Flecainide F 861 hydrochloride RN: 3717-88-2 MF: C24H25N04. HCI MW: 427.93 EINECS: 223-066-4 LD,,: 28 mgkg (M, i.v.); 740 mgkg (M, p.0.); 25 mglkg (R, i.v.); 1040 mglkg (R, p.0.) salicylic propiony! P-propionyloxy- acid chloride benzoic acid 3-propionyl- salicylic acid (1) , 180-190 OC SOC12 I + b b n 0 0 sodium / CH3 benzoote benzoic anhydride 0 8-carboxy-3- methylflavone Reference(s): US 2 921 070 (Recordati; 12.1.1960; CH-prior. 5.1 1.1957). 8-chloroformyl- 1-(2-hydraxy- alternative synthesis: US 3 350 41 1 (Seceph; 31.10.1967; I-prior. 10.10.1963). Flavaxate Formulation(s): f. c. tabl. 200 mg; tabl. 100 mg (as hydrochloride) 3-methylflovone (11) ethy1)piperidine Tmde Name(s): D: Spasuret (Sanofi Winthrop) 1: Cistalgan (Recordat$ J: Bladderon (Nippon F: Urispas (Negma) comb. Shinyaku) GB: Urispas (Shire) Genurin (Recordati) USA: Urispas (SmithKline Beecham) Flecainide ATC: COlBC04 Use: antiarrhythmic RN: 54143-55-4 MF: C17H,F,N,03 MW: 414.35 CN: N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide acetate RN: 54143-56-5 MF: C17H20F,N203 . C2H402 MW: 474.40 862 F Fleroxacin O\\ 0 CF3 NOHC03 H2N4 H 0 + /s\( - F~C o ~~c-0 -I pyridine 2.5-dihydroxy- 2.2.2-trifluoro- 2.2,2-trifluoroethyl benzoic acid ethyl trifluoro- 2.5-bis(2.2.2-trifluoro- methonesulfonote eth0xy)benzoote (1) I Flecoinide Reference(s): DE 2 5 13 916 (Riker; prior. 27.3.1975). US 3 900 481 (Riker; 19.8.1975; prior. 1.4.1974). US 3 655 728 (Riker; 1 1.4.1972; prior. 22.7.1970). US 4 005 209 (Riker; 25.1.1975; prior. 27.5.1975). Bannit, E.H. eta].: J. Med. Chem. (JMCMAR) 18, 1130 (1975); 20, 821 (1977). Fomiulation(s): amp. 50 rng; tabl. 50 rng, 100 rng (as acetate) Trade Name(s): D: Tarnbocor (3M Medica; GB: Tarnbocor (3M Health J: Tarnbocor (Eisai) 1982) Care; 1983) USA: Tambocor (3M; 1985) F: FlCcai'ne (3M SantC; 1984) I: Almarytrn (Synthelabo; 1986) Fleroxacin (AM 833; Ro 23-6240; Megalocin) ATC: JOlMAO8 Use: antibacterial RN: 79660-72-3 MF: C,,H,,F,N,O, MW: 369.34 LD,,,: 20.4 mglkg (R, i. v.]; >4 glkg (R, p. 0.); 21.7 rnglkg (M, i. v.); >4 glkg (M, p. 0.); >I glkg (dog, p. 0.) CN: 6,8-Difluoro-l-(2-fluoroethyl)-l,4-dihydro-7-(4-rnethyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylicacid monohydrochloride RN: 79660-53-0 MF: C,,H,,F,N,O, . HCl MW: 405.80 6,7,8-trifluoro-4- 1 -bromo-2- hydroxy-3-quinoline- fluoroethone corboxylic acid (cf. lomefloxocin) 6.7.8-trifluoro-l- (2-fluoroethy1)-1.4- dihydro-4-oxoquinoline 3-corboxylic ocid (I) Floctafenine F 863 Reference(s): ' a BE 887 574 (Kyorin Pharm.; appl. 19.2.198 1; BE-prior. 19.8.1980). 1 ZA 8 502 065 (Kyorin Pharm.; appl. 20.3 1985; ZA-prior. 20.3.1985). b ES 2 010 862 (Inke S A.; appl. 13.2.1989). purification and recovery using porous absorbents: PO8 259 541 (Kyorin Seiyaku; appl. 23.3.1995). synthesis offluorine-labeled fleroxacin: Livni, E. et al.: Nucl. Med. Biol. (NMBIEO) 20 (I), 883-897 (1993) N-rnethyl- Formulation(s): amp. for inj. 400 mg; f. c. tabl. 200 mg, 400 mg; tab!. 200 mg, 400 mg; v1al400 mg1100 ml Fleroxocin Trade Name(s): D: Quinodis (Rochel Griinenthal) piperozine Floctafenine ATC: N02BG04 Use: analgesic RN: 23779-99-9 MF: CmHl,F3N204 MW: 406.36 EINECS: 245-881-4 LD,,: 180 mglkg (M, i.v.); 1960 mglkg (M. p.0.): 160 mglkg (R, i.v.); 535 mglkg (R, p.0.); >1 glkg (dog, p.0.) CN: 2-[[8-(trifluoromethyl)-4-quinolinyl]amino]benzoic acid 2,3-dihydroxypropyl ester 2-trifluoro- diethyl ethoxy- methyl- methylenemalonote oniline 864 F Flomoxef 3-ethoxycarbonyl-4- hydroxy-8-trifluoro- methylquinoline (I) 4-hydroxy-8- trifluoromethyl- auinoline HOTo O<CH, H3C NaH, toluene -, 111 4-chloro-8- methyl trifuoromethyl- anthronilate quinoline (11) '33 Floctatenine DE 1 815 467 (Roussel-Uclal; appl. 18.12.1968; F-prior. 29.12.1967,29.3.1968, 23.8.1968). US 3 644 368 (Roussel-Uclaf; 22.2.1972; F-prior. 29.12.1967,23.8.1968). US 3 818 090 (Roussel-Uclaf; 22.2.1972; prior. 7.7.1971). Formulation(s): tabl. 200 mg Trade Name(s): D: Idarac (Roussel; 1978); F: ldarac (Roussel Diamant; I: Idarac (Roussel; 1977) wfm 1976) Flomoxef (6315-S) ATC: J0lC Use: antibacterial (p-lactam antibiotic) RN: 99665-00-6 MF: C,,HlRF2N,O7S, MW: 496.47 CN: (6R-ci.~)-7-[[[(difluoromethyl)thio]acetyl]amino]-3-[[[l-(2-hydroxyethyl)-lH-tetrazol-5-yl]thio]methyl]- 7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Flomoxef F 865 @ side choin I: NaOC2H5 I. KOH Fyc! 0 C2H50H 0 2. HCI F F~s,,~~~~~~ - F S-COOH F Y F chloro- difluoro- methane ethyl (difluoro- rnethylthio)ocetate (difluorornethyl- thio)acetic acid (I) ethanalomine carbon disufide methyl N-(2-hydroxy- ethyl)dithiocorbornate (11) 1-(2-hydroxyethy1)- 1H-tetrozole-5-thiol (IV) 8 final product: NoOCH,, DMF N- diphenylrnethyl 7a-banzarnido-3- chlorornethyl-1 -oxo- 3-cepkm-4-corboxylote (cf. latomoxef synthesis) p-rnethyl- benzyl chloroforrnote 866 F Flopropione hypochlorite PI"?!; 1. PC15, pyridine 1. I, pyridine 2. NaHCO, VII CH3 ~suji, T. et a].: J. Antibiot. (JANTAJ) 38, 466 (1984). US 4 532 233 (Shionogi; 30.7.1985; J-prior. 23.12.1982). DOS 3 345 989 (Shionogi; appl. 20.12.1983; J-prior. 23.12.1982). EP 128 536 (Shionogi; appl. 7.6.1984; J-prior. 14.6.1983). purification: DOS 3 503 303 (Shionogi; appl. 31.1.1985; J-prior. 2.2.1984). Formulation(s): vial (dry substance for inj.) 500 mg, lg Trade Name(s): J: Flumarin (Shionogi) Flopropione ATC: A03A Use: antispasmodic RN: 2295-58-1 MF: C,H,,O, MW: 182.18 EINECS: 218-942-8 LD,,,: 300 mglkg (M, i.v.); 2780 mglkg (M, p.0.); 246 mg/kg (R, i.v.); 2380 mglkg (R, p.0.) CN: 1 -(2,4,6-trihydroxypheny1)- 1-propanone Florantyrone F 867 phloroglucinol propionitrile Flopropione Reference(s): Canter et al.: J. Chem. Soc. (JCSOA9) 1931, 1245. Shinoda, K.: Yakugaku Zasshi (YKKZAJ) 35,235 (1927). Howells et a].: J. Am. Chem. Soc. (JACSAT) 54, 2451 (1932). pharmacology: Cahen, R.; Boucherie, A,: C. R. Seances Soc. Biol. Ses Fil. (CRSBAW) 157, 112 (1963). Formukztion(s): cps. 40 mg; gran. 80 mg/g, 160 mg/g Trade Name(s): J: Chlonarin (Kanebo) Cospanon (Eisai) Colenfupan (Nichiiko) Pasmus (Daiichi) generic Florantyrone ATC: A03A Use: choleretic RN: 519-95-9 MF: C2,H1,O3 MW: 302.33 EINECS: 208-279-2 CN: y-0x0-8-fluoranthenebutanoic acid succinic fluoronthene onhydride I Florantyrone Reference(s): US 2 560 425 (Miles Labs.; 195 1; prior. 