethylamino)propyl]methylamino]androst-5-en-3-ol dihydrochloride R 1249-84-9 MF: C2SHuN20 . 2IICl MW: 461 .S6 LD,,,: 380 rng/kg (M, p.0.); 470 mg/kg (R, p.0.) 156 A Azacyclonol prasterone 3-dimethylomino- formic acid (9. v.1 propylomine FHO YH3 N-N\CH3 LiA\H+ dioxone, lithium oluminum hydride 178-[[3-(dimethylomino)propyl]- formylomino]ondrost-5-en-38-01 (I) Rejerence(s): US 3 084 156 (Searle; 2.4.1963; prior. 30.1 1.1961,28.3.1961). Counsell, R.E. et al.: J. Med. Pharm. Chem. (JMPCAS) 5, 1224 (1962) Trade Name(s): USA: Ornitrol (Searle); wfm Azacyclonol Use: anxio~ytic RN: 115-46-8 MF: CIuH2,N0 MW: 267.37 EINECS: 204-092-5 LD,,: 177 mg/kg (M, i.v.); 650 mg/kg (M, p.0.) CN: a,a-diphenyl-4-piperidinemethanol hydrochloride RN: 1798-50-1 MF: C,,HZ1NO. HC1 MW: 303.83 EINECS: 217-284-9 LD,,,: 121 mglkg (M, i.v.); 650 mglkg (M, p.0.) phenylmognesium ethyl a,a-diphenyl- Azocyclonol bromide isonicotinote 4-pyridinemethonol Reference(s): US 2 804 422 (Merrell; 1957; prior. 1954). Forrnulation(s): amp. 5 mglml (as hydrochloride); tabl. 20 mg Trade Name(s): F: Frenquel (Merrell) J: Frenquel (Shionogi) Azapetine A 157 Azapetine ATC: C04AX30 Use: sympatholytic, vasodilator RN: 146-36-1 MF: C,,H,,N MW: 235.33 EINECS: 205-667-3 LD,,: 27 mglkg (M, i.v.); 460 mglkg (M, p.0.); 50 mglkg (dog, i.v.) CN: 6,7-dihydro-6-(2-propeny1)-5H-dibenz[c,e]azepine phosphate (1:l) RN: 130-83-6 MF: C17H17N. H,P04 MW: 333.32 LD,,: 26 mglkg (M, i.v.); 460 mglkg (M, p.0.): 50 mag (dog, i.v.) 2.2'-dimethyl- 2,2'-bis(broma- biphenyl methy1)biphenyl diphenic acid diphenic anhydride EINECS: 204-997-5 Azapetine COOH diphenamic acid (1) 200 OC I b &o lithium 8 Er"%~2, ' NH allyl bromide n aluminum - hydride diphenimide 6.7-dihydro-5H- dibenz[c,e]azepine Reference(s): a US 2 619 484 (Hoffmann-La Roche; 1952; appl. 1950). b US 2 693 465 (Hoffmann-La Roche; 1954; appl. 1953). Formulation(s): tabl. 25 mg Trade Name(s): D: Ilidar (Roche); wfm Azapropazone (Apazone; Cinnopropazone) ATC: MOlAX04 Use: anti-inflammatory, analgesic RN: 13539-59-8 MF: C,6H20N40, MW: 300.36 EINECS: 236-913-8 LD,,: 680 rnglkg (M, i.v.); 1080 mgkg (M, p.0.); 660 mglkg (R, i.v.); 1800 mglkg (R, p.0.) CN: 5-(dimethylamino)-9-methyl-2-propyl-1 H-pyrazolo[l,2-a][] ,2,4]benzotnazine- l,3(2H)-dione 158 A Azatadine 4-methyl-2- nitrooniline 3-dimethylomino-7- methyl-1,2-dihydro- 1,2,4-benzotriozine (I) NC, P43 HZ, Roney-Ni Y 4 b I CH, dimethyl- 3-dimethylomino-7methyl- cyonomide 1,2,4-benzotriozine 1 -oxide diethyl propyl- molonote Ampropozone US 3 349 088 (Siegfried AG; 24.10.1967; CH-prior. 22.10.1963). Mixich, G.: Helv. Chim. Acta (HCACAV) 51, 532 (1968). Formulation(s): cps. 150 mg, 200 mg, 300 mg; tabl. 600 mg Trade Name(s): D: Tolyprin (Du Pont Pharma) GB: Rheumox (Wyeth) F: Prolixan (J. Logeais); wfm I: Prolixan (Malesci); wfm J: Sinnamin (Nippon Chemiphar) Azatadine ATC: R06AX09 Use: antihistaminic RN: 3964-81-6 MF: C20H22N2 MW. 290.41 CN: 6,ll-dihydro-1 l-(l-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine dimaleate RN: 3978-86-7 MF: C2,H2,N2. 