Bracco J: Conraxin Takeda I: Isteropac E.R... benzenedicarboxamide dimethyl 5-nitro- 3-amino- 1,2- 5-nitro-N,N'-bis2,3- isophtholate propanediol dihydroxypropy1- from glycide isophthal
Trang 1Iodamide 1 1081
I locetomic ocid I
H C 0
HZ Roney-Ni '? CH3
g N 3 - c 0 o ~ L iodine p
monochloride
Reference(s):
FR 5 997 M (Dagra; appl 23.11.1966; prior 25.11.1965, 26.5.1966)
I 7 CH3
#"%OOH
I
''4%
Fonnulation(s): tabl 500 mg, 750 mg
Trade Name(s):
D: Cholebrine F: CholCbrine (Schering); USA: Cholebrine (Mallinckrodt);
1: Colebrin (Schering); wfm
Iodamide
(Jodamid)
ATC: V08AA03 Use: X-ray contrast medium
RN: 440-58-4 MF: C12H,,13N204 MW: 627.94 EINECS: 207-125-1
LD,,: >7 glkg (M, p.0.);
>7 glkg (R, p.0.)
meglurnine salt
RN: 18656-21-8 MF: C,,H,,13N204 C7H17N0, MW: 823.16 EINECS: 242-480-6
4-chloro- 2.2-dichloro-N-
benzoic hydroxymethyl-
acid acetomide
3-aminamethyl- 4-chlorobenzoic ocid (I)
dichlora- 0
NH2 potassium H3CKN
Trang 21082 1 Iodoxamic acid
Reference(s):
US 3 360 436 (Eprova; appl 12.1 1.1963; CH-prior 23.1 1.1962,9.8.1963)
GB 1 002 344 (Eprova; appl 3.10.1963; CH-prior 23.1 1.1962,9.8.1963)
DE 1 273 747 (Eprova; appl 24.9.1963; CH-prior 23.1 1.1962)
Fornzulation(s): amp 300 mg, 380 mg, 420 mg (as meglumine salt)
Trade Name(s):
D: Uromiro (Heyden); wfm Opacist E.R (Bracco) J: Conraxin (Takeda) I: Isteropac E.R (Bracco) Uromiro (Bracco)
Use: X-ray contrast medium (cholangiography) RN: 31127-82-9 MF: C26H2,1,N20,0 MW: 1287.92 EINECS: 250-478-1
LD,,,: 13.65g/kg(M,i.v.)
CN: 3,3'-[(I ,16-dioxo-4,7,10,13-tetraoxahexadecane-l,l6-diyl)diimino]bis[2,4,6-triiodobenzoic acid]
meglumine salt (1:2)
RN: 51764-33-1 MF: C2,H2,16N20,0 2C7HI7NO, MW: 1678.35 EINECS: 257-398-6
N C ~ C H ~ + H O O ~ + O ~ ~ ~ + ~ N C ~ O f i O - O f i O - C N
acrylonitrile triethylene glycol 4,7,10,13-tetrooxahexadecane-
dinitrile (I)
1 H2S0,, C2H50H
4,7,10,13-tetrooxahexadecanedioyl chloride (11)
dirnethyl-
COOH ocetornide
3-amino-2.4.6-
triiodobenzoic
ocid
COOH 1
DE 1 937 21 1 (Bracco; appl 22.7.9969)
Formulation(s): amp 3.66 g, 5.49 g, 8.06 g, 9.91 g, 12.09 g (as meglurnine salt)
Trang 3Iofendylate 1 1083
Trade Name(s):
D: Endomirabil (Byk Gulden); I: Endobil (Bracco)
Iofendylate
(Iophendylate)
ATC: V08AD04 Use: X-ray contrast medium (myelography) RN: 99-79-6 MF: C,,H,,I02 MW: 416.34 EINECS: 202-787-8
LD,,,: 21 00 mglkg (R, p.0.)
CN: 4-iodo-t-methylbenzenedecanoic acid ethyl ester
I
benzene
Reference(s):
U S 2 348 23 1 (Eastman Kodak; 1944; appl 1940)
Formulation(s): inj sol
Trade Name(s):
GB: Ethiodan (Allen & USA: Pantopaque (Lafayette);
Ioglycamic acid
(Acide ioglycamique)
ATC: VO8ACO3 Use: X-ray contrast medium RN: 2618-25-9 MF: C,,H,oI,N207 MW: 1127.71 EINECS: 220-048-8
CN: 3.3'-[oxybis[(l -oxo-2,l -ethanediyl)imino]]bis[2,4,6-triodobenzoic acid]
meglumine salt (1:2)
RN: 14317-18-1 MF: CI,H,,I,N,07~ 2C,H,,NOS MW: 1518.14
3-amino-2,4,6- diglycolic chloride loglycamic acid
triiodobenzoic
Trang 41084 1 Iohexol
Reference ( s ) :
US 2 776 241 (Schering AG; 1957; D-prior 1952)
US 2 853 424 (Schering AG; 1958; D-prior 1952)
DE 936 928 (Schering AG; appl 1952)
DE 962 698 (Schering AG; appl 1952)
DE 962 699 (Schering AG; appl 1953)
DE 1 006 428 (Schering AG; appl 1955)
Formulation(s): amp 0.17 g/ml (as rneglumine salt)
Trade Name(s):
D: Biligram (Schering); wfm GB: Biligram (Schering Bilivison (Schering); wfm Bilivistan (Schering); wfm Chemicals); wfm Bilivistan (Schering); wfm F: Biligram (Schering); wfm I: Biligram (Schering); wfm
Use: X-ray contrast medium RN: 66108-95-0 MF: C,yH2613N30y MW: 821.14 EINECS: 266- 164-2
LD,,: 50 g/kg (M, i.v.); >20 g/kg (M, p.0.);
25.235 g/kg (R, i.v.); >20 g k g (R, p.0.);
>20 g k g (dog, i.v.)
