Phenglutarimidc P 161 1 S0CI2 H3c~ooH thionyl ' H3C CI ureo K chloride 0 0 0 2-phenylbutyric ocid Pheneturide 1 Reference(s): DRP 249 241 (Bayer; 1910). Kushner, S. et al.: J. Org. Chem. (JOCEAH) 16, 1283 (1951). opfical active isomers: CH 374 644 (Lab. Sapos; appl. 30.10.1958). Trade Narne(s): F: Trinuride (Robert et I: Lircapil (Lira)-comb.; generic Carri6re)-comb.; wfm wfm GB: Benuride (Bengue); wfrn J: Sepotence Pulv. (Kanto) ~hen~lutarimide ATC: N04AA09 Use: anliparkinsonian RN: 1156-05-4 MF: C,,HxN202 MW: 288.39 EINECS: 214-587-8 LD,,,: 1200 rngkg (M, p.0.) CN: 3-[2-(diethylamino)ethyl]-3-phenyl-2.6-piperidinedione monohydrochloride RN: 1674-96-0 MF: C,,H2,N2O,.HC1 MW: 324.85 EINECS: 216-819-3 LD,,: 1200 mgkg (M, p.0.) amide benzyl 2-diethylamino- 4-diethylomino-2-phenyl- cyanide ethyl chloride butyronitrile (1) H3C-0 H5Cs-CH2-N+(CH,), OH- I + &\ b 0 CH2 benzyltrimethyl- ammonium hydroxide acrylic acid methyl ester 1. KOH H 2. CH,COOH. H,SO, o N o NrCH3 '1 . 1612 P Phenindamine Reference(s): US 2 664 424 (Ciba; 1953; CH-prior. 1950). Trude Name(s): D: Aturbal (Ciba); wfm GB: Aturbane (Ciba); wfm Phenindamine ATC: R06AX04 Use: antiallergic, antihistaminic RN: 82-88-2 MF: C,,H,,N MW: 261.37 EINECS: 201-443-4 LD,,; 265 mglkg (M, p.0.) CN: 2,3,4,9-te~rahydro-2-methyl-S)-phenyl-1H-indeno[2,1-c]pyridine tartrate (1:l) RN: 569-59-5 MF: C,,H,,N. C,H60, MW: 41 1.45 EINECS: 209-320-7 LD,,: 18 mgkg (M, i.v.); 265 mgtkg (M, p.0.); 280 mglkg (R, p.o.1 5? + H,C-NH, + O=CH, + 0 CH, aceto- methyl- form- 6.p-(rnsthylirnino phenona ornine aldehyde (pr~pia~henons) conc. HBr H2 . Roney-Ni I + Reference (s): US 2 470 108 (Roche; 1949; appl. 1947). Fortnulation(s): tabl. 25 mg (as tartrate) Trade Nainefs): D: Fluprim (Roche)-comb.; GB: Thephorin (Sinclair) wfm USA: Nolahist (Camrick) Nolamine (Carnrick) Pheniramine ATC: R06AB05 Use: antihistaminic RN: 86-21-5 MF: CI6H2,N2 MW: 240.35 EINECS: 201-656-2 LD5,: 48 mglkg (M, i.v.) CN: N,N-dimethyl-y-phenyl-2-pyridinepropanamine Pheniramine P 1613 maleate (1:l) RN: 132-20-7 MF: C16H2,N2 .C4H404 MW: 356.42 EINECS: 205-051-4 LD,,,: 268 mglkg (M, p.0.); 520 mglkg (R, p.0.) p-aminosalicylate (1:l) RN: 3269-83-8 MF: C,,H2,N2. C7H7N03 MW: 393.49 EINECS: 221-888-8 LD,,: 48 mgkg (M, i.v.) 1. NoNH2 2. CI- /CH3 Y sodium 1. sodium omide benzyl P-chloro- cyanide pyridine (2-dimethylominoethyl)- phenyl(2-pyridy1)oceto- nitrile (U) amide 2. 2-(dimethylomino)- phenyl(2-pyridyl)- ethyl chloride (I) acetonitrile Pheniromine I 1. NoNH2 2.1 1. sodium amide benryl pyridine 2-benzylpyridine chloride (olong with 4-benzylpyridine) Reference(s): US 2 567 245 (Schering Corp.; 1951; prior. 