Mebendazole M 121 1 CI 2-(4-chlorabenzoyl)- ethylene- benzoic acid diamine pyridine (1) 4'-chlora-2- 1 Maiindol / (2-imidazolin- 2-yl)-benzo- phenane Reference(s): DOS 1 770 030 (Sandoz; appl. 22.3.1968; USA-prior. 23.3.1967). US 3 597 445 (Sandoz-Wander; 3.8.1971; appl. 19.6.1968). US 3 763 178 (American Home Products; 2.10.1973; appl. 5.9.1968; prior. 15.9.1965.2.9.1966, 14.3.1967). alternative syntheses: DOS 1 795 105 (Sandoz; appl. 10.8.1968; USA-prior. 15.8.1967,3.5.1968). DOS 1 814 540 (Sandoz; appl. 12.12.1968; USA-prior. 18.12.1967, 23.7.1968). DOS 1 930 488 (Sandoz; appl. 16.6.1969; USA-prior. 19.6.1968). Formulation(s): tabl. 1 mg, 2 mg Trade Name(s): D: Teronac (Wander); wfm I: Mazildene (Lifepharma); USA: Sanorex (Sandoz); wfm GB: Tcronac (Wander); wfm wfm Mebendazole ATC: P02CAOl Use: anthelmintic RN: 31431-39-7 MF: C,,H,,N,O, MW: 295.30 EINECS: 250-635-4 LD,,,: 620 mglkg (M, p.0.); 714 mg/kg (R, p.0.); 1280 mgkg (dog, p.0.) CN: (5-benzoyl1H-bznzimidazol-2-y1)carbamic acid met!iyr! ester 1212 M Mebeverine 4-chloro- benzophenone 4-chloro-3-nitro- benzophenone 4-amino-3-nitro- benzophenone (I) 3.4-diomino- benzophenone (11) S NH, C1 0, NoOH, pH 8 S NH, H,C' 'fH a tt2sO4 + 'f CH3 - H3c' Y 0 N~0\cH3 0 S-methylthiouronium- methyl sulfate chloroformote methyl S-methyl- isothioureo-N- corboxylate (111) I Mebendazole Rejkrence(s): DE 2 029 637 (Janssen; appl. 16.6.1970; USA-prior. 20.6.1969). US 3 657 267 (Janssen; 18.4.1972; prior. 20.6.1969). Formulation(s): chewable tabl. 100 mg; susp. 100 mg/5 ml; tabl. 100 mg, 500 mg Trade Name(s): D: Surfont (Ardeypharm) GB: Vermox (Janssen-Cilag; J: Mebendazol (Janssen Vermox (Janssen-Cilag; 1976) Kyowa) 1976) I: Vermox (Janssen; 1979) USA: Vermox (Janssen; 1975) Mebeverine ATC: A03AA04 Use: antispasmodic RN: 3625-06-7 MF: C2sH35NOs MW: 429.56 EINECS: 222-830-4 LD,,: 24 mglkg (M, i.v.); 995 mgkg (M, p.0.) CN: 3,4-dimethoxybenzoic acid 4-[ethyl[2-(4-methoxyphenyl)-1-methylethyl]amino]butyl ester hydrochloride RN: 2753-45-9 MF: C2sH35N05 . HCI MW: 466.02 EINECS: 220-400-0 LD,,: 17.7 mgkg (R, i.v.); 1540 mglkg (R, p.0.) Mebhydrolin M 1213 H,. Pt NH2 + ~O\CH~ -, ~O'CH~ L, I HF? / ethyl 3-chloro- formylpropionote ethyl- (4-methoxypheny1)- 2-ethylamino- omine acetone 1 -(4-rnethoxypheny1)- propane J - K-N n lithium N - LH3 olonate 'cH3 Reference (s): DE 1 126 889 (N. V. Philips; appl. 20.1 1.1958; NL-prior. 23.1 1.1957). 3,4-dimethoxy- alternative synthesis: GB 1 009 082 (N. V. Philips; appl. l9.10.1961; NL-prior. 22.10.1960). Mebeverine Formulation(s): cps. 100 mg; drg. 135 mg; s. r. cps. 200 mg (as hydrochloride); susp. 10 mg benzoyl chloride Trade Name(s): D: Duspatal (Solvay Duspatal~n (Solvay; as Fy bogel Mebeverine Arzneimittel; as hydrochloride) (Reckltt & Co1man)-comb. hydrochloride)-comb. Spasmopriv (Irex; as I: Duspatal Duphar (UCM) F: Colopriv (Biotherapie; as hydrochloride) hydrochloride) GB: Colofac (Solvay) Mebhydrolin ATC: R06AX15 Use: antihistaminic RN: 524-81-2 MF: C,,H,,,N, MW: 276.38 EINECS: 208-364-4 CN: 2,3,4,5-tetrahydro-2-methyI-5-(phenylmethyl)-1H-pyrido[4,3-b]indole naphthalene-1,s-disulfonate (2:l) RN: 6153-33-9 MF: C,,H2,N2. 