Mesna M 1261 medical use for treatment of dermatological disorders: EP 352 826 (Gist-Brocades; appl. 1.5.1989; N-prior. 5.5.1988). medical use for treatment of psoriasis: EP 291 159 (Dak-Lab.; appl. 31.3.1988; GB-prior. 1.4.1987). medical use for treatment of colitis ulcerosa and Crohn's disease: WO 8 102 671 (Ferring; appl. 20.3.1980). medical use for treatment of coronary circulation diseases: WO 8 903 216 (Ferring; appl. 13.10.1988; DK-prior. 14.10.1987). soluble pharmaceutical formulations: DOS 3 151 196 (K. H. Bauer; appl. 23.12.1981). US 4 664 256 (Ferring; 12.5.1987; prior. 6.9.1983). controlled-release formulation: EP 131 485 (Rowel1 Lab.; appl. 6.6.1984; USA-prior. 7.7.1983). Formulation(s): rectal susp. 2g/30 ml, 4 g/60 ml; suppos. 250 mg, 500 mg; tabl. 250 mg, 400 mg, 500 mg Trade Name(s): D: Asacolitin (Henning Berlin) Claversal (Merckle; SmithKline Beecham) Pentasa (Ferring) Salofalk (Falk) F: Pentasa (Ferring) Rowasa (Solvay Pharma) GB: Asacol (SmithKline Salofalk (Interfalk) Beecham) J: Pentasa (Kyorin; Nisshin Pentasa (Yamanouchi) Kyorin) Salofalk (Thames) USA: Asacol (Procter & Gamble) I: Asacol (Giuliani) Pentasa (Hoechst Marion Claversal (Smith Kline & Roussel) French) Rowasa (Solvay) Pentasa (Brocades) Mesna ATC: R05CB05; V03AFO1 Use: detoxificant, mucolytic agent RN: 19767-45-4 MF: C2H,Na03S, MW: 164.18 EINECS: 243-285-9 LD,,: 1720 mgkg (M, i.v.); 6102 m@g (M, p.0.); 15 10 mgkg (R, i.v.); 4440 mgkg (R, p.0.) CN: 2-mercaptoethanesulfonic acid free acid RN: 3375-50-6 MF: C2H,03S2 MW: 142.20 EINECS: 222-167-0 thiourea Z-brorno- ethanesulfonic acid I Mesna Reference(s): US 2 695 310 (Lever Brothers; 1954; appl. 1951). Schramm, C.H. et al.: J. Am. Chem. Soc. (JACSAT) 77,6231 (1955). US 3 567 835 (UCB; 2.3.1971; GB-prior. 7.5.1965) - only medical use. from ethylenesulfide and sodium hydrogen sulfite: Reppe, W.: Justus Liebigs Ann. Chem. (JLACBF) 601, 127 (1956) from 2-chloroethanesulfonic acid and NaSH: DRP 619 299 (Henkel; appl. 1933). 1262 M Mesoridazine deroxicanr for rherapy wirh cyclophosphamide and ifosfamide: DAS 2 756 018 (ASTA-Werke; appl. 14.12.1977). salts with amines (muco1ytic.s): DAS 1 620 629 (UCB; appl. 5.5.1966; GB-prior. 7.5.1965). Formulation(s): amp. 100 mglml, 600 mg; tabl. 400 mg, 600 mg Trade Name(s): D: Mistabronco (UCB) GB: Urimitexan (ASTA Uromitexan (ASTA Uromitexan (ASTA Medica Medica) Medica) AWD) I: Ausobronc (Biotekfarma) J: Uromitexan (Shionogi) F: Mucofluid (UCB) Mucofluid (UCB) USA: Mesnex (Bristol-Myers Uromitexan 400 (ASTA Mucolene (Formenti) Squibb) Medica) Mesoridazine ATC: - N05AC03 Use: psychosedative, antipsychotic RN: 5588-33-0 MF: C,,H2,N20S2 MW: 386.58 LD,,,: 26 mglkg (M, i.v.); 560 mglkg (M, p.0.); 644 mglkg (R, p.0.) CN: 10-[2-(1-methyl-2-piperidinyI)ethyl]-2-(methylsulfinyl)-lOH-phenothiazine monobenzenesulfonate RN: 32672-69-8 MF: C,,H,,N2OS2. C,H,O,S MW: 544.76 0 CH, H Y hydrogen peroxide 2-methylthio- acetic phenothiozine anhydride 1. sodium arnide 2-methylsulfinyl- phenothiozine (11) 2. 