Hexobendine H 101 1 Reference(s): DRP 595 175 (I. G. Farben; 193 1). DRP 590 175 (I. G. Farben; 1932). Formulation(s): amp. 0.5g15 g (10 %) (as sodium salt) Trade Name(s): D: Dormopan (Bayropharm)- F: Dormopan (Bayer- J: Cyclopan (Teikoku comb.; wfm Pharma)-comb.; wfm Kagaku-Nagase) Evipan (Bayer); wfm Noctivane (Vaillant- Oltopan (Dainippon) Stodinox (Lorem)-comb.; Defresne); wfm Ouropan Soda (Shionogi) wfm GB: Evidorm (Winthrop); wfm USA: Sombulex (Riker); wfm Hexobendine ATC: COIDX06 Use: coronary vasodilator RN: 54-03-5 MF: C,oHuN,O1o MW: 592.69 EINECS: 200-189-1 LD,,,: 34 mgkg (R, i.v.) CN: 3,4,5-trimethoxybenzoic acid 1,2-ethanediylbis[(methylimino)-3,l-propanediyl] ester dihydrochloride RN: 50-62-4 MF: C,oHuN,O,o. 2HCl MW: 665.61 EINECS: 200-054-7 LD,,: 35.2 mgkg (M, i.v.); 682 mgkg (M, p.0.); 52 mgkg (R, i.v.); 2550 mgkg (R, p.0.) methyl N.N'-dimethyl- acrylote ethylenediornine 1012 H Hexocyclium metilsulfate Reference(s): DE 1 217 397 (Lentia; appl. 26.3.1962). I1 + H3C-0 0 3.4,5-trimethoxy- benzoyl chloride' N,N-bis-(3-hydroxypropy1)-1,2-ethylenediamine from 1,2-dichloroethane and 3-aminopropanol: DAS 2 042 320 (Lentia; appl. 26.8.1970). 04VN@N~0 I 0 CH3 0-CH3 0'CH3 Hexobendine Formulation(s): amp. 10 mg; tabl. 30 mg, 60 mg Trade Name(s): D: Card-Instenon (Byk Reoxyl (Byk Gulden); wfm Ustimon (Merck- Gulden)-comb.; wfm F: Hityl (Biosedra)-comb.; Cltvenot); wfm Instenon (Byk Gulden)- wfm I: Flussicor (Farmalabor); comb.; wfm wfm Hexocyclium metilsulfate ATC: A03AB10 Use: antispasmodic, anticholinergic RN: 115-63-9 MF: C,,H,,N,O . CH,O,S MW: 428.59 EINECS: 204-097-2 LD,,,: 8900 pg/kg (M, 1.v.) CN: 4-(2-cyclohexyl-2-hydroxy-2-phenylethyl) 1,l-dimethylpiperazinium methyl sulfate (salt) 2-bromo- 1 -methyl- 4-methyl- 1 -(2-0x0- ocetophenane piperozine 2-phenylethy1)piperozine (1) dimethyl sulfote 1 Hexacycliurn mctilsulfote Reference(s): US 2 907 765 (Abbott; 6.10.1959; prior. 10.9.1956) Forrnulation(s): drops; f. c. tabl. 25 mg Hexoprenaline H 101 3 Trade Name(s): D: Traline retard (Abbott); F: Traline (Abbott); wfm USA: Tral (Abhott); wfm wfm I: Tral (Abbott); wfm Hexoprenaline ATC: R03AC06; R03CC05 Use: bronchodilator RN: 3215-70-1 MF: C22H32N20, MW: 420.51 CN: 4,4'-[1,6-hexanediylbis[imino(l-hydroxy-2,1-ethanediyl)]]bis[1,2-benzenediol] dihydrochloride RN: 4323-43-7 MF: C,,H,,N,O, .2HCI MW: 493.43 EINECS: 224-354-2 LD,: 88 mgkg (M, i.v.); 2036 mglkg (M, p.0.); 58 mglkg (R, i.v.); 10 glkg (R, p.0.) sulfate RN: 30117-45-4 MF: C22H,2N,0,.xH2S0, MW: unspecified EINECS: 250-057-2 NWdibenzyl- 2-chloro-3',4'- hexameihylene- dihydroxy- diomine ocetophenone Reference(s): DE 1 215 729 (Lentia; appl. 14.6.1963). US 3 329 709 (Osterr. Stickstoffwerke; 4.7.1967; A-prior. 