Oxyfedrine 0 1531 USA: OxyContin (Purdue Pharma) Percocet-5 (Endo) Percodan (Endo)-comb. generics and combination Roxicodone (Roxane) preparations Tylox (Ortho-McNeil) Oxyfedrine ATC: COlDX03 Use: coronary therapeutic RN: 15687-41-9 MF: CI9H2,NO3 MW: 313.40 CN: [R-(R*,S*)]-3-[(2-hydroxy-l-methyl-2-phenyethyl)amino]-l-(3-methoxyphenyl)-l-propanone hydrochloride RN: 16777-42-7 MF: C,,H23N03 . HC1 MW: 349.86 EINECS: 240-828-1 LD,,,: 23 mgkg (M, i.v.); 510 mglkg (M, p.0.); 46 mgkg (R, i.v.); 500 mag (R, p.0.); 50 mgkg (dog, i.v.); 200 mglkg (dog, p.0.) 3-methoxyaceto- poroforrn- L-norephedrine Oxyfedrine phenone aldehyde Refermce(s): DE 1 493 574 (Degussa; appl. 3 1.3.1962). US 3 225 095 (Degussa; 21.12.1965; D-prior. 3 1.3.1962). Formulation(s): amp. 4 mgl2 ml; f. c. tabl. 8 mg, 24 mg (as hydrochloride) Trade Name(s): D: Ildamen (ASTA Medica F: Modacor (I.S.H.); wfm Ildamen (Sir); wfm AWD) I: Ildamen (Farmades); wfm J: Ildamen (Chugai) Oxymesterone (Oxymestrone; Methandrostenediolone) ATC: G03B Use: anabolic RN: 145-12-0 MF: CZOH3003 MW: 318.46 EINECS: 205-646-9 CN: (17~)-4,17-dihydroxy-17-methylandrost-4-en-3-one V H20,. OsO,, (CH,),C-OH hydrogen osmium tert- peroxide, tetroxide, butanal 0 4~,5~,17~-tiihydroxy-l7-me~hyl-3- ondrostanone (I) 1532 0 Oxymetazoline KOH, CH30H I Oxyrnesterone u H2S04. CH30H KOH, CH30H b I Reference(s): US 3 060 201 (Farrnitalia; 23.10.1962; GB-prior. 6.6.1958). firmnlation(s): tabl. 5 mg Trade Narne(s): D: Olocortina (Montedison Oranabol (Montedison J: Farma)-comb.; wfm Farma); wfm I: Anamidol (Iwaki); wfm Anamidol (Iwaki) Oranabol (Sumitorno) Oxymetazoline ATC: ROlAA05; R01AB07; SOlGA04 Use: rhinological therapeutic (vasoconstrictor) RN: 1491-59-4 MF: C16HHN20 MW: 260.38 EINECS: 216-079-1 LD,,: 2700 pglkg (M, i.v.); 800 pglkg (R, p.0.) CN: 3-[(4,5-dihydro-lH-imidazol-2-yl)methyl]-6-(1,1-d1rnethylethyl)-2,4-dirnethylphenol monohydrochloride RN: 23 15-02-8 MF: Cl,H24N20 . HCl MW: 296.84 EINECS: 219-015-0 LDs,): 4700 pg/kg (M, p.0.); 1070 pglkg (R, i.v.); 680 pglkg (R, p.0.) 6-lert-butyl-2.4- paraforrn dimethylphenol aldehyde Oxymetholone 0 1533 NoCN sodium H3C c~3 ethylenediomine cyanide 4-tert-butyl-3-hydroxy- Oxyrnetozaline 2.6-dimethylbenzene- acetanitrile Reference(s): US 3 147 275 (E. Merck AG; 1.9.1964; D-prior. 