Prednicarbate P 1 69 1 alternative synthesis: US 3 935 213 (Pfizer; 27.1.1976; prior. 5.12.1973). DOS 2 457 911 (Pfizer; appl. 4.12.1974; USA-prior. 5.12.1973). DOS 2731 737 (Pfizer; appl. 11.7.1977; USA-prior. 6.8.1976). US 4 062 844 (Pfizer; 13.12.1977; appl. 20.9.1976). US 4 138 561 (Bristol-Myers; 6.2.1979; prior. 30.9.1977). BE 861 821 (Fermion; appl. 14.l2.1977; SF-prior. 15.1 2.1976). BE 861 822 (Ferrnion; appl. 14.12.1977; SF-prior. 15.12.1976). a-form: US 4 092 315 (Pfizer; 30.5.1978; appl. 1.3.1976). DAS 2 708 192 (Pfizer; appl. 25.2.1977; USA-prior. 1.3.1976). anhydrous crystalline form: DE 3 429 415 (Orion; appl. 9.8.1984; FL-prior. 25.6.1984). US 4 816 455 (Heumann Pharrna; 28.3.1989; appl. 3.3.1987; EP-prior. 21.3.1986). Formuhtion(s): s. r. cps. 1 rng, 2 rng, 4 rng, 6 rng; tabl. 0.5 mg, 1 rng, 2 mg, 5 rng (as hydrochloride) Trade Name(s): D: Adversuten (ASTA Medica Polypressl-forte (Pfizer)- GB: Hypovase (Invicta; 1974) AWD) comb. I: Minipress (Pfizer; 1978); Duramipress (durachernie) ~razosin-ratiodharm wfrn Eurex (Sanofi Winthrop) (ratiopharrn) J: Minipress (Pfizer Taito; Minipress (Pfizer; 1977) F: Alpress LP (Pfizer) 1981) Minipress (Pfizer; 1979) USA: Minipress (Pfi7er) Prednicarbate (Hoe 777) ATC: D07AC18 Use: topical glucocorticoid, steroidal anti- inflammatory RN: 73771-04-7 MF: C2,H3,0, MW. 488.58 EINECS: 277-590-3 CN: (1 1 P)- 17-[(ethoxycarbonyl)oxy]-1 I-hydroxy-21-(I -oxopropoxy)pregna-1,4-diene-3,20-dione prednisolone tetraethyl (q v.1 orthocorbonote prednisolone 17.21 -diethy1 orihocarbonote (I) CH3COOH. CI ~20 8 / vcH3 propionyl , 1- MeH H H 0 ' chloride 0&Lc~3 Me NO 0-CH, Me H / ,' H H prednisolone Prednicorbote 17-ethylcarbonote 1692 P Prednimustine Reference(s): Stache, U. et al.: Arzneim Forsch. (ARZNAD) 35 (11), 1753 (1985). EP 742 (Hoechst; appl. 27.7.1978; D-prior. 4.8.1977). DE 2 735 110 (Hoechst; appl. 4.8.1977). US 4 242 334 (Hoechst: appl. 21.2.1979; D-prior. 4.8.1977). Formulation(s): cream 2.5 mgll g; ointment 2.5 mgll g; sol. (in aqueous ethanol, 20 %) 2.5 mgll g Trade Name(s): D: Dermatop (Hoechst) I: Dermatop (Hoechst Marion USA: Dermatop (Hoechst Marion Roussel) Roussel) Prednimustine ATC: LOlAA08 Use: antineoplastic RN: 29069-24-7 MF: C,5H45C12N0, MW: 646.65 EINECS: 249-410-3 LDs,,: 530 mglkg (R, p.o.) CN: (1 1 ~)-21-[4-[4-[bis(2-chloroethyl)arnino]phenyl]-I-oxobutoxy]-l1,17-dihydroxypregna-1,4-diene-3,20- dione prednisolone (9 v.) 4-[4-[bis(2-chloraethyl)amino]phenyl]- butyric anhydride Prednimustine (I) Reference(s): DOS 2 001 305 (A B Leo; appl. 13.1.1970; GB-prior. 