Propiram P 1731 COOH COOH CI-CO-O-CH2-CH(CH,)2, N(C2H5)3 isobulyl chloroformate, triethylamine 2-phenoxybutyric 6-arninopenicillanic acid acid I Propicillin Reference(s): GB 877 120 (Beecham; appl. 10.5.1960; USA-prior. 25.5.1959,22.10.1959). GB 899 199 (Pfizer; appl. 7.1.1960; USA-prior. 28.9.1959). GB 904 576 (Bayer; appl. 24.1 1.1960; D-prior. 4.12.1959). GB 958 478 (Beecharn; appl. 28.2.1963; USA-prior. 13.3.1962). DE 1 143 817 (Beecharn; appl. 25.5.1960; USA-prior. 25.5.1959, 22.10.1959) DE 1 154 805 (Bayer; appl. 24.10.1961). DE 1 159 449 (Griinenthal; appl. 22.3.1961). Fomulation(s): f. c. tabl. 280 rng, 700 rng; syrup 70 rng; tabl. 125 mg, 140 rng, 280 mg, 700 rng (as potassium salt) Trade Name(s): D: Baycillin (Bayer Vital) Ultrapen (Pfizer); wfm Trescillin (Beecham- Pluscillin (Bayropharm) 1: Bayercillin (Bayer); wfm Fujisawa) F: Brocilline (Nativelle); wfm J: Oracillin (Takeda) GB: Brocillin (Beecham); wfrn Synthepen-P (Meiji) Propiram ATC: NO2 Use: analgesic RN: 15686-91-6 MF: C16H2sN,0 MW: 275.40 EINECS: 239-775-7 LD5": 290 mglkg (M, s.c.); 366 rng/kg (R, s.c.) CN: N-[l-rnethyl-2-(l-piperidinyl)ethyl]-N-2-pyridinylpropanamide fumarate (1:l) RN: 13717-04-9 MF: C,,H,,N,O . C4H404 MW: 391.47 EINECS: 237-270-6 LD,,: 48.2 rnglkg (M, i.v.); 874 mglkg (M, p.0.); 63.8 rnglkg (R, i.v.); 1289 mglkg (R, p.0.); 1 glkg (dog, p.0.) Q sodium Q % H3cq CI amide HN N Y 9 2-amino- 2-chloro-l- pyridine piperidino- propane 2-(2-piperidino-l - rnethylethylornino)- pyridine (I) prapianic anhydride I propiram / Reference(s): US 3 163 654 (Bayer; 29.12.1964; D-prior. 13.4.1961). FR 1 492 761 (Bayer; appl. 13.4.1962; D-prior. 13.4.1961). combinations: US 4 479 956 (Analgesic Assoc.; 30.10.1984; appl. 26.4.1983). Trade Name(s): I: Algeril (Bayer); wfrn Yropiverine (P4) ATC: G04BD06 Use: anticholinergic, treatment of incontinence RN: 60569-19-9 MF: C2,H,,N0, MW: 367.49 CN: a-Phcnyl-a-prupoxybenzeneacetic acid 1 -methyl-4-piperidinyl ester hydrochloride RN: 54556-98-8 MF: C,,H2,N0,. HCl MW: 403.95 1 -methyl-4- piperidinol (11) diethyl oxolote ethyl benzilote (I) (cf. benoctyzlne synthesis) Propofol P 1733 COOH. 11 SOC12 benzen; clpN isoproponol SOClp -b 111 + N \cH3 benzilic ocid 1 -methyl-4- chloropiperidine alternative synthesis of ethyl benzilote (I): bensaldehyde benzoin benzil Reference(s): a DD 106 643 (C. Starke et al.; appl. 12.7.1973; DD-prior. 12.7.1973). Laphin, 1.1. et al.: Khim. Khim. Tekhnol. (SSAKAG) 30 (7), 27-36 (1987). b Klosa, J.; Delmar, G.: J. Prakt. Chem. (JPCEAO) 16,7 1-82 (1962). pharmaceutical preparation: DE 2 937 489 (C. Starke, G. Schubert; appl. 17.9.1979; DD-prior. 