Iopanoic acid

Modify Date: 2025-08-20 10:32:31

Iopanoic acid structure	Common Name	Iopanoic acid
	CAS Number	96-83-3	Molecular Weight	570.93200
	Density	2.426g/cm3	Boiling Point	529.1ºC at 760mmHg
	Molecular Formula	C₁₁H₁₂I₃NO₂	Melting Point	153 °C
	MSDS	Chinese USA	Flash Point	273.8ºC
	Symbol	GHS07	Signal Word	Warning

Use of Iopanoic acid

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

Name	2-[(3-amino-2,4,6-triiodophenyl)methyl]butanoic acid
Synonym	More Synonyms

Description	Iopanoic acid is an inhibitor of 5'-Deiodinase and also an iodinated contrast medium.
Related Catalog	Signaling Pathways >> Others >> Others Research Areas >> Endocrinology
Target	5'-Deiodinase[1]
In Vitro	The thyrotropin-releasing-hormone (TRH)-induced thyrotropin (TSH) release from the pituitary fragments is inhibited by 3,5,3'-triiodothyronin (T3) (10-7 M), by triiodothyroacetic acid (10-7 to 10-7 M), and by high concentrations of iodide (10-4 or 10-5 M). Iopanoic acid has no significant effect at the concentrations tested[2].
In Vivo	Iopanoic acid (IOP) administration to pregnant rats during days 18 and 19 postconception does not modify litter size (controls: 11.8±0.5 fetusesldam, Iopanoic acid-treated: 11.6±0.6 fetusesldam) or body weight at day 20 (controls: 3.27±0.12 g, Iopanoic acid-treated: 3.42±0.20 g). Iopanoic acid treatment produces a significant blockage of 5'-Deiodinase (5'D) activity in interscapular brown adipose tissue (IBAT) and brain; in contrast, liver 5'D is not modified. 3,5,3'-triiodothyronin (T3) content is similar in IBAT and slightly increased in brain and liver nuclei of Iopanoic acid-treated fetuses when compare with control fetuses at day 20 (p<0.05). However, when administered to adult rats, Iopanoic acid produces a significant reduction in IBAT nuclear T3 content and plasma T3 concentration. Iopanoic acid inhibition of IBAT 5'D activity in fetuses at term is as effective as at day 20[1].
Cell Assay	Rat pituitary fragments are superfused by Medium-199. After a 90 min equilibration period, the superfusion is continued for 135 min with or without inclusion into the superfusion medium of 3,5,3'-triiodothyronin (T3) 10-7 M, triiodothyroacetic acid (TRIAC) (stock solution 10-4 M in 20% methanol, final concentrations 10-8 to 10-6 M), Iopanoic acid (stock solution 10-3 M in 0.2 M NaOH, final concentrations 10-7 to 10-5 M), or potassium iodide 10-7 to 10-4 M. The superfusion is followed by a 6-min pulse of thyrotropin-releasing-hormone (TRH)[2].
Animal Admin	Wistar rats initially weighing 180 to 200 g are used. The administration of Iopanoic acid (IOP) is started at day 18 of gestation. Pregnant rats are injected subcutaneously with 10 mg of Iopanoic acid every 12 h, from day 18 of gestation to 12 h before they are killed on the morning of day 20 or 22 of gestation. Control animals receive the vehicle solution with identical timing. Iopanoic acid effectiveness in decreasing interscapular brown adipose tissue (IBAT) nuclear 3,5,3'-triiodothyronin (T3) is assessed by Iopanoic acid (IOP) administration to adult male rats (220 to 250 g body weight) following the same dose and time schedule as in pregnant dams during two days. Caesarean sections are performed at 18 (only untreated animals), 20 and 22 days of gestation. Fetuses are killed by decapitation, and IBAT, brain, and liver are removed. Tissue samples are immediately frozen in liquid nitrogen with the exception of brown fat from several 22 day-old fetuses, which is directly homogenized in 0.25 M sucrose for mitochondria isolation[1].
References	[1]. Tuca A, et al. Inhibition of iodothyronine 5'-deiodinase by iopanoic acid does not block nuclear T3 accumulation during rat fetal development. Pediatr Res. 1994 Jan;35(1):91-5. [2]. Szabolcs I, et al. Effects of triiodothyronine, triiodothyroacetic acid, iopanoic acid and iodide on the thyrotropin-releasing hormone-induced thyrotropin release from superfused rat pituitary fragments. Acta Endocrinol (Copenh). 1991 Oct;125(4):427-34.