23.1.1969). Formularion(s); cps. 10 rng, 50 mg; tabl. 10 mg, 100 mg Trade Narne(s): D: Sterecyt (Pharmaleo); wfm F: Sttrkocyt (Roger Bellon); wfm Prednisolamate ATC: H02AB06 Use: glucocorticoid RN: 5626-34-6 MF: C2,H3,N06 MW: 473.61 EINECS: 227-064-4 CN: N,N-diethylglycine (1 1P)-I l,17-dihydroxy-3,20-dioxopregna-1.4-dien-21 -yl ester Prednisolone P 1693 hydrochloride RN: 17140-01-1 MF: C2,H3,N06 . HCI MW: 510.07 -I prednisalone dieihyl- amine chloroacetyl chloride GB 862 370 (Pfizer; valid from 1957; USA-prior. 1956). DE 1 037 451 (Schering AG; appl. 1957). __* alternative synthesis: Pancrazio, G.; Sbarigia, G.: Farmaco, Ed. Prat. (FRPPAO) 16, 190 (1961). Prednisolompte Formulation(s): tabl. 5 mg Trade Name(s): D: Deltacortril-intravenos (Pfizer); wfm - Prednisolone ATC: A07EA01; C05AA04; D07AA03; D07XA02; H02AB06; R01AD02; ROlAD52; SO1 BAO4; SOlCB02; S02BA03; S03BA02 Use: glucocorticoid RN: 50-24-8 MF: C21H280s MW: 360.45 EINECS: 200-021-7 LD,,: 180 mglkg (M, i.v.); 1680 mglkg (M, p.0.); 120 mgkg (R, i.v.) CN: (1 1 ~)-11,17,21-trihydroxypregna-l,4-diene-3,20-dione acetate RN: 52-21-1 MF: C,,H3,06 MW: 402.49 EINECS: 200-134-1 LD5,,: 3500 mgkg (M, s.c.); >240 mglkg (R, s.c.) 1694 P Prednisolone hydrollostone 21 -ocetote A, collidine I + hydrocortisone Br,. CH,COOH + bromine I Prednisolone 21 -oretole microbiologicol dehydrogenation [Cotyneboctcrium haagii (ATCC 7005)] or SeO, , mi / H H 1 Prednisolone I a US 2 897 216 (Schering Corp.: 1959; prior. 1952). starting material: The Merck Index, 12th Ed., 815 (1996). b US 3 134 718 (Schering Corp.; 26.5.1964; appl. 12.12.1963; prior. 1 1.8.1954). Wettstein, A. et al.: Helv. Chim. Acta (HCACAV) 39, 734 (1956). Nobile, A. et al.: J. Am. Chem. Soc. (JACSAT) 77,4184 (1955). DAS 1 135 899 (Schering AG; appl. 20.5.1960). alternative synthesis: US 4 041 055 (Upjohn; 9.8.1977; appl. 17.1 1.1975). Formulation(s): amp. 10 mg/ml, 25 mglml, 50 mglml (as acetate); eye drops 1.2 mg/ml, 10 mglrnl (as acetate); ointment 5 mglg, 100 mglg; suppos. 100 mg (as acetate); syrup 15 mgl5 ml; tabl. 1 mg, 5 mg, 20 mg Trade Name(s): D: Alferm (Schoning-Berlin)- comb. Decaprednil (Orion Pharma) Decortin H (Merck) Dontisolan (Hoechst) Dura Prednisolon (durachemie) Hefasolon (Hefa Pharma) Prednabene (Merckle) Inflanefran (Pharm- Prednihexal (Hexal) Allergan) Predni-H-injekt Klismacort (bene- (Sanorania) Arzneimittel) Predni-H-Tablinen Linola (Wolff) (Sanorania) Preclal (Artesan; Cassella- Predni-POS (Ursapharm) med) Prednisolone sodium phosphate P 1695 Prednisolon "Ferring" (Ferring) Prednisolon "Lentia" (Lentia) Prednisolon Augensalbe Jenapharm (Jenapharm) Prednisolut (Jenapharm) Soh-Decortin (Merck) Ultracortenol (CIBA Vision) combination preparations F: Deliproct (Schering; as caproate)-comb. Dtrinox (Thtrabel Lucien pharrna)-comb. combination preparations GB: Deltacortril (Pfizer) Deltastab (Knoll) Hydrocortancyl cp stc (Roussel) Hydrocortancyl susp