2C4H404 MW: 522.55 EINECS: 223-615-8 LD,,,: 165 mglkg (M, p.0.); 440 n~gkg (R, p.0.) phenyloceto- ethyl nitrile nicotinote benzyl 3-pyridyl ketone (I) H,N-NHZ. NOOH. diethylene glycol, "z02, CH3COOH 235-240 'C Azathioprine A 159 H~C/O\ /P 0//S'O-~H3 2.85 OC 1 .H~C-N>M~CI , THF 3. NaCN . HZO 2. HCI. H20 U. b 111 1. 1-methyl-4-piperidyl- magnesium chloride 2-cyano-3-phen- ethylpyridine Reference(s): US 3 301 863 (Schering Corp.; 31 .l.l967; prior. 24.4.1963, 13.12.1963, 21.12.1964, 18.3.1965). US 3 326 924 (Schering Corp.; 20.6.1967; prior. 24.4.1963, 13.12.1963). US 3 357 986 (Schering Corp.; 12.12.1967; prior. 24.4.1963, 13.12.1963, 19.9.1966). US 3 366 635 (Schering Corp.; 30.1.1968; prior. 24.4.1963, 13.12.1963). US 3 419 565 (Schering Corp.; 31.12.1968; prior. 24.4.1963, 19.9.1966). 7H3 polyphosphoric 'acid & - improvedprocess for 2-cyano-3-phenethylpyridine: US 4 954 632 (SmithKline Beecham Corp.; 4.9.1990; prior. 2.12.1987, 10.2.1989). Villani, F.J. et al.: J. Med. Chem. (JMCMAR) 15, 750 (1972). 7% N ,8- Formulation(s): syrup 0.5 mg (as dimaleate); tabl. 1 mg (azatadine maleate) Trade Name(s): GB: Optimine (Schering- USA: Trinalin (Key Pharm.)- Plough) comb. Azathioprine ATC: LOlBB; L04AXO1 Use: antineoplastic, immunosuppressive RN: 446-86-6 MF: C,H7N70,S 'MW: 277.27 EINECS: 207-175-4 LD,,,: 1389 mglkg (M, p.0.); 535 mglkg (R, p.0.) CN: 6-[(I-methyl-4-nitro-1 H-imidazol-5-yl)thio]-lH-purine rnercaptopurine 5-chloro-1 -methyl- (q v.) 4-nitraimidozole 1 Azathioprine US 3 056 785 (Burroughs Wellcome; appl. 2.10.1962; prior. 21.3.1960). 4 160 A Azelaic acid Formulation(s): amp. 50 mg; f. c. tabl. 50 mg, 25 mg; lyo. 54.1 mg Trade Narne(s): D: Azamedac (medac) F: Imurel (Glaxo Wellcome) I: lmuran (Wellcome) Imurek (Glaxo Wellcome) GB: Azamune (Penn) J: Imuran (Tanabe) Zytrim (Isis Puren) Imuran (Glaxo Wellcome) USA: Imuran (Glaxo Wellcome) Azelaic acid ATC: DlOAX03; Dl 1AX Use: topical treatment of hyperpigmentary disorders and skin cancers, acne therapeutic RN: 123-99-9 MF: CYH,,O4 MW: 188.22 EINECS: 204-669-1 LD,,: >5 gkg (R, p.0.) CN: nonanedioic acid disodium salt RN: 17265-13-3 MF: C,H,,Na,O, MW: 232.19 EINECS: 241-298-4 calcium salt (1:l) RN: 14488-58-5 MF: CYHl4CaO, MW: 226.29 KOH d I glyceral triricinoleate . perrnanganate ricinaleic acid (I) 1 Azelaic acid (CH2),-COOH KMn04, KOH H~c-(cH~)~~ b T)H patassiurn technical process 1. 03, 02, 20-40°C HOOC~COOH aleic acid pelarganic acid Reference(s): a Hill, J.W.; McEwen, W.L.: Org. Synth. (ORSYAT), Coll. Vol. 2, 53 (1943). b Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed., Vol. A8, 526. . 5-( dimethylamino )-9 -methyl-2-propyl-1 H-pyrazolo[l,2-a][] ,2,4]benzotnazine- l,3(2H)-dione 158 A Azatadine 4-methyl- 2- nitrooniline 3-dimethylomino- 7- methyl-1,2-dihydro- 1,2,4-benzotriozine. 5 2-8 8-0 MF: Cl,H,,N,O, MW: 366.41 EINECS: 20 0-1 5 6-1 LD,,: 9300 pglkg (M, i.v.); 1320 mglkg (M, p.0.); 1902 mgkg (R, p.0.) CN: endo-(f )-3 -( 3-hydroxy-l-oxo-2-phenylpropoxy )-8 ,8-dimethyl-8-azoniabicyclo[3.2.l]octane. 44 6-8 6-6 MF: C,H7N70,S 'MW: 277.27 EINECS: 20 7-1 7 5-4 LD,,,: 1389 mglkg (M, p.0.); 535 mglkg (R, p.0.) CN: 6-[ (I-methyl-4-nitro-1 H-imidazol-5-yl)thio]-lH-purine rnercaptopurine 5-chloro-1