11.6.1963). Formulation(s): aerosol 5.7 mg (as sulfate); amp. 0.005 mg, 0.025 mg; tabl. 0.5 mg (as sulfate) Trade Name(s): D: Etoscol (Byk Gulden); wfm I: Tocolysan (Byk Gulden; as J: Leanal (Yoshitomi; as sulfate) sulfate) Hexylcaine RN: 532-77-4 MF: C,6H,3N0, MW: 261.37 CN: I-(cyclohexylamino)-2-propanol benzoate (ester) ATC: NOlB Use: local anesthetic hydrochloride RN: 532-76-3 MF: C,,H2,N02. HCI MW: 297.83 EINECS: 208-544-2 LD,,: 23 mglkg (M, i.v.); 1080 mglkg (M, p.0.) Reference(s): US 2 486 374 (Sharp & Dohme; 1949; prior. 1944). Cope, A. et al.: J. Am. Chem. Soc. (JACSAT) 66,1453 (1944). benzoyl 1 -cyclohexylarnino- Formulation(s): amp. 1 %, 2 %; sol. (as hydrochloride) Hexylcaine Trade Name(s): USA: Cyclaine (Merck Sharp & Dohme); wfrn chloride 2-proponol hydrochloride Hexylresorcinol ATC: R02AA12 Use: anthelmintic, antiseptic RN: 136-77-6 MF: C,,H,,O, MW: 194.27 EINECS: 205-257-4 LD,,,: 1040 mgkg (M, p.0.); 550 mglkg (R, p.0.) CN: 4-hexyl- l,3-benzenediol resorcinol hexonoic acid Reference(s): DRP 488 419 (Sharp & Dohme; appl. 1923; USA-prior. 1923). DRP489 117 (Sharp & Dohme; appl. 1925; USA-prior. 1925). Dohme, A.R.L. et al.: J. Am. Chem. Soc. (JACSAT) 48, 1688 (1926). Twiss, D.: J. Am. Chem. Soc. (JACSAT) 48,2206 (1926). Formulation(s): cream 20 mg; drg. 2.4 mg; ointment 4.3 mg Trade Name(s): D: Hexamon (Beiersdorf- Mycatox (Bremer-Efeka)- Lil1y)-comb.; wfm comb.; wfm Jodo-Muc (Merz & Co.); GB: Kamillosan (Norgine)- wfm comb.; wfm CH3 Hexylresorcinol I: Oxana (Biologici Italia); wfrn Histapyrrodine ATC: R06AC02 Use: antihistaminic, antiallergic RN: 493-80-1 MF: C,,H,,N, MW: 280.42 EINECS: 207-781-9 CN: N-phenyl-N-(phenylmethy1)- 1-pyrrolidineethanamine L-Histidine H 1015 monohydrochloride RN: 61 13-17-3 MF: CI9H2,N2 . HC1 MW: 31 6.88 EINECS: 228-079-9 N-(%chloroethyl)- N-benzyl- pyrrolidine aniline hydrochloride Reference(s): US 2 623 880 (H. Hopff et al.; 1952; D-prior. 1948). GB 659 730 (BASF; appl. 1949; D-prior. 1948). Fonnulation(s): tabl. 25 mg (as hydrochloride) Histapyrrodine I Trade Name(s): D: Calcistin (Boehringer Calcistin (Hestia)-comb. Mannh.)-comb. with with calcium lactate; wfm calcium lactate; wh F: CrBme domistan vit. F (Servier); wfm. Domistan (Servier); wfm I: Calcistin (Roehringer Biochemia)-comb.; wfm ATC. M01 Use: essential proteinogen amino acid (for mfusion solutions), dletary supplement RN: 71-00-1 MF: C,H,N,O, MW: 155.16 EINECS: 200-745-3 LD,,,: >2 glkg (M, i.v.); >I5 gkg (M, p.0.); >2 g/kg (R, i.v.); >I5 gkg (R, p.0.) CN: L-histidine monohydrochloride monohydrate RN: 5934-29-2 MF: C,H,N,O,. HC1. H,O MW: 209.63 LD,,: >1.677 glkg (M, i.p.) Isolation from hydrolysates of blood meal by ion-exchange