I Sobrerol S 1881 / Trade Name(s). J: Son~filan (Ta~to Pfizer) Sobrerol (Pinolhydrat) ATC: R05CB07 Use: respiratory stimulant, secretolytic, mucolytic RN: 498-71-5 MF: C,,,H,,O, MW: 170.25 EINECS: 207-868-1 LD,,,: 580 mg/kg (M, i.v.) CN: 5-hydroxy-a,a,4-trimethyl-3-cyclohexene-l-methanol (+)-u-pinene (2)-a-pinene 1 Sobrem oxide H3C peroxyacetic H3C H3C acid H3C Reference(s): US 2 815 378 (Glidden; 3.12.1957; appl. 12.6.1-953). DE 1 096 348 (FMC; appl. 26.10.1959). DE 2 114 138 (C. Corvi; appl. 24.3.1971; I-prior. 17.4.1970). 0 H medical use: DE 2 166 355 (Camillo Corvi; appl. 24.3.1971; I-prior. '17.4.1970). GB 1 176 817 (C. Corvi; appl. 8.12.1967; NL-prior. 9.12.1966). Forrnulation(s): cps. 200 mg; gran. 100 mg, 300 mg; suppos. 20 mg, 100 mg, 200 mg; syrup 0.8 % Trade Name(s): I: Fluental (Corvi)-comb. Sobrepin (Roche) Polimucil (Po1i)-comb. Sopulmin (Scharper) Sobuzoxane (MST 16) ATC: LO1 Use: antineoplastic, topoisomerase II- inhibitor RN: 98631-95-9 MF: C22H74N4010 MW: 514.53 LD,,,: >I glkg (M, p.0.); >5 g/kg (R, p.o.1; >3 g/kg (dog, p.0.) CN: carbonic acid 1,2-ethanediylbis[(2,6-dioxo-4,1-piperazinediyl)methylene] bis(2-methylpropyl) ester 1,2-bis(3,5-dioxo- piperazin-1 -yl)- ethane (from ethylenediomine tetraacetic acid) 1.2-bis(4-hydroxymethyl- 3,5-dioxopiperozin-1 -yl)- ethone (I) 1882 S Sodium aurothiomalate Refercnce(s): EP 140 327 (Zenyaku Koguo Co.; appl. 23.10.1984; J-prior. 3 1.10.1983). isobutyl chlaroformote E-ondution(s): sachets containing gran. 400 mg, 800 mg, 1200 mg, 1600 mg Soburoxone Trade Nume(s): J: Perazolin (Zenyaku Koguo) Sodium aurothiomalate (Gold Sodium Thiomalate) ATC: MOlCBOl Use: gold therapeutic (antirheumatic, antiarthritic) RN: 12244-57-4 MF: C,H,Au04S . xNa MW: unspecified EINECS: 235-479-7 CN: sodium [mercaptobutanedioato(2-)]aurate(2-) free acid RN: 24145-43-5 MF: C,H,Au04S MW: 346.14 EINECS: 246-034-1 HS COOH Aul + LEL. 1 1 'COOH gald(l) thiornolic iodide ocid Sodium aurothiornalote I Fonnulution(s): amp. 10 mg, 20 mg, 50 mg Trade Natne(s): D: Tauredon (Byk Gulden; GB: Myocrisin (IHC) USA: Myochrysine (Merck) By k Tossc) J: Kidon (Ono) Sodium dioctyl sulfosuccinate ATC: A06A (Dioctyl sodium sulfosuccina~e; Docusatc sodium) Use: laxative, detergent, emulgator, cerumenoly tic RN: 577- 1 1-7 MF: C,,H,,NaO,S MW: 444.57 EINECS: 209-406-4 CN: sulfobutanedioic acid 1,4-bis(2-ethylhexyl) ester sodium salt Ip Sodium dioctyl sulfosuccinate S 1883 calcium salt RN: 128-49-4 MF: C40H74CaO14S, MW: 883.23 EINECS: 204-889-8 potassium salt RN: 7491-09-0 MF: C20H,7K0,S MW: 460.67 EINECS: 231-308-5 COOH $ + COOH furnaric acid NaHSO, 1 b sodium hydrogen sulfite Reference(s): CH3 2-ethyl- l -hexan01 bis(2-ethylhexyl) furnarate (1) I Sodium dioctyl sulfosuccinote US 2 028 091 (American Cyanamid; 1936; appl. 1933). US 2 176 423 (American Cyanamid; 1939; appl. 1936). calcium salt: US 3 035 973 (Lloyd Brothers Inc.; 1962; appl. 1958). Formulation(s): drg. 5 mg; drinking amp. 50 mg, 100 mg; suppos. 