Menadione sodium bisulfite M 1241 Trade Narne(s): F: Bilkaby (Lehning) J: generic - Menadione sodium bisulfite ATC: ~11 (Menaphthone sodium bisulfite) Use: ant~hemorrhagic vitamin RN: 130-37-0 MF: C,,H,Na05S MW: 276.24 EINECS: 204-987-0 CN: 1,2,3,4-tetrahydro-2-methyl-1,4-dioxo-2-naphthalenesulfonic acid sodium salt 0 Menadione sadium bisulfite Reference(s): Moore, M.B.: J. Am. Chem. Soc. (JACSAT) 63,2049 (1941). Baker, B.R. et al.: J. Am. Chem. Soc. (JACSAT) 64, 1096 (1942). Menotti, A.R.: J. Am. Chem. Soc. (JACSAT) 65, 1209 (1943). US 2 367 302 (Abbott; 1945; appl. 1940). Forrnulation(s): amp. 1 mg, 2 mg, 3 mg, 10 mg, 50 mg Trade Narne(s): D: Chloramsaar (Chephasaar)- Poly-Vitamin-Saar F: ArhCmapectine vitaminCe comb.; wfm (Chephasaar)-comb.; wfm (Gal1ier)-comb.; wfm Geriatrie-Mulsin (Mucos)- Prenatal (Cyanamid)- CCpCvit K (UCB)-comb.; comb.; wfm comb.; wfm wfm Lentinorm (Kano1dt)- Tetracycletten (Voigt); wfm I: Vitamina K Salf (Salf) comb.; wfm J: Menadione Inj. (Nord) Use: anesthetic (combination ingredient in antitussives and expectorants) RN: 2216-51-5 MF: C,,,H,,O MW: 156.27 EINECS: 218-690-9 LD,,: 3400 mgkg (M, p.0.); 3300 mgkg (R, p.0.) CN: [1R-(la,2~,5)]-5-methyl-2-(l-methylethyl)cyclohexanol isolation from peppermint oils, contoining 70-80 % free menthol, by freezing ond recrystollizotion @ from (+)-citronellol (contoining at 80 % in citronellol) (+)-citronellol (I) (-)-isopulegol (II) (+)-neoiso- (+)-isoiso- (+)-neoisoiso- pulegol (111) pulegol (IV) pulegol (V) HZ, Raney-Ni I1 pyrolysis 111 + IV + v 1 lhyrnal (+)-menthol (VI) (f)-neornenthol (f)-isamenthal recycling! epimerization to the mtia (?)-menthol : (2)-neomenthol : (+)-isamentho1 = 6 : 3 : 1 under hydrogenation conditions: separation of (?)-menthol by distillotion 1. fract. crystallization 0 pyridine 2. hydrolysis with NaOH 6 . H~c/*'cH~ (+)-menthy1 benzoate (+)-Menthol can be racemized under thymol hydrogenation conditions (also with Raney-Ni). Referencefs): review: Ullmanns Encykl. Tech Chem., 4. Aufl., Vol. 20,220. b DAS 1 197 081 (A. Boake Roberts & Co.; appl. 31.10.1963). c racemute resolution of (+_)-menthy1 benzoate: DOS 2 109 456 (Haarmann & Reimer; appl. 27.2.1971). Mepacrine M 1243 Formulation(s): cream 0.042-1 %; drg. 1 mg; ointment, sol. in numerous concentrations; powder 1 % Trade Name(s): D: numerous combination I: numerous combination Thera-Gesic (Mission). preparations preparations comb. F: numerous combination USA: Listerine (Warner- numerous combination preparations Lambert)-comb. preparations GB: numerous combination Panalgesic Gold (ECR)- preparations comb. Mepacrine (Quinacrine; Atebrin) ATC: PO1 AX05 Use: antimalarial RN: 83-89-6 MF: C2,H3,CIN30 MW: 399.97 EINECS: 201-508-7 LD,,: 50mgkg (M,i.v.); 1320mgkg(M,p.o.) CN: ~-(6-chloro-2-methoxy-9-acridinyl)-N1,NL-diethyl-l ,4-pentanediamine dihydrochloride RN: 69-05-6 MF: C,3H,oC1N,0~ 2HCI MW: 472.89 EINECS: 200-700-8 LD,,: 38 mgkg (M, i.v.); 557 mglkg (M, p.0.); 29 mgkg (R, i.v.); 660 mgkg (R, p.0.) Cu. K2C03 COOH + J+J"CH~ PocI, CI HzN c I phosphorus H oxychloride 2.4-dichloro- 4-methoxy- benzoic acid oniline Reference (s): DRP 553 072 (I. G. Farben; appl. 1930). Wingler, A.: Angew. Chem. (ANCEAD) 61,49 (1949). 