chromatography. Reference(s): Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed., Vol. A2, 70. Vickery, M.B.: J. Biol. Chem. (JRCHA3) 143.77 (1942). Formulation(s): sol. 0.25 gI100 ml (as hydrochloride) 1016 H Homatropine Trade Name(s): D: Histinorm (A.S.); wfm USA: NephrAmine (R & D) Homatropine (Omatropina) ATC: SOlFA05 Use: anticholinergic, antispasmodic, mydriatic RN: 87-00-3 MF: C,,H,,NO, MW: 275.35 EINECS: 201-716-8 CN: a-hydroxybenzeneacetic acid endo-(f)-8-methy1-8-azabicyclo[3.2.1]oct-3-y1 ester hydrobromide RN: 51-56-9 MF: C1,H,,NO, . HBr MW: 356.26 EINECS: 200-105-3 LD,,,: 107 mglkg (M, i.v.) COOH COOH - co2 OHC) + H3C-NH2 + OHC COOH succin- methyl- ocetonedi- tropinone-2.4- tropinone (I) oldehyde omine corboxylic dicorboxylic acid acid Hz, Ran,-Ni H'%9 OH I N _____* H~C' = (f )-rnondelic ocid H tropine Reference(s): DRP 95 853 (E. Tauber; appl. 1896). Homatropine Ladenburg, A,: Justus Liebigs Ann. Chem. (JLACBF) 217,75 (1883). Chemnitius, F.: J. Prakt. Chem. (JPCEAO) 117, 142 (1927). tropinone synthesis: Robinson, R.: J. Chem. Soc. (JCSOA9) 111,762 (1917); 111, 876 (1917). Schopf, C.: Angew. Chem. (ANCEAD) 50,779 (1937). racernate resolution: Werner, G.; Miltenberger, K.: Justus Liebigs Ann. Chem. (JLACBF) 631, 163 (1960). Formulation(s): eye drops 1 %; eye ointment 1 % (as hydrobromide) Trade Name(s): D: Homatropin POS 1 % I: Omatr Br (Formulario J: Homatropine Augentropfen (Ursapharm) Naz.; Tariff. Nazionale) hydrobromide (Torii) GB: Minims Homatropine Omatropina Lux coll. Hydrobromide (Chauvin) (Allergan) Homatropine methylbromide H 1017 Homatropine methylbromide (Methylhornatropine bromide) ATC: A07AA54 Use: anticholinergic, antispasmodic RN: 80-49-9 MF: C,7H24BrN03 MW; 370.29 EINECS: 201-284-0 LD,,: 1400 mgkg (M, p.0.); 12 mgkg (R, i.v.); 1200 mglkg (R, p.0.) CN: endo-3-[(hydroxyphenylacetyl)oxy]-8,8-dimethyl-8-azoniabicyclo[3.2. ]]octane bromide Reference(s): Cahen, R.L.; Tvede, K.: J. Pharmacol. Exp. Ther. (JPETAB) 105, 166 (1952). homatropine methyl Formulalion(s): eye drops I %, 2 %, 5 %; syrup 1.5 mg/5 ml, 5 mg15 ml; tabl. 1.5 mg, 5 mg Hornatropine methylbromide Trade Name(s): F: Entercine (Robapharm)- Ulfon (Lafon)-comb.; wfm I: Novatropina (ASTA comb.; wfm Vagantyl (Robapharm)- Medica) Supadol (Lederlej-comb.; comb.; wfm USA: Hycodan (Endo) wfm GB: APP (Consolidated); wfm Surparine (Licardy)-comb.; Vagantyl (Robapharm)- w fm comb.; wfm (9. v.) bromide Homofenazine ATC: NOSAK Use: neuroleptic, psychosedative RN: 3833-99-6 MF: C2,H,,F3N,0S MW: 451 S6 CN: hexahydro-4-[3-[2-(trifluoromethy1)- 10H-phenothiazin-10-yllpropyll-I H-1,4-diazepine-l -ethanol dihydrocldoride RN: 1256-01-5 MF: C23H2nF3N30S . 