30.9.1960). Formulation(s): doses spray 0.5 mg; drops 10 mgI100 ml; gel 0.5 mg; nasal drops 10mg/100 ml, 25 mg1100 ml, 50 mgI100 ml; spray 50 mg/100 ml (as hydrochloride) Trade Name(s): D: Nasivin (Merck) Nasivinetten (Merck) Vistoxyn (Pharm-Allergan) Wick Sinex (Wick Pharma) F: Aturgyl (SynthClabo) Sinex Lachartre (Lachartre) GB: Actifed Nasale (Wamer- Lambert) Afrazine (Kirby-Warrick); wfrn Atom01 (Allen & Hanburys); wfrn Iliadin-Mini (Merck); wfrn Oxilin (Allergan) Rino Calyptol (RhBne- Poulenc Rorer) I: Nasivin (Bracco) Triaminic Nasale (Novartis Consumer Health) Vicks Simcx Spray (Procter & Gamble)-comb. J: Nasivin (Merck-Chugai) USA: 4-Way Long Acting Nasal Spray (Bristol-Myers); wfm Afrin (Schering); wfrn Dristan Long Lasting Nasal Spray (Whitehall); wfrn Neo-S ynephrine (Winthrop); wfm Oxymetholone (Hydroxymetholone) ATC: A14AA05 Use: anabolic RN: 434-07-1 MF: C2,H,20, MW: 332.48 EINECS: 207-098-6 LD,,: >I glkg (R, i.p.) CN: (5a,17~)-17-hydroxy-2-(hydroxymethylene)-17-methylandrostan-3-one rnestonolone (9. v.) formic acid ethyl ester sodium I ' " oq hydride I Oxyrnetholone I Referencers): DE 1070 632 (Syntex; appl. 30.1.1957; MEX-prior. 7.2.1956). Ringold, H.J. et al.: J. Am. Chem. Soc. (JACSAT) 81,427 (1959). For.rnulation(s): tabl. 50 mg Trade Name(s): D: Pardroyd (Parke Davis); Plenastril (Griinenthal); F: Nastenon (Syntex-Daltan); wfm wfm wfm 1534 0 Oxymorphone GB: Anapolon (Syntex) J: Adroyd (Parke Davis- Anadrol (Shionogi) Sankyo) USA: Anadrol (Unimed) Oxymorphone (Oxy dimorphone) ATC: A14AA05 IJse: analgesic RN: 76-41-5 MF: C,,H1,NO, MW: 301.34 EINECS: 200-959-7 LD,,,: 172 mglkg (M, i.v.) CN: (5a)-4,5-epoxy-3,14-dihydroxy-l7-methylmorphinan-6-one hydrochIoride RN: 357-07-3 MF: C17H19N0,. HCl MW: 337.80 thebaine '14-hydroxycodeinone (cf. oxycodone synthesis) oxycodone (I) (alternative synthesis. cf. oxycodone synthesis) Oxymorphone u Refercncc(s): US 2 806 033 (M. J. Lewenstein and U. Weiss; 1957; appl. 1955). Formulation(s): amp. 1 mglml, 1.5 mglml; suppos. 5 mg (as hydrochloride) Trade Name(s): USA: Numorphan (Endo) Oxypendyl ATC: A04 IJse: anti-emetic RN: 5585-93-3 MF: C,,,H,N40S MW: 370.52 CN: 4-[3-(1OH-pyrido[3,2-b][l,4]benzothiazin- 10-yl)propyl]- 1-piperazineethanol dihydrochloride RN: 17297-82-4 MF: C2,H2,N40S~ 2HCl MW: 443.44 EINECS: 241-326-5 LD,,,: 75 mgkg (M, i.v.); 735 mglkg (M, p.0.); 16 10 mglkg (R, p.0.) Oxypertine 0 1535 ti ('NH 2. CI-NJ 1. sadium amide 2. 