6,9-dichloro-2- 2-omino-5-diethyl- Formulation(s): tabl. 100 mg Mepocrine Trade Natir~ls): F: Colla&nan (Sobio)-comb.; Tenicridine (Norgan); wfm wfm USA: Atabrine (Winthrop); wfm methoxyacridine (1) aminopentone 1244 M Mepartricin Mepartricin (Methylpartricin) RN: 11 121-32-7 MF: C,,H,,N,O,, MW: 1141.36 LD,,: 11.1 mglkg (M, i.p.); 4300 pglkg (M, i.v.); >2 glkg (M, p.0.) CN: partricin methyl ester 1. ferrnentotion of Streptornyces oureofociens 2. rnethylotion with excess of diozornethone ATC: AOlAB16; DOlAA06; GOlAA09 Use: polyene antibiotic (for treatment of Reference(s): DE 2 154 436 (Spa; appl. 2.1 1.1971; GB-prior. 3.1 1.1970). GB 1 359 473 (Spa; appl. 3.1 1.1970). GB 1 406 774 (Spa; appl. 15.2.1973). GB 1 462 442 (Spa; appl. 29.8.1974). DE 2 406 628 (Spa; appl. 12.2.1974; GB-prior. 15.2.1973). US 3 773 925 (Spa; 20.11.1973; appl. 3.1 1.1971; GB-prior. 3.11.1970) Bruzzese, T. et al.: Experientia (EXPEAM) 28, 1515 (1972). Pandey, R.C. et al.: J. Antibiot. (JANTAJ) 30, 158 (1973). Tweit, R.C. et al.: J. Antibiot. (JANTAJ) 35, 997 (1982). water soluble formulation: GB 1 413 256 (Spa; appl. 14.5.1973). GB 1 463 348 (Spa; appl. 3.9.1974). medical use for treatment of benign prostatic hypertrophy: US 4 237 117 (Spa; 2.12.1980; prior. 6.1 l.l978,5.lO.l979). candidal and trichomonal gynaecological infections, treatment of benign prostatic hypertrophy) liposomal formulation: WO 89 103 677 (Board of Regents; Univ. of Texas Syst.; appl. 27.10.1988; USA-prior. 27.10.1987). structure of partricin: Tweit, R.C. et al.: J. Antibiot. (JANTAJ) 35, 997 (1982). Formulation(s): tabl. 50000 iulg, 40 mg; vaginal cream 5000 iulg; vaginal tabl. 25000 iu. Trade Name(s): 1: Ipertrofan (SPA; 1986) Montricin (SPA; 1988 as Tricandil (SPA; 1975) sodium lauryl sulfate) Me~enzolate bromide M 1245 Mepenzolate bromide ATC: A03AB12 Use: anticholinergic RN: 76-90-4 MF: C2,H2,BrN03 MW: 420.35 EINECS: 200-992-7 LD,,,: 9800 @kg (M, i.v.); 900 mglkg (M, p.0.); 22 mgkg (R, i.v.); 742 mg/kg (R, p.0.) CN: 3-[(hydroxydiphenylacetyl)oxy]-1,1-dimethylpiperidinium bromide Reference(s): US 2 918 408 (Lakeside Labs.; 1959; prior. 1950). 3-chlom- benzilic 3-benziloyioxy- Formulation(s): tabl. 7.5 mg, 15 mg, 25 mg Mepenzolate bromide Trade Name(s): 1 -methyl- acid 1 -methylpiperidine piperidine F: Cantil (Roger Bellon); wfm Colum (Jamco) J: Eftoron (Maruko Seiyaku) GB: Cantil (M.C.P. Enterocantril (RBS Sachicoron (Zensei) Pharmaceuticals); wfm Pharma)-comb. Tendalin (Nihon Yakuhin) I: Cantril Lakeside (Roger Enterocantril (Roger Trancolon (Fujisawa) Bellon) Bellon)-comb. USA: Cantil (Hoechst Marion Colibantil (Tosi-Novara) Gastropidil (Fabo) Roussel) Mephenesin ATC: M03BX06 Use: muscle relaxant RN: 59-47-2 MF: c,,H,,o~ MW: 182.22 EINECS: 200-427-4 LD,,: 175 mg/kg (M, i.v.); 720 mgkg (M, p.0.); 133 mglkg (R, i.v.); 625 mgkg (R, p.0.) CN: 3-(2-methy1phenoxy)- 1,2-propanediol o-cresol (1) 3-chloro-1,2- propanediol 1246 M Mephenytoin Mephenesin 0 glycide Reference(s): a Marie, E.R.: J. Chem. Soc. (JCSOA9) 101, 310 (1912). b GB 628 497 (British Drug Houses; appl. 1948). Formulation(s): drg. 250 mg; tabl. 500 mg Trade Nnrne(s): D: Dolo Visano (Kade) Traumalgyl Relaxar (Bouty) F: Algipan Baume (Darcy)- (Pharmad6veloppement)- Relaxar Linimento comb. comb. (Bouty)-comb. DCcontractyl (Synthe1abo)- GB: Myanesin (Duncan, J: Curaresin (Kyoto) comb. Flockhart); wfm Myanol (Chugai) 1: Mefenesina (Tariff. Myoserol (Sankyo) Integrativo) USA: Tolserol (Squibb); wfm Mephenytoin (Methoin) ATC: N03AB04 Use: antiepileptic, anticonvulsant RN: 50-12-4 MF: CI2Hl4N2O2 MW: 218.26 EINECS: 200-012-8 LD,,,: 440 mglkg (M, p.0.); 850 mgkg (R, p.0.) CN: 5-ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione benzyl diethyl corbonote ethyl a-phenyl- (1) cyonide cyonoocetote ethyl bromide 2-cyono-2-phenyl- butyromide dimethyl sulfote (In) I Mephenytoin 5-ethyl-5- phenylhydontoin (U) Mepindolol M 1247 + NoCN + (NH4)2C03 propiophenone Reference(s): Ehrhart-Ruschig, Vol. 1, 196. DRP 309 508 (Chem. Fabrik von Heyden; appl. 1914). FR 769 667 (Sandoz; 1934). Formulation(s): tabl. 100 mg Trade Name(s): D: Mesantoin (Sandoz); wfm GB: Mesantoin (Sandoz); wfm USA: Mesantoin (Sandoz); wfrn F: SCdantoinal (Sandoz); wfm I: Mesantoina (Sandoz); wfm Mepindolol ATC: C07AA14 Use: beta blocking agent, antianginal RN: 23694-81-7 MF: C,,H22N20, MW: 262.35 EINECS: 245-831-1 CN: l-[(l-methylethyl)amino]-3-[(2-methyl-1H-indol-4-yl)oxy~-2-propanol sulfate RN: 56396-94-2 MF: C3,H,N404 . H2S04 MW: 622.78 4-benzyloxyindole-2- corboxylic acid 4-benzyloxy-2-di- methylaminornethyl- indole (I) methyl iodide 4-benzyloxy-2- methylindole 4-hydroxy-2-methyl- indole (Ill) 1248 M Mepitiostane H H C NH2 NoOH Y CH3 isopropyl- one VI epichloro- hydrin (N) 1 CH3 Mepindolol I 8' 0+ , benzoyl peroxide NoHCO,, OMSO N-brorno- b CHO H,c/O succinimide H,c/O H,c/O 2-methyl-3- nitroonisole 2-methoxy-6- nitrobenzyl bromide 2-rnethoxy-6- nitrobenz- oldehyde (W) nitro- ethane 1 -(2-methoxy-6- 4-methoxy-2- nitropheny1)-2- methylindole nitroprop-1 -ene NoOH 1 + N + v Fl Reference(s): a GB 1 260 907 (Sandoz; appl. 23.5.1969; BR-prior. 7.6.1968). Seemann, F. et al.: Helv. Chim. Acta (HCACAV) 54, 241 1 (1971). b DOS 2 905 054 (Schering AG; appl. 8.2.1979). combination with hydrochlorothiazide: DOS 3 027 392 (Schering AG; appl. 17.7.1980). Formulation(s): f. c. tabl. 2.5 mg, 5- mg (as sulfate) Trade Namefs): D: Corindocomb (Schering) Corindolan (Schering; as I: Betagon (Schering; as comb. with sulfate) sulfate) hydrochlorothiazide Mepicor (Corvi; as sulfate) Mepitiostane ATC: L02BA Use: antiestrogen, antineoplastic RN: 21362-69-6 MF: C,,H,,O,S MW: 404.66 CN: (2a,3a,5a,17~)-2,3-epithio-17-[(l-methoxycyclopentyl)oxy]androstane Mepivacaine M 1249 p-toluenesulfonic ocid tert-butanal H H epithiostonol 1 -methoxy- (q v.) cyclopentene ( Mepitiostane I Reference(s): DE 1 668 659 (Shionogi; appl. 27.1.1968; J-prior. 