Penmesterol P 1581 Trade Name(s): F: Penetracyne Midy (Clin- Midy); wfrn I: Idrociclin (Biagini); wfrn Lisomicina (Borromeo); wfrn Nikeciclina (Panther-Osfa Chemie); wfrn Penetracyn (Midy); wfrn Peniltetra 500 (Panther- Sieromicin (Sierochimica); Osfa Chemie); wfm wfm Prestociclina (Chemil); Tetrasolvina (Nouvo Cons. wfm Sanit. Naz.); wfm Singramicina (Mitim); wfm Valtomicina (Midy; as pipacycline guajacol glycolate) Boniciclina (Boniscontro & Gazzone); wfrn Penmes terol (Penmestrol) ATC: G03B Use: androgen RN: 67-81-2 MF: C25H3u02 MW: 370.58 EINECS: 200-670-6 CN: (17~)-3-(cyclopentyloxy)-17-methylandrosta-3,5-dien-17-01 I. HC(OC,H,),. H,C~SO,H 2. OH b 1. orthoformic ocid triethyl ester 2. cyclopentyl alcohol 3-cyclopentyloxy-17-0x0-3.5- androstadiene (I) Reference(s): FR-M 568 (Francesco Vismara; appl. 31.8.1960; D-prior. 4.5.1959; GB-prior. 15.10.1959). US 3 019 241 (A. Ercoli; 30.1.1962; D-prior. 4.5.1959). methylmagnesium bromide alternative synthesis: DAS 1 159 940 (Francesco Vismara; appl. 10.7.1961; I-prior. 9.5.1961) addition to DE 1 119 264. Penmesterol Trade Name(s): F: Pandrocine (Sptcia); wfrn Pentaerythrityl tetranitrate (Pentanitrolum) ATC: A06AD14 Use: coronary vasodilator RN: 78-11-5 MF: C5HuN,01, MW: 316.14 EINECS: 201-084-3 LD,,: >5 g/kg (M, i.p.) CN: 2,2-bis[(nitrooxy)methyl]- 1,3-propanediol dinitrate (ester) 1582 P Pentagastrin pentoerythritol I Pentaerythrilyl tetranitrate Referetzce(s): US 2 370 437 (Du Pont; 1945; prior. 1943). Fortnulation(s): drg. 40 mg; s. r. tabl. 80 mg; tabl. 50 mg, 80 mg Trade Narne(s): D: Dilcoran 80 (Godecke); wfm and following combination preparations: Adenolanat (Herbrand); wfrn Adenopurin Herbrand (Herbrand); wfrn Dilcoran 80 S Retard (Godecke); wfrn Gilucor (Giulini); wfrn Govil (Stada); wfrn Klimax-H Taeschner, -N Taeschner (Taeschner); wfrn Nirason (Ravensbcrg); wfrn Nitro-Crataegutt (Schwabe); wfrn Nitro-Novodigal (Beiersdorf); wfrn Nitro-Sandolanid (Sandoz); wfrn Opticardon (UCB); wfm Pentaneural (Wyeth); wfm Pentrium (Hoffmann-La Roche); wfrn - Pheracor (Kanoldt); wfrn Stenoppressin (Efeka); wpm VisanoCor (Kadc); wfrn F: Nitrodex (Dexo) GB: Mycardol (Sanofi Winthrop) 1: Ajmetril (Inverni della Beffa)-comb. Peritrate Sincron. (Teofarma) J: Hasethrol (Shionog) Hypothurol (N~ssin) Pectolcx (Shionogi) USA: Duotrate (Marion), wfm Metranil Duracap (Meyer); wfm Neo-Corovas (Amfre- Grant); wfrn Pent aery thrl to1 Tetranitrate (Philips Roxane); wfrn Pentritol (Armour); wfm Perispan (USV); wfm Peritratc (Parke Davis; Warner Chilcott); wfm SK-PETN (Smith Kline & French); wfrn Vasltol (Rowell); wfm Pentagastrin ATC: V04CG04 Use: gastric secretion diagnostic RN: 5534-95-2 MF: C,,H,,N,O,S MW: 767.91 EINECS: 226-889-7 CN: N-[(1,1-dimethyIethoxy)carbonyl]-~-alanyl-~-tryptophyl-~-rnethionyl-~-a-aspartyl-~-phenylalaninamide Pentagestrone acetate P 1583 I Boc Boc Boc Boc I Pentogastrin Reference(s): Davey, J.M. et al.: J. Chem. Soc. C (JSOOAX) 1966,555. US 3 896 103 (ICI; 22.7.1975; GB-prior. 