benzenedicarboxamide
dimethyl 5-nitro- 3-amino- 1,2- 5-nitro-N,N'-bis(2,3-
isophtholate propanediol dihydroxypropy1)-
(from glycide isophthalomide ond ommonia)
5-amino-N,N8-bis(2.3- 5-amino-2.4.6-triiodo-
dihydroxyprapy1)- N,N'-bis(2,3-dihydroxy-
isophthalamide (I) propy1)isophthalamide
1 NaOCH,
2 H O / \ ~ C I
OH
5-acetamido-2.4.6-triiodo-
N.Na-bis(2.3-dihydroxy-
Iohexol
Trang 5Iopamidol 1 1085
Reference(s):
DE 2 726 196 (Nyegaard; appl 10.6.1977; GB-prior 11.6.1976)
US 4 250 113 (Nyegaard; 10.2.1981; GB-prior 11.6.1976)
Fomularion(s): amp 240 mg, 300 mg, 350 mg
Trade Name(s):
Use: X-ray contrast medium RN: 60166-93-0 MF: C,7H2213N308 MW: 777.09 EINECS: 262-093-6
LD,,,: 33 glkg (M, i.v.); >49 glkg (M, p.0.);
22.044 glkg (R, i.v.);
35 g/kg (dog, i.v.)
benzenedicarboxamide
COOH
ICI
Hz"4 chloride
5-orninoiso-
phtholic ocid
5-ornino-2.4.6- triiodoiso- phthalic acid
H,c,$cl dirnethylacetornide,
0 CH,
K
0
L-2-acetoxy-
propionyl
chloride
(from L-lactic
acid)
1 dirnethylacetarnide, tributylornine
2-ornino-1.3-
DE 2 547 789 (Savac; appl 24.10.1975; CH-prior 13.1 2.1974)
US 4 001 323 (Savac; 4.1.1977; CH-prior 13.12.1974)
Trang 61086 1 Iopanoic acid
Fortnulution(s): amp 200 mg, 300 mg, 370 mg
Trade Narne(s):
D: Solutrast (Byk Gulden; GB: Niopam (Merck; 1982); J: Iopamiron (Nippon
F: Iopamiron (Schering; 1982) I: Giastromiro (Bracco) USA: Isovue (Squibb); wfm
Iopamiro (Bracco)
Iopanoic acid
(Acidum iopanoicum)
ATC: V08ACO6 Use: X-ray contrast medium RN: 96-83-3 MF: C,,H,,I3NO2 MW: 570.93 EINECS: 202-539-9
LDs,,: 320 mglkg (M, i.v.); 6600 mglkg (M, p.0.);
280 mglkg (R, i.v.); 1540 mglkg (R, p.0.)
CN: 3-amino-a-ethyl-2,4,6-triiodobenzenepropanoic acid
monosodium salt
RN: 2497-78-1 MF: Cl1H,,I,NNaO2 MW: 592.92 EINECS: 219-683-3
LD,,,: 296 m g k g (M, i.v.); 1602 mglkg (M, p.0.);
332 mgikg (R, i.v.); 2986 mglkg (R, p.0.)
0 0
sodium butyrote
3-nitro- butyric anhydride a-ethyl-3-nitro-
2-(3-orninobenzy1)- butyric ocid
NH2 monochloride
Reference(s):
US 2.705 726 (Sterling Drug; 1955; prior 1949)
I
I
NH2
For~nulation(s): cps 500 mg (as sodium salt); powder 375 mglg (as calcium salt)
Trade Name(s):
D: Telepaque (Winthrop); wfm I: Cistobil (Bracco) Molpaque (Tokyo Tanabe) F: TClCpaque (Winthrop); Telepaque (Winthrop); wfm Telepaque (Kodama)
GB: Telepaque (Winthrop); wfm Leabar (Toyo S.-Ono)
Trang 7Iophenoic acid 1 1087
Iophenoic acid
(Acidum iophenoicum; Iophenoxic acid)
RN: 96-84-4 MF: Cl,Hl,1303 MW: 571.92
LD,,: 374 mglkg (M, i.v.); 1850 mglkg (M, p.0.);
2 glkg (R, p.0.);
203 m g k g (dog, i.v.)
