Iodamide 1 1081 I locetomic ocid I HC 0 HZ. Roney-Ni '? CH3 gN3-c0o~ Lp iodine monochloride NO2 NH2 Reference(s): FR 5 997 M (Dagra; appl. 23.11.1966; prior. 25.11.1965, 26.5.1966). H3C O I 7 CH3 #"%OOH I ''4% Fonnulation(s): tabl. 500 mg, 750 mg Trade Name(s): D: Cholebrine F: CholCbrine (Schering); USA: Cholebrine (Mallinckrodt); (Mundipharma); wfm wfm wfm 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.) CN: 3-(acetylamino)-5-[(acetylamino)methyl]-2,4,6-triiodobenzoic acid meglurnine salt RN: 18656-21-8 MF: C,,H,,13N204 . C7H17N0, MW: 823.16 EINECS: 242-480-6 COOH COOH COOH 4-chloro- 2.2-dichloro-N- benzoic hydroxymethyl- acid acetomide 3-aminamethyl- 4-chlorobenzoic ocid (I) COOH COOH H , Pd-C KICI2 III Z b dichlora- 0 NH2 potassium H3CKN 0 I iodate 1082 1 Iodoxamic acid I Iodornide I 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) Iodoxamic acid ATC: V08ACOl 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 NC~CH~ + HOO~+O~~~~ + NC~OfiO-OfiO-CN acrylonitrile triethylene glycol 4,7,10,13-tetrooxahexadecane- dinitrile (I) 1. H2S0,, C2H50H 2. NaOH ,7 4,7,10,13-tetrooxahexadecanedioyl chloride (11) dirnethyl- COOH ocetornide 3-amino-2.4.6- triiodobenzoic ocid COOH 1 Iodoxarnic ocid I 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) Iofendylate 1 1083 Trade Name(s): D: Endomirabil (Byk Gulden); I: Endobil (Bracco) wfm J: Cholegrafin (Takeda) 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 + H2COcH H3C 0-c~~ I iodo- ethyl 10-undecylenate lofendylate benzene Reference(s): US 2 348 23 1 (Eastman Kodak; 1944; appl. 1940). Formulation(s): inj. sol. Trade Name(s): GB: Ethiodan (Allen & USA: Pantopaque (Lafayette); Hanburys); wfm wfm 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 acid 1084 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 Iohexol ATC: V08AB02 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 gkg (R, p.0.); >20 gkg (dog, i.v.) CN: 5-[acetyl(2,3-dihydroxypropyl)amino]-~,~-bis(23-dihydroxypropy1)-24,6-trioo-1,3- 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. HO/\~CI OH 5-acetamido-2.4.6-triiodo- N.Na-bis(2.3-dihydroxy- Iohexol propyl)isophtholamide (11) Iopamidol 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): D: Accupaque (Nycomed) F: Omnipaque (Nycomed; J: Lumopaque (Winthrop) Omnipaque (Schering; 1986) Omnipaque (Daiichi) 1983) I: Omnipaque (Schering; USA: Omnipaque (Winthrop- 1985) Breon); wfm Iopamidol ATC: V08AB04 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.) CN: (S)-N,~-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-l ,3- benzenedicarboxamide COOH ICI Hz"4 chloride I 10 5-orninoiso- phtholic ocid 5-ornino-2.4.6- triiodoiso- phthalic acid H,c,$cl dirnethylacetornide, I + 0 CH, K 0 L-2-acetoxy- propionyl chloride (from L-lactic acid) 1. dirnethylacetarnide, tributylornine 2-ornino-1.3- propanediol I loparnidol 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). 1086 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 1981) wfm Schering) 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 mgkg (M, i.v.); 1602 mglkg (M, p.0.); 332 mgikg (R, i.v.); 2986 mglkg (R, p.0.) 0 0 sodium butyrote qCHO + (U-OJ-CH3 - NO2 CH3 NO2 3-nitro- butyric anhydride a-ethyl-3-nitro- benzoldehyde cinnornic acid (I) 2-(3-orninobenzy1)- butyric ocid HZ. Roney-Ni ICI 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) wfin J: Ace-Line (Maruishi) USA: Telepaque (Winthrop); wfm GB: Telepaque (Winthrop); wfm Leabar (Toyo S Ono) Iophenoic 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 mgkg (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- benzaldhyde cinnamic acid (1) sodium arnalgorn ICI 1- Tic-' OH monochloride 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 I0p yd0l ATC: V08AD02 Use: X-ray contrast medium RN: 5579-92-0 MF: C,H91,N0, MW: 420.97 EINECS: 226-968-6 CN: 1-(2,3-dihydioxypropyl)-3,5-diiodo-4(1H)-pyridinone 3.5-diiodo-4(1 H)- glycide I lopydol pyridone (I) I (cf. diodone synthesis) 1 -chloro-2.3- propanediol 1088 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- wfm comb. with iopydone; wfm Kodama)-comb. with F: Hydrast (Guerbet)-comb. iopydone 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 CN: 3-(acetylamino)-2,4,6-triiodo-5-[(methylamino)carbonyl]benzoic acid 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 Hz, Pd-C ICI I * H2N iodine 0 CH3 manochloride Reference(s): Hoey, G.B. et al.: J. Med. Chem. (JMCMAR) 6,24 (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 Iotrolan I 1089 Trade Name(s): D: Conray (Byk Gulden); wfm I: Angio-Conray 80 (Bracco) Conray (Mallinckrodt); F: Contrix 28 (Guerbet); wfm Conray (Bracco) wfm GB: Conray (May & Baker); J: Angio-Conray (Daiichi) Cysto-Conray wfm Conray (Daiichi) (Mallinckrodt); wfm Gastro-Conray (May & USA: Angio-Conray Vascoray (Mallinckrodt); Baker); wfm (Mallinckrodt); wfm wfm - - I0tr0lan ATC: V08AB06 (DL-31 17; Iotrol) Use: X-ray contrast medium (water 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.) CN: 5,5'-[1,3-dioxo-1,3-propanediylbis(methylimino)]bis[N,N'-bis[2,3-dihydroxy-1-(hydroxymethyl)propyl]- COOH OVCl S0CI2 HOOC OIH 2.4.6-triiodo-5- methylomino- isophtholic acid 01' I I 0 5-amino-6-hydroxy CH, CH, 1,3-dioxepane (11) 1090 1 Iotroxic acid 90% aq. CFxCOOH 111 * 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. 40 OC. 5 h liq.NH3, 120 "C, 4 h IV 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; I: Isovist (Schering) 19 87) Iotroxic acid ATC: V08AC02 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.) CN: 3,3'-[oxybis[2,I-ethanediyloxy(l-oxo-2,l-ethanediyl)imino]]bis[2,4,6-triiodobenzoic acid] tetroethylene glycol 3.6.9-trioxaundecanedioic ocid . (dog, i.v.) CN: 5-[ acetyl(2,3-dihydroxypropyl)amino ]-~ ,~-bis(23-dihydroxypropy1 )-2 4,6-trioo-1, 3- benzenedicarboxamide dimethyl 5-nitro- 3-amino- 1, 2- 5-nitro-N,N'-bis(2, 3- isophtholate. (S)-N,~-bis[2-hydroxy- 1-( hydroxymethyl)ethyl ]-5 -[ (2-hydroxy-1-oxopropyl)amino ]-2 ,4,6-triiodo-l , 3- benzenedicarboxamide COOH ICI Hz"4 chloride I 10 5-orninoiso- phtholic ocid 5-ornino-2.4. 6-. 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