inj (Roussel) Precortisyl forte (Hoechst) Pred forte (Allergan) Scheriproct (Schering; as hexanoate)-comb. 1: Biodeltacortilen (SIFT)- comb. Meticortelone (Schering- Plough) Solprene (Farmigea) J: Codelcortone (Merck- Banyu) Deltacortil (Taito Pfizer) Delta Prenin (Sumitomo) Donisolone (Sankyo) Lavine (Tatsumi) Prednisolone Cream (Toho) Prednisolon Ophthalmic Oint (Nilten) Predonine (Shionogi) Scherisolon Inj. (Nihon Schering) Scherisolon Tab. (Nihon Schering) numerous combination preparations USA: Predniso (Roxane) Prelone (Muro) Prednisolone sodium phosphate ATC: H02AB06 Use: glucocorticoid RN: 125-02-0 MF: C2,H2,Na20,P MW: 484.39 EINECS: 204-722-9 LDS,: 360 mglkg (rabbit, i.v.) CN: (1 1 P)-ll,l7-dihydroxy-21-(phosphonooxy)pregna- 1,4-diene-3,20-dione disodium salt free acid RN: 302-25-0 MF: C,,H2,0,P MW: 440.43 EINECS: 206-120-1 prednisolone (q v.) -8- 1. Od-F;-U , pyridine Cl 2. ocidic ion exchonger. NoHCO, b 1. dimorpholinophosphinic chloride prednisolone 21 -phosphate (monosodium solt) (1) Prednisolone sodium phosphote 1 Reference(s): DE 1 134 075 (Merck AG; appl. 26.1 1.1959). 1696 P Prednisolone sodium succinate alternurive synrheses: US 2 789 1 17 (Merck & Co.; 1957; appl. 1957). US 2 870 177 (Merck & Co.; 1959; appl. 1954). US 2 932 657 (Merck k Co.; 12.4.1960; appl. 30.7.1957). US 2 936 313 (Glaxo; 10.5.1960; appl. 18.11.1958; GB-prior. 19.1 1.1957). Forrnulation(s): amp. 33.6 mg/5 ml, 53.75 mg15 ml; eye drops 0.5 g1100 ml; oral sol. 6.7 mg15 ml Trade Narne(s): D: Hefasolon (Hefa Pharma) Phortisolone (Fumouze); Prednesol (Glaxo Prednabene wfm Wellcome) Injektionslosung (Merckle) Solucort (Merck Sharp & Predsol (Evans) F: Colicort (Merck Sharp & Dohme-Chibret) I: Solprene (Farmigea)-comb. Dohme-Chibret)-comb. GB: Minims Prednisolone J: Prozorin (Takeda) Deturgylone (SynthC1abo)- (Chauvin) USA: Optimyd (Medeva)-comb. comb. Prednisolone sodium succinate ATC: H02AB06 Use: glucocorticoid RN: 1715-33-9 MF: C25H31NaOR MW: 482.51 EINECS: 216-995-1 LD,,: 1125 mgkg (M, i.v.); 770 mgkg (R, i.v.) CN: (1 1 P)-2 1 -(3-carboxy- 1 -oxopropoxy)-l 1 ,17-dihydroxypregna-1,4-diene-3,20-dione monosodium salt free acid RN: 2920-86-7 MF: C2,H,,0, MW: 460.52 EINECS: 220-861-8 prednisolone (9. v.) quinoline succinic anhydride ( Prednisolone sodium succinate DAS 1 045 400 (Pfizer; appl. 1956; USA-prior. 