Products Categories
CAS No.: | 60166-93-0 |
---|---|
Name: | Iopamidol |
Article Data: | 17 |
Molecular Structure: | |
Formula: | C17H22I3N3O8 |
Molecular Weight: | 777.09 |
Synonyms: | 1,3-Benzenedicarboxamide,N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-,(S)-;1,3-Benzenedicarboxamide,N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[[(2S)-2-hydroxy-1-oxopropyl]amino]-2,4,6-triiodo-(9CI);Gastromiro;Iopamidol 300;Iopamiro;Iopamiro 370;Iopamiron 300;Iopamiron 370;Isovue;Isovue 300;Isovue 370;Jopamiron 200;Niopam;Niopam 300;Oypalomin;Oypalomin 150;Solutrast;Solutrast 370; |
EINECS: | 262-093-6 |
Density: | 2.281 g/cm3 |
Melting Point: | >320 °C (dec) |
Boiling Point: | 785.3 °C at 760 mmHg |
Flash Point: | 428.8 °C |
Solubility: | 473.7g/L(25 oC) |
Appearance: | White Crystalline Powder |
PSA: | 188.45000 |
LogP: | -0.15950 |
Iopamidol
Conditions | Yield |
---|---|
With sodium hydroxide for 0.166667h; | 99% |
With water; sodium hydroxide at 40℃; pH=~ 11; | 76.4% |
With water; sodium hydroxide at 40℃; pH=Ca. 11; | 76.4% |
Stage #1: S-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-(acetyloxy)-1-oxo-propyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide With water; sodium hydroxide In ISOPROPYLAMIDE at 35℃; for 7h; Stage #2: With hydrogenchloride In ISOPROPYLAMIDE; water pH=~ 7; | |
With water; sodium hydroxide at 35℃; pH=12; | 159 g |
Iopamidol
Conditions | Yield |
---|---|
With Amberlite IRA400 In water for 32h; pH=6 - 7; Product distribution / selectivity; Smiles Rearrangement; | 95% |
With Amberlite IRA400 In water for 32h; Smiles Aromatic Rearrangement; | 95% |
With sodium methylate In methanol; N,N-dimethyl-formamide at 25℃; Smiles rearrangement; | 89% |
With potassium hydroxide In methanol; water |
S-(-)-5-[[2-(acetyloxy)-1-oxopropyl]amino]-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride
serinol
Iopamidol
Conditions | Yield |
---|---|
In ISOPROPYLAMIDE at 8 - 20℃; for 10h; | 94% |
Stage #1: S-(-)-5-[[2-(acetyloxy)-1-oxopropyl]amino]-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride; serinol at 44 - 48℃; for 48 - 70h; Stage #2: With water at 52 - 57℃; for 2 - 4h; | 78% |
Iopamidol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: phosphorus pentachloride / ISOPROPYLAMIDE / 6 h / 40 °C 2: triethylamine / ISOPROPYLAMIDE / 6 h / 50 °C 3: sodium hydroxide; water / 40 °C / pH ~ 11 View Scheme | |
Multi-step reaction with 3 steps 1: phosphorus pentachloride / N,N-dimethyl acetamide / 6 h / 40 °C 2: triethylamine / N,N-dimethyl acetamide / 6 h / 50 °C 3: water; sodium hydroxide / 40 °C / pH Ca. 11 View Scheme |
2,4,6-triiodo-5-aminoisophthalic acid
Iopamidol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ISOPROPYLAMIDE / 22 h / 20 - 50 °C 2: phosphorus pentachloride / ISOPROPYLAMIDE / 6 h / 40 °C 3: triethylamine / ISOPROPYLAMIDE / 6 h / 50 °C 4: sodium hydroxide; water / 40 °C / pH ~ 11 View Scheme | |
Multi-step reaction with 4 steps 1: N,N-dimethyl acetamide / 22 h / 20 - 50 °C 2: phosphorus pentachloride / N,N-dimethyl acetamide / 6 h / 40 °C 3: triethylamine / N,N-dimethyl acetamide / 6 h / 50 °C 4: water; sodium hydroxide / 40 °C / pH Ca. 11 View Scheme |
S-(-)-5-[[2-(acetyloxy)-1-oxopropyl]amino]-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride
Iopamidol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl acetamide / 6 h / 50 °C 2: water; sodium hydroxide / 40 °C / pH Ca. 11 View Scheme |
Iopamidol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl acetamide / 18 h / 30 - 35 °C / Inert atmosphere; Large scale 2: sodium hydroxide; water / N,N-dimethyl acetamide / Large scale View Scheme |
Iopamidol
Conditions | Yield |
---|---|
With water; sodium hydroxide In N,N-dimethyl acetamide Large scale; | 992 g |
Iopamidol
Conditions | Yield |
---|---|
With water; sodium hydroxide In N,N-dimethyl acetamide Large scale; | 992 g |
Iopamidol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N,N-dimethyl acetamide / 18 h / 20 °C / Inert atmosphere 2: water / N,N-dimethyl acetamide / 1 h 3: sodium hydroxide; water / 35 °C / pH 12 View Scheme |
