Heparin H 1001 Uzara plus (Uzara)-comb.; GB: Quixalin (Squibb); wfm w fm USA: Quinolor (Squibb); wfm Heparin ATC: BOIABOI; C05BA03 Use: anticoagulant, antithrombotic RN: 9005-49-6 MF: [C,,H,,N,O,sS,]x MW: unspecified EINECS: 232-681-7 LD,,,: 500 mglkg (M, i.v.); 1950 mglkg (R, p.0.) CN: mucopolysaccharide polysulfuric acid ester sodium salt RN: 9041-08- 1 MF: unspecified MW: unspecified LD,: 2800 mgikg (M, i.v.); >5 gkg (M, p.0.); 391821 idkg (R, i.v.); >779000 idkg (R, p.0.); I glkg (dog, i.v.) calcium salt RN: 37270-89-6 MF: unspecified LD,,: A0 gkg (M, i.v.); >40 gikg (R, i. v.) magnesium salt RN: 54479-70-8 MF: unspecified MW. unspecified MW: unspecified I Heparin (molar mass 6000-20000, according to origin) From animal tissue, especially bovine lung and liver (e. g. autolysis of comminuted tissue parts, heating with ammonium sulfate in alkaline solution, filtration and acidification yield heparin as complex with protein, removal of fat with alcohol and treatment with trypsine for the purpose of decomposition of proteins, precipitation with alcohol and various purification methods). Reference(s): review: Hind, H.G.: Manuf. Chem. (MACSAS) 34,510 (1963). purification: US 2 884 358 (Southerm California Gland Co; 28.4.1959; appl. 22.4.1957), US 2 989 438 (Uclaf; 20.6.1961; appl. 29.12.1958). DE 1 195 010 (Ormonoterapia Richter; appl. 12.5.1962). US 3 016 331 (Ormonoterapia Richter; 9.1.1962; I-prior. 28.1.1960). US 4 119 774 (AB Kabi; 10.10.1978; appl. 2.3.1977). GB 1 539 332 (AB Kabi; appl. 4.3.1977; S-prior. 5.3.1976). Formulation(s): amp. 12500 iu, 20000 iu, 50000 iu, 60000 iu; cream, eye drops and eye ointment 30000 iu, 60000 iu, 150000 iu (as sodium salt or calcium salt); syringe 5000 iu, 7500 iu. Trade Name(s): D: Calciparin (Sanofi Winthrop) Heparin-lnjekt (Immuno) Heparin-Na (Braun Melsungen; medac; Nattermann; ratiopharm) Heparin Novo (Novo) Heparin POS (Ursapharm) Heparin Riker (Riker) Liquemin (Roche) Thrombareduct (Azuchemie) Thrombophob (Knoll) Traumalitan (3M Med~ca; as sodium salt) Vetren (Klinge) numerous generic and combination preparations F: Calciparin (Sanofi Winthrop; as calcium salt) Dioparine (ThCa; as sodium salt) NCoparyl Framycttine (CIBA Vision 0phthalmics)-comb. numerous generic and combination preparations GB: Canusal (CP Pharm.) Clexane (RhGne-Poulenc Rorer) Fragmin (Pharmacia & Upjohn) Hepsal (CP Pharm.) Monoparin (CP Pharm.) generic and combination preparations I: Ateroclar (Mediolanum) Chemyparin (SIT) Clarisco (Schwarz) Disebrin (Allergan) Eparina (Tariff. Integrativo; Bristol-Myers Squibb; Manetti Roberts; Parke Davis) Eparinovis (Intes) Essaven Gel (RhGne- Poulenc Rarer)-comb. Flebs Crema (Pierre Fabre Phar.)