1948). US 2 676 964 (Schering Corp.; 1954; prior. 1950). DE 830 193 (Farbw. Hoechst; appl. 1948). DE 832 153 (Farbw. Hoechst; appl. 1948). Formulution(s): drg. 75 mg (as maleate) Trade Name(s): D: Avil (Albert-Roussel, Rhinosovil (ELI Rho GB: Daneral (Hoechst; as Hoechst) Arznei)-comb. with maleate) Konjunktival Thilo naphazoline nitrate I: Inhiston (Biomedica Augentropfen (Aleon)- F: Fervex Oberlin (0berlin)- Foscama) comb. with naphazoline comb. Senodin-An (Bristol-Myers hydrochloride Triaminic (Novartis)-comb. Squibb)-comb. 161 4 P Phenmetrazine Tetramil (Farn1igea)-comb. USA: Naphcon A (A1con)-comb. Triaminic (Novartis Triaminic (Novartis)-comb. Poly-Histine D (Sanofi)- Consumer)-comb. J: Chlor-Trimeton (Schering) comb. Phenmetrazine (Oxazi~nedrine) ATC: N06B Use: psychostimulant RN: 134-49-6 MF: C,lH15N0 MW: 177.25 EINECS: 205-143-4 LD,,,: 125 mg/kg (M, p.0.); 370 mglkg (R, p.0.) CN: 3-methyl-2-phenylmorpholine hydrochloride RN: 1707-14-8 MF: C,,H,,NO.HCI MW: 213.71 EINECS: 216-950-6 LD,,: 71 mgkg (M, i.v.); 165 mgkg (M, p.0.); 165 mg/kg (R, p.0.) propiophenone a-bromopropio- phenone a-[benzyl(Z-hydroxyethy1)- ominalpropiophenone (I) 2-(2-hydroxyethyl- amino)-1-phenyl-1- propanol I Phenrnetrazine Keference(s): US 2 835 669 (Boehringer lng.; 1958; D-prior. 1952). Formulation(s): drg. 30 mg Trade Name(s): D: Catilon (Ravensberg)- J: Cafilon (Yamanouchi)- comb.: wfm comb. F: Catilon (Merck-C1Cvenot)- USA: Preludin (Roehringer Ing.); comb.; wfm wfm Phenobarbital (Phenemalum; Phenobarbitone) ATC: N03AA02 Use: hypnotic, sedative, anticonvulsant RN: 50-06-6 MF: C,,H,,N,O, MW: 232.24 EINECS: 200-007-0 LD,,: 218 mglkg (M, i.v.); 137 mag (M, p.0.); 209 mgkg (R, i.v.); 162 mglkg (R, p.0.); 150 mg/kg (dog, p.0.) CN: 5-ethyl-5-phenyl-2,4,6(1H,3H,SH)-pyrimidinetrione Phenobarbital P 1615 monosodium salt RN: 57-30-7 MF: Cl,HllN,NaO, MW: 254.22 EINECS: 200-322-3 LD,,: 226 mglkg (M, i.v.); 200 mglkg (M, pa); 83 mg/kg (R, i.v.); 150 mg/kg (R, p.0.) calcium salt RN: 7645-06-9 MF: C12H12N20, . xCa MW: unspecified EINECS: 231-583-1 magnesium salt RN: 7645-05-8 MF: CI2H,,N2O, . xMg MW: unspecified benzyl ethanol cyanide (I) phenylacetic ocid ethyl ester (11) oxalic ocid diethyl ester phenyloxalacetic acid diethyl ester phenylmalonic acid diethyl ester (111) ethyl ethylphenylmolonic bromide (1V) acid diethyl ester J. HZN NHZ nl + H3C '-Br urea (V) I Phenobarbital H diethyl carbonate a-cyanaphenylacetic 2-cyano-2-phenyl- acid ethyl ester butyric acid ethyl ester (VI) phenoborbitol- 4-imine Reference(s): DRP 247 952 (Bayer; 191 1). US 2 358 072 (Kay-Fries; 1944; appl. 1941). Formulation(s): amp. 200 mglml (as monosodium salt); tabl. 15 mg, 100 mg 1 16 1 6 P Phenolphthalein Trade Name(s): D: Lepinal (ASTA Medica AW D) Lepinalelten (ASTA Medica AWD) Luminal (Desitin) Luminaletten (Desitin) Maliasin (Knoll; as salt with propylhexedrine (=barbexaclonum)) Phenaemal (Desitin) Phenaemaletten (Desitin) F: Aparoxal (Veyron et Froment) GardCnal (Specia) GB: Cantil with phenobarbitone (M.C.P.)