25.6.1964,9.3.1965). 8-Ala OCP Formulation(s): amp. 0.25 mg12 ml 9-Alo Trp Met Asp Phe Trp H OCH3 0CH3 Boc NHNH2 H Trade Name(s): Phe H NH2 NH2 NH2 NH2 NH2 NH2 Met Asp z Boc 0CP H D: Gastrodiagnost (Merck); GB: Peptavlon (ICI); wfm USA: Peptavlon (Wyeth-Ayerst) wfm J: Pentagastrin (Sumitomo F: Peptavlon (Zeneca) Chem.) OBz 2-/OCP OBz / Pentagestrone acetate (Pentagestroni acetas) ATC: GO3 Use: progestogen RN: 1178-60-5 MF: C,,H4,04 MW: 440.62 CN: 17-(acetyloxy)-3-(cyclopentyloxy)pregna-3,5-dien-2O-one 1584 P Pentamidine pyridlne , HCI 0 17-ocetoryprogesterone cyclopentanol I Pentogestrone acetate I Reference(s): DAS 1 167 830 (Francesco Vismara; appl. 18.1.1961; I-prior. 6.2.1960). alternative syntheses: US 3 019 241 (A. Ercoli; 30.1.1962; D-prior. 4.5.1959). DAS 1 159 940 (Franccsco Vismara; appl. 10.7.1961; 1-prior. 9.5.1961) addition to DE 1 119 264. Trade Narne(s): I: Gestovis (Vister); wfm Pentamidine ATC: POlCXOl Use: chemotherapeutic (protozoal infections) RN: 100-33-4 MF: C,,HZ4N4O2 MW: 340.43 EINECS: 202-841-0 LD,,: 50 mgkg (M, i.p.) CN: 4,4'-[1,5-pentanediylbis(oxy)]bis[benzenecarboximidamide] diisethionate RN: 140-64-7 MF: C,,H24N402. 2C2H604S MW: 592.69 EINECS: 205-424-1 LD5,: 15.1 mglkg (M, i.v.) 4-hydroxybenzo- 1.5-dibromo-' 1.5-bis(4-cyonophenoxy)- nitrile pentane pentone (I) 1. HCI. C2H,0H 2. NH,, C2H50H I - Pentomidine 1 Referencers): GB 507 565 (May & Baker; appl. 1938). Ashley, J.N. et al.: J. Chem. Soc. (JCSOA9) 1942, 103. Fonnulation(s): vial 120 rng, 300 mg Pentapiperide P 1585 Trade Name(s): D: Pentacarinat (Glaxo Pneumopent aerosol Pentam 300 (Lyphomed); Wellcome; RhGne-Poulenc (Italchimici) wfm Rorer) J: Benambax (RhGne- Pneumopent (Rh6ne- F: Pentacarinat (Bellon) Poulenc-Chugai) Poulenc Rorer); wfm GB: Pentacarinat (GHC) USA: Pentacarinate (RhBne- I: Pentacarinat (RhBne- Poulenc Rorer); wfm Poulenc Rorer) Pentam (Fujisawa); wfm Pentapiperide ATC: N04A Use: antispasmodic, anticholinergic RN: 7009-54-3 MF: C,,H,,NO, MW 289.42 EINECS: 230-286-4 CN: a-(1 -methylpropyl)benzeneacetic acid 1-methyl-4-piperidinyl ester hydrogen fumarate (1:l) RN: 635-32-5 MF: CI8H2,NO2. C4H404 MW: 405.49 EINECS: 21 1-233-4 methyl sulfate RN: 7681-80-3 MF: C,,H,oN02. CH,04S MW: 415.55 EINECS: 231-678-8 LD,,: 7500 @kg (M, i.v.); 435 mglkg (M, p.0.); 720 mgkg (R, p.0.) 