2-(2-ch~oroethyl)- 1 -methylpiperidine Mesoridazine US 3 084 '161 (Sandoz; 2.4.1963; CH-prior. 10.3.1960). Formulafion(s): amp. 25 mg; drg. 5 mg; tabl. 10 mg, 25 mg, 100 mg (as monobenzenesulfonate) Mestanolone M 1263 Trade Name(s): F: Lidanil (Salvoxyl-Wander); USA: Serentil (Boehringer Ing.) wfm Mestanolone ATC: A14 Use: anabolic, androgen RN: 521-1 1-9 MF: C,0H,202 MW: 304.47 EINECS: 208-302-6 LD,,,: >3 glkg (M, p.0.); >3 glkg (R, p.0.) CN: (Sa, UP)- 17-hydroxy- 17-methylandrostan-3-one ondrosterone methylmagnesium bromide I Mestonolone I CrO, I chromium(V1) oxide methyltestosterone (9. v.) .& H H O H CrO, 11 v. Mestanolone chrom~um(M) oxide 1 Reference (s): a GB 464 396 (Schering AG; appl. 1935). Ruzicka, L. et al.: Helv. Chim. Acta (HCACAV) 18,994, 1487 (1935). starting material: The Merck Index, 676 (Rahway 1976). b US 2 763 670 (Syntex; 1956, MEX-prior. 1954). Fortnulation(s): 10 - 30 mglday 1264 M Mesterolone Trade Name(s): GB: Androstalone (Roussel); Methyantalon (Sanwa) Tantarone (Mohan) w fm Prohormo (Toyo Pharmar) Yonchlon Syr. (Santen- J: Andoron (Sawai) Protenolon (Showa) Yamanouchi) Mestalone (Hokuriku) Restore (Tokyo Tanabe) Mesterolone ATC: G03BBOI Use: androgen RN: 1424-00-6 MF: C2,H,202 MW: 304.47 EINECS: 215-836-3 CN: (la,5a,17~)-17-hydroxy-l-methylandrostan-3-one Hz, Roney-Ni pyridine ____, benzoyl chloride ondroslenolone ocetote 1. KOH 2. Brz LiCI. DMF ___, ___, 170-hydroxy-3-0x0- 5a-ondrost-1 -ene (IV) methylmagnesium iodide Reference(s): DE 1 152 100 (Schering AG; appl. 23.12.1960), Mestranol M 1265 alternative syntheses: DE 1 122 944 (Schering AG; appl. 6.4.1960). DE 1 13 1 667 (Schering AG; appl. 21.7.1960). Formulation(s): tabl. 25 mg, 50 mg Trade Name(s): D: Proviron (Schering) F: Proviron (Schering) I: Pro-Viron (Schering) Vistimon (Jenaphann) GB: Proviron (Schering) Mestranol ATC: GO3 Use: estrogen (in combination with progestogen as oral contraceptiva) RN: 72-33-3 MF: C,,H,,O, MW: 310.44 EINECS: 200-777-8 LD,,: >10 gkg (M, p.0.); >lo gkg (R, p.0.) CN: (17a)-3-methoxy-l9-norpregna-l,3,5(10)-trien-20-yn-17-01 3-0-methylestrone acetylene I Mestronol I Reference(s): US 2 666 769 (Searle; 1954; appl. 1952). Colton, F.B. et al.: J. Am. Chem. Soc. (JACSAT) 79, 1123 (1957). DE 1 096 354 (Schering AG; appl. 1.8.1959). Formulation(s): drg. 0.05 mg, 0.08 mg; tabl. 0.05 mg Trade Name(s): D: Gestamestrol (Hermal- Chemie)-comb. Ortho-Novum (Janssen- Ci1ag)-comb. I: Ovosiston (Jenaphann) F: MCtrulhe (Sear1e)-comb.; wfrn MCtrulkne-test (Sear1e)- comb.; wfrn Noracycline (Ciba-Geigy)- comb.; wfrn Orgaluton (Organon)- comb.; wfrn O.V. 28 (Biosedra)-comb.; wfrn GB: Menophase (Searle) Norinyl- 1 (Sear1e)-comb. Ortho-Novin 1/50 (Janssen- J: Ci1ag)-comb. Elan (Valeas)-comb.; wfrn Franovul (Francia Farm.)