1 -(3-chloropropyl)- 10H-pyrido[3,2-b]- piperazine 10-(3-piperazinopropy1)- [I ,4]benzothiazine 1 OH-pyrido[3,2-b]- [1,4]benzothiazine (I) ethylene Oxypendyl chlorahydrin Referenceis): DE 1 063 603 (Degussa; appl. 3.12.1957). Formulation(s): vial 25 mg Trade Nameis): D: Pervetral (Homburg); wfm Oxypertine ATC: NOSAEO1 Use: neuroleptic, antipsychotic RN: 153-87-7 MF: C23H29N302 MW: 379.50 EINECS: 205-818-3 LD,,: 2300 mg/kg (M, p.0.); 1 glkg (K, p.0.) CN: 5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1 -piperazinyl)ethyl]-1H-indole 1. CI-CO-0-CHZ-CH(CH,), i. HN~N~ , H3c-0334hc;3 H3C-0 1. chloroformic acid isobutyl ester /N7 5,K-dimethoxy-2-methyl- 3-indolylacetic ocid (from levulinic acid and 3.4-dimethoxyphenylhydrozine) 1536 0 Oxyphenbutazone LiAIH, lithium alanate Reference(s): DE 1 445 151 (Sterling Drug; appl. 23.9.1960; USA-prior. 25.9.1959). BE 595 341 (Sterling Drug; appl. 23.9.1960; USA-prior. 25.9.1959). Formulation(s): tabl. 40 mg Trade Nurne(s): D: Forit (Winthrop); wfm GB: Integrin (Winthrop); wfm USA: Font (Sterling Winthrop); F: Equipertine (Winthrop); J: Font (Daiichi) wfm wfm Oxyphenbutazone ATC: MOlAA03; M02AA04; SOIBC02 Use: anti-inflammatory RN: 129-20-4 MF: C,,H2,N,0, MW: 324.38 EINECS: 204-936-2 LD,,,: 52 mgkg (M, I.v.); 330 mglkg (M, p.0.); 68 mgkg (R, i.v.); 329 mgkg (R, p.0.); 178 mglkg (dog, i.v.) CN: 4-butyl-l-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione monohydrate RN: 7081-38-1 MF: C,yH,oN203 . H20 MW: 342.40 4-benzyloxyhydrazo- butylmalonic acid benzene diethyl ester I Oxyphsnbutozone Oxyphencyclimine 0 1537 Referencc(s): US 2 745 783 (Geigy; 1956; CH-prior. 1950). Formulation(s): suppos. 250 mg, 500 mg Trade Namc(s): D: Californit (Merckle); wfm Dolo-Phlogase (Adeny1chemie)-comb.; wfrn Imbun (Merckle); wfrn Oxyphenbutazon- ratiopharm (ratiopharm); wfrn Oxyphenbutazon S tada (Stada Chemie); wfrn Phlogase (Adeny1chemie)- comb.; wfrn Phlogistol (Helopharm); wfm Phlogont (Azuchemie); wfrn Tanderil (Geigy); wfm F: Tandtril (Geigy); wfrn GB: Tandacote (Geigy); wfrn Tanderil (Geigy); wfrn Tanderil (Zyma); wfrn Tanderil Chloramphenicol (Zyma); wfrn I: Artroflog (Magis); wfm Butaflogin (Chimipharma); wfrn Butaspirone (Brocchieri); wfrn Butilene (Francia Farm.); wfrn Difmedol'Gel (UCM- Difme)-comb.; wfm Flogistin (Scharper); wfm Flogitolo (Isnardi); wfrn Flogodin (Firma); wfm lridil (Farmila); wfm lsobutil (Panthcr-Osfa Chemie); wfm Neo-Farmadol (Ottolenghi); wfm Pirabutina (Ellea); wfrn Piraflogin (Jamco); wfrn Poliflogil (Farmacobiologico); wfm Tanderil (Geigy); wfm Validil (Von Boch); wfm J: Tanderil (Ciba-Geigy- Fujisaw a) Tantal (Sawai) USA: Oxalid (USV); wfm Oxyphenbutazone Tablets (Bolar; Bioline); wfrn Tandearil (Geigy); wfin Oxyphencyclimine ATC: A03AAOl Use: anticholinergic RN: 125-53-1 MF: C20H2nN203 MW: 344.46 EINECS: 204-743-3 CN: a-cyclohexyl-a-hydroxybenzeneacetic acid (1,4,5,6-tetrahydro-l-methyl-2-pyrimidinyI)methyl ester monohy drochloride RN: 125-52-0 MF: C2,H2,N2O3~ HCI MW: 380.92 EINECS: 204-742-8 LD,,: 80 mgkg (M, i.v.); 860 mglkg (M, p.0.); 88 mgkg (R, i.v.); 1370 mgtkg (R, p.0.); 47 mgkg (dog, i.v,); 1 g/kg (dog, p.0.) 