28.1.1967). US 3 567 713 (Shionogi; 2.3.1971; appl. 26.1.1968; J-prior. 28.1.1967). Trade Name(s): J: Thioderon (Shionogi; 1979) Mepivacaine ATC: NOIBBO~ Use: local anesthetic RN: 22801-44-1 MF: C,5H22N20 MW: 246.35 CN: (+)-N-(2,6-dimethylphenyl)-l-methyl-2-piperidinecarboxamide monohydrochloride RN: 1722-62-9 MF: C,,HZ2N2O . HC1 MW: 282.82 EINECS: 217-023-9 LD,: 32 mgkg (M, i.v.) ' ethyl 1-methyl / CH3 I piperidine- 2.6-dimethyl- ethyl- aniline mognesium bromide picolinic acid 2.6-xylidide (cf. bupivocaine synthesis) Mepivocoine H,. Pt-C. HCI (cH20)n . H~. Pd-C - aldehyde pipecalinic acid 2,6-xylidide 1250 M Meprednisone Reference(s): a US 2 799 679 (AB Bofors; 1957; S-prior. 1955). Ekenstam, 9. af et al.: Acta Chem. Scand. (ACHSE7) 11, 1183 (1957). Rinderknecht, H.: Helv. Chim. Acta (HCACAV) 42, 1324 (1959). b DOS 2 726 200 (Bofors; appl. 10.6.1977; S-prior. 22.6.1976). US 4 110 33 1 (Bofors; 29.8.1978; S-prior. 22.6.1976). analogous method with methylation before hydrogenation ofpyridine nucleus: GB 826 668 (Crookes Labs.; appl. 1955). D-(-)-mepivacaine: DOS 2 259 517 (Bofors; appl. 5.12.1972; USA-prior. 6.12.1971). Formulation(s): amp. 0.5 %, 1 %, 2 96, 3 %, 4 % (as hydrochloride) Trade Name(s): D: Meaverin (RhGne-Poulenc F: Carbocaine (Astra; as Mepident (Parke Davis) Rorer) hydrochloride) Mepiforan (Bieffe Medital) Mecain (curasan) GB: Estradurin (Lundbeck)- - Mepimynol (Molteni) Mepivastesin (Espe) comb.; wfm Optocain (Bayer) Scandicain (Astra) I: Carbocaina (Astra-Simes) J: Carbocain (Yoshitomi) numerous combination Carbocaina adrenalina USA: Polocaine (Astra; as preparations (Pierrel)-comb. hydrochloride) Meprednisone ATC: H02AB15 Use: glucocorticoid RN: 1247-42-3 MF: CzzH,,O, MW: 372.46 EINECS: 214-996-1 CN: (16P)-17,21 -dihydroxy-16-methylpregna-l,4-diene-3,11,20-trione _____, 1. diazo- . methane 4. OH- - 2. acetic anhydride. perchlaric acid 3. peroxobenzoic acid , 11 1. bromine 3. N-brama- succinimide . 2369 4-8 1-7 MF: C,,H22N20, MW: 262.35 EINECS: 24 5-8 3 1-1 CN: l-[(l-methylethyl)amino ]-3 -[ (2-methyl-1H-indol-4-yl)oxy ~-2 -propanol sulfate RN: 5639 6-9 4-2 MF: C3,H,N404 . H2S04 MW: 622.78 4-benzyloxyindole- 2-. nitroonisole 2-methoxy- 6- nitrobenzyl bromide 2-rnethoxy- 6- nitrobenz- oldehyde (W) nitro- ethane 1 -( 2-methoxy- 6- 4-methoxy- 2- nitropheny1 )-2 - methylindole nitroprop-1 -ene NoOH 1 +. glucocorticoid RN: 124 7-4 2-3 MF: CzzH,,O, MW: 372.46 EINECS: 21 4-9 9 6-1 CN: (16P )-1 7,21 -dihydroxy-16-methylpregna-l,4-diene-3,11,20-trione _____, 1. diazo- . methane 4. OH- - 2. acetic anhydride.