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Home > Encyclopedia > (±)-Iopanoic acid

(±)-Iopanoic acid

pharmaceutical raw materials
(±)-Iopanoic acid structure

(±)-Iopanoic acid 

structure
  • CAS No:

    96-83-3

  • Formula:

    C11H12I3NO2

  • Chemical Name:

    (±)-Iopanoic acid

  • Synonyms:

    Benzenepropanoic acid,3-amino-α-ethyl-2,4,6-triiodo-;Hydrocinnamic acid,3-amino-α-ethyl-2,4,6-triiodo-;3-Amino-α-ethyl-2,4,6-triiodobenzenepropanoic acid;3-Amino-α-ethyl-2,4,6-triiodohydrocinnamic acid;2-(3-Amino-2,4,6-triiodobenzyl)butyric acid;3-(3-Amino-2,4,6-triiodophenyl)-2-ethylpropanoic acid;Copanoic;2-Ethyl-3-(3-amino-2,4,6-triiodophenyl)propionic acid;Iodopanic acid;Iodopanoic acid;Iopanoic acid;Jopagnost;Telepaque;α-Ethyl-β-(3-amino-2,4,6-triiodophenyl)propionic acid;3-(3-Amino-2,4,6-triiodophenyl)-2-ethylpropionic acid;Colepax;Iopanoicum;Cholevid;Iopagnost;Bilijodon;Choladine;Cistobil;(±)-Iopanoic acid;NSC 41706;2-[(5-Amino-2,4,6-triiodophenyl)methyl]butanoic acid;2-[(3-Amino-2,4,6-triiodophenyl)methyl]butanoic acid;2-(3-Amino-2,4,6-triiodobenzyl)butanoic acid;17879-93-5

  • Categories:

    Active Pharmaceutical Ingredients  >  Diagnostic Agents

Description

Iopanoic acid is an inhibitor of 5'-Deiodinase and also an iodinated contrast medium.


Iopanoic acid is a monocarboxylic acid.|Iopanoic acid contains iodine and is useful as a contrast medium in cholecystography.|Radiopaque medium used as diagnostic aid.

(±)-Iopanoic acid Basic Attributes

570.93

570.93

202-539-9

758646|41706

DTXSID6023159

POWDER

V - Various

2922499990

Characteristics

63.32000

4.31710

2.426g/cm3

155.2 °C

529.1ºC at 760mmHg

273.8ºC

1.732

348.3mg/L(37 ºC)

2-8°C

FAINTLY AROMATIC

TASTELESS

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

Safety Information

NONH for all modes of transport

1

20/21/22

22-26-36/37/39

NW5075000

DARKENS ON EXPOSURE TO LIGHT

P301 + P312 + P330

H302

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 40 companies from 1 notifications to the ECHA C&L Inventory.

Toxicity

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.

Drug Information

Contrast Media|ORALLY AS A RADIOPAQUE MEDIUM IN CHOLECYSTOGRAPHY. ALTHOUGH NOT THE METHOD OF CHOICE, IT MAY ALSO BE USED FOR ORAL CHOLANGIOGRAPHY.|USUAL REGIMEN IS TO GIVE PT FAT-FREE EVENING MEAL FOLLOWING WHICH IOPANOIC ACID IS ADMIN APPROX 10 HR BEFORE TIME SCHEDULED FOR ROENTGENOGRAPHY. IMMEDIATELY AFTER ROENTGEN EXAM, PT IS GIVEN HIGH-FAT MEAL & ADDITIONAL EXPOSURES ARE MADE...TO EVALUATE CONTRACTION OF GALL BLADDER & TO VISUALIZE PATENCY OF EXTRAHEPATIC DUCTS. WHEN LATTER STRUCTURES ARE OF PARTICULAR INTEREST, DOSE OF IOPANOIC ACID MAY BE INCR TO 5 OR 6 G. DOSE--3 TO 6 G; USUAL, 3 G.|TYROPANOATE 3 G, IOCETAMIC ACID 4.5 G, IOPANOIC ACID 3 G & IOCETAMIC ACID 3 G, WERE EVALUATED IN 800 PT. IOCETAMIC ACID IS AS RELIABLE & EFFECTIVE AS TYROPANOATE OR IOPANOIC ACID IN CHOLECYSTOGRAPHY. 3 G DOSE PRODUCES CHOLECYSTOGRAMS AS SATISFACTORY AS 4.5 G WITH LOWER INCIDENCE OF CRAMPS.