-comb. Franol (Winthrop)-comb. Gardenal (May & Baker) Luminal (Winthrop) Parabal (Sinclair) Phenomet (Woodward) I: Bellergil (Novartis)-comb. Comizial (Ogna) Gardenale (RhBne-Poulenc Rorer) Luminale Bracco (Bracco) Luminalette (Bracco) Neurobiol (Teofarma)- comb. Teofilcolina Sedativo (Sa1fa)-comb. numerous combination preparations J: Linasen (Daiichi) Phenobal (Fujinaga- Sankyo) USA: Arco-Lase Plus (Arco)- comb. Bellatal (Richwood)-comb, Donnatal (Robins)-comb. Quadrinal (Knoll)-comb. further combination preparations Phenolphthalein ATC: A06AB04 (Dihydroxyphthalophenone; Fenolftalein) Use: laxative RN: 77-09-8 MF: C,,H,,O, MW: 318.33 EINECS: 201-004-7 CN: 3,3-bis(4-hydroxypheny1)-l(3H)-isobenzofuranone phthalic phenol anhydride Baeyer, A. v.: Justus Liehigs Ann. Chem. (JLACBF) 202, 68 (1880). Formularion(s): drg. 30 mg; emulsion 1.3 g/100 g Trade Name(s): D: F: GB: Agarol (Warner-Lambert)- comb. Darmol (Omegin) Vencipon (Artesan)-comb. Boldolaxine (Charpentier) comb.; wfrn Pluribiase (Bouchara)- comb.; wfrn Purganol Daguin (Saunier- Daguin); wfrn Agarol (W. R. Warner)- comb.; wfrn Alophen (Parke Davis)- comb.; wfrn Kest (Berk)-comb.; wfrn Veracolate (W. R. Warner)- comb.; wfrn 1: Agarbil (0ttolenghi)- comb.; wfrn Agarol (Parke Davis)- comb.; wfrn Amaro lassat. Giuliani (Giuliani)-comb.; wfrn Bilagar (Schiapparelli Farm.)-comb.; wfrn Bom-bon (Montefarmac0)- comb.; wfrn Cofetto Falqui (Falqui); wfrn Crisolax (Lifepharma); wfrn Emulsione lass. Fama (Fama)-comb.; wfrn Enteroton lass. (Panthox & Burck)-comb.; wfrn Euchessina (Antonetto)- comb.; wfrn Flambax emuls. (AG1PS)- comb.; wfrn Fructine Vichy (Lirca)- comb.; wfrn Lilo 40 cioccolatini (Giu1iani)-comb.; wfm Neopurges (IFC1)-comb.; wfrn Ormobol (Ciba)-comb.; wfrn Purgante Falqui (Falqui)- comb.; wfrn Phenoperidine P 1617 Purgestol (Zoja)-comb.; J: Eva1 (Nippon Shinyaku)- Evac-Q-Kit (Savage)-comb. wfm comb. Modane (Savage) Reolina (IN)-comb.; wfm Laxatol (Shionogi)-comb. Ricinagar (0ttolenghi)- USA: Agora1 (Warner-Lambert)- comb.; wfm comb. Phenoperidine (Fenoperidine) ATC: NOlAH04 Use: analgesic RN: 562-26-5 MF: C2,H2,N03 MW: 367.49 EINECS: 209-229-2 CN: l-(3-hydroxy-3-phenyIpropyl)-4-phenyl-4-piperidinecarboxylic acid ethyl ester hydrochloride RN: 3627-49-4 MF: C2,H2,N03 . HCI MW: 403.95 EINECS: 222-846-1 LD,,: 64 mgkg (M, i.p.) acclaphenane parafarm- aldehyde carborylic acid ethyl ester hYdrachloride . 