10 rng; syrup 20 mg/5 ml; tabl. 2.5 mg, 5 mg, 50 mg Trade Narnefs): D: Agaroletten (Warner- Lambelt)-comb. Florisan (Boehringer 1ng.)- comb. Laxagetten (ct- Arzneimitte1)-comb. Otowaxol (Norgine)-comb. Potsilo (Stark, Konstanz)- comb. Tirgon (Woe1m)-comb. further combination preparations F: Jamylbne (Expanpharm) Norgalax (Norgine Pharma) GB: Klyx (Ferring); wfm Solivax (Concept); wfm numerous combination preparations I: Dorbantyl (Robins)-comb.; wfm Fisiolax (Manetti Roberts)- comb.; wfm Ikelax (1keton)-comb.; wfn~ Lambanol (Zi1liken)- comb.; wfm Sorbichs (Pharkos)-comb ; wfm Tiplcol (Blomedica Foscama)-comb.; wfm J: Bulkosol (Elsai) USA: Colace (Roberts) Modane Plus (Savage) Modane Soft (Savage) Peri-Colace (Roberts) Senokot-S (Purdue Frederick) genencs and further combination preparations 1884 S Sodium picosulfate Sodium pk0~dfd.e ATC: A06AB08 (Natrium-picosulfat; Picosulfate sodium; Sodium Use: laxative picosulphate) RN: 10040-45-6 MF: C,,H,,NNa,O,S, MW: 481.41 EINECS: 233-120-9 LD,,,: 1600 mglkg (M, i.v.); 14.5 g/kg (M, p.0.); 1450 mg/kg (R, i.v.); 17 g/kg (R, p.0.) CN: 4,4'-(2-pyridinylmcthy1ene)bisphenol bis(hydrogen sulfate)(ester) disodium salt 1. CIS03H, pyridine 2. NaOH _______* 1. chlarosulfonic acid 0 H 2-(4.4'-dihydroxybenz- hydly1)pyridine (cf, bisacodyl) US 3 528 986 (De Angeli; 15.9.1970; appl. 22.8.1966). alternative synthesis (with amidosulfonic acid or pyridine sulfur ~rioxide adducr) DOS 1 904 322 (Dr. K. Thomae; appl. 29.1.1969). Formulution(.sJ: drg. 5 mg; drops 7.5 mglml; tabl. 1.25 mg, 5 mg Trade Namc.(s): D: Agiolax (Madaus) Regulax (Krewel Dalcolax (Boehringer Ing.) Meuielbach) Laxoberal (Boehringer GB: Laxoberal (Windsor) Ing.) Picolax (Felling)-comb. Mandrolax Pico (Dolorgiet) I: Falquigut (Falqui) Midro (Midro) Gocce Antonetto (Antonetto) Gocce Lassative Aicardi (SIT) Guttalax (Fher) Sofalcone (SU-88) ATC: A02B Use: ulcer therapeutic RN: 64506-49-6 MF: C,,H,,,O, MW: 450.53 LD,,,: 131 mglkg(M,i.v.);>10g/kg(M, p.0.); 105 mglkg (R, i.v.); >I0 g/kg (R. p.0.); >20 glkg (dog, p.0.) CN: (5-[(3-methyl-2-butenyl)oxy]-2-[3-[4-[(3-methyl-2-butnyl)oxy]phenyl]-I-oxo-2- propenyl]phenoxy]acetic acid OH 0 KOH or K2C0,/acetone 2'.4'-dihydroxy- prenyl bromide acetophenone Sorbitol S 1885 ethyl bromo- ocetote 2'-ethoxycorbonylmethoxy- 4'-(3-methyl-2-buienyloxy)- ocetophenone (11) Sofolcone 1 Reference(s): DE 2 705 603 (Taisho; appl. 10.2.1977; J-prior. 13.2.1976). US 4 085 135 (Taisho; 18.4.1978; appl. 11.2.1977; J-prior. 13.2.1976). synthesis of intermediate I: Kyogoku, K, et al.: Chem. Pham. Bull. (CPBTAL) 27, 2943 (1979). Formulation(s): cps. 50 mg, 100 mg; gran. 10 % Trade Name(s): I: Solon (Taisho; 1984); wfm Sorbitol (D-Glucitol) RN: 50-70-4 MF: C6H& MW: 182.17 CN: ~-glucitol ATC: A06Ati07; B05CX02; V04CCO1 Use: osmotic, laxative EINECS: 200-061-5 OH Sorbitol ~llmanns Encykl. Tech. Chem., 4. Aufl., Vol. 24,772. Formulation(sj: sol. 13.4 gl67.5 ml, 400 gll0OO ml; clysma 200 gllOO0 ml; susp. 48 gll20 ml, 96 