112C,,H,0,S2 MW: 841.07 EINECS: 228-170-3 LD,,,: 40 mglkg (M, i.v.) 1214 M Mebutamate HCI, C2H50H ON,NH2 + oNCH3 b 0 N-benzyl-N- 1 -methyl- Mebhydrolin phenylhydrozine 4-pipendone Ref'erence(s): GB 721 171 (Bayer; appl. 1952; D-prior. 1951). Fomulation(s): drg. 50 mg, 76 mg (as napadisilate); s. r. tabl. 150 mg; susp. 50 mg; tabl. 50 mg Trade Namds): D: Omcril(Bayer);wfm GB: Fabahistin (Baycr); wfm Omeril (Tropon-Dome I: lncidal (Bayropharm) Hollister Stier); wfm J: Incidal (Yoshitomi) Mebutamate ATC: N05BC04 Use: neurosedative, antihypertensive RN: 64-55- 1 MF: C,,H,,lN20, MW: 232.28 EINECS: 200-587-5 LD,,,: 550 mglkg (M, p.0.); 1160 mgkg (R, p.0.) CN: 2-methyl-2-(1-methylpropy1)-1,3-propancdiol dicarbamate LiAIH, h3cA0~o,cH, lithium H3C CH~O alonate H3C CH3 2-sec-butyl-2- methylpropone- 1,3-diol (I) ethyl corbamate Mebutamate Rejerence(s): US 2 878 280 (Carter Products; 17.3.1959; prior. 29.11.1955). Formulation(s): tabl. 300 mg Trade Nameis): F: Dtvalknc (Dexo)-comb. J: Mega (Ono) Dormate (Wallace); wfm 1: Sigmafon (Lafare) USA: Capla (Wallace); wfm Mecamylamine M 1215 Mecamylamine (Dimecamine) ATC: C02BBOl Use: ganglionic blocker, antihypertensive RN: 60-40-2 MF: Cl,H21N MW: 167.30 EINECS: 200-476-1 LD,,: 11.9 mglkg (M, i.v.); 90 mglkg (M, p.0.) CN: N,2,3,3-tetramethylbicyclo[2.2.l]heptan-2-amine hydrochloride RN: 826-39-1 MF: C,,H,,N. HC1 MW: 203.76 EINECS: 212-555-8 LD,,,: 14 mgkg (M, i.v.); 92 mglkg (M, p.0.); 21 mgkg (R, i.v.); 208 mgkg (R, p.0.) comphene hydrocyonic 2-(formylomino)- Mecomylomine ocid isocamphane Reference(s): US 2 831 027 (Merck & Co.; 1958, prior. 1955). Stein, G.A. et al.: J. Am. Chem. Soc. (JACSAT) 78, 1514 (1956). Fi~rrnulation(s): tabl. 2.5 mg (as hydrochloride) Trade Name(s): D: Mevasine (Sharp & GB: lnversine (Merck Sharp & USA: Inversine (Merck Sharp & Dohme); wfm Dohme); wfm Dohme) F: Inversine (Merck Sharp & J: Mevasine (Meiji) Dohme); wfm Mecillinam ATC: JOlCAll Use: antibiotic RN: 32887-01-7 MF: C,,H,,N,O,S MW: 325.43 EINECS: 251-277-1 CN: [2S-(2a,5a,6~)]-6-[[(hexahydro-1H-azepin-l-yl)methylene]amino]-3,3-dimethyl-7-oxo-4-thia-l- azabicyclo[3.2.0]heptane-2-carboxylic acid COOH 0-Si-CH3 + H3C-Si-N-Si-CH, b I I y3 CH3 CH, H3C-Si-N I HH CH3 6-orninopenicillonic hexamethyldisilazone (1) ocid 12 16 M Meclofenamic acid 1 -formyl- hexahydro- azepine Reference(s): DOS 2 055 53 1 (Loevens; appl. 11.1 1.1970; GB-prior. 11 .I 1.1969, 8.7.1970). GB 1 293 590 (Loevens; appl. 11.1 1.1969, 8.7.1970; valid from 10.1 1.l97O). Formula~ion(s): amp. 0.2 g, 0.4 g, 0.5 g, 1 g Trade Name(s): GB: Selexidin (Burgess); wfm Selexidin (Leo); wfm USA: Coactin (Roche); wfm Meclofenamic acid ATC: M01 AG04; M02AA 18 Use: anti-inflammatory, antirheumatic, antipyretic RN: 644-62-2 MF: CI4H,,C1,NO, MW: 296.15 EINECS: 211-419-5 LD,,,: 100 mglkg (R, p.0.) CN: 2-[(2,6-dichloro-3-metbylpbenyl)amino]benzoic acid monosodium salt RN: 6385-02-0 MF: C,4H,oC1,NNa0, MW: 318.14 EINECS: 228-983-3 potassium 2.6-dichloro- 2-brorno- 3-methyl- benzoate aniline Meclofenamic acid I Referencefs): DE 1 149 015 (Parke Davis; appl. 22.6.1961; USA-prior. 