1. NoNH2 NoOH 1. sodium arnide H3C 2. 2-brornobutone CH3 benzyl cyonide 3-methyl-2-phenyl- pentonenitrile "Q , pyridine S0Cl2 I thionyl H3C 4-hydroxy-1 -methyl- chloride CH30 piperidine 3-methyl-2-phenyl- pentonoyl chloride US 2 987 517 (Cilag-Chemie AG; 6.6.1961; D-prior. 20.4.1954). Trade Name(s): 3-methyl-2-phenyl- pentonoic ocid (I) Pentopiperide I F: Cryltne (Auclair); wfm Togestal (Biosedra)-comb.; 1: Crilin (Ayerst); wfm wfm USA: Perium (Rover); wfm 1586 P Pentazocine Pentazocine ATC: N02ADOI Use: analgesic RN: 359-83-1 MF: C,,H2,N0 MW: 285.43 EINECS: 206-634-6 LD,,,: 19.8 mg/kg (M, i.v.); 205 mglkg (M, p.0.); 21 mg/kg (R, i.v.); l 1 I0 mglkg (R, pa.) CN: (2a,6a,11 R*)- 1,2,3,4,5.6-hexahydro-6,1 l-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocin-8- hydrochloride RN: 2276-52-0 MF: C,,H2,N0 . HCI MW: 321.89 EINECS: 218-896-9 LD,,,: 126 mglkg (M, s.c.) lactate (1:l) RN: 17 146-95-1 MF: C,,H,NO . C&03 MW: 375.5 1 EINECS: 241-209-9 LD,,,: 103 mglkg (M, i.p.) H3C y - 4-methoxybenzyl- CH3 magnesium chloride 3,4-dimethyl- methyl 1 -3.4-lrimethyl- pyddine iodide pyridiniurn iodide 7H3 HBr H HZ. Pd BrCN decomposition I H3C, o ax! b ,,0%NJ~3 II H3C CH, bcF CH31 2-(4-methoxybenzy1)- 2'-hydroxy-2,5,9- 1,3,4-trimethyl- l,2,5.6- trirnethylbenzo- tetrohydropyridine 6-morphen Rrference(s): BE 61 1 000 (Sterling Drug; appl. 30.1 1.1961; USA-prior. 1.12.1960). Archer, S. et al.: J. Med. Chem. (JMCMAR) 7, 123 (1964). 2'-hydroxy-5.9- 1 -brorno-3-methyl- dirnethylbenro- 2-butene Forn~ularion(s): amp. 30 mg/ml; cps. 50 mg, 56.4 mg; suppos. 50 mg; tabl. 25 mg Pentozocine Trade Nanze(s): D: Fortral (Winthrop) GB: Fortagesic (Sanofi F: Fortal (Sanofi Winthrop) Winthrop; as hydrochloride) Fortral (Sterwin; as hydrochloride) Pentetrazol P 1587 I: Pentalgina (Pierrel) TaIwintab (Sanofi Pentagin (Sankyo) Talwin (Pierrel) Winthrop) USA: Talacen (Sanofi) Talwin (Sanofi Winthrop) J: PeItazon (Grelan) Talwin (Sanofi) Pentetrazol (Pentylenetetrazol) ATC: R07AB03 Use: analgesic, circulatory stimulant RN: 54-95-5 MF: C6H,,N4 MW: 138.17 EINECS: 200-219-3 LD,,: 31.4 mglkg (M, i.v.); 88 mgkg (M, p.0.); 45 mgkg (R, i.v.); 140 mg/kg (R, p.0.) CN: 6,7,8,9-tetrahydro-5H-tetrazolo[1,5-alazepine c%apro- dirnethyl loctorn sulfate N.N' Pentetrazal 2-methoxy-A'- 2-hydrazino-A '- tetrahydroazepine tetrahydraazepine (I) Reference(s): Schmidt, K.F.: Ber. Dtsch. Chem. Ges. (BDCGAS) 57,704 (1924). Stolle, R.: Ber. Dtsch. Chem. Ges. (BDCGAS) 63, 1032 (1930). alternative syntheses (azide method): DRP 427 858 (Knoll; appl. 1923). DRP 439 041 (Knoll; appl. 1924). DRP 455 585 (Knoll; appl. 1925). DRP 