1955)-withdrawn. continuation of DE 1 013 648 Forrnularion(s): amp. 10 mg, 25 mg, 100 mg (as free acid); amp. 10 mglml, 25 mglml, 50 mg/ml, 100 mglml, 250 mgl5 ml, 250 mg/lO ml, 500 mgl5 ml, 500 mgllO ml, 1000 mg1.5 ml, 1000 mgll0 ml Prednisolone sodium sulfobenzoate P 1697 p- - Trade Name(s): D: Aquapred (Winzer)-comb. Solo-Decortin H (Merck) J: Predonine, water sol. Hostacortin H sol. I: Endoprenovis (Vister) (Shionogi) (Hoechst) Ibisterolon Iniett. (IBI) IJSA: Meticortelone sol. Realin Supp. (Geigyl Policort (Lepetit)-comb. (Schering); wfm Thomae)-comb. Soludacortin (Bracco) Prednisolone sodium sulfobenzoate ATC: H02AB06 Use: glucocorticoid RN: 630-67-1 MF: C,,H,,Na09S MW: 566.60 EINECS: 21 1-141-4 CN: (1 1 ~)-ll,l7-dihydroxy-21-[(3-sulfobenzoyl)oxy]pregna- 1,4-diene-3,20-dione monosodium salt prednisolone methonesulfonyl (9. v.1 chloride sodium 3-sulfo- benzoate Prednisolone sodium 21-sulfobenzoote Reference(s): US 3 037 034 (Roussel-Uclaf; 29.5.1962; appl. 21.4.1960; F-prior. 24.4.1959). alternative synthesis: US 3 032 568 (Roussel-Uclaf; 1.5.1962; appl. 15.3.1961; prior. 13.4.1959). Formulation(s): collutorium 22.5 mgl3 m1;clysma 20 mg; eye ointment 30 mgl4 g; foam 20 mg Trade Name(s): D: Cortiphenicol Positex (Ursapharm)- Tergynan (Bouchara)- (Saarstickstoff-Fato1)- comb.; wfm comb. comb.; wfm F: DCsocort (Chauvin)-comb. GB: Predenema (Pharmax) Phoscortil-Klys Solupred (HoudC) Predfoam (Pharmax) (Biotherax)-comb.; wfm I: Rexidina (Bouty)-comb. Prednisolone steaglate (Prednisolone stearoylglycolate) ATC: H02AB06 Use: glucocorticoid RN: 5060-55-9 MF: C4,H,O8 MW: 684.96 EINECS: 225-763-9 CN: (1 1 P)- 11 ,l7-dihydroxy-21-[[[(1-oxooctadecyl)oxy]acetyl]oxy]pregna-1,4-diene-3,20-dione 1698 P Prednisolone tebutate 0 dioxane. pyridine + C,&~y(CH2)16-CH3 - 0 prcdnisolone steoroylglycoloyl (9. v.) chloride Prednisolone steoglote Reference(s): US 3 171 846 (Carlo Erba; 2.3.1965; I-prior. 10.7.1962). Girardi, P.N. et al.: Arzneim Forsch. (ARZNAD) 16, 162 (1966). Formulation(s); nasal drops 0.25 % Trude Name(s): F: Rollsone (Bellon); wfm Estilsona (Erba); wfm Siutisane (Erba); wfm GB: Sintisone (Farmitalia Carlo Glistelone (Erba); wfm Verisone (Tiber); wfm Erba); wfm Glitisone (Vis); wfm I: Erbacort (Erba); wfm Prenisei (Cifa); wfm Prednisolone tebutate ATC: H02AB06 Use: . glucocorticoid RN: 7681 -14-3 MF: C,,H,,O, MW: 458.60 EINECS: 23 1-661-5 CN: (1 10)-21-(3,3-dimethyl-1 -oxobutoxy)-l 1,17-dihydroxypregna-1,4-diene-3,20-dione pyridine CI CH3 prednisolone tert-butyl- (q v.) acetyl chloride Reference(s): US 2 736 734 (Merck & Co.; 1956; prior. 1955). Prednisolone tebutotc DE 1 135 904 (Merck & Co.; appl. 1956; USA-prior. 1955). Formulation(s): susp. 20 mglml Trade Name(s): USA: Hydeltra-TBA (Merck Sharp & Dohme) Prednisolone 2 1-trimethvlacetate P 1699 Prednisolone 214rimethylacetate (Prednisolon 2 1 -pivalate) ATC: H02ABO6 Use: glucocorticoid RN: 1107-99-9 MF: C2,H,,0, MW: 444.57 EINECS: 214-172-1 CN: (1 1 P)-21-(2,2-dimethyl- l-oxopropoxy)-l 1 ,17-dihydroxypregna-I,4-diene-3,20-dione dH CHCI3. pyridine H i 0' prednisolone trirnethylocetyl (4. v.1 chloride I Prednisolone 21 -trirnethylocetote