12.1.1961). US 3 313 848 (Parke Davis; 11.4.1967; prior. 12.1.1961, 18.9.1962, 18.6.1964). Formularion(s): cps. 50 mg, 100 mg; suppos. 200 mg (as sodium salt) Trade Name(s): I: Movens (lnverni della Meclomen (Warner- Beffa); wfm Lambert); wfm USA: Meclomen (Parke Davis); Meclomen (Parke Davis; as wfm sodium salt); wfm generic Meclofenoxate M 12 17 Meclofenoxate (Centrophenoxine) ATC: N06BXO1 Use: neuroenergetic RN: 51-68-3 MF: Cl,H1,ClNO3 MW: 257.72 EINECS: 200-116-3 LD,,: 1750 mglkg (M, p.0.); 2600 mglkg (R, p.0.) CN: (4-chlorophenoxy)acetic acid 2-(dimethy1amino)ethyl ester hydrochloride RN: 3685-84-5 MF: Cl,H,,ClN03 . HCl MW: 294.18 EINECS: 222-473-4 LD,,,: 330 mg/kg (M, i.v.); 1750 mglkg (M, p.0.); 865 mg/kg (R, p.0.) Thuillier, G.; Rumpf, P.; Thuillier, J.: C. R. Hebd. Seances Acad. Sci. (COREAF) 249,2081 (1959). FR 398 M (Centre Nat'l. Recherche Sci., appl. 15.4.1959). 4-chlorophenoxy- 2-(dimethylomino)- Formulation(s): amp. 250 mg, 500 mg, 2 g (as hydrochloride); drg. 200 mg, 500 mg; f. c. tabl. 100 mg, 250 mg Meclofenoxate Trade Name(s): D: CERUTIL (Isis Pharma) F: Lucidril (Lipha SantC; as J: Lucidril (Dainippon) Helfergin (Promonta hydrochloride) Meclon (Toho) Lundbeck; Isis Pharma; as GB: Lucidril (Reckitt & Mecroeat (Hishiyama) hydrochloride) Colman); wfm Proseryl (Funai) I: Lucidril (Bracco); wfm acetic acid ethyl chloride Mecloqualone ATC: N05C Use: hypnotic, sedative RN: 340-57-8 MF: C,,HllCIN,O MW: 270.72 EINECS: 206-432-8 LDTo: 470 mgtkg (M, p.0.) CN: 3-(2-chlorophenyl)-2-methyl-4(3~)-quinazolinone N-acetyl- 2-chloro- anthranilic aniline acid I Mecloqualone Jackman, G.B. et al.: J. Pharm. Pharmacol. (JPPMAB) 12,528 (1960). Klosa, J.: J. Prakt. Chem. (JPCEAO) 14 [4], 84 (1961). 1218 M Meclozine Trude Narne(s): F: Nubarhe (Diamant); wfm Meclozine (Histamethizine; Meclizine) ATC: R06AE05 Use: antihistaminic RN: 569-65-3 MF: C2,H2,C1N2 MW: 390.96 EINECS: 209-323-3 LD,,: 1650 mgkg (M, p.0.); 1750 mgkg (R, p.0.) CN: I-[(4-chlorophenyl)phenylmethyl]-4-[(3-methylphenyl)methyl]piperazine dihydrochloride RN: 1104-22-9 MF: C2,H2,C1N2 . 2HC1 MW: 463.88 EINECS: 214-164-8 LDs,,: 1600 mgkg (M, p.0.) dihydrochloride monohydrate RN: 3 1884-77-2 MF: C2,H2,C1N2 .2HC1 H20 MW: 481.90 3-methyl- 1 -(4-chlorobenz- benzoldehyde hydry1)piperazine Hz. Raney-Ni H3C I Meclozine H3C Reference(s): US 2 709 169 (UCB; 1955; B-prior. 1951). Formulution(s): drg. 12.5 mg; suppos. 