- comb.; wfrn Luteolas (Serono)-comb.; wfrn Lyndiol (Ravasini Organon)-comb.; wfm USA Metrulen (SPA)-comb.; wfrn Ortho-Novum (Cilag- Chemie)-comb.; wfrn Ovaras (Serono)-comb.; wfrn Regovar (Recordati); wfrn Devocin (Shionogi) Enavid (Dainippun)-comb. Lutedione (Teikoku Zoki)- comb. Lyndiol (Organon-Sankyo)- comb. Norluten D (Shionogi)- comb. Nelova (Warner Chi1cott)- comb. Norethin (Roberts)-comb. Norinyl (Sear1e)-comb. Ortho-Novum (Ortho- McNei1)-comb. Mesulfen (Thianthol) ATC: D 1OABO5; P03AA03 Use: topical scabicide, antipruritic RN: 135-58-0 MF: C,,H,,S, MW: 244.38 EINECS: 205-202-4 CN: 2,7-dimeththianthrene 1. NoNOZ 2. KI. H,SO, H3C S03H H3C 0 3-sulfonic acid sulfonic acid HI. C,H,OH. H3C SO2H bis(2-iodo-5-methyl- Mesulfen phenyl) disulfide L I Reference(s): Barber, H.J.; Smiles, S.: J. Chem. Soc. (JCSOA9) 1928, 1141. alternaiive synfhesis (from toluene, sulfur and AICl,): DE 365 169 (Bayer; appl. 1919). Fo~mulation(s): ointment 5-25 % Trade Name(s): D: Citemul (Medopharm) I: Mitigal (Bayropharm); Mitigal (Sigurth); wfrn wfrn J: Scabol (Daiichi) Mesuximide (Methsuximide) ATC: N03AD03 Use: antiepileptic RN: 77-41-8 MF: C,,H,,NO, MW: 203.24 EINECS: 201-026-7 LD,,: 900 rnglkg (M, p.0.) CN: 1,3-dirnethyl-3-phenyl-2,5-pyrrolidinedione methyl ocetophenone cyonoocetate cyanide Keference(s): US 2 643 257 (Parke Davis; 1953; prior. 1950). Miller, C.A.; Long, L.M.: J. Am. Chem. Soc. (JACSAT) 73,4895 (1951); 75,373 (1953). Formulation(s): cps. 150 mg, 300 mg Trade Name(s): D: Petinutin (Parke Davis) GB: Celontin (Parke Davis); USA: Celontin (Parke Davis) wfm Metaclazepam (Brometazepam; Metuclazepam) ATC: NOSBA Use: anxiolytic, benzodiazepine derivative RN: 8403 1-17-4 MF: Cl,Hl,BrC1N20 MW: 393.71 . LD,,: 1578 mgkg (M, p.0.) CN: 7-bromo-5-(2-chlorophenyl)-2,3-dihydro-2-(methoxymethyl)-l-methyl-1H-l,4-benzodiazepine monohydrochloride RN: 61802-93-5 MF: C,,H,,BrC1N20 . HC1 MW: 430.17 EINECS: 263-234-4 LD,,: 1578 mgkg (M, p.0.) N-phenyl-N-methyl- 2-hydroxy-1.3- diaminopropone N-phenyl-N-methyl-Na- (2-ch1orobenzoyl)-2-hydroxy- 1.3-diaminopropane (I) FH3 FH3 POCI, I + u phosphoryl chloride 1268 M Metacvcline N-bromo- succinimide Reference(s): BE 799 001 (Kali-Chemie; appl. 2.5.1973; D-prior. 3.5.1972). DOS 2 520 937 (Kali-Chernie; appl. 10.5.1975). US 4 098 786 (Kali-Chemie; 4.71978; appl. 23.9.1976; D-prior. 3.5.1972). US 4 244 869 (Kali-Chemie; 13.1.1981; D-prior. 3.5.1972, 10.5.1975). Liepmann, H. et al.: Eur. J. Med. Chem. (EJMCAS) 11, 501 (1976). medicul use as analgesic: EP 96 320 (Kali-Chemie; appl. 28.5.1983; D-prior. 5.6.1982). Formulation(s): drops 10 mglml; tabl. 5 mg, 10 mg (as hydrochloride) Trade Name(s): D: Talis (Kali-Chemie; 1990); wfm Metacycline (Methacycline; Mtthylbnecycline) ATC: JOIAAOS Use: antibiotic RN: 914-00- 1 MF: C2,H2,N208 MW: 442.42 EINECS: 213-017-5 LD,,: 660 mglkg (R, i.p.) CN: [4S-(4a,4aa,5a,5ac1,12aa)]-4-(dimethyamino)- 1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a- pentahydroxy-6-methylene-l,l l -dioxo-2-naphthacenecarboxamide monohy drochloride RN: 3963-95-9 MF: C22H22N208 . HCl MW: 478.89 EINECS: 223-568-3 LD,,: 193 mg/kg (M, i.v.); 3450 mglkg (M, p.0.); 202 mg/kg (R, i.v.); >2 glkg (R, p.0.) 