521 870 (Knoll; appl. 1929). DRP 537 739 (Knoll; appl. 1928). DRP 538 981 (Knoll; appl. 1926). DRP 543 025 (Knoll; appl. 1927). DRP 545 850 (Knoll; appl. 1927). DRP 574 943 (Knoll; appl. 1932). DRP 576 327 (Knoll; appl. 1930). DRP 61 1 692 (Chinoin; appl. 1934). Formulation(s): drops 100 mglg Trade Name(s): D: Afpred (Hefa-Frenon)- comb.; wfm Cardaminol (Reinecke)- comb.; wfrn Cardiazol (Knoll); wfm F: Indovert (Do1orgiet)-comb.; w fm I: Jasivita (Bolder)-comb.; wfrn Poikiloton (Lomapharm)- comb.; wfrn Sympatocard (Boehringer 1ng.)-comb.; wfrn DCsintex-Pentazol (M. Richard); wfrn Cardiazol (Knoll); wfrn Cardiazol Paracodina (Knoll)-comb.; wfrn Tetracor (Chinoin); wfrn Tetrazol (Lisapharma); wfrn J: Cardiazol (Sankyo) Pentazol (Yashima) USA: Analeptone (Reed & Carnrick); wfrn Benizol (1CI)-comb. with nicotinic acid; wfrn 1588 P Penthienate methobromide Geroniazol (Philips Nico-Metrazol (Knoll)- Vita-Metrazol (Knoll)- Roxane)-comb. with comb. with nicotinic acid; comb. with vitamin B nicotinic acid; wfm wfm complex; wfm Metrazol (Knoll); wfm Rovite Tonic (Rotex); wfm Penthienate methobromide (Penthienate bromide) ATC: A03AB Use: antispasmodic RN: 60-44-6 MF: C,,H,,BrNO,S MW: 420.41 EINECS: 200-478-2 LD,,,: 16 mgkg (M, i.v.); 2080 mglkg (M, p.0.) CN: 2-[(cyclopentylhydroxy-2-thienylacetyl)oxy]-N,N-diethyl-N-methylethanaminium bromide thiophene chloroglyoxylic 2-thienylglyoxylic ocid ethyl ester acid ethyl ester ethyl chloride cyclopentyl- cyclopentyl-2- magnesium thienylglycolic bromide acid 2-thienylglyoxylic ocid (I) methyl cyclopentyl-2-thienyl- glycaiic ocid 2-diethyl- arninoethyl ester (U) Penthienate methobromide Referencefs): US 2 541 634 (Univ. of Michigan; 1951 ; prior. 1946). bromide Formulation(s): tabl. 5 mg Trade Name(s): GB: ~onodral (Winthrop); wfm J: Monodral (Nakataki) USA: Monodral (Winthrop); wfm Pentifylline (Hexyltheobromine) ATC: C04ADO1 Use: vasodilator RN: 1028-33-7 MF: C,,H2,N402 MW: 264.33 EINECS: 213-842-0 LD;,,: 1040 mglkg (M, p.0.) CN: l-hexyl-3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione Pentobarbital P 1589 Reference(s): DE 860 217 (Chemische Werke Albert; appl. 1950). '3'3 theobrornine hexyl chloride alternative synthesis: SU 202 152 (K. Chkhikoadze et al.; appl. 17.9.1966). C"3 Pentifylline combination with inositol hexanicotinate: GB 1 129 134 (Sterling Winthrop; valid from 3.1 1.1965; prior. 4.1 1.1964). combination with nicotinic acid: GB 815 969 (Chemische Werke Albert; valid from 1958; USA-prior. 