Molecular Structure of Iopamiron (CAS NO.60166-93-0):
IUPAC Name: 1-N,3-N-bis(1,3-dihydroxypropan-2-yl)-5-[[(2S)-2-hydroxypropanoyl]amino]-2,4,6-triiodobenzene-1,3-dicarboxamide
Empirical Formula: C17H22I3N3O8
Molecular Weight: 777.0853
H bond acceptors: 11
H bond donors: 8
Freely Rotating Bonds: 15
Polar Surface Area: 107.08Å2
Index of Refraction: 1.738
Molar Refractivity: 137.2 cm3
Molar Volume: 340.6 cm3
Surface Tension: 86.5 dyne/cm
Density: 2.281 g/cm3
Flash Point: 428.8 °C
Enthalpy of Vaporization: 119.83 kJ/mol
Boiling Point: 785.3 °C at 760 mmHg
Vapour Pressure: 5.57E-26 mmHg at 25°C
Melting point: >3200C (dec)
EINECS: 262-093-6
Product Categories: Diagnostic; Intermediates & Fine Chemicals; Pharmaceuticals
InChI
InChI=1/C17H22I3N3O8/c1-6(28)15(29)23-14-12(19)9(16(30)21-7(2-24)3-25)11(18)10(13(14)20)17(31)22-8(4-26)5-27/h6-8,24-28H,2-5H2,1H3,(H,21,30)(H,22,31)(H,23,29)/t6-/m0/s1
Smiles
C(=O)(NC(CO)CO)c1c(c(C(=O)NC(CO)CO)c(c(c1I)NC(=O)[C@H](C)O)I)I
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | intravenous | 35gm/kg (35000mg/kg) | Farmaco, Edizione Scientifica. Vol. 32, Pg. 835, 1977. | |
man | TDLo | intraspinal | 214uL/kg (0.214mL/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP | American Journal of Emergency Medicine. Vol. 12, Pg. 329, 1994. |
man | TDLo | intravenous | 600mg/kg/3S-C (600mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) CARDIAC: CHANGE IN RATE | Archives of Internal Medicine. Vol. 147, Pg. 2208, 1987. |
man | TDLo | intravenous | 1657mg/kg (1657mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Annals of Internal Medicine. Vol. 107, Pg. 116, 1987. |
mouse | LD50 | intracrebral | 3gm/kg (3000mg/kg) | Farmaco, Edizione Scientifica. Vol. 32, Pg. 835, 1977. | |
mouse | LD50 | intraperitoneal | 40825mg/kg (40825mg/kg) | United States Patent Document. Vol. #4001323, | |
mouse | LD50 | intravenous | 33gm/kg (33000mg/kg) | SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 12(Suppl, |
mouse | LD50 | oral | > 49gm/kg (49000mg/kg) | Drugs in Japan Vol. -, Pg. 104, 1990. | |
mouse | LD50 | subcutaneous | > 49gm/kg (49000mg/kg) | Drugs in Japan Vol. -, Pg. 104, 1990. | |
rabbit | LD50 | intravenous | 20gm/kg (20000mg/kg) | Farmaco, Edizione Scientifica. Vol. 32, Pg. 835, 1977. | |
rabbit | LD50 | parenteral | 510mg/kg (510mg/kg) | United States Patent Document. Vol. #4001323, | |
rabbit | LD50 | unreported | > 245mg/kg (245mg/kg) | Journal of the American College of Toxicology. Vol. 9, Pg. 563, 1990. | |
rat | LD | oral | > 49gm/kg (49000mg/kg) | Farmaco, Edizione Scientifica. Vol. 32, Pg. 835, 1977. | |
rat | LD50 | intraarterial | 13268mg/kg (13268mg/kg) | United States Patent Document. Vol. #4001323, | |
rat | LD50 | intracrebral | 2449mg/kg (2449mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 200, 1995. | |
rat | LD50 | intraperitoneal | 35gm/kg (35000mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 12(Suppl, |
rat | LD50 | intravenous | 22044mg/kg (22044mg/kg) | Acta Radiologica, Supplementum. Vol. 370, Pg. 41, 1987. | |
rat | LD50 | subcutaneous | > 49gm/kg (49000mg/kg) | Drugs in Japan Vol. -, Pg. 104, 1990. | |
rat | LDLo | parenteral | 2041mg/kg (2041mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 22, Pg. 769, 1994. |
Iopamiron , with CAS number of 60166-93-0, can be called (S)-N,N'-bis(2-Hydroxy-1-(hydroxymethyl)ethyl)-2,4,6-triiodo-5-lactamidoisophthalamide ; 1,3-Benzenedicarboxamide, N,N'-bis(2-hydroxy-1-(hydroxymethyl)ethyl)-5-((2-hydroxy-1-oxopropyl)amino)-2,4,6-triiodo-, (S)- ; Iopamidol-200 in plastic container ; L-(+)-N,N'-Bis(2-hydroxy-1-hydroxymethylethyl)-2,4,6-triiodo-5-lactamide isophthalamide ; L-5alpha-Hydroxypropionylamino-2,4,6-triiodoisophthalic acid di(1,3-dihydroxy-2-propylamide) ; L-5alpha-Idrossipropionilamino-2,4,6-triiodoisoftal-di(1,3-diidrossi-2-propilamide) . It is a white crystalline powder, used as nonionic radiocontrast medium.