Iopanoic Acid

FAINTLY AROMATIC

TASTELESS

POWDER

CREAM-COLORED SOLID; SOL IN DIL ALKALI, 95% ALC, OTHER ORG SOLVENTS /DL-ISOMER/

INSOL IN WATER; SOL IN CHLOROFORM & ETHER; SOL IN SOLN OF ALKALI HYDROXIDES & CARBONATES

MELTS WITH DECOMP BETWEEN 152 DEG & 158 °C

CRYSTALS; SPECIFIC OPTICAL ROTATION (ETHANOL, 2%): -5.2 +/- 0.1 DEG @ 20 °C/D; MP: 162-163 °C /L-ISOMER/

CRYSTALS; SPECIFIC OPTICAL ROTATION (ETHANOL, 2%): +5.1 +/- 0.1 DEG @ 20 °C/D; MP: 162 °C /D-ISOMER/

DARKENS ON EXPOSURE TO LIGHT

171.5 Ų [M]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID6023159]

172.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

IMAP assessments - Benzenepropanoic acid, 3-amino-.alpha.-ethyl-2,4,6-triiodo-: Environment tier I assessment；IMAP assessments - Benzenepropanoic acid, 3-amino-.alpha.-ethyl-2,4,6-triiodo-: Human health tier I assessment

Acute Tox. 4 (100%)

RESULTS INDICATE THAT HEPATIC METABOLISM OF IOPANOATE TO ITS GLUCURONIDE IS DECREASED BY ETHER & PENTOBARBITAL ANESTHESIA IN COMPARISON TO URETHANE ANESTHESIA OR DECEREBRATION.

A SINGLE CASE HAS BEEN REPORTED OF POOR RADIOGRAPHIC VISUALIZATION OF THE GALL BLADDER DUE APPARENTLY TO AN INTERACTION BETWEEN IOPANOIC ACID AND CHOLESTYRAMINE WITHIN THE GUT.

IOPANOIC ACID ADMIN RESULTS IN INCR SULFOBROMOPHTHALEIN (BSP) RETENTION, PROBABLY BY COMPETING WITH BSP FOR CONCN AND EXCRETION BY THE LIVER.

STUDIES ON THE FACTORS THAT INFLUENCE THE INTESTINAL ABSORPTION OF CHOLECYSTOPAQUES REVEALED THAT CHOLESTYRAMINE DECREASED THE ABSORPTION OF IOPANOIC ACID. IOPANOIC ACID WAS ABSORBED RELATIVELY SLOWLY & EXCRETED AT A CONSTANT RATE.

IN HEALTHY SUBJECTS, TEMPORAL CHANGES IN THE RESPONSES OF SERUM TSH & PROLACTIN (PRL) TO A FIXED DOSE OF TRH (SYNTHETIC TSH-RELEASING HORMONE, 500 MUG, IV) WERE STUDIED & SERUM T4, T3, & RT3 CONCN WERE ASSESSED BEFORE, IMMEDIATELY AFTER, & THEN AT WEEKLY INTERVALS AFTER THE 3 DAILY DOSES OF IOPANOIC ACID. BOTH BASAL & TRH-STIMULTED TSH CONCN WERE INCREASED AT THE END OF THE PERIOD OF IP ADMIN. SERUM T3 CONCN WAS DECREASED.

OCCASIONALLY, NAUSEA & DIARRHEA &, RARELY, DYSURIA HAVE FOLLOWED ITS ADMIN. A MILD STINGING SENSATION DURING URINATION MAY OCCUR. HYPERSENSITIVITY REACTIONS INVOLVING THE SKIN, MUCOUS MEMBRANE, AND A SYSTEMIC SERUM SICKNESS-TYPE REACTION HAVE BEEN REPORTED.

MEDIA USED FOR GI ROENTGENOGRAPHY & AGENTS ADMIN ORALLY MAY CAUSE NAUSEA, VOMITING, & DIARRHEA. ACUTE TUBULAR NECROSIS HAS BEEN REPORTED TO BE THE CONSEQUENCE OF INGESTION OF CERTAIN GALLBLADDER DYES. /IODINATED CONTRAST MEDIA/

ONSET OF ACUTE IODIDE POISONING MAY OCCUR IMMEDIATELY OR SEVERAL HR AFTER ADMIN. ANGIOEDEMA IS OUTSTANDING SYMPTOM, & SWELLING OF LARYNX MAY LEAD TO SUFFOCATION. MULTIPLE CUTANEOUS HEMORRHAGES MAY BE PRESENT. ALSO MANIFESTATIONS OF SERUM-SICKNESS TYPE HYPERSENSITIVITY, SUCH AS FEVER, ARTHRALGIA, LYMPH NODE ENLARGEMENT, & EOSINOPHILIA, MAY APPEAR. THROMBOTIC THROMBOCYTOPENIC PURPURA & FATAL PERIARTERITIS NODOSA ATTRIBUTED TO HYPERSENSITIVITY TO IODIDE HAS BEEN DESCRIBED. /IODINE PREPN/

AUTHORS REPORT A CASE OF A MIDDLE-AGED FEMALE WITH SEVERE THROMBOCYTOPENIA FOLLOWING ORAL CHOLECYSTOGRAPHY WITH IOPANOIC ACID, A WIDELY USED CONTRAST MEDIUM. A BONE MARROW ASPIRATE SHOWED INCREASED NUMBERS OF MEGAKARYOCYTES, SUGGESTING A THROMBOCYTOPENIA DUE TO ENHANCED PERIPHERAL DESTRUCTION OF PLATELETS.