CN: a-ethyl-3-hydroxy-2,4,6-triiodobenzenepropoic acid
ATC: V08AD Use: X-ray contrast medium
3-hydroxy- butyric anhydride a-ethyl-3-hydroxy-
1 -
Tic-'
2-(3-hydroxybenzyl)- butyric acid
Iophenoic ocid
Reference(s):
US 2 931 830 (Sterling Drug; 5.4.1960; appl 20.3.1952)
GB 726 987 (Sterling Drug; appl 1953; USA-prior 1952)
Trade Name(s):
USA: Teridax (Schering); wfm
Use: X-ray contrast medium RN: 5579-92-0 MF: C,H91,N0, MW: 420.97 EINECS: 226-968-6
3.5-diiodo-4(1 H)- glycide I lopydol
(cf diodone
synthesis)
1 -chloro-2.3-
Trang 81088 1 Iotalamic acid
Reference(s):
DRP 579 224 (I G Farben; appl 1930)
Formulation(s): vial 20 mg 3,5-diiodo-4(1H)-pyridonelml in comb with iopydol
Trade Name(s):
D: Hydrast (Byk Gulden); I: Hytrast (Byk Gulden)- J: Hydrast (Guerbet-
with iopydone; wfm
Iotalamic acid
(Iothalamic acid; Acide iotalamique)
ATC: V08AA04 Use: X-ray contrast medium RN: 2276-90-6 MF: CllH913N204 MW: 613.92 EINECS: 218-897-4
monosodium salt
RN: 1225-20-3 MF: C,,H,13N2Na04 MW: 635.90 EINECS: 214-955-8
LD,,,: 19.2g/kg(M,i.v.)
meglumine salt
RN: 13087-53-1 MF: C,,H,13N204 C7H17N0, MW: 809.13 EINECS: 235-998-9
LD,,,: 8.1 glkg (M, i.v.);
10.5 glkg (R, i.v.)
dimethyl 5-nitro-
isophtholote
monomethyl 5-nitroisophtholote
0 CH3 manochloride
Reference(s):
Hoey, G.B et al.: J Med Chem (JMCMAR) 6 , 2 4 (1963)
US 3 145 197 (Mallinckrodt; 18.8.1964; appl 26.6.1961; prior 25.8.1960)
GB 994 215 (Mallinckrodt; appl 18.8.1961; USA-prior 25.8.1960)
acetyl
Formularion(s): sol 17 %, 24 %, 36 %, 43 %, 60 %, 66.8 %, 80 % (as meglumine salt)
lotolomic acid chloride
Trang 9Iotrolan I 1089
Trade Name(s):
D: Conray (Byk Gulden); wfm I: Angio-Conray 80 (Bracco) Conray (Mallinckrodt);
GB: Conray (May & Baker); J: Angio-Conray (Daiichi) Cysto-Conray
Gastro-Conray (May & USA: Angio-Conray Vascoray (Mallinckrodt);
- -
soluble, non-ionic, for myelography and contrast enhancement in CT) RN: 79770-24-4 MF: C3,H,,I,N,0,0 MW: 1626.24
LD,,: > 26 g/kg (M, i.v.);
12.7 g/kg (R, i.v.)
S0CI2 HOOC
2.4.6-triiodo-5-
methylomino-
isophtholic acid
0 1 ' I I 0 5-amino-6-hydroxy
CH, CH,
1,3-dioxepane (11)
Trang 101090 1 Iotroxic acid
90% aq CFxCOOH
preparotion of 11:
2.2-dimethoxy- 1.2-dihydroxy- 2.2-dimethyl-
propane 2-butene 4.7-dihydro-1.3-
dioxepin (N)
H3C-CN, CH,OH, 30% H202
4 0 O C 5 h liq.NH3, 120 "C, 4 h
I V
acetonitrile, hydrogen peroxideb H3C 0
octone
The epoxidation step can also be performed with m-chloroperoxybenzoic acid in CH2C12
Reference(s):
US 4 341 756 (The Regents of the Univ of Calif.; 27.7.1982; prior 3 1.1.1980, 17.4.1980)
EP 33 426 (The Regents of the Univ of Calif.; appl 30.12.1980; USA-prior 3 1.1.1980, 17.4.1980)
preparation of trans-2,2-dimethyl-5-amino-6-hydroxy-l,3-dioxepane:
US 4 439 613 (The Regents of the Univ of Calif.; 27.5.1984; prior 31.1.1980, 17.4.1980,5.4.1982)
review:
Dawson, P.; Howell, M.: Br J Radiol (BJRAAP) 59,987 (1986)
Fortnulation(s): vial 10 ml and 20 ml(513 mglml), 10 ml (641 mglml)
Trade Name(s):
D: Isovist (Schering; 1988) J: Isovist (Nihon Schering;
Use: X-ray contrast medium RN: 51022-74-3 MF: C22H,,I,N20, MW: 1215.82 EINECS: 256-917-3
LD,,: 2820 mglkg (M, i.v.); >9 g/kg (M, p.0.);
4190 mg/kg (R, i.v.); >9 g/kg (R, p.0.)