9.10.1978). transdermal formulation: JP04 266 821 (Rido Chem.; appl. 22.2.1991) Formulatior~(s): drg. 5 mg, 15 mg (as hydrochloride) Trade Narne(s): D: Mictonetten (Apogepha) Mictonorm (Apogepha) Propofol (Disoprofol; ICI-35868) ATC: NOlAXlO Use: anesthetic (injectible) RN: 2078-54-8 MF: CI2H,,O MW: 178.28 EINECS: 218-206-6 LD,,: 50mgkg (M, i.v.); 1100 mgfkg (M, p.0.); 42 mgkg (R, i.v.); 500 mg/kg (R, p.0.) CN: 2,6-bis(1-methylethy1)phenol Reference(s): US 2 831 898 (Ethyl Corp.; 1958). Kolka, A.J. et al.: J. Org. Chem. (JOCEAH) 21,712 (1956); 22,642 (1957). Kealy, T.J.; Coffman, D.D.: J. Org. Chem. (JOCEAH) 26, 987 (1961). Carlton, J.K.; Bradbury, W.C.: J. Am. Chem. Soc. (JACSAT) 78, 1069 (1956). phenol propylene Propofol I 1734 P Propoxycainc Trade Name(s): D: Disoprivan (Glaxo Propofol-Fresenius GB: Diprivan (Zeneca) Wellcome; Zeneca) (Fresenius-Klinik) I: Diprivan (Zeneca) Klimofol (IVAmed) Propofol-Parke Davis J: Diprivan (Zeneca) Propofol-Abbott (Abbott) (Parke Davis) USA: Diprivan (Zeneca) F: Diprivan (Zeneca) Propoxycaine ATC: NOlBA Use: local anesthetic RN: 86-43-1 MF: C,,H,N,O, MW: 294.40 EINECS: 201-670-9 LD,,: 9 mglkg (M, i.v.) CN: 4-amino-2-propoxybenzoic acid 2-(diethy1amino)ethyl ester monohydrochloride RN: 550-83-4 MF: C,,H,,N,O,. HCl MW: 330.86 EINECS: 208-988-7 LD,,,: 7417 bglkg (M, i.v.) methyl 4-nitro- propyl benzene- solicylote sulfanote COOH H~C-N"+~' + , \ 0ficti3 <CH3 - NO2 H3c-N-F NO2 4-nitro-2-propoxy- 2-diethylomino benzoic acid (I) ethyl chloride 1 Prapoxycoine I Rcfcrence(s): US 2 689 248 (Sterling Drug; prior. 1950). Trade Nume(s): IISA: Blockain (Breon); wfm Ravocaine (Cook-Waite)- comb.; wfm Propranolol P 1735 Propranolol ATC: C07AA05 Use: beta blocking agent RN: 525-66-6 MF: C,,H2,N02 MW: 259.35 EINECS: 208-378-0 LD,,: 28.1 mgkg (M, i.v.); 289 mgkg (M, p.0.); 23 mgkg (R, i.v.); 660 mgkg (R, p.0.) CN: 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol hydrochloride RN: 318-98-9 MF: C,,H,,N02 . HCI MW: 295.81 EINECS: 206-268-7 LD,,: 18 mgkg (M,i.v.); 320mglkg (M,p.o.); 21 mgkg (R, i.v.); 466 mglkg (R, p.0.) + 1 -naphthol (1) @ 1. 11 2. NaOH 1 - 0 isopropyl- epichloro- 1 -chloro-3- ornine (111) hydrin (11) (1 -nophthoxy)- 2-proponol 3-(1 -naphkhoxy)- propylene oxide Rejerence(s): DE 1 493 847 (ICI; prior. 18.1 1.1963). US 3 337 628 (ICI; 22.8.1967; GB-prior. 23.1 1.1962). GB 994 918 (ICI; appl. 23.11.1962; valid from 28.10.1963). GB 995 800 (ICI; appl. 23.1 1.1962; valid from 28.10.1963). retard form: US 4 138 475 (ICI; 6.2.1979; GB-prior. 1.6.1977). Propronolol Formulation(s): amp. 5 mgl5 ml; f. c. tabl. 10 mg, 20 mg, 40 mg, 80 mg; s. r. cps. 60 mg, 80 mg, 120 mg, 160 mg; tabl. 10 mg, 25 mg, 40 mg, 80 mg (as hydrochloride) Traa'e Name(s): D: Beta-Tablinen (Sanorania) Dociton (Rhein-Pharma; Zeneca) Efektolol (Brenner-Efeka) Elbrol (Pfleger) Indobloc (ASTA Medica AWD) Obsidian (Isis Pharma) Probabloc-401-80 (Azupharma) Propanur 20140180 (Henning Berlin) Prophylux (Hennig) Propranolol-Gry (Gry) Sagittol40/80/160 (Sagitta); wfm various generics and combination preparations F: Avlocardyl (Zeneca; 1967) HCmipralon (Urpac-Astier) GB: Beta-Prograne (Tillomed) Inderal LA (Zeneca; 1965) Inderetic (Zeneca)-comb. lnderex (Zeneca)-comb. Probeta LA (Trinity) Propanix LA (Ashbourne) I: Inderal (Zeneca; 1967) J: Caridolol (Sankyo Zoki) Inderal (Sumitomo) Kemi (Otsuka) Pylapron (Kyorin) 1736 P Proovlhexedrine USA: Inderal (Wyeth-Ayerst; Inderide (Wyeth-Ayerst)- generics 1967) comb. with hydrochlorothiazide Propylhexedrine ATC: A08A; N07A Use: sympathomimetic, appetite depressant RN: 101-40-6 MF: CIoH2,N MW: 155.29 EINECS: 202-939-3 CN: N,a-dimethylcyclohexaneethanamine hydrochloride RN: 1007-33-6 MF: CloH21N . HC1 MW: 191.75 EINECS: 213-753-7 (+)-base RN: 3595-1 1-7 MF: CloH2,N MW: 155.29 EINECS: 222-741-0 (+)-hydrochloride RN: 6192-98-9 MF: C,oH21N. HCI MW: 191.75 EINECS: 228-246-6 LD,,: 70 mglkg (M, i.p.) N,a-dirnethyl- benzeneethanornine Reference(s): DE 949 657 (Knoll; appl. 1954). DE 970 480 (Knoll; appl. 1940). Zenitz, B.L. et al.: J. A;. Chem. Soc. (JACSAT) 69, 11 17 (1947) alternative synrhesis: US 2 454 746 (Smith Kline & French; 1948; appl. 1947). Formularion(s): drg. 25 mg Trade Name(s): D: Eventin (Minden); wfm GB: Benzedrex (Smith Kline & USA: Benzedrex (Smith Kline & French); wfm French); wfm Prop yliodone ATC: V08AD03 Use: X-ray contrast medium RN: 587-61-1 MF: CloHII12N0, MW: 447.01 EINECS: 209-603-5 LD,,: 300 mglkg (M, i.v.); >18 glkg (M, p.0.) CN: 3,5-diiodo-4-0x0-l(4H)pyridineacetic acid propyl ester Propylthiouracil P 1737 H (COOH iodine I chloroocetic acid I 1 0 0 4(1H)-pyridone 3.5-diiodo-4(1 H)- pyridone I Propyliodone Reference(sJ: GB 517 382 (ICI; appl. 1938). BE 5 16 687 (Glaxo; appl. 1953; GB-prior. 1952). Formulation(s): susp. 10 g120 ml, vial 50 % Trade Name(s): 0 3.5-diiodo-4-0x0- 1.4-dihydropyridino- acetic ocid (I) D: Dionosil (Glaxo); wfm Propyliodon-Cilag (Cilag- J: Dionosil (Torii) Chemie); wfm Propylthiouracil ATC: H03BA02 Use: antithyroid drug RN: 51-52-5 MF: C,HloN20S MW: 170.24 EINECS: 200-103-2 LD,,: 1250 mgikg (R, p.0.) CN: 2,3-dihydro-6-propyl-2-thioxo-4(1H)-pyrimidinone ethyl 3-oxocoproote thioureo I Propylthiouiocil I Reference(s): Anderson, G.W. et al.: J. Am. Chem. Soc. (JACSAT) 67,2197 (1945). Formularion(s): tabl. 25 mg, 50 mg Trade Name(s): D: Thyreostat I1 (Herbrand F: Propylthiouracil Diamant J: Propacil (Chugai) HerstellerIBerlin-Chemie (Diamant); wfm Thiuragyl (Tokyo Tanabe) Vertrieb) I: Propycil (Sir); wfm USA: Propylthiouracil (Lederle) 1738 P Propyphenazone Propgphenazone (Isopropylantipyrin) ATC: N02BB04 Use: analgesic, antipyretic RN: LD,,,: CN: 479-92-5 MF: C,+H,,N,O MW: 230.31 EINECS: 207-539-2 960 mglkg (M, p.o.1; 860 mglkg (R, p.0.) 1,2-dihydro- 1,s-dimethyl-4-(I -methylethyl)-2-phenyl-3H-pyrazol-3-one ethyl phenyl- 3-methyl-l- ocetoocetote hydrozine phenyl-5-b2 pyrozolone 4-isopropyl-3- methyl- 1 -phenyl- 5-b2-pyrozolone (1) dimethyl sulfote 1 Prapyphenozone I Reference(s): DRP 565 799 (Hoffmann-La Roche; appl. 1931). DE 962 254 (Riedel-deHaen; appl. 1954). Formulntion(s): cps. 400 mg; suppos. 