Density	2.426g/cm3
Boiling Point	529.1ºC at 760mmHg
Melting Point	153 °C
Molecular Formula	C₁₁H₁₂I₃NO₂
Molecular Weight	570.93200
Flash Point	273.8ºC
Exact Mass	570.80000
PSA	63.32000
LogP	4.31710
Index of Refraction	1.732
Storage condition	2-8°C

Iopanoic acid MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MW5075000

CHEMICAL NAME :: Hydrocinnamic acid, 3-amino-alpha-ethyl-2,4,6-triiodo-

CAS REGISTRY NUMBER :: 96-83-3

BEILSTEIN REFERENCE NO. :: 2220381

LAST UPDATED :: 199710

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C11-H12-I3-N-O2

MOLECULAR WEIGHT :: 570.94

WISWESSER LINE NOTATION :: ZR BI DI FI C1Y2&VQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 86 mg/kg/1W-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: ARDEAC Archives of Dermatology. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.82- 1960- Volume(issue)/page/year: 123,387,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting Blood - thrombocytopenia Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 18,221,1981

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1540 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 14,232,1969

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1520 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: -,103,1990

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 280 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 14,232,1969

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6600 mg/kg

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

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 13,997,1970

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1230 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: -,103,1990

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 320 mg/kg

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

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 13,997,1970 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2200 mg/kg

SEX/DURATION :: female 1-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: ATSUDG Archives of Toxicology, Supplement. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) No.1- 1978- Volume(issue)/page/year: 7,425,1984

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Precautionary Statements	P301 + P312 + P330
Risk Phrases	20/21/22
Safety Phrases	S22-S26-S36/37/39
RIDADR	NONH for all modes of transport
RTECS	NW5075000
HS Code	2922499990

2-[(3-aminophen...

CAS#:16623-25-9

Iopanoic acid

CAS#:96-83-3

Literature: Journal of the American Chemical Society, , vol. 71, p. 3753

Butanoic acid,2...

CAS#:5253-02-1

Iopanoic acid

CAS#:96-83-3

Literature: Journal of the American Chemical Society, , vol. 71, p. 3753

Precursor 2
CAS#:16623-25-9 2-[(3-aminophen... CAS#:5253-02-1 Butanoic acid,2...
DownStream 1
CAS#:100850-30-4 ethyl 2-[(3-ami...

HS Code	2922499990
Summary	HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

Regulation and function of deiodinases during decidualization in female mice.

Endocrinology 155(7) , 2704-17, (2014)

Thyroid dysfunction during human pregnancy is closely related to serious pregnancy outcome. However, the regulation and function of thyroid hormones during early pregnancy are largely unknown. We foun...

Crystallographic analysis reveals the structural basis of the high-affinity binding of iophenoxic acid to human serum albumin.

BMC Struct. Biol. 11 , 18, (2011)

Iophenoxic acid is an iodinated radiocontrast agent that was withdrawn from clinical use because of its exceptionally long half-life in the body, which was due in part to its high-affinity binding to ...

Liquid chromatography-electrospray ionization mass spectrometry for direct identification and quantification of iophenoxic acid in serum.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 832(1) , 144-57, (2006)

A liquid chromatographic-electrospray ionization mass spectrometric technique was developed for direct quantitation of iophenoxic acid (IA) in serum. IA was spiked into canine, feline, bovine, equine,...

Name: Primary qHTS assay for inhibitors of alpha-synuclein gene (SNCA) expression
Source: NCGC
External Id: SNCA-p-activity-luciferase

Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN

Name: Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: lu...
Source: 824
External Id: CYP273

Name: Increase the activity of the Burkholderia fixLJ 2-component system
Source: ICCB-Longwood/NSRB Screening Facility, Harvard Medical School
Target: Burkholderia multivorans
External Id: HMS1625

Name: Fluorescence-based cell-based primary high throughput screening assay to identify pos...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_PAM_FLUO8_1536_1X%ACT PRUN

Name: qHTS Assay for Small Molecule Inhibitors of the Human hERG Channel Activity
Source: NCGC
External Id: HERG01

Name: qHTS for Inhibitors of TGF-b: Cytotox Counterscreen
Source: NCGC
Target: N/A
External Id: SