Bcnzphetamine B 21 1 F: Cutacnyl (Galderma) Eclaran (Pierre Fabre) EffacnC (Roche-Posay) Pannogel (Labs. CS) Panoxyl (Stiefel) I: GB: Acnezide (Galderma) Acnidazil (Janssen-Ci1ag)- comb. Benzamycin (Biog1an)- comb. Nericur (Schenng) Panoxyl (Stiefel) Quinoderm (Quinoderm)- comb. Quinoped (Quinoderm)- comb. Acnidazil (Fisons ' 1talchimici)-comb. Benoxid (Brocades) Benzac (Galderma) Benioil Peros (Formulario Naz.) Benzomix (Savoma) Fatroxid (Fatro) Reloxyl (Rdc) USA: Benzac (Galderma) Benzagel (Dermik) Benzamycin (Dermik) Bcnzashave (Medicis) Brevoxyl (Stiefel) Desquam-E (Westwood- Squibb) Desquam-X (Westwood- Squibb) PanOxyl (S tiefel) Triaz (Medicis) Vanoxide-HC (Dermik) Benzphetamine Use: appetite depressant RN: 156-08-1 MF: C,,H,,N MW: 239.36 LDSO: 227 mglkg (M, p.0.); 160 mglkg (R, p.0.) CN: (+)-N,a-dimethyl-N-(phenylmethyl)benzeneethanamine hydrochloride RN: 541 1-22-3 MF: C,,H,,N . HCI MW: 275.82 EINECS: 226-489-2 Reference(s): US 2 789 138 (Upjohn; 1957; prior. 1952). (+)-deaxyephedrine benzyl chloride Formulation(s): tabl. 25 mg, 50 mg Benzphetarnine Trade Name(s): F: Inapelyl (Upjohn); wfm GB: Didrex (Upjohn); wfm Benzquinamide ATC: NOSAK Use: anti-emelic, tranquilizer RN: 63-12-7 MF: C22H32N20S MW: 404.51 CN: 2-(acety1oxy)-N,N-diethyl- 1,3,4,6,7, I1 b-hexahydro-9,1O-dimcthoxy-2H-benzo[n]quinolizine-3- carboxamide 2-(3,4-dimethoxy- diethyl rnalonote ethyl N-(3,4-dimethoxy- pheny1)ethylamine phenethy1)malonamate (I) 212 B Benzquinamide ethyl 3.4-dihydro-6.7-di- methaxy-1 -isoquinoline- acetate ethyl 1,2.3,4-tetrahydro- 6,7-dirnethoxy-1- isoquinolineocetate (11) ethyl ocrylate ethyl 1-ethoxycorbonylrnethyl- 1,2,3.4-tetrahydro-6,7-dimethoxy- 2-isoquinolineprapionote [Ill) ethyl 1.3.4.6.7.1 1 b-hexohydm- N.N-diethyl-1.3.4.6.7,ll b-hexahydro-9.10. dimethoxy-2-0x0-2H- 9,lO-dimethaxy-2-0x0-2H- benzo[o]quinalizine- 3-corboxylote benzo[a]quinolizine-3-corboxamide (N) H2. Roney -Ni -___+ benzo[a]quinolizine-3-corboxornide (V) acetic anhydride / Benquinornide I Rejierence(s): US 3 053 845 (Pfizer; appl. 29.8.1961). US 3 055 894 (Pfizer; appl. 9.3.1960). BE 621 895 (Pfizer; appl. 29.8.1962; USA-prior. 9.3.1960,29.8.1961). DE 1 303 628 (Pfizcr; appl. 30.5.1962; USA-prior. 29.8.1961.6.9.1961) starting material: Brossi, A. eta].: Helv. Chim. Acta (HCACAV) 41, 119 (1958). L'nrmrrlntinnlcJ. nmn 50 mu Benzthiazide B 213 Trade Name(s): D: Promecon (Endopharm) Promecon (Searle) USA: Emete-Con (Roerig) Benzthiazide (Benzothiazide; Benztiazide) ATC: C03 Use: diuretic, antihypertensive RN: 91-33-8 MF: C,5H,4C1N304S3 MW: 431.95 EINECS: 202-061-0 LD,,: 410mg/kg(M, i.v.); >5 glkg (M, p.0.); 422 mglkg (R, i.v.); >10 glkg (R, p.0.); >5 gtkg (dog, p.0.) CN: 6-chloro-3-[[(phenylmethyl)thio]methyl]-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,l-dioxide 5-chloro-2.4-diomino- chloro- 7-ominonulfonyl-6-chloro-3-(chlo;omethyl)- sulfonylaniline acetaldehyde 2H-1.2.4-benzothiadiozine 1.1-dioxide (I) Formulation(s): cps. 25 mg benzyl Trade Name(s): D: Sali-Raufuncton (Minden)- Tensimic (Roussel); wfm Regulon (Yamanouchi) comb.; wfm GB: Dytide (Pharmark)-comb. F: Diteriam (Roussel)-comb. with triamterene with triamterene; wfm J: Fovane (Taito Pfizer) Benzthiozide Benzydamine mercapton ATC: AOlAD02; G02CC03; MOlAX07; M02AA05; M02AX Use: analgesic, antipyretic, anti- inflammatory RN: 642-72-8 MF: C,,H,,N,O MW: 309.41 EINECS: 211-388-8 LD,: 25 mg/kg (M, i.v.); 460 mglkg (M, p.0.); 950 mglkg (R, p.0.) CN: N,N-dimethyl-3-[[l-(phenylmethyl)-1H-indazol-3-yl]oxy]-l-propanamine monohydrochloride RN: 132-69-4 MF: C,,H2,N3O . HCl MW: 345.87 EINECS: 205-076-0 LD,,,: 33 mg/kg (M, i.v.); 440 mglkg (M, p.0.); 43.5 mg/kg (R, i.v.); 740 mglkg (R, p.0.) 214 B Benzyl alcohol 1. HCI. NoN02 2.NoHS03 0 methyl benzyl onthronilate chloride 1. NoOCH3 2. CI-N~~~~ CH3 I 1. sodium methylote 2. 3-dimethylomino- propyl chloride methyl 2-benzyl- ominobenzaote Benzydomine 1 -benzyl-3-hydroxy- 1 H-indozole (I) 1 382 855 (Angelini Francesco; appl. 21.2.1964; I-prior. 9.8.1963). Formulation(s): amp. 25 mg; cps. 50 mg; cream 30 mg; drg. 50 mg; drops 50 mg; liquid 1.5 mg; powder 500 mg (as hydrochloride) Trade Narne(s): D: Tantum (Solvay Arzneimittel) F: Opalgyne (Innothtra) GB: Difflam (3M; as hydrochloride) I: Afloben (Esseti) Berzirin (Fater) Ginesal (Farmigea) J: Leucorsan (Zil1iken)-comb. Multum (Lampugnani) Benzyrin (Yoshitomi) Saniflor (Esseti) Enzamin (Kowa) Tantum Biotic (Ange1ini)- Epirotin (Nakataki) comb. with tetracycline Lilizin (Beppu) Verax (Tosi-Novara) Riripen (Daiichi) numerous combination Salyzoron (Hishiyama) preparations Sanal (Sana) Ant01 (Seiko Eiyo) Benzidan (Nikken) Benzyl alcohol ATC: R02AD (Alcoholum benzylicum; Phenylcarbinolum) Use: disinfectant, local anesthetic RN: 100-51-6 MF: C,H,O MW: 108.14 EINECS: 202-859-9 LD,,: 324 mglkg (M, i.v.j; 1360 mglkg (M, p.0.); 53 mgkg (R, i.v.); 1230 mgkg (R, p.0.) CN: benzenemethanol benzyl chloride Benzyl olcohol L Reference(s): Ullmanns Encykl. Tech. Chem., 4. Aufl., Vol. 8,437. Formulation(s): amp. 1 %, 2 %; cream 1 %; sol. 1 g1100 g Benzyl benzoate B 2 15 Trade Name(s): D: Spitacid (Henke1)-comb. GB: Pabrinex (Link)-comb. Foille (Delalande Isnardi) numerous combination Sudocrem (Tosara)-comb. comb. preparations I: Borocaina (Schiapparelli) Benzyl benzoate (Benzoesaurebenzylester) ATC: P03AXOl Use: scabicide, pharmaceutic agent RN: 120-51-4 MF: CI4Hl2O2 MW: 212.25 EINECS: 204-402-9 LD,,,: 1400 yUkg (M, p.0.); 1700 yL1kg (R, p.0.); >22440 mglkg (dog, p.0.) CN: benzoic acid phenylmethyl ester sodium benzyl benzooie chloride I Benzyl benzooie I Rejerence(s): Tharp, I.D. et al.: Ind. Eng. Chem. (IECHAD) 39, 1300 (1947). Formulation(s): emulsion 250 mg Trade Name(s): D: Acarosan (Allergopharma) Anusol HC (Warner- I: Antiscabbia Candioli a1 Antiscabiosum Mago KG Lambert)-comb. D.D.T. terap. (Candio1i)- (Strathmann) Ascabiol (RhGne-Poulenc comb. F: Ascabiol (Evans Medical) Rorer) Benz Be (Formulario Naz.; GB: Anugesic HC (Parke Tariff. Integrativo) Davis)-comb. Benzyl mustard oil (Oleum tropaeoli) ATC: SOlAA Use: antibiotic RN: 622-78-6 MF: C,H,NS MW: 149.22 EINECS: 210-753-9 LD,,,: 150 mg/kg (M, s.c.) CN: (isothiocyanatomethy1)benzene bemylomine omrnonium N-benzylthioureo hydrachloride rhodonide Rejerence(s): Ullmams Encykl. Tech. Chem., 4. Aufl., Vol. 23, 156 216 B Benzylpenicillin Trade Name(s): D: Soledurn (Cassella-rned)- comb. Benz ylpenicillin (Penicillin G) ATC: JOlCE01; JOlHA; SOlAA14 Use: antibiotic RN: 61-33-6 MF: C,,H,,N2O4S MW: 334.40 EINECS: 200-506-3 LD,,: 329 mglkg (M, i.v.); >5 &/kg (M, p.0.); 8 glkg (R, p.0.) CN: [2S-(2a,Sa,6~)]-3,3-dirnethyl-7-oxo-6-[(phenylacetyl)arnino]-4-thia-l-azabicyclo[3.2.0]heptane-2- carboxylic acid monosodium salt RN: 69-57-8 MF: C,,H,,N,NaO,S MW. 356.38 EINECS: 200-7 10-2 LD,,: 1500 rngkg (M, i.v.); >4 glkg (M, p.0.); 3020 mgkg (R, i.v.); 6916 rnglkg (R, p.0.) monopotassium salt RN: 113-98-4 MF: C,,H,,KN,04S MW: 372.49 EINECS: 204-038-0 LD,,: 240 rnglkg (M, i.v.); 6257 mgkg (M, p.0.); 243 mglkg (R, i.v.1; 8900 mgkg (R, p.0.) COOH Benzylpenicillin From fermentation solutions of Penicillium notatum Westling or Penicillium chrysogenum Thorn by addition of phenylacetic acid as precursor. Reference(s): Ehrhart, Ruschig IV, 286 ff. Formulation(s): eft'. tabl. 653.6 rng; f. c. tabl. 392.2 me, 653.6 rng, 982.32 rng; lyo. for syrup 1986.59 mg Trade Name(s): D: Megacillin (Griinentha1)- comb. Penicillin Heyl (Heyl) Prevecillin (Griinentha1)- (clemizol-penicillin) Tardocillin (Bayer)- (benzathine- benzylpenicillin) F: Biclinocilline (Sanofi Winthrop)-comb. Extencilline (Specia)- (benzathine- benzylpenicillin) Penicilline G Diarnant (Roussel Diarnant) GB: Bicillin (Yamanouchi)- comb. with procaine penicillin G Crystapen (Britannia) I: Benzil (Formulario Naz.) Penicillina Icar (SrnithKline Beecham) Penicillina Sod Farm (Farrnitalia) Penicillina Squibb (Bristol- Myers Squibb) J: Bicillin G (Wyeth-Banyo) USA: Bicillin (Wyeth-Ayerst). (benzathine- benzylpenicillin) Pen (Wyeth-Ayerst)- (penicillin V potassium) Pfizerpen G (Pfizer)- (penicillin G potassium) Sugracillin (Upjohn) Wycillin (Wyeth-Ayerst). (procaine-benzylpenicillin) Bephenium hydroxynaphthoate B 2 17 Bephenium hydroxynaphthoate ATC: ~02~x02 Use: anthelmintic RN: 3818-50-6 MF: C17H22N0 . CllH703 MW: 443.54 EINECS: 223-306-8 CN: N,N-dimethyl-N-(2-phenoxyethyl)benzenemethanamium 3-hydroxy-2-naphthoate (1:l) sodium 2-(dimethylomino)- N-(2-phenoxyethy1)- phenolate ethyl chloride dimethylomine Reference(s): US 2 918 401 (Rorroughs Wellcome; 22.12.1959; GB-prior. 29.3.1956). DE 1 117 600 (Wellcome Found.; appl. 21.3.1957; GB-prior. 