-comb. Heparin Collirio (Farmigea) Idracemi Eparina (Farmigea)-comb. Lioton (Menarini) Liquemin (Roche; as sodium salt) Luxazone Eparina (Allergan)-comb. Normoparin (Opocrin) Venotrauma (Also)-comb. Viteparin (Teofarma)- comb. numerous generic preparations J: Caprocin (Mitsui; as calcium salt) Depo-Heparin (Upjohn- , Kodama; as sodium salt) Hepacarin (Eisai) Heparigen (Mukasa-Torii) Heparin Sodium (Tokyo Tanabe) Novo Heparin (Novo- Kodama) Panheprin (Nippon Abbott) numerous generic preparations USA: Heparin-Sodium (Wyeth- Ayerst) Hep-Lock (Elkins-Sinn) Hepronicate ATC: C04 Use: vasodilator RN: 7237-81-2 MF: C2,H3,N,06 MW: 505.57 LD,,,: 5 glkg (M, p.0.) CN: 3-pyr~d~necarboxylic acid 2-hexyl-2-[[(3-pyr1d1nylcarbonyl)oxy]methyl]-1,3-propaned1yl ester octanol 1 + pyridine 0 HO~OH H 0 2-hexyl-2-hydroxy- methyl- 1,3- proponediol (I) nicotinoyl Hepronicote chloride Heptabarb H 1003 Reference(s): US 3 384 642 (Yoshitomi; 21.5.1968; J-prior. 18.11.1964, 12.10.1965) Formulation(s): tabl. 100 mg Trade Name(s): I: Megrin (Yoshitomi) Heptabarb ATC: NOSCA~I (Heptabarbital; Heptabarbitone; Heptamalum) Use: hypnotic. sedative RN: 509-86-4 MF: Cl3HI8N2O3 MW: 250.30 EINECS: 208-107-6 LD,,: 180 mglkg (M, i.v.); >800 mglkg (M, p.0.); >S glkg (R, p.0.); 105 mglkg (dog, i.v.) CN: 5-(l-cyclohepten-l-yl)-5-ethyl-2,4,6(1H,3H,SH)-pyrimidinetrione H$"B~ , NOOCH~ +I CN ethyl bromide cyclo- methyl methyl heptanone cyanoocetate 1 -cycloheptenyl- cyanaacetate urea ( Heptobarb I Reference(s): FR 870 714 (Geigy; appi. 1941 ; Palestine-prior. 1940). DE 756 489 (Geigy; appl. 1941 ; Palestine-prior. 1940). Forrnulation(s): tabl. 200 mg Trade Name(s): D: Medomin (Geigy); wfm F: Medomine (Geigy); wfm GB: Medomin (Gcigy); wfm Heptaminol ATC: COlDX08 Use: cardiotonic, sympathomimetic RN: 372-66-7 MF: C8Hl9NO MW: 145.25 EINECS: 206-758-0 LD,,,: 1250 mgikg (M, i.p.) CN: 6-amino-2-methyl-2-heptanol hydmchloride RN: 543-15-7 MF: C,H,,NO. HCI MW: 181.71 EINECS: 208-837-5 LD,,: 900 mglkg (M, i.p.) 1004 H Hetacillin 180 OC H3C,p,yCH3 conc. HCI H3C~CH3 OHC-NH2-b 0 CH3 OHC/NH CH3 6-methyl- forrnarnide 5-hepten-2-one ~ejizrence(s): Dceuvre, I.; Pozat, I.: C. R. Hebd. Seances Acad. Sci. (COREAF) 224,286 (1947). Formulation(s): amp. 250 mg, 500 mg; drg. 50 mg; drops 50 mg/ml;tabl. 150 mg (as hydrochloride) Trade Name(s): D: Normotin (0TW)-comb. DCbmmyl (Pierre Fabre numerous combination Perivar (Intersan)-comb. Sant6)-comb. preparations F: Amptcyclal (Sargel) Sureptil (SynthClab0)- I: Coreptil (Delalande comb. Isnardi) Hetacillin ATC: JOlCA18 Use: antibiotic RN: 3511-16-8 MF: C,,HZ3N3O4S MW: 389.48 EINECS: 222-512-5 CN: [2S-[2a,5a,6~(S*)]]-6-(2,2-dimethyl-5-oxo-4-pheny-l-imidazolidinyl)-3,3-dimethyl-7-oxo-4-thia-l- azabicyclo[3.2.0]heptane-2-carboxylic acid monopotassium salt RN: 5321 -32-4 MF: C,,H,KN,04S MW: 427.57 EINECS: 226-182-3 LD,,,: 650 mglkg (M, i.v.); >15 gkg (M, p.0.); >1400 mgkg (R, i.v.); >I0 gikg (R, p.0.); 2200 mgkg (dog, 1.v.); >4 gkg (dog, p.0.) ONa , CH, ornp~c~ll~n sod~urn salt acetone Hetac~ll~n (q v) Reference(s): US 3 198 804 (Bristol-Myers; 3.8.1965; appl. 6.1.1965; prior. 