1957). usefor stabilization of vitamins: DOS 1 8 10 705 (Chemische Werke Albert; appl. 25.1 1.1968). retard form: DE 1 617 418 (Chemische Werke Albert; appl. 16.12.1967). oral pharmaceutical formulation: DOS 2 520 978 (Hoechst; appl. 10.5.1975). Formulation(s): s. r. drg. 400 mg Trade Name(sJ: D: Cosaldon (Albert-Roussel, Cosaldon (Albert-Roussel, J: Tonostan (Tokyo Tanabe)- Hoechst)-comb. with Hoechst) comb. with nicotinic acid retinol palmitate F: Cosadon (Hoechst)-comb. with nicotinic acid; wfm Pentobarbital (Mebumalum; Pentobarbitone) ATC: NOSCAOI Use: hypnotic RN: 76-74-4 MF: cI1HIRN2o3 MW: 226.28 EINECS: 200-983-8 LD,: 65 mgkg (M, i.v.); 170 mglkg (M, p.0.); 125 mglkg (R, p.0.); 50 mgkg (dog, i.v.) CN: 5-ethyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione monosodium salt RN: 57-33-0 MF: C,,H,,N2Na03 MW: 248.26 EINECS: 200-323-9 LD,,,: 8 1 mglkg (M, i.v.); 239 mgkg (M, p.0.); 65 mgkg (R, i.v.); 118 mglkg (R, p.0.); 65 mgkg (dog, p.0.) calcium salt RN: 7563-42-0 MF: C,,H,,N,O, . xCa MW: unspecified EINECS: 231-460-2 1590 P Pentorex 2-bromapentane ethylmalonic acid diethyl ester ethyl(1 -rnethylbutyl)- rnalanic acid diethyl ester (1) urea I Pentaborbital Reference(s): DRP 293 163 (Bayer; 1915). GB 650 354 (Geigy; appl. 1948) - method Formulation(s): cps. 50 mg, 100 mg; sol. 50 mglml; suppos. 60 mg, 120 mg (as sodium salt) Trade Name(s): D: Isoptin S (Knoll)-comb.; wfrn Migrexa (Sanorania)- comb.; wfrn Nembutal (Abbott); wfrn Neodorm (Minden); wfrn Norkotral (Desitin)-comb.; wfm F: GB : Omka-Nacht Tabletten (Heyden)-comb.; wfrn Praecicalm (Molimin); wfrn Priatan (Minden)-comb.; wfrn Repocal (Desitin); wfrn Nembutal (Abbott); wfrn Nembutal (Abbott); wfrn Pentorex (Phenpentermine) I: Isoptin S (Knoll)-comb.; wfrn Nembutal (Abbott); wfm J: Mintal (Tanabe) Nembutal (Dainippon) USA: Nembutal (Abbott) Pentobarbital Sodium (Wyeth-Ayerst) ATC: A08A Use: appetite depressant RN: 434-43-5 MF: C,,H,,N MW: 163.26 EINECS: 207-102-6 CN: a,a,P-trimethylbenzeneethanamine hydrogen tartrate (2:l) RN: 22876-60-4 MF: CIIHI7N. 1/2C4H,06 MW: 476.61 3-0x0-2-phenyl- rnethylrnagnesium 3-methyl-2-phenyl- butane bromide 3-butanal (I) . secretion diagnostic RN: 553 4-9 5-2 MF: C,,H,,N,O,S MW: 767.91 EINECS: 22 6-8 8 9-7 CN: N-[(1,1-dimethyIethoxy)carbonyl ]-~ -alanyl-~-tryptophyl-~-rnethionyl-~-a-aspartyl-~-phenylalaninamide Pentagestrone. R* )- 1,2,3,4,5.6-hexahydro-6,1 l-dimethyl- 3-( 3-methyl-2-butenyl )-2 ,6-methano-3-benzazocin- 8- hydrochloride RN: 227 6-5 2-0 MF: C,,H2,N0 . HCI MW: 321.89 EINECS: 21 8-8 9 6-9 LD,,,: 126 mglkg (M,. C04ADO1 Use: vasodilator RN: 102 8-3 3-7 MF: C,,H2,N402 MW: 264.33 EINECS: 21 3-8 4 2-0 LD;,,: 1040 mglkg (M, p.0.) CN: l-hexyl-3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione Pentobarbital P 1589