29.3.1956, ,24.1.1957). bephenium chloride (I) sodium 3-hydmxy- Formulation(s): gran. 2.5 g, 4.33 g; powder 5 g Bephenium hydroxynophthoote Trade Namefs): 2-no~hthoote D: Alcopar (Wellcome); wfm J: Alcopar-P (Wellcome- USA: Alcopara (Borroughs F: Alcopar (Wellcome); wfm Tanabe) Wellcome); wfm GB: Alcopar (Wellcome); wIm Bepridil ATC: C02DE; C08EA02 Use: calcium channel blocker, antianginal RN: 64706-54-3 MF: C2,H3,N20 MW: 366.55 EINECS: 256-384-7 LD,: 1955 mgkg (M, p.0.); 23,s mgtkg (M, i.v.) CN: a-[(2-methylpropoxy)methyl]-N-phenyl-N-(phenylmethyl)-l-pyrrolidineethanamine monohydrochloride RN: 68099-86-5 MF: C24H,4N20 . HCl MW: 403.01 EINECS: 268-472-2 monohydrochloride monohydrate RN: 74764-40-2 MF: C2,H,,N20 . HCI . H,O MW: 421.03 LDsn: 23.5 mglkg (M, i.v.); 1955 mg/kg (M, p.0.); >21.3 mg/kg (R, i.v.); 6850 mg/kg (R, p.0.) (+)-form RN: 110143-74-3 MF: C2,H,,N20 MW: 366.55 (-)-form RN: 110143-75-4 MF: C2,H3,N20 MW: 366.55 (*)-form RN: 89035-90-5 MF: C2,H3,N,0 MW: 366.55 218 B Betacarotene epichloro- isobutonol glycide isobutyl ether 1 -(2-hydroxy-3-iso- hydrin butoxypropyl)pyrrolidine (1) SOCIZ. CHCI3 I thionyl chloride u N-benzyloniline I Bepridil Reference(s): DOS 2 3 10 918 (CERM; appl. 5.3.1973; F-prior. 6.3.1972). DE 2 802 864 (CERM; ap& 13.1.1978; F-prior. 25.1.1977). US 3 962 238 (CERM; 8.6.1976; appl. 27.2.1973; F-prior. 6.3.1972). GB 1 377 327 (CERM; appl. 27.2.1973; F-prior. 6.3.1972). GB 1 595 031 (CERM; appl. 13.1.1978; F-prior. 25.1.1977). Formulation(s): tabl. 100 mg Trade Narne(s): F: Cordium (Riom; 1981) J: Bepricor (Nippon Organon; USA: Vascor (Ortho-McNeil; as Sankyo; as hydrochloride hydrochloride) hydrate) Betacarotene @-Carotene; Betacarotin; p-Carotin) ATC: D02BBO1 Use: provitamin A RN: 7235-40-7 MF; C4&, MW: 536.89 EINECS: 230-636-6 CN: (all-E)-l,l'-(3,7,12,16-tetramethyl-l,3,5,7,9,11,13,15,17-octadecanonaene- 1,18-diyl)bis[2,6,6- trimethylcyclohexene] 1 Roche: "oldehyde C,," triethyl (cf. retinol synthesis) orthoformate (I) Betacarotene B 219 ethyl vinyl ether ethyl 1 -propenyl ether H,C CH CH CH, BrMg-C=C-MgBr H3P4, dbxane. H20 wCHO (from HCrCH and C,Hs-UpBr) V b Vl -CH, acetylenebis(mognesium bromide) Hz, Pd-Pb . vI1 H3 Lindlar catalyst 15-dehydro-@-carotene (VI) 80-100 "C in petraleum ether ______, Betacarotene EI 15-cis-@-carotene (VII) I Betacarotene I 220 B Betacarotene 2 BASF: retinol (VIII) triphenyl- (4. v.) phosphine KOH. CH,OH H202. K CO Ix - FJ Mn02 H3C WI OHC 4 \ ' CH, CH,~~~ CH3 retinal 1.4-dibromo- trimethyl 2-butene phosphite tetramethyl 2-butene- 1 -4-diylbisphosphonate HsC-0 3. H*O/H+ - XI 1. sodium methylate 2. rnethylglyoxal diethyl ocetol CH H~C CH~ CH, f3 OHC -HO + ydr, + FI CH3 - (all-E)-2.7-dirnethyl-2.4.6- triphenylphosphinylide octotrienediol (XI) from vinyl-8-ionol (cf. retinol synthesis) 3 Rhone-Poulenc: sodium benzenesulfinote retinyl phenyl sulfone (XII) . b-hexohydm- N.N-diethyl-1.3.4.6.7,ll b-hexahydro-9.10. dimethoxy- 2-0 x 0-2 H- 9,lO-dimethaxy- 2-0 x 0-2 H- benzo[o]quinalizine- 3-corboxylote benzo[a]quinolizine-3-corboxamide (N) H2. Roney -Ni -_ __+. anti-emelic, tranquilizer RN: 6 3-1 2-7 MF: C22H32N20S MW: 404.51 CN: 2-( acety1oxy)-N,N-diethyl- 1,3,4,6,7, I1 b-hexahydro-9,1O-dimcthoxy-2H-benzo[n]quinolizine- 3- carboxamide 2-( 3,4-dimethoxy-. CllH703 MW: 443.54 EINECS: 22 3-3 0 6-8 CN: N,N-dimethyl-N-(2-phenoxyethyl)benzenemethanamium 3-hydroxy-2-naphthoate (1:l) sodium 2-( dimethylomino )- N-(2-phenoxyethy1 )- phenolate ethyl chloride