g1240 ml Trade Name($ j: D: 1 x klysma Sorbit Klistier Sorbitol-Infusionslosung numerous combination (Pharmacia & Upjohn) 40 (Braun Melsungen) preparations Mikroklist (Pharmacia & Yal (Trommsdorff) F: Arnilose (ATC Pharma) Upjohn)-comb. 1886 S Sorivudine HCpagrume (Rosa- Phy topharma) HCpargitol (ElertC) Sorbitol Aguettant (Aguettant) Sorbitol Delalande (S ynthelabo) numerous combination preparations GB: Glandosane (Fresenius)- comb. Relaxit (Crawford)-comb. combination preparations only I: Sorbilande (Delalande) numerous combination preparations J: Sorbit Inj. (Nikken Kagaku) D-Sorbitol Solution (Maruishi) Sorbit TS Inj. (Termo) USA: Actidose (Paddock)-comb. Sorbitol Sodium (Pharmaceutical Associates) Sorivudine (BVAU) Use: antiviral RN: 77 181-69-2 MF: C,,H,,BrN,O, MW: 349.14 LD,,,: >8 glkg (R, p. 0.); >2 glkg (R, s. c.); >10 glkg (M, p. 0.); >5 glkg (M, s. c.); >5 glkg (dog, p. o.) CN: (~)-l-~-~-Arabinofuranosyl-5-(2-bromoethenyl)-2,4(1H,3H)-pyrimidinedione I 0 H 1 -8-D-orabino- parafarrn- furanosyluracil (I) aldehyde (11) HCI or NaOH ____) I OH 5-(hydroxyrnethy1)- 1 -8-D-arabinofuranosyl- uracil (In) 0 0 0 HCI, dioxone 111 0'g3 2. BuLi, 11 1 triphenyl- phosphine 2. butyllithiurn. paraform- 0 H aldehyde Br2. DMF IV * I Sorivudine Sorivudine S 1887 1. 11, HCI 2. o2 I b OH 5-formyl-l-p-D- arobinafuronosyl- uracil (V) 2. NaOH, H20, dioxane N -co2 ______, Sorivudine pyridine , DMSO 2. NaOH. H20, dioxone VI1 b I Sorivudine 1 r bromine. 1.2-dichlaroethane Reference{s): a EP 031 128 (Yamasa Shoyu; appl. 1.7.1981; J-prior. 19.12.1979). b JP 59 163 39.5 (Yamasa Shoyu Co.; appl. 14.9.1984; J-prior. 8.3.1983). c JP 58 062 195 (Yamasa Shoyu Co.; appl. 14.4.1983; J-prior. 8.10.1981). d DD 280 763 (Akademie der Wissenschaften der DDR; appl. 18.7.1990; DD-prior. 4.8.1981). nurleic acid related compounds: Robins, M.J., Manfredini, S.: Tetrahedron Lett. (TELEAY) 31 (39), 5633 (1990). .facile uccess to 2'-0-acetylprodrugs of l-(~-~-arabinofuranosyl) 5(E)-(2-bromovinyl)uracil: Baraldi, P.G.; Bazzanini, R.; Manfredini, S.; Simoni, D.; Robins, M.J.: Tetrahedron Lett. (TELEAY) 34 (19), 3177 (1993). .rynrhesis and antiviral activity of(@-5-(2-bromoviny1)uracil: De Clercq, E. et a].: J. Med. Chem. (JMCMAR) 29,213 (1986) Formulation{s): tabl. 50 mg Trade Nume(s): J: Usevir (Nippon Shoji KaishdEisai; 1993); wfm Sotalol ATC: C07AA07 Use: beta blocking agent, anlianginal, antihypertensive RN: 3930-20-9 MF: CI,H,,N2O3S MW: 272.37 LD,,,: 166 mglkg (M, 1.v.) CN: N-[4-[l-hydroxy-2-[(1-methylethyl)amino]ethyl]phenyl]methanesu1f011amide monohydrochloride RN: 959-24-0 MF: C,2H20N20$ .HCI MW: 308.83 EINECS: 213-496-0 LD,,,: 2600 mgkg (M. p.0.); 3450 mglkg (R, p.0.) methonesulfonyl aniline methanesulfon- chloride onilide Refc.rence(s): Uloth, R.H. el a].: J. Med. Chem. (JMCMAR) 9, 88 (1966) Sparfloxacin S 1889 1 Formdotion(s): amp 20 mg/2 m1. 