25.1.1963). Formulation(s): amp. 250 mg, 500 mg, 1 g; tabl. 50 mg (as potassium salt) Trade Name(s): D: Penplenum (Bristol); wfm Etadipen (Ghimas)-comb. J: Natacillin (Banyu) F: Versapen (Allard); wfm with dicloxacillin; wfm USA: Versapen (Bristol); wfm I: Dicloeta (Lusopharma)- Versaclox (Bristo1)-comb. comb. with dicloxacillin; with dicloxacillin; wfm wfm Versapen (Bristol); wfm Heteronium bromide H 1005 Heteronium bromide AX: A03 Use: anticholinergic RN: 7247-57-6 MF: C, *H,,BrN03S MW: 41 2.35 LDs,,: 3576 mgkg (R, p.0.) CN: 3-[(hydroxyphenyl-2-thienylacety1)oxyl-1 ,l-dimethylpyrrolidinium bromide NaOCH,, n-C7HI6 sodium 0 H OH methylate I-methyl- phenyl- 3-pyrrolidinol (2-thieny1)- glycolic acid H,C-Br 1 b methyl bromide I Heteroniurn bromide us3 138 614 (Eli Lilly; 23.1.1964; prior. 18.12.1961, 3.8.1960). slarting material: US 2 830 997 (A. H. Robins; 1958; prior. 1956). Formulation(s): tabl. 1 mg Trade Name(s): I: Quentar (Ravizza)-comb. USA: Hetrum Bromide (Lilly); with oxazepam; wfm - wfm Hexachlorophene ATC: D08AE01 Use: topical antiinfective, disinfectant, parasiticide RN: 70-30-4 MF: C,,H6c160, MW: 406.9 1 EINECS: 200-733-8 LD,,: 67 mgkg (M, p.0.); 7500 @kg (R, i.v.); 56 mglkg (R, p.0.) CN: 2,2'-methylenebis[3,4,6-trichlorophenol] 1006 H Hexafluronium bromide I. oleurn I I 2. NaOH + (CH,O), 3. t12s04 , 1 clmcl 1 CI CI CI Refirence(s): . US 2 250 480 (B. T. Bush; 1941; appl. 1939). US 2 435 593 (B. 1: Bush; 1948; appl. 1945). US 2 8 12 365 (Givaudan Corp.; 1957; prior. 1951, 1954). 2,4.5-trichloro- poroform- Forniulation(s): cream 0.5 g1100 g; emulsion 0.5 gt100 g; lotion 0.5 gt100 g Hexachlorophene Trade Narne(s): D: Aknefug (Wolff) GB: Dermalex (Sanofi Phisohex disinf (Magg~om- Aknefug (Wo1ff)-comb. Winthrop)-comb. W1nthrop)-comb., wfm I with estrad~ol Ster-Zac D.C. (Seton) Vestene (Eurospital); wfm F: Acnestrol (Po1rier)-comb. 1: Etaproctene (Ange1ini)- USA: pHisoHex (Sanofi) comb.; wfm phenol oldehyde f Hexafluronium bromide ATC: ~03~~05' (Hexafluorenium bromide) Use: muscle relaxant RN: 3 17-52-2 MF: C,,H,,Br2N2 MW: 662.55 EINECS: 206-265-0 LD,,. 1760 pglkg (M, I.v.); 280 mglkg (M, p.0.) I CN: N,N-di-9H-fluoren-9-yl-N,N,N,W-tetramethyl- 1.6-hexanediam~nrum dihromide 9-bromo- 1,6-bis(dimethy1- fluorene amin0)hexane Hexafluronium bromide Reference(s): 1 US 2 783 237 (Irwin, Neisler & Co.; 1957; prior. 