100 mg, 200 mg, 300 mg, 400 mg; tabl. 500 mg Trade Name(s): D: Avamigran (ASTA Medica AWD) Demex (Berlln-Chemie) Eufibron (Berlin-Chemie) Isoprochin (Mcrckle) Saridon (Roche Nicholas)- comb. and circa 150 more generics and combination preparations F: Polypirine (Lehning)- comb. I: Caffalgina (Home)-comb. Flexidone (Po1i)-comb. Influvit (Recordati)-comb. Micranet (0gna)-comb. Mind01 (Merck-Bracco)- comb. Neo-Optalidon (Novartis)- comb. Omniadol (Montefarrnaco)- comb. Optalidon confetti (Novartis)-comb. Ribelfan (Pharmacia & Upjohn)-comb. Saridon (Roche)-comb. Spasmocibalgina (Novanis)-comb. Spasmoplus (Novartis)- comb. Uniplus (Ange1im)-comb. Veramon (Sofar)-comb, Vit~algin (Boots H.M. VIT1)-comb. Propyramazine bromide ATC: AO~ Use: antispasmodic RN: 145-54-0 MF: C2,,H2,BrN20S MW: 419.39 EINECS: 205-657-9 LD,,,: 80 mg/kg (M, i.p.) CN: l-methyl-l-[l-methyl-2-oxo-2-(lOH-phenothiazin-lO-yl)cthyl]pyrrolidinium bromide Proquazone P 1739 phenothiozine 2. 2-bromopropionyl bromide (1) methyl I Propyromozine bromide bromide Referencefs): US 2 615 886 (Astra; 1952; prior. 1951). Formulation(s): tabl. 25 mg; vial 10 mglml Trade Name(s): F: Diaspasmyl (Diamant); wfm Proquazone ATC: MOlAX13 Use: analgesic, anti-inflammatory RN: 22760-18-5 MF: CI,HI8N2O MW: 278.36 EINECS: 245-203-7 LD,,: 930 mgkg (M, p.0.); 759 mglkg (R, p.0.) CN: 7-methyl-l-(l-methylethyl)-4-phenyl-2(1H)-quinazolinone 1. HISO+ H2N~0 , CH3COOH H3C NH2 _____, 0 urea 2-amino-4-methyl- benzophenone P-isopropylomino- 4-methylbenzo- phenone Reference(s): US 3 723 432 (Sandoz-Wander; 27.3.1973; prior. 29.8.1966,4.5.1967,4.10.1967,26.2.1968, 1.7.1968, 12.11.1968). DE 1 805 501 (Sandoz; appl. 26.10.1968; USA-prior. 30.10.1967, 26.2.1968, 1.7.1968). alternative synthesis: US 3 549 635 (Sandoz-Wander; 22.12.1970; prior. 26.2.1968, 1.7.1968). DOS 1 909 110 (Sandoz; appl. 24.2.1969; USA-prior. 26.2.1968, 1.7.1968). 1740 P Proscillaridin 2-isopropylamino-4-methylbenzophenone: US 3 845 128 (Sandoz; 29.10.1974; prior. 30.10.1967, 5.8.1970). DOS I 81 8 01 2 (Sandoz; appl. 26.10.1968; USA-prior. 3O.lO.l967,26.2.1968, 1.7.1968). US 4 071 557 (Sandoz; 31.1.1978; appl. 29.1.1976). Formulation(s): cps. 200 mg, 300 mg; suppos. 300 mg Trade Name(s): D: Biarison (Sandoz); wfm Proscillaridin (Proscillaridin A) ATC: COlABOl Use: cardiac glycoside RN: 466-06-8 MF: C,,H,,O, MW: 530.66 EINECS: 207-370-4 LD,,: 4.7 mglkg (M, i.v.); 30.5 mg/kg (M, p.0.); 9 mg/kg (R, i.v.); 56 mglkg (R, p.0.) CN: (3~)-3-[(6-dcoxy-a-~-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide enzymatic hydralysis (p-glucosidose) _____* glucoscilloren A (from Scillo moritimo L.) enzymatic hydrolysis (scillorenose or strophonthobiore or Coronillo enzymes or fungo1 enzymes) OH OH scllloren A (I) I Proscilloridin @ from Urgineo burkei Baker . 47 9-9 2-5 MF: C,+H,,N,O MW: 230.31 EINECS: 20 7-5 3 9-2 960 mglkg (M, p.o.1; 860 mglkg (R, p.0.) 1,2-dihydro- 1,s-dimethyl- 4-( I -methylethyl )-2 -phenyl-3H-pyrazol-3-one ethyl phenyl- 3-methyl-l-. Use: antispasmodic RN: 14 5-5 4-0 MF: C2,,H2,BrN20S MW: 419.39 EINECS: 20 5-6 5 7-9 LD,,,: 80 mg/kg (M, i.p.) CN: l-methyl-l-[l-methyl-2-oxo- 2-( lOH-phenothiazin-lO-yl)cthyl]pyrrolidinium bromide. mglkg (R, p.0.) + 1 -naphthol (1) @ 1. 11 2. NaOH 1 - 0 isopropyl- epichloro- 1 -chloro- 3- ornine (111) hydrin (11) (1 -nophthoxy )- 2-proponol 3-( 1 -naphkhoxy )- propylene oxide