ioxaglic acid

Names

[ Name ]:
ioxaglic acid

[Synonym ]:
Ioxaglic acid
3-[[2-[[3-[acetyl(methyl)amino]-2,4,6-triiodo-5-(methylcarbamoyl)benzoyl]amino]acetyl]amino]-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodobenzoic acid

Biological Activity

[Description]:

Ioxaglic acid (P-286) is negatively charged contrast agent, is useful as an inverse indicator for glycosaminoglycan (GAG) used in computed tomography (CT). Ioxaglic acid can be used for imaging of human osteoarthritic cartilage via quantitative assessment of glycosaminoglycan content[1][2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[In Vivo]

Ioxaglic acid is sensitive to the GAG gradient observed in cartilage and is able to measure similar concentrations of GAG[2].

[References]

[1]. Gonsette RE, et, al. New contrast media in cerebral angiography: animal experiments and preliminary clinical studies. Invest Radiol. Nov-Dec 1980;15(6 Suppl):S270-4.

[2]. Baer K, et, al. Spectral CT imaging of human osteoarthritic cartilage via quantitative assessment of glycosaminoglycan content using multiple contrast agents. APL Bioeng. 2021 Apr 1;5(2):026101.

Chemical & Physical Properties

[ Density]:
2.545g/cm3

[ Boiling Point ]:
887.9ºC at 760 mmHg

[ Melting Point ]:
302°C

[ Molecular Formula ]:
C₂₄H₂₁I₆N₅O₈

[ Molecular Weight ]:
1268.88000

[ Flash Point ]:
490.8ºC

[ Exact Mass ]:
1268.57000

[ PSA ]:
194.24000

[ LogP ]:
4.69100

[ Index of Refraction ]:
1.786

[ Water Solubility ]:
Very slightly soluble in water, slightly soluble in ethanol (96 per cent), very slightly soluble in methylene chloride. It dissolves in dilute solutions of alkali hydroxides.

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DG0922000

CHEMICAL NAME :: Benzoic acid, 3-((((3-(acetylmethylamino)-2,4,6-triiodo-5-((methyla mino)carbonyl)benzoyl) amino)acetyl)amino)-5-(((2-hydroxyethyl)amino)carbony l)-2,4,6-triiodo-

CAS REGISTRY NUMBER :: 59017-64-0

LAST UPDATED :: 199509

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C24-H21-I6-N5-O8

MOLECULAR WEIGHT :: 1268.90

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 13300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,99,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 13300 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Lungs, Thorax, or Respiration - respiratory stimulation Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 19,2411,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 102 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 18,474,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >37300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 18,474,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >13300 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Lungs, Thorax, or Respiration - respiratory stimulation Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 19,2411,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >10700 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 18,474,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >10700 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 18,474,1987 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 168 gm/kg/35D-C

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - changes in lung weight Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 19,2427,1985 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 1431 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 19,2463,1985

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 4320 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - sex ratio

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 19,2463,1985

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Articles

Computed tomography detects changes in contrast agent diffusion after collagen cross-linking typical to natural aging of articular cartilage.

Osteoarthr. Cartil. 19(10) , 1190-8, (2011)

The effect of threose-induced collagen cross-linking on the mechanical and diffusive properties of cartilage was investigated in vitro. In particular, we investigated the potential of Contrast Enhance...

Hyperosmolaric contrast agents in cartilage tomography may expose cartilage to overload-induced cell death.

J. Biomech. 45(3) , 497-503, (2012)

In clinical arthrographic examination, strong hypertonic contrast agents are injected directly into the joint space. This may reduce the stiffness of articular cartilage, which is further hypothesized...

Acute thyrotoxicosis secondary to destructive thyroiditis associated with cardiac catheterization contrast dye.

Thyroid 21(4) , 443-9, (2011)

Thyrotoxicosis caused by destructive thyroiditis is self-limited and results from the subacute release of preformed thyroid hormone. Common etiologies include painful subacute thyroiditis and silent (...

Related Compounds

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