1953). Frtio(): amp. 20 mgln~l. 1 Trade Name(s): J: Mylaxen (Nippon Shoji); USA: Mylaxen (Mallinckrodt); Mylaxen (Wallace); wfm wfm wfm b Hexamethonium chloride H 1007 Hexamethonium chloride ATC: C02 Use: ganglionic blocker, antihypertensive RN: 60-25-3 MF: CI2H3,Cl2N2 MW: 273.29 EINECS: 200-465-1 LD,,,: 26.7 mglkg (M, i.v.); 35 mgkg (dog, i.v.) CN: N, N, N,N,N,N-hexamethyl- 1,6-hexanediaminium dichloride hexamethylenediamine dimethyl sulfate hexarnethanium sulfate (1) hexamethonium hydroxide I Hexomethonium chloride OH- OH- NaOH, C2H50H H3C\+/~~3 , , , H3C\+ CH3 Reference(s): DE 900 097 (May & Baker; appl. 195 1 ; GB-prior. 1950). CI- CI- H3C\+ Formulation(s): oral: 0.5 gld Trade Name(s): D: Raucombin forte (Voigt); Gastrometonio (Fabo; as w fm iodide); wfm 1: Gastrometonio (Fabo); J: Methobromin w fm (Yamanouchi); wfm Hexcarbacholine bromide (Carbolonium bromide) ATC: M03 Use: muscle relaxant RN: 306-41-2 MF: C,,H,,,Br,N,O, MW: 536.35 CN: N,N,N,N,N,N-hexamethyl-4,13-dioxo-3,14-dioxa-5,12-diazahexadecane-,16-diaminium dibromide H thionyl H H hem- ethylene methylene- carbonate diamine 1008 H Hexestrol ": 1. KBr I 1 1. potassium bromide 2. trimelhylamine H 1 Hexcorbacholine bromide 1 Reference(s): . DE 1 021 842 (Osterr. Stickstoffwerke; appl. 1954; A-prior. 1953). Formulation(s): amp. 2 mglml Trade Narne(s): D: lmbretil (Hormon- Chemie); wfm Hexestrol ATC: GO3 Use: estrogen, antineoplastic (hormonal) RN: 84-16-2 MF: C1XH2202 MW: 270.37 EINECS: 201-518-1 LDs": 1 g/kg (M, p.0.); >2 glkg (R, p.0.) CN: (R*,S*)-4,4'-(1,2-diethyl-l,2-ethanediyl)bisphenol @W3r, ether, toluene, CoCI2 b H C \O dBr phenylmagnesium cobalt(8) bromide chloride 1 -bromo-1-(4-meth- oxypheny1)propone (I) (cf. diethylstilbestrol synthesis) HI 11 * hydrogen iodide 1 Hexestrol 1 1. metals (Na. Mg. Ai, or Fe) 2. HI 1 1. (sodium, magnesium, aluminum, or iron) 2. hydrogen iodide Hexetidine H 1009 Reference(s): a Kharasch, M.S.; Kleimann, M.: J. Am. Chem. Soc. (JACSAT) 65,491 (1943) b Dodds, E.C. et a].: Proc. R. Soc. London, Ser. B (PRLBA4) 218,253 (1940). Bernstein, S.; Wallis, E.S.: J. Am. Chem. Soc. (JACSAT) 62, 2871 (1940). Buu-Hoi', N.G.; Hoan, N.G.: J. Org. Chem. (JOCEAH) 14, 1023 (1949). US 2 357 985 (Research Corp; 1944; appl. 1940). GB 523 320 (Boots; appl. 1938). FR 855 879 (Lab. Franc;. de ChimiothCrapie; appl. 1939). starting material: Bemstein, S.; Wallis, E.S.: J. Am. Chem. Soc. (JACSAT) 62,2871 (1940). alternative syntheses: Dockcn, A.M.;. Spielman, M.A.: J. Am. Chem. Soc. (JACSAT) 62,2163 (1940). US 2 392 852 (Lilly; 1946; prior. 1941). US 2 402 054 (Lilly; 1946; prior. 1941). US 2421 401 (Hoffmann-La Roche; 1947; S-prior. 