1948). Trade Name(s): I: Bilyn (Janus); wfm Idroepar (Beolet); wfm USA: Zanchol (Searle); wfm Cistoplex (Borromeo); wfm J: Zanchol (G.D Dainippon) Floredil ATC: COlDB Use: coronary vasodilator RN: 53731-36-5 MF: Cl,H2,N0, MW: 295.38 CN: 4-[2-(3,5-diethoxyphenoxy)ethyl]morpholine 868 F Flosequinan 2-morpholino- 3,5-diethoxy- I Floredil ethyl chloride phenol Reference (s): DOS 2 020 464 (Orsymonde; appl. 27.4.1970; GB-prior. 29.4.1969). Fnrmulation(s): cps. 200 mg Trude Name(s): F: Carfonal (Lafon); wfm Flosequinan (BTS 49037; BTS 49465) ATC: COlDBOl Use: vasodilator, antihypertensive RN: 76568-02-0 MF: CllH,oFN02S MW: 239.27 CN: 7-Fluoro- 1 -methyl-3-(methylsulfiny1)-4(1H)-quinolinone cu, cuc12. H20 F H COCI~ FaC' + H2N-CH1 b + I COOH 2-chloro-4-fluoro benzoic ocid 4-fluoro-N- methylonthranilic ocid 7-fluoro-1 -methyl- trirnethyl- 3.1 -benzoxozine- sulfoxonium 2.4-dione (I) iodide trimethyl orthoformate (111) dirnethyloxosulfonium 4-fluoro-2-(methylomino)- benzaylmethylide (11) I Flosequinan I Fluanisone F 869 111 I + II Flosequinan 0 - Fq3,cH3 - 0 0 dirnsyl sodium 1 -[4-fluoro-2- (methylomina)phenyl]- 2-(methylsulfinyl)- ethanone "Q"" + 3-fluoro- aniline phxO-ph IV d diphenyl ether Reference (s): methyl (methylthi0)- acetate methyl 3-(3-fluoro- aniline)-2-(methylthb- acrylate (IV) ?\ 1. H3C, ,S/O'CH~ 0 \b 2. MCPBA. CHZCIZ - Flosequinan 1. dimethyl sulfate 0 2. 3-chloroperbenzoic acid a DE 3 011 994 (Boots; appl. 27.3.1980; GB-prior. 27.3.1979). b,cBirch, A.M. et al.: J. Chem. Soc., Perkin Trans. 1 (JCPRB4) 1994, 387. EP317 149 (Boots; appl. 7.1 1.1988; GB-prior. 18.11.1987). Formulation(s): tabl. 50 mg, 100 mg Trade Name(s): GB: Manoplax (Boots) Fluanisone ATC: NOSAD09 Use: neuroleptic RN: 1480-19-9 MF: C2,H2,FN202 MW: 356.44 EINECS: 216-038-8 LDg: 25 mgikg (M, i.v.); 550 mglkg (M, p.0.); 20 mgkg (R. i.v.) CN: l-(4-fluorophenyl)-4-[4-(2-methoxyphenyl)-l-piperazinyl]-l-butanone I -(2-rnethoxy- 4-chloro-4'-fluoro- Fluonisone pheny1)piperazine butyrophenone 870 F Fluazacort Reference(s): DAS 1 185 6 15 (Janssen; appl. 25.3.1960; USA-prior. 26.3.1959). US 2 997 472 (Janssen; 22.8.1961; prior. 26.3.1959). Formulation(s): sol. 6.25 rnglrnl Trade Name(s): D: Sedalande (Delalande); F: Saalande (Delalande); wfrn wfrn Fluazacort (Azacortid) ATC: D07AB Use: topical glucocorticoid, anti- inflammatory RN: 19888-56-3 MF: C,sH,oFNO, MW: 459.51 EINECS: 243-400-2 LD,,,: 54 mgkg (M, s.c.); 580 rnglkg (R, s.c.) CN: (1 1~,16~)-21-(acetyloxy)-9-fluoro-11-hydroxy-2'-methyl-5'H-pregna-1,4-dieno[l7,16-d]oxazole-3,20- dione 3p-ocetoxy-11.20- dioxo- 16-pregnene (from hecogenin. cf. olfoxolone synthesis) pyridine + I 1. NoBH, 2. HCI, CHJOH CH3S02CI, O CH DMF, , ,, MXN+'HJ collidine . 6,8-Difluoro-l-(2-fluoroethyl)-l,4-dihydro- 7-( 4-rnethyl-1-piperazinyl )-4 -oxo-3-quinolinecarboxylicacid monohydrochloride RN: 7966 0-5 3-0 MF: C,,H,,F,N,O, . HCl MW: 405.80 6,7,8-trifluoro- 4-. ethyl)dithiocorbornate (11) 1-( 2-hydroxyethy1 )- 1H-tetrozole-5-thiol (IV) 8 final product: NoOCH,, DMF N- diphenylrnethyl 7a-banzarnido- 3- chlorornethyl-1 -oxo- 3-cepkm-4-corboxylote (cf. latomoxef. 6,7,8-trifluoro- 4- 1 -bromo- 2- hydroxy-3-quinoline- fluoroethone corboxylic acid (cf. lomefloxocin) 6.7.8-trifluoro-l- (2-fluoroethy1 )-1 . 4- dihydro-4-oxoquinoline 3-corboxylic ocid (I)