2-chloroocetimidic acid 3-methylomino- 2-chloromethyl-1 -methyl- methyl ester propylamine 1,4,5,64etrahydropyrimidine (I) hydrochloride a-cyclohexyl-a- I Oxyphemyclimine phenylglycolic acid 1538 0 Oxyphenisatin acctate Reference(s): GB 795 758 (Pfizer; appl. 1956; USA-prior. 1955). DE 1 058 515 (Pfizer; appl. 1956; USA-prior. 1955). Formulariorr(s); drg. 5 mg (as hydrochloride) Trade Narne(s): D: Orbigastril (Roerig); wfm Orbigastril (Roerig)-comb. with meprobamate F: Daritran (0podex)-comb.; wfm Manir (Valpan); wSm GB: Daricon (Pfizer); wfm I: Gastrised (Benvegna)- comb.; wfm Madil (Beolet); wfm Ulcelac (Sigurtl)-comb.; w fm Vagogastrin (Benvegna); wfm combination preparations; wfm J: Daricon (Taito Pfizer) Inomaru-S (Sawai) Norma (Sankyo) USA: Daricon (Beecham- Massengill); wfm Daricon (SmithKline Beecham; as hydrochloride); wfm Daricon PB (Beecham- Massengill)-comb. with phenobarbital; wfm Enarax (Roerig)-comb. with hydruxyzine; wfm Gastrix (Rowell); wfm Gastrix Wffhenobarbital (Rowell)-comb. with phenobarbital; wfrn Vistrax (Pfizer)-comb. with hydroxyzine Oxyphenisatin acetate (Diphesatine; Acetphenolisatin) ATC: A06A Use: laxative RN: 1 15-33-3 MF: C,,H,9N0, MW: 401.42 EINECS: 204-083-6 CN: 3,3-bis[4-(acetyloxy)phenyl]-l,3-dihydro-2H-indol-2-0ne isatin phenol ocetic onhydride I Oxyphenisotin acelole Reference(s): DRP 406 210 (Hoflmann-La Koche; appl. 1923; CH-prior. 1922). DRP 447 539 (Hoffmann-La Roche; appl. 1924; CH-prior. 1924). DRP 482 435 (Hoffmann-La Ruche; appl. 1928). Fortnulation(s): tabl. 5 mg Trade Nume(s J: , , D: Bisco-Zitron (Aiscova); Darmoletten (Ornegin); wsm wfm Laxatan forte (Divapharma); wfm Obstilax (Zirkulin); wfm Oxyphenonium bromide 0 1539 Schokolax (Dallmann); numerous combination Veripaque (Winthrop); wfm wfm preparations; wfm USA: lsocrin (Warner Chilcott); Vinco- Abfiihrperlen F: LaxCnia (Dumesny)-comb.; wfm (Krehayn); wfm w fm Lavema (Winthrop); wfm GB: Bydolax (Moore); wfrn Oxyphenonium bromide ATC: A03AB03 Use: anticholinergic, antispasmodic RN: 50-10-2 MF: C,,H,,BrNO, MW: 428.41 EINECS: 200-010-7 LD,,,: 30 mgkg (M, i.v.); 400 mglkg (M, p.0.); 13.2 mglkg (R, i.v.); 995 mgkg (R, p.0.) CN: 2-[(cyclohexylhydroxyphenylacetyl)oxy]-N,N-diethyl-N-methylethanaminium bromide a-cyclohexylphenyl- 2-diethylomino- glycolic acid ethonol a-cyclohexylphenylglycolic acid 2-diethylominoethyl methyl ester ester (I) Reference(s): CH 259 958 (Ciba; appl. 1944). methyl bromide Formulation(s): drg. 10 mg; tabl. 5 mg Oxyphenonium bromide Trade Name(s): D: Antrenyl (Ciba); wfm Ossitetra Sciroppo GB: Antrenyl (Ciba); wfm (Pierrel); wfm I: Antrenil (Ciba); wfm USA: Antrenyl (Ciba); wfm Oxypyrronium bromide ATC: A03AB Use: anticholinergic, antispasmodic RN: 561-43-3 MF: C,,H,,BrNO, MW: 426.40 EINECS: 209-219-8 LD,,,: 18 mgkg (M, i.v.); 1040 mglkg (M, p.0.); 27.5 mglkg (R, i.v.); 780 mglkg (R, p.0.) CN: 2-[[(cyclohexylhydroxyphenylacetyl)oxyJmethyl]- 1,l-dimethylpyrrolidinium bromide 1540 0 Oxyquinoline 1. H,C-NH, . C2H50H HBr, 5- 10 OC 0 2. NaOH CHI BreOKCH3 1. methylomine tetrohydrofurfuryl ocetate 2,5-dibromoomyl ocetote a-cyclohexylphenyl- a-cyclohexylphenyl- glycolic acid methyl glycolic acid ester (1-methyl-2-pyrrolidiny1)- methyl ester Br-CH, ___, methyl bromide I Oxypyrronium bromide Referencc(s); GB 859 260 (Beecham; appl. 1957; valid from 1958). 2-hydroxymethyl- I-methylpyrrolidine: GR 820 503 (Beecham; appl. 1956; valid from 1957). Formzdation(s): 3 mg, 6 mg Trade Name(s): F: Immetropan (Dausse); wfm J: Immetro (Fujisawa) Oxyquinoline (Oxinc) ATC: AOlAB07; D08AH03; G01AC30; R02AA14 Use: antiseptic, disinfectant RN: 148-24-3 MF: C9H7N0 MW: 145.16 EINECS: 205-71 1-1 LD,,,: 20 g/kg (M, p.0.); 1200 mgkg (R, p.o.1 CN: 8-quinolinol hydrochloride RN: 16862-1 1-6 MF: C,H7N0. HCI MW: 181.62 EINECS: 240-884-7 sulfate (2:l) RN: 134-3 1-6 MF: C,H,NO . 112H,SO, MW: 388.40 EINECS: 205-137-1 LD,,,: 280 mdkg (M, p.0.); 1200 mgkg (R, p.0.) 0""' . H,S04 + HO"Y-OH , OH nitrobenzene (Skraup synthesis) 2-amino- glycerin Oxyquinoline phenol Referertce(s): DRP 14 976 (Z. H. Skraup; 1881). . 313.40 CN: [R-(R*,S*) ]-3 -[ (2-hydroxy-l-methyl-2-phenyethyl)amino]-l-(3-methoxyphenyl)-l-propanone hydrochloride RN: 1677 7-4 2-7 MF: C,,H23N03 . HC1 MW: 349.86 EINECS: 24 0-8 2 8-1 LD,,,: 23. RN: 149 1-5 9-4 MF: C16HHN20 MW: 260.38 EINECS: 21 6-0 7 9-1 LD,,: 2700 pglkg (M, i.v.); 800 pglkg (R, p.0.) CN: 3-[ (4,5-dihydro-lH-imidazol-2-yl)methyl ]-6 -( 1,1-d1rnethylethyl )-2 ,4-dirnethylphenol. RN: 15 3-8 7-7 MF: C23H29N302 MW: 379.50 EINECS: 20 5-8 1 8-3 LD,,: 2300 mg/kg (M, p.0.); 1 glkg (K, p.0.) CN: 5,6-dimethoxy-2-methyl- 3-[ 2-( 4-phenyl-1 -piperazinyl)ethyl ]-1 H-indole