2HCl MW: 524.48 EINECS: 21 5-017-0 LD,,,: 73.5 mglkg (M, i.v.); 790 mglkg (M, p.0.); 102 mglkg (R, i.v.); 880 mgkg (R, p.0.) 2-trifluoromethyl phenothiazine 2. I -(3-chloropropyl)- hexahydro- 1,4-diazepine phenothiazine (1) 1018 H Hydralazine Reference(s): DE 1 160 442 (Degussa; appl. 18.2.1960). US 3 040 043 (Degussa; 19.6.1962; D-prior. 18.3.1959). 2-chloro- Formulation(s): tabl. 3 mg (as hydrochloride) Homofenorine Trade Name(sj: D: Pasaden (Homburg); wfm Seda-Ildamen (Homburg)- I: Pasaden (Farmades); wfm comb.; wfrn ethanol J Hydralazine ATC: C02DB02 Use: antihypertensive RN: 86-54-4 MF: C,H,N4 MW: 160.18 EINECS: 201-680-3 LD,,,: 52mgkg(M,i.v.); 122mgkg(M,p.o.); 34 mgkg (R, i.v.); 90 mglkg (R, p.0.); 50 mgkg (dog, i.v.); 100 mglkg (dog, p.0.) CN: l(2H)-phthalazinone hydrazone monohydrochIoride RN: 304-20-1 MF: C8H,N4. HC1 MW: 196.64 EINECS: 206-151-0 LD,,,: 84mgkg(M,i.v.); 188mg/kg(M,p.o.); 34 mgkg (R, i.v.) 0 1. Cl, 0 2. H20 hydrazine 0 phtholic phthalide onhydride hydrate (I) phthalozone (11) Reference(s): US 2 484 029 (Ciba; 1949; CH-prior. 1945). DE 848 818 (Ciba; CH-prior. 1945). Formulation(s): amp. 20 mg; drg. 10 rng, 25 mg, 50 mg; tabl. 25 mg, 50 mg (as hydrochloride) Hydrochlorothiazide H 1019 Trade Name(s): D: Docidrazin (Rhein-Pharma; Zenecabcomb. I~npresso-Puren (Isis Puren)-comb. pertenso (Fournier Pharma)-comb. Treloc (Astra1Promed)- comb. Trepress (Novartis ~harma)-comb. Td-Normin (Zeneca)- comb. GB: Apresoline (Novartis; as hydrochloride) I: Apresolin Retard (Novartis; as hydrochloride) J: Anaspasmin (Vitacain) Aprelazine (Kaigai) Apresoline (Novartis) Aprezine (Kanto) Basedock D (Sawai) Deselazine (Kobayashi Kako) Diucholin (Toyama) Homoton (Horii) Hypatol (Yamanouchi) Hypos (Nippon Shinyaku) Pressfall (Nissin) Propectin (Maruishi) Solesorin (Hishiyama) USA: Hydralazine Hydrochloride (SoloPak) Hydra-Zide (Par) Hydrochlorothiazide ATC: C03~~03 Use: diuretic RN: 58-93-5 MF: C7H8CIN304S2 MW: 297.74 EINECS: 200-403-3 LDso: 590 mgfkg (M, i.v.); 1175 rnglkg (M, p.0.); 990 mglkg (R, i.v.); 2750 mglkg (R, p.0.); 250 mglkg (dog, i.v.) CN: 6-chloro-3,4-dihydro-2H- l,2,4-benzothiadiazine-7-sulfonamide 1,l-dioxide 4-amino-6-chloro- poraform- benzene-1,S- aldehyde disulfarnide Hydrochlorothiazide 0 0 Hydrochlorothiazide + q. HCHO 5 CI chlorothiazide formaldehyde (4. v.) Reference(s): a US 3 163 645 (Ciba; 29.12.1964; appl. 25.9.1964; prior. 9.4.1958). Stevens, G. de et al.: Experientia (EXPEAM) 14,463 (1958). b US 3 164 588 (Merck & Co.; 5.1.1965; GB-prior. 19.6.1959). alternative syntheses: US 3 025 292 (Merck & Co.; 13.3.1962; prior. 