Reference(s): CH 398 585 (Ciba; appl. 1956). Formulation(s): ophthalmic ointment 5 mglml (0.5 %) Trade Name(s): D: Ultracortenol (Ciba); wfm Varecort (Zyma-Blaes)- comb.; wfm Prednisone ATC: A07EA03; H02AB07 Use: glucocorticoid RN: 53-03-2 MF: C2,H2,0, MW: 358.43 EINECS: 200-160-3 LD,,: 600 mg/kg (M, i.m.); 135 mglkg (M, i.p.); 101 mglkg (M, s.c.) CN: 17.21-dihydroxypregna-l,4-diene-3,11,20-trione dihydrocortisone 21 -ocetote (cf. cortisone synthesis) 1. collidine. 3% 3.5-lutidine 2. KHCO, I b Prednisone 1700 P Prednival acetate microbiological dehydrogenation OyoH [Corynebocterium simplex] &OH or seo2 H H selenium dioxide 0' Reference(s): a US 2 897 216 (Schering Corp.; 1959; prior. 1952). Applezweig, N.: Steroid Drugs, Vol. 1, 66 (New York, London, Toronto 1962). starting material: Applezweig, N.: Steroid Drugs, Vol. 1,66 (New York, London, Toronto 1962). b US 3 134 718 (Schering Corp.; 26.5.1964; appl. 12.12.1963; prior. 11.8.1954). Wettstein, A. et al.: Helv. Chim. Acta (HCACAV) 39, 734 (1956). review: Ullmanns Encykl. Tech. Chem., 4. Aufl., Vol. 13, 54. Formulation(s): cream 5 mglg; eye drops 2 mg/g in comb. with chloramphenicole; suppos. 5 mg, 10 mg, 30 mg, 100 mg; syrup 5 mgl5 ml, 25 mglml, 50 mglml; tabl. 1 mg, 5 mg, 20 mg, 50 mg Trade Name(s): D: Decortin (Merck) Oleomycetin-Prednison Augentropfen (Winzer)- comb. Prcdnison "Dorsch" (Orion Pharma) Prednison "Ferring" (Pharmagalen) Prednison "Sanhelios" (Borner) Predni-Tablinen (Beiersdorf-Tablinen) Predni-Tablinen (Sanorania) Rectodelt (Trommsdorff) F: Cortancyl (Roussel) GB: Decortisyl (Roussel); wfm Delta-Butazolidin (Geigy). comb.; wfm J: Delta-Butazolidin (Ciba- Geigy-Fujisawa)-comb. USA: Liquid Pred (Muro) Lisacort (Fellows) Sterapred (Merz) generics Prednival acetate (Prednisolone 17-0-valerate) ATC: H02AB Use: glucocorticoid RN: 72064-79-0 MF: C,,H3,0, MW: 486.61 EINECS: 276-312-8 LDs(,: >3 &/kg (M, p.0.); >4 g/kg (R, p.0.) CN: (1 1P)-21-(acety1oxy)-1 l-hydroxy-17-[(l-oxopentyl)oxy~pregna-1,4-diene-3,20-dione prednival KN: 15 180-00-4 MF: C,,H3,0, MW: 444.57 EINECS: 239-228-2 LD,,,: 490 mg/kg (M, s.c.) prednisolone (4. v.) trimethyl orthovolerate . 2906 9-2 4-7 MF: C,5H45C12N0, MW: 646.65 EINECS: 24 9-4 1 0-3 LDs,,: 530 mglkg (R, p.o.) CN: (1 1 ~ )-2 1-[ 4-[ 4-[ bis(2-chloroethyl)arnino]phenyl]-I-oxobutoxy]-l1,17-dihydroxypregna-1,4-diene-3,2 0-. 7681 -1 4-3 MF: C,,H,,O, MW: 458.60 EINECS: 23 1-6 6 1-5 CN: (1 10 )-2 1-( 3,3-dimethyl-1 -oxobutoxy)-l 1,17-dihydroxypregna-1,4-diene-3,20-dione pyridine CI CH3 prednisolone tert-butyl- (q. steroidal anti- inflammatory RN: 7377 1-0 4-7 MF: C2,H3,0, MW. 488.58 EINECS: 27 7-5 9 0-3 CN: (1 1 P )- 1 7-[ (ethoxycarbonyl)oxy ]-1 I-hydroxy-2 1-( I -oxopropoxy)pregna-1,4-diene-3,20-dione prednisolone