0.5 mg, 1 rng, 2 mg, 5 rng as hydrochloride Trade Names: D: Adversuten ASTA Medica Polypressl-forte Pfizer- GB: Hypovase Invicta; 1974 Duramipress durachernie ~razosin-ratiodharm wfrn E
Trang 1Prednicarbate 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)
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
H H
0&Lc~3
Me NO 0-CH,
Me H
Trang 21692 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
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
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
Trang 3Prednisolone 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 -
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 m g k g (M, s.c.);
>240 mglkg (R, s.c.)
Trang 41694 P Prednisolone
hydrollostone
21 -ocetote
A, collidine
hydrocortisone
Br, CH,COOH
+ bromine
I Prednisolone 21 -oretole
microbiologicol dehydrogenation [Cotyneboctcrium haagii
/ H H
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)
Preclal (Artesan; Cassella- Predni-POS (Ursapharm) med)
Trang 5Prednisolone 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)
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 O d - 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)
Trang 61696 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
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
Use: glucocorticoid RN: 1715-33-9 MF: C25H31NaOR MW: 482.51 EINECS: 216-995-1
LD,,: 1125 m g k g (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
Trang 7Prednisolone sodium sulfobenzoate P 1697
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
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):
comb.; wfm F: DCsocort (Chauvin)-comb GB: Predenema (Pharmax)
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
Trang 81698 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
I: Erbacort (Erba); wfm Prenisei (Cifa); wfm
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)
Trang 9Prednisolone 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
0'
prednisolone trirnethylocetyl
(4 v.1 chloride
I Prednisolone 2 1 -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
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,
Trang 101700 P Prednival acetate
microbiological dehydrogenation
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 , 6 6 (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.)
orthovolerate