26.11.1958). purification: US 3 043 840 (Merck & Co. 10.7.1962; appl. 14.10.1359). Formulatioiz(s): tabl. 12.5 mg, 25 mg, 50 mg, 100 mg 1020 H Hydrocodone Trade Name(s): D: Disalunil (Berlin-Chemie) diu melusin (Schwarz)- comb. Esidrix (Novartis Pharma) HCT-ISIS (Isis Puren) numerous generics and combination preparations F: Acuilix (ParKe Davis)- comb. Briazide (Pierre Fable)- comb. Esidrex (Novartis) Moducren (Merck Sharp & Dohme-Chibret)-comb. Moduretic (Du Pont Pharma)-comb. Prestole (SmithKline Beecham)-comb. Zestoretic (Zeneca)-comb. numerous generics and combination preparations GB: Hydrosaluric (Merck Sharp & Dohme) numerous combination preparations I: Accuretic (Parke Davis)- comb. Acediur (Guidotti)-comb. Aceplus (Bristol-Myers Squibb)-comb. Acequide (Recordati)- comb. Acesistem (Sigma-Tau)- comb. Aldactazide (SPA)-comb. Condiuren (Neopharmed)- comb. Esidrex (Novartis) lndroclor (Formulario . Naz.) Medozide (Malexi)-comb. Moduretic (Merck Sharp & Dohme)-comb. Prinzide (Du Pont)-comb. Quinazide (Malesci)-comb. Raunova Plus (SmithKline Beecham)-comb. Selozide (Astra)-comb. Spiridazide (SIT)-comb. Vasoretic (Merck Sharp & Dohme)-comb. Zestoretic (Zeneca)-comb. combination preparations J: Chloth~a (Iwaki) Dichlotride (Merck-Banyu) Esidrex (Novartis-Takeda) Maschitt (Showa Shinyaku) Mikorten (Zensei) Newtolide (Towa) Pantemon (Tatsumi) USA: Hydrochlorothiazide (Lederle) HydroDIURIL (Merck Sharp & Dohme) Hydropres (Merck Sharp & Dohme)-comb. Oretic (Abbott) . Timolide (Merck Sharp & Dohme)-comb. generic and combination preparations Hydrocodone ATC: R05DA03 Use: antitussive, narcotic analgesic RN: 125-29-1 MF: C,*H,,NO, MW: 299.37 EINECS: 204-733-9 LD,,,: 8.57 mglkg (M, s.c.); CN: (5a)-4,5-epoxy-3-methoxy-l7-methylmorphinan-6-one bitartrate hydrate RN: 34195-34-1 MF: C,,H,,NO,. C4H60c 5/2H20 MW: 988.99 LD,,,: 375 mglkg (R, p.0.) hydrochloride RN: 25968-91-6 MF: C,,H21N0,. HCl MW: 335.83 EINECS: 247-382-7 Pd or Pt, A isomerizotion CH3 Reference(s): Ehrhart, Ruschig I, 1 19-120. DRP 607 93 1 (Knoll; 1935). DRP 6 17 238 (Knoll; 1935). DRP 623 821 (Knoll; 1935). codeine Formulation(s): amp. 15 mglml (as hydrochloride); syrup 5 mg/5 ml, 100 mg15 ml; tabl. 5 mg, 10 mg (as bitartrate hydrate) Hydrocodone . EINECS: 20 4-0 9 7-2 LD,,,: 8900 pg/kg (M, 1.v.) CN: 4-( 2-cyclohexyl-2-hydroxy-2-phenylethyl) 1,l-dimethylpiperazinium methyl sulfate (salt) 2-bromo- 1 -methyl- 4-methyl- 1 -( 2-0 x 0- ocetophenane. hexahydro- 4-[ 3-[ 2-( trifluoromethy1 )- 10H-phenothiazin-10-yllpropyll-I H-1,4-diazepine-l -ethanol dihydrocldoride RN: 125 6-0 1-5 MF: C23H2nF3N30S . 2HCl MW: 524.48 EINECS: 21 5-0 1 7-0 LD,,,:. p.0.); 250 mglkg (dog, i.v.) CN: 6-chloro-3,4-dihydro-2H- l,2,4-benzothiadiazine-7-sulfonamide 1,l-dioxide 4-amino-6-chloro- poraform- benzene-1,S- aldehyde disulfarnide Hydrochlorothiazide