4-phenylpiperidinc-4- carboxylic acid ethyl ester (I) Hp, PtO or NoBH4 I b Phenoperidine US 2 951 080 (Eli Lilly; 30.8.1960; prior. 5.8.1957). US 2 962 501 (Merck & Co.; 29.1 1.1960; prior. 19.9.1956). Formulution(s): amp. 10 mg/lO ml, 2 mg/2 ml Trade Nume(s): F: R. 1406 (Janssen); wfm R. 1406 (LeBrun); wfm GB: Operidine (Janssen); wfm Phenoxybenzamine ATC: C04AX02 Use: vasodilator, antihypertensive RN: 59-96-1 MF: C,,HzzCINO MW: 303.83 EINECS: 200-446-8 LD,,: 1535 mgkg (M, p.0.); 2500 mg/kg (R, p.0.) CN: N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)benzenemethanamine 16 18 P Phenoxymethylpenicillin hydrochloride RN: 63-92-3 MF: C,,H,,CINO . HCI MW: 340.29 EINECS: 200-569-7 LD,,: 63.75 mglkg (M, i.v.); 900 mglkg (M, p.0.) phenol propylene 1-phenoxy-2- 1 -phenoxy-2- oxide proponol propyl cMoride (1) + H2N~oH -*- myO CH3 chloride ethonolomine N-(1 -methyl-2- phenoxyethyl)- ethonolomine CH3 chloride N-benzyl-N-(1 -methyl-2- Phenoxybenzamine phenoxyethyl)ethanolomine (11) Reference(s): US 2 599 000 (Smith Kline &French; 1952; prior. 1950). Fortnulation(s): cps. 1 mg, 5 mg, 10 mg (as hydrochloride) Trade Nante(s): D: Dibcnzyran (Procter & GB: Dibenyline (Smith Kline & USA: Dibenzyline (SmithKline Gamble) French); wfm Beecham) Phenoxymethylpenicillin (Penicillin V) ATC: JOlCE02 Use: antibiotic RN: 87-08-1 MF: C,,H,,N,O,S MW: 350.40 BINECS: 201-722-0 LD,,,: 6.578 g/kg (M, p.0.); >1.775 glkg (R, i.v.); >2.22 glkg (R, p.0.) CN: [2S-(2a,5a,6~)]-3,3-dimethyl-7-oxo-h-[(phenoxyacetyl)amino]-4-th1a-1-azabicyclo[3.2.0]he~tane-2- carboxylic acid monopotassium salt RN: 132-98-9 MF: C,,H,,KN,O,S MW: 388.49 EINECS: 205-086-5 LD,,,: 1 glkg(M,i.v.); >4g/kg(M, p.0.); 71.04 glkg (R, p.0.) calcium salt (2:l) RN: 147-48-8 MF: C,2H,,CaN40,0S2 MW: 738.85 EINECS: 205-689-3 Phenprobamate P 161 9 COOH Phenoxyrnethylpenicillin L From fermentation solutions of Penicilliurn notaturn Westling or Penicillium chrysogenum Thom by addition of phenoxyacetic acid as precursor substancc. Reference(s): US 2 479 295 (Lilly; 1949; prior. 1946). US 2 479 296 (Lilly; 1949;.prior. 1946). US 2 562 410 (Lilly; 1951 ; prior. 1946). US 2 941 995 (Beecham; 1960; GB-prior. 1957). partial synthesis: US 3 159 617 (A. D. Little; 1.12.1964; prior. 