50 mg; tabl. 12.5 mg, 25 mg, 50 mg (as dihydrochloride) Trade Nurne(s): D: Bonamine (Pfizer; as hydrochloride) Diligan (Rodleben; Vedim; as hydrochloride)-comb. Peremesin (Bristol-Myers Squibb; as hydrochloride) Postadoxin (Rodleben; as hydrochloride)-comb. Postafen (UCB; as . hydrochloride) F: Agyrax (Medim; as hydrochloride) GB: Ancolan (Duncan, Flockhart); wfm Ancoloxin (Duncan, Flockhart)-comb.; wfm I: Neo-Istafene(UCB-Smith); wfm J: Bonamine (Taito Pfizer) Taizer (Taito Pfizer) USA: Antivert (Pfizer; as hydrochloride) Bonine (Pfizer; as hydrochloride) Mecobalamin (Methylcobalamin) ATC: V03AB Use: vitamin B ,,-preparations RN: 13422-55-4 MF: C,,H,lCoN,301,P MW: 1344.41 EINECS: 236-535-3 CN: cobinamide Co-methyl deriv. hydroxide dihydrogen phosphate (ester) inner salt 3'-ester with 5,6- dimethyl- 1 -a-D-ribofuranosyl-1 H-benzimidazole Mecobalamin M 1219 Zn/NH,CI or Zn/CH,COOH or NaBH, (under exclusion of 02) , I hydroxocobalarnin (4. v.1 hydridocabalarnin (1) Mecabalarnin ' + H3C-I Mecobalarnin u Mecabalarnin Ezl ~iller, 0.; Miiller, G.: Biochem. Z. (BIZEA2) 336, 299 (1962). Dolphin, D.H.; Johnson, A.W.: Proc. Chem. Soc., London (PCSLAW) 1963,311. Dolphin, D.H.; Johnson, A.W.: J. Chem. Soc. (JCSOA9) 1965,2174. Boos, R.N. et al.: Science (Washington, D.C.) (SCIEAS) 117,603 (1953). Smith, E.L. et al.: Nature (London) (NATUAS) 194, 1175 (1962). 1220 M Mecysteine hydrochloride review: Bernhauer, K. et al.: Angew. Chem. (ANCEAD) 75,1145 (1963). Formulation(s): tabl. 500 pg; vial 10 pg, 500 pg Trade Name(s): F: Algobaz (Labaz) J: Calomide-Me LyomCthyl (Bouchara) (Yamanouchi) MCthylcobaz (Labaz) Cobamain (Kyowa) Cobametin (Sankyo) Hitocobamin-M (Hishiyama) Vancomin (Dainippon) Mecysteine hydrochloride Use: mucolytic agent RN: 18598-63-5 MF: C,H,NO,S . HCl MW: 171.65 EINECS: 227-208-6 LD,,: 2300 mgkg (M, p.0.) CN: L-cysteine methyl ester hydrochloride mecysteine RN: 2485-62-3 MF: C,H,NO,S MW: 135.19 EINECS: 219-625-7 L-cysteine hydrochloride rnonohydrote I Mecysteine hydrochloride I L-cystine dirnethyl ester dihydrochloride Reference(s): a Bergmann, M.; Michalis, G.: Ber. Dtsch. Chem. Ges. (BDCGAS) 63,987 (1930). b Zervas, L.; Theodoropoulos, D.M.: J. Am. Chem. Soc. (JACSAT) 78, 1359 (1956). Formulation(s): drg. 100 mg; suppos. 100 mg, 200 mg; tabl. 0.05 g, 0.1 g Trade Name(s): F: Acthiol J. (JoulliC); wfm Ectazis (Nichiiko) GB: Visclair (Sinclair) Epecoal (Beppu) I: Actiol (SIT) Epectan (Seiko) Donatiol (AG1PS)-comb. Equverin (Nissin) J: Aslos-C (Nissin) Fustant (Kanto) Fuszemin S (Taiyo) Higlomin (Wakamoto) Jeorgen (Sanwa) Moltanine (Toho K Tokyo Tanabe) . RN: 3288 7-0 1-7 MF: C,,H,,N,O,S MW: 325.43 EINECS: 25 1-2 7 7-1 CN: [2S-(2a,5a,6~) ]-6 -[ [(hexahydro-1H-azepin-l-yl)methylene]amino ]-3 ,3-dimethyl-7-oxo-4-thia-l- azabicyclo[3.2.0]heptane-2-carboxylic. antihistaminic RN: 52 4-8 1-2 MF: C,,H,,,N, MW: 276.38 EINECS: 20 8-3 6 4-4 CN: 2,3,4,5-tetrahydro-2-methyI- 5-( phenylmethyl )-1 H-pyrido[4,3-b]indole naphthalene-1,s-disulfonate (2:l) RN: 615 3-3 3-9 MF: C,,H2,N2 hypnotic, sedative RN: 34 0-5 7-8 MF: C,,HllCIN,O MW: 270.72 EINECS: 20 6-4 3 2-8 LDTo: 470 mgtkg (M, p.0.) CN: 3-( 2-chlorophenyl )-2 -methyl-4(3~)-quinazolinone N-acetyl- 2-chloro- anthranilic aniline