No indication of carcinogenicity to humans (not listed by IARC).

V - Various；V08 - Contrast media；V08A - X-ray contrast media, iodinated；V08AC - Watersoluble, hepatotropic x-ray contrast media；V08AC06 - Iopanoic acid

QV - Various；QV08 - Contrast media；QV08A - X-ray contrast media, iodinated；QV08AC - Watersoluble, hepatotropic x-ray contrast media；QV08AC06 - Iopanoic acid

.../IT/ SUPPRESSES THYROID FUNCTION IN EUTHYROID AND HYPERTHYROID INDIVIDUALS.

TSH INDUCED SECRETION OF 3,3'-DIIODOTHYRONINE, 3',5'-T2, & 3,5-T2 BY PERFUSED DOG THYROID WAS DETERMINED. IOPANOATE (10-5 MOLAR) & IPODATE (10-5 MOLAR), BOTH INHIBITORS OF PERIPHERAL IODOTHYRONINE DEIODINATION, INHIBITED 3,3'-DIIODOTHYRONINE SECRETION.

THE ABILITY OF ROENTGENOGRAPHIC CONTRAST AGENTS TO INHIBIT BINDING OF (125)I-LABELED T3 TO NUCLEAR RECEPTORS WAS STUDIED DURING INCUBATION OF RAT LIVER NUCLEI OR NUCLEAR EXTRACTS IN VITRO & AFTER IP ADMIN OF THE AGENTS IN VIVO. IOPANOIC ACID INHIBITED BINDING OF T3-(125)I IN VITRO.

CHANGES IN CONCN OF TSH, THYROXINE, T3, & REVERSE T3 IN SERUM WERE EXAMINED IN 21 MALE EUTHYROID SUBJECTS AFTER ORAL ADMIN OF 3 G/DAY OF IOPANOIC ACID. CONCN OF TSH, THYROXINE, & REVERSE T3 INCREASED, WHEREAS CONCN OF T3 DECREASED AFTER ADMIN OF IOPANOIC ACID.

...IOPANOIC ACID...& TYROPANOIC ACID...IN DOGS & MAN...IDENTIFIED AS ESTER GLUCURONIDES. ... POORLY ABSORBED IN CATS... IOPANOIC ACID...PREVIOUSLY... FOUND...TRANSFORMED INTO...WATER-SOL CONJUGATE IN CATS & RE-EXAMINATION OF PROBLEM ESTABLISHED LIMITED GLUCURONIC ACID CONJUGATION OF IOPANOIC & TYROPANOIC ACIDS.

Substances used to allow enhanced visualization of tissues.

AFTER INGESTION, IT IS ABSORBED PROMPTLY, UNDERGOES CONJUGATION WITH GLUCURONIC ACID IN LIVER, IS CONCENTRATED & STORED IN GALLBLADDER, & IS ELIMINATED IN BILE.

FAILURE OF IOPANOIC ACID TO REACH DIAGNOSTIC CONCN IN BILE AFTER.../ORAL/ DOSES HAS BEEN SHOWN TO BE DUE, IN PART @ LEAST, TO IRREGULAR ABSORPTION. ABSORPTION OF.../ORAL/ DOSED IOPANOIC ACID IN DOGS WAS INCR IN PRESENCE OF BILE SALTS & SODIUM SALT FORM OF THIS AGENT IS ABSORBED MORE UNIFORMLY THAN FREE ACID.

BILIARY EXCRETION RATE OF SODIUM IOPANOATE FITTED BY COMPUTER TO MICHAELIS-MENTEN EQUATION AGAINST ITS UNBOUND PLASMA CONCN AVG MAX VALUE 0.85 MU MOLAR/KG/MIN, & KM VALUE 0.253 MU MOLAR. UNCHANGED IN MONKEY BLOOD & MAINLY NA IOPANOATE ESTER GLUCURONIDE IN BILE.

MAX EXCRETION OF IOPANOIC ACID INTO BILE OF UNANESTHETIZED DOGS WITH BILE FISTULA WAS CLOSELY CORRELATED TO EXCRETION RATE OF BILE SALTS.

For more Absorption, Distribution and Excretion (Complete) data for IOPANOIC ACID (6 total), please visit the HSDB record page.

MEDICATION

A MIXT OF M-NITROBENZALDEHYDE, BUTYRIC ANHYDRIDE, AND SODIUM BUTYRATE IS HEATED IN XYLENE AT REFLUX FOR 12 HR TO EFFECT A PERKIN CONDENSATION YIELDING M-NITRO-ALPHA-ETHYLCINNAMIC ACID. THE ACID IS EXTRACTED WITH AQ ALKALI AND REDUCED WITH HYDROGEN IN THE PRESENCE OF RANEY NICKEL. THE RESULTING M-AMINO-ALPHA-ETHYLHYDROCINNAMIC ACID IS IODINATED WITH IODINE MONOCHLORIDE IN ACETIC ACID SOLN AND CRUDE IOPANOIC ACID THUS FORMED IS PURIFIED BY CRYSTALLIZATION FROM ETHYL ACETATE.

TABLETS USP: 500 MG.

US PATENT 2,705,726 (1955 TO STERLING DRUG).