IT IS CONTRAINDICATED IN PT WITH ACUTE NEPHRITIS AND UREMIA, SINCE IT IS ELIMINATED BY THE KIDNEYS. IT SHOULD NOT BE ADMIN WHEN DISORDERS OF THE GI TRACT EXIST WHICH PREVENT ABSORPTION OF THE MEDIUM.|IOPANOIC ACID APPEARS TO COMPETE WITH BILIRUBIN FOR HEPATIC UPTAKE, RESULTING IN TRANSIENT ELEVATIONS OF SERUM BILIRUBIN.|CONTRAST NEPHROPATHY IS AN ADVERSE ALTERATION IN RENAL FUNCTION INDUCED BY INTRAVASCULAR CONTRAST MEDIA. THE INCIDENCE OF CONTRAST NEPHROPATHY IN THE GENERAL HOSPITALIZED POPULATION IS ABOUT 5%, & IS ASSOCIATED WITH PREEXISTING RENAL INSUFFICIENCY & DIABETES MELLITUS. AS MANY AS TWO-THIRDS OF PATIENTS WITH CHRONIC RENAL FAILURE MAY EXPERIENCE AN ACUTE DETERIORATION IN RENAL FUNCTION FOLLOWING EXPOSURE. DIABETIC PATIENTS WITH PREEXISTING RENAL INSUFFICIENCY ARE AT AN EVEN GREATER RISK; ABOUT 75% OF SUCH PATIENTS WILL EXPERIENCE RENAL COMPLICATIONS. IN MULTIPLE MYELOMA THE RISK OF CONTRAST-INDUCED RENAL FAILURE IS LOW, & PROBABLY INVOLVES A DIFFERENT PATHOGENESIS THAN SEEN IN OTHER CASES OF CONTRAST NEPHROPATHY. PERIPHERAL VASCULAR DISEASE, HYPERTENSION, OLD AGE & LARGE & REPEATED DOSES OF CONTRAST MAY INCREASE THE RISK IN SUSCEPTIBLE PATIENTS.

Substances used to allow enhanced visualization of tissues. (See all compounds classified as Contrast Media.)

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.

...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.

.../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.

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.

Acid, Iodopanoic

(±)-Iopanoic acid Use and Manufacturing

Methods of Manufacturing

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.

Uses

antiulcer

TABLETS USP: 500 MG.

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

ANALYSIS OF RADIOLOGICAL CONTRAST MEDIA, INCLUDING IOPANOIC ACID, BY REVERSE-PHASE ION-PAIR HIGH-PRESSURE LIQUID CHROMATOGRAPHY. SPECTROPHOTOMETRIC ANALYSIS OF THE ELUATES WAS AT 240 NM.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:570.93
XLogP3:3.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:570.8002
Monoisotopic Mass:570.8002
Topological Polar Surface Area:63.3
Heavy Atom Count:17
Complexity:277
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Drug Function and Efficacy

This product is a diagnostic drug, an organic iodine compound. After oral absorption into the body, it absorbs more X-rays than the surrounding soft tissue structures, forming density contrast and developing under X-ray irradiation. After oral administration, this product is mainly secreted by the liver and flows into the gallbladder with a concentrating function. After concentration, the gallbladder morphology and function can be displayed under X-rays.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • China Resources Double-Crane Pharmaceutical Co., Ltd.

    China China
    Active
  • Shanghai Qingping Pharmaceutical Co., Ltd.

    China China
    Active
  • BRACCO IND CHIMICA SPA

    United States United States
    Inactive

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