0 SO3 - pyridine- sulfur trioxide complex oxytetracycline (1) Metahexamide M 1269 "2F2 I. hydrogen fluoride Metacycline Reference(s): US 2 984 686 (Pfizer; 16.5.1961; appl. 19.12.1960). US 3 026 354 (Pfizer; 20.3.1962; prior. 15.12.1960). cf. also doxycycline Formulation(s): cps. 150 mg, 300 mg; drops 100 mg; susp. 100 mg (as hydrochloride) Trade Name(s): D: Rondo-Bron (Mack)- Physiomycine (Laphal) J: Adramycin (Sanko) comb.; wfm GB: Rondomycin (Pfizer); wfm Rondomycin (Taito Pfizer) Rondo-Bron (Mack)-comb. I: Esarondil (Terapeutico USA: Rondomycin (Wallace); with guaiphenesin; wfm M.R.) wfm Rondomycin (Mack); wfm Rotilen (Terapeutico Mil.) F: Lysocline (Parke Davis) Stafilon (AGIPS) Metahexamide ATC: AlOBBlO Use: antidiabetic RN: 565-33-3 MF: C,,H,,N,O,S MW: 3 11.41 EINECS: 209-276-9 CN: 3-amino-N-[(cyclohexylamino)carbonyl]-4-methylb~namide 3-ocetylomino- ethyl 4-methylbenzene- chloroformote suMonarnide + cyclohexyl- arnine DMF d KOH + Metahexornide GB 831 043 (Boehringer Mannh.; appl. 1958; D-prior. 1957). Formulation(s): tabl. 100 mg 1270 M Metamizole sodium Trade Narnefs): F: Isodiane (Servier); wfm Metamizole sodium ATC: N02BB02 RN: LD,,: CN: Use: analgesic, antipyretic, anti- inflammatory 68-89-3 MF: C,,H,,N,NaO,S MW: 333.34 EINECS: 200-694-7 2197 rng/kg (M, i.v.); 2891 mglkg (M, p.0.); 2182 mgkg (R, i.v.); 3 g/kg (R, p.0.) [(2,3-dihydro- 1,5-dimethyl-3-0x0-2-phenyl- 1 H-pyrazol-4-yl)methylamino]rnethanesulfonic acid sodium salt monohydrate RN: 5907-38-0 MF: C,,H,,N,NaO,S . H,O MW: 351.36 metamizole RN: 50567-35-6 MF: C,,H,,N,O,S MW: 3 11.36 EINECS: 256-627-7 4-amino-2.3-dimethyl- benzoldehyde 4-benzylidenomino-2.3-dimethyl- 1 -phenyl-5-A'-pyrozolone 1 -phenyl-5-~'-pyrazolone (I) (cf. ominophenozone synthesis) dimethyl sulfote 4-benzylidenemethylamrnonio-2.3-dimethyl- 1 -phenyl-5-~'-pyrorolone methyl sulfote (II) Metamizole sodium u Referencefs): Ehrhart, Ruschig, I, 17 1. DRP476 663 (I.G. Farben; 1922). DRP 421 505 (I.G. Farben; appl. 1920), DRP 467 627 (I.G. Farben; appl. 1921). DRP 476 643 (I.G. Farben; appl. 1921). . 6180 2-9 3-5 MF: C,,H,,BrC1N20 . HC1 MW: 430.17 EINECS: 26 3-2 3 4-4 LD,,: 1578 mgkg (M, p.0.) N-phenyl-N-methyl- 2-hydroxy-1. 3- diaminopropone N-phenyl-N-methyl-Na- (2-ch1orobenzoyl )-2 -hydroxy-. C,,H,,N,O,S MW: 3 11.36 EINECS: 25 6-6 2 7-7 4-amino-2.3-dimethyl- benzoldehyde 4-benzylidenomino-2.3-dimethyl- 1 -phenyl-5-A'-pyrozolone 1 -phenyl- 5-~ '-pyrazolone (I) (cf. ominophenozone. 1-1 7-4 MF: Cl,Hl,BrC1N20 MW: 393.71 . LD,,: 1578 mgkg (M, p.0.) CN: 7-bromo- 5-( 2-chlorophenyl )-2 ,3-dihydro- 2-( methoxymethyl)-l-methyl-1H-l,4-benzodiazepine monohydrochloride RN: 6180 2-9 3-5