1.3.1957, 1.5.1959). Formulation(s): f. c. tabl. 1000000 iu 1500000 iu; susp. 300000 id5 ml; syrup 250000iu, 500000 iu; tabl. 664 mg (as potassium salt) Trade Nanze(s): D: Arcasin (Engelhard) F: Isocillin (Hoechst) Ispenoral (Rosen Pharrna) GB: Megacillin oral (Griinenthal) P-Mega-Tablinen (Sanorania) V-Tablopen (ASTA Medica AWD) numerous generics Oracllline (Schwarz) Ospen (Novartis) Apsin VK (A.P.S.); wfrn Bicillin (Yamanowhi)- comb. I: Crystapen V (Britannia) Distaquaine V-K (Dista); J: wfm USA: Econopen V (Beck); wfm Icipen (ICI); wfm Penagen (Genethic); wfrn Stabilin V-K (Boots); wfrn Ticillin V-K (Ticen); wfrn V-Cil-K (Lilly); wfrn Fenospen (Pharmacia & Upjohn) Newcillin (Takeda) Pen Vee (Wyeth-Ayerst) Pfizerpen (Pfi 7er) Phenprobamate ATC: M03BA01 Use: muscle relaxant, tranquilizer RN: 673-31-4 MF: C,,H,,NO, MW: 179.22 EINECS: 211-606-1 LD5,,: 320 mgkg (M, i.v.); 840 mglkg (M, p.0.); 11 10 mgkg (R, p.0.) CN: benzenepropanol carbamate 1. COCI* 1. phasgene 3-phenyl- 1 -propon01 Phenprobomote Reference(s): GB 837 718 (Siegfried AG; appl. 6.5.1958; D-prior. 9.5.1957). Fomulation(s): tabl. 200 mg 1620 P Phenprocoumon Trade Name(s): D: Dolo Prolixan (Siegfried)- J: Actiphan (Teisan) Spalpane (Sawai) comb.; wfm Ansepron (Fuso) Spantol (Nippon Gamaquil (Siegfried); wfm Neurosedan (Sato) Chemiphar) F: Diaflexol (Pal1lusseau)- Paraquick (Ohta) Tatartan (Nissin) comb.; wfm Phencol (Towa) Phenprocoumon ATC: ROIAA04 Use: anticoagulant RN: 435-97-2 MF: C,,H,,O, MW: 280.32 EINECS: 207-108-9 LD,,: 32 mgkg (M, i.v.); 190 mglkg (M, p.0.); 200 mglkg (R, p.0.) CN: 4-hydroxy-3-(l-phenyIpropyl)-2H-l-benzopyran-2-one 0 CH, 9' 0 0 2-ocetoxybenzoyl (1 -phenylpropyl)malonic chloride ocid diethyl ester (sodium solt) CH3 (2-ocetoxybenzoyl)(l -phenyl- propyl)molonic acid diethyl ester (1) NaOCHJ 1 'CH, 3,4-dihydro-2.4-dioxo-3- (1 -phenylpropyl)-3-1 -benzo- pyron-3-corboxylic acid ethyl ester oq. NoOH __+ Phenprocournan US 2 701 804 (Hoffrnann-La Rache; 1955; CH-prior. 1952). uiternative synthesis: US 2 872 457 (Wisconsin Alumni Research; 1959; appl. 1956). resolution of racemate: US 3 239 529 (Wisconsin Alumni Research; 8.3.1966; appl. 1.3.1962). Formulation(s): f. c. tabl. 3 mg; tabl. 3 mg Trade Name(s): D: Falithrom (Hexal) Marcumar (Roche) USA: Liquamar (Organon); wfm . EINECS: 20 1-4 4 3-4 LD,,; 265 mglkg (M, p.0.) CN: 2,3,4,9-te~rahydro-2-methyl-S)-phenyl-1H-indeno[2,1-c]pyridine tartrate (1:l) RN: 56 9-5 9-5 MF: C,,H,,N. C,H60, MW: 41 1.45 EINECS: 20 9-3 2 0-7 LD,,:. EINECS: 20 9-2 2 9-2 CN: l-(3-hydroxy-3-phenyIpropyl )-4 -phenyl-4-piperidinecarboxylic acid ethyl ester hydrochloride RN: 362 7-4 9-4 MF: C2,H2,N03 . HCI MW: 403.95 EINECS: 22 2-8 4 6-1 LD,,: 64. proponol propyl cMoride (1) + H2N~oH -* - myO CH3 chloride ethonolomine N-(1 -methyl- 2- phenoxyethyl )- ethonolomine CH3 chloride N-benzyl-N-(1 -methyl- 2- Phenoxybenzamine phenoxyethyl)ethanolomine