1943). review: Solmssen, U.V.: Chem. Rev. (Washington, D. C.) (CHREAY) 36,481 (1945). Fonulation(s): pessaries 10 mg Trade Name(s): D: Malun (Temm1er)-comb.; wfm GB: F: Cycloestrol (Bruneau); J: wfm Micro-cristaux Cycloestrol USA: (Bruneau); wfm Synthrogene (Gerda); wfm Hexestrol and Phenorbital Synthovo (Boots); wfm (Jenkins)-comb.; wfm Robal (Chugai; as Hexestrol WlButabarb diacetate) (Bowman)-comb.; wfm Estra-Plex (Rowell); wfm Vagi-Plex (Rowell)-comb.; wfrn Hexetidine ATC: AOlAB12 Use: antiseptic antifungal RN: 141-94-6 MF: C2,H4,N3 MW: 339.61 EINECS: 205-513-5 CN: 1,3-bis(2-ethylhexyl)hexahydro-5-methyl-5-pyrimidinamine nitro- form- 2-methyl-2-nitro- ethane oldehyde (I) propane-1.3-diol I Hexetidine Reference(s): US 2 415 047 (Commercial Solvents; 1947; appl. 1945). US 3 054 797 (Commercial Solvents; 18.9.1962; prior. 1 1.10.1961), Senkus, M.: J. Am. Chem. Soc. (JACSAT) 68,161 1 (1946). 1010 H Hexobarbital pur$cation: DE 2 01 1 078 (Godecke; appl. 9.3.1970). DAS 2 355 917 (Meditest; appl. 8.1 1.1973). DOS 2 709 929 (Dolorgiet; appl. 8.3.1977). DOS 2 310 337 (Wiilfing; appl. 1.3.1973). DAS 2 323 150 (Wiilfing; appl. 8.5.1973). salts with aromatic acids: GB 1 538 603 (Doll; appl. 5.1 1.1976; D-prior. 6.11.1975, 3.6.1976, 16.6.1976). US 4 141 968 (Doll; 27.2.1979; D-prior. 16.6.1976). US 4 142 050 (Doll; 27.2.1979; D-prior. 6.1 1.1975,3.6.1976). nicotinate: DOS 2 310 338 (Wiilfing; appl. 1.3.1973). Fortnulation(s): sol. 100 mg1100 ml, 200 mg1100 ml; spray 0.1 dl00 g; vaginal tabl. 10 mg Trade Namc(s): D: Anginasin Spray (0pfermann)-comb. De-menthasin (Scheurich)- comb. Doreperol (Rentschler) F: Givalex (Norgine)-comb. Hexetidin Gurgellosung (ratiopharm) Hexoral (Warner-Lambert) Nifluril (UPSA) Hcxoral Spray (Warner- GB: Oraldene (Wamer- Lambert) Lambert) generic I: Oraseptic (Parke Davis) Collu-Hextril (Warner- USA: Sterisil (Warner Chilcott); Lambert) wfm Givalex (Norgine)-comb. Hextril (Warner-Lambert) Hexobarbital ATC: NO1 AF02; N05CA16 Use: hypnotic, sedative RN: 56-29- 1 MF: C,,Hl6N,O3 MW: 236.27 EINECS: 200-264-9 LD,,,: 133 mglkg (M, i.v.); 468 mglkg (M, p.0.) CN: 5-(1 -cyclohexen- 1 -yl)- 1,s-dimethyl-2,4,6(1 H,3H,SH)-pyrimidinetrione sodium salt RN: 50-09-9 MF: C12H1,N,Na0, MW: 258.25 EINECS: 200-009-1 LD,,,: 165 mglkg (M, i.v.); 1325 mglkg (M, p.0.); 1 gikg (R, p.0.) O+ /O'CH~ H~c.~/~+~ , NoOCH3 g + OyO- CH3 HN(C2H!j), b 3Lr3 11 'C N dimethyl sulfate (I) cyclo- methyl methyl hexonone cyono- 1 -cyclohexenyl- acetate cyonoocetate H + H2NKN\CN N H \ NH methyl 2-cyano- dicyono- 2-(1 -cyclohexenyl)- diomide propionate (11) . 351 1-1 6-8 MF: C,,HZ3N3O4S MW: 389.48 EINECS: 22 2-5 1 2-5 CN: [2S-[2a,5a,6~(S*)] ]-6 -( 2,2-dimethyl-5-oxo-4-pheny-l-imidazolidinyl )-3 ,3-dimethyl-7-oxo-4-thia-l- azabicyclo[3.2.0]heptane-2-carboxylic. RN: 37 2-6 6-7 MF: C8Hl9NO MW: 145.25 EINECS: 20 6-7 5 8-0 LD,,,: 1250 mgikg (M, i.p.) CN: 6-amino-2-methyl-2-heptanol hydmchloride RN: 54 3-1 5-7 MF: C,H,,NO. HCI MW: 181.71 EINECS: 20 8-8 3 7-5 LD,,:. relaxant RN: 3 1 7-5 2-2 MF: C,,H,,Br2N2 MW: 662.55 EINECS: 20 6-2 6 5-0 LD,,. 1760 pglkg (M, I.v.); 280 mglkg (M, p.0.) I CN: N,N-di-9H-fluoren-9-yl-N,N,N,W-tetramethyl- 1.6-hexanediam~nrum