40 mgl4 ml; tab1 40 mg, 80 mg, 160 mg, 240 mg Tmde Name(s): D: CorSotalol (durachemie) Darob (Knoll) Gllucor (Solvay Arzne~mlttel) Sotalex (Brlstol-Myers Squ~bb) Sotazlden (Bristo1)-comb. Tachytalol (ASTA Medlca AWD) various generics Tolerzide (Bristol-Myers)- F: Sotalex (Bristol-Myers comb.; wfm Squibb) I: Betades (Farmades) GB: Beta-Cardone (Evans) Sotalex (Bristol-Myers Sotacor (Bristol-Myers Squibb) Squibb) USA: Betapace (Berlex; as Sotazide (Rristol-Myers)- hydrochloride) comb.; wfm I: Sparfloxacin ATC: JOIMAOI) (AT-4140; Ci-978; CP 103826; PD-13 1501; RP-64206) antlbacterla' RN: 110871-86-8 MF. C,9H22F2N40, MW: 392.41 LD,. >5 glkg (R, p. 0.); >2 glkg (R, s c.); >2 glkg (M, p. 0.); >2 glkg (M, s. c.); > 600 mglkg (dog, p. 0.) CN: ns-5-Amino-I-cyclopropyl-7-(3,s d1methyl-l-piperaz1nyl)-6,8-difluoro-1,4-dihydr~-4-~~~-3- qulnolinecarboxylic acid , , HJC-OyO-CH3 O-CH, 2. D-~''2. diethyl ether 'kOVcH, F 1. ethyl orthoformote FOO 2. cyclopropylornine pentofluoro- molonote ethyl pentofluoro- benzoic ocid benzoylacetote K,C03. CH,CN 2. HS. Pd-C. C2H50H 0uCH3 1. benrylomine FOO FOO (1) ethyl 5.6.7.8-tetrafluoro- corboxylote 5-omino- lcyclopropyl- 6,7,8-trifluoro-4-0x0- 1,4-dihydroquinoline- 3-corboxylic acid (In) cis-2,6-dimethyi- I Sparfloxacin HNq Ill + pyridine H3C Ad+ piperazine I HN v H~~~~~J), F COOH H,N 0 Ref~rence(s): Miyamoto, T. et al.: J. Med. Chem. (JMCMAR) 33, 1645.1656 (1990). EP 221 463 (Dainippon; appl. 23.10.1986; J-prior. 29.10.1985). synthesis of ethyl pentafluorobenzoylacetate: Clay, R.J.; Collom, T.A.; Karride, G.L.; Wemple, J.: Synthesis (SYNTBF) 3,290 (1993) Forntulution(s): f. c. tabl. 200 mg; tabl. 100 mg, 150 mg Trade Nante(s): D: Zagam (Rhhe-Poulenc J: Spara (Dainippon) USA: Zagam (Rh8ne-Poulenc Rorer) Zagam (Dainippon) Rorer) F: Zagam (Specia) Spectinomycin (Actinospectacin) AX: JOIXXO4 Use: antibiotic RN: 1695-77-8 MF: C,,H,N2O7 MW: 332.35 EINECS: 216-91 1-3 LDio: 2 glkg (M, i.v.); >5 glkg (R, p.0.) CN: [2R-(2a,4afi,5afi,6fi,7fi,8fi,9a,9aa,I0afi)]-decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)~ 4H-pyrano[2,3-b][1,4]benzodioxin-4-one dihydrochloride pentahydrate RN: 22189-32-8 MF: C,,Hz4N20,, 2HCI . 5H20 MW: 495.35 LD,,,: >I 0 mglkg (M, p.0.); - >5 glkg (R, p.0.) Spectinomycin Froin culture of Streptontyces spectubilis. Reference(s): US 3 206 360 (Upjohn; 14.9.1965; prior. 18.6.1962). US 3 234 092 (Upjohn; 8.2.1966; prior. 20.10.1959). US 3 272 706 (Upjohn; 13.9.1966; prior. 2.8.1961). US 3 819 485 (Abbott; 25.6.1974; appl. 3.7.1972). . (dog, p. 0.) CN: ns-5-Amino-I-cyclopropyl- 7-( 3,s d1methyl-l-piperaz1nyl )-6 ,8-difluoro-1,4-dihydr ~-4 -~ ~ ~-3 - qulnolinecarboxylic acid , , HJC-OyO-CH3 O-CH, 2. D-~''2. diethyl. (~)-l- ~-~ -Arabinofuranosyl- 5-( 2-bromoethenyl )-2 ,4(1H,3H)-pyrimidinedione I 0 H 1 -8 -D-orabino- parafarrn- furanosyluracil (I) aldehyde (11) HCI or NaOH ____) I OH 5-( hydroxyrnethy1 )-. mucolytic RN: 49 8-7 1-5 MF: C,,,H,,O, MW: 170.25 EINECS: 20 7-8 6 8-1 LD,,,: 580 mg/kg (M, i.v.) CN: 5-hydroxy-a,a,4-trimethyl-3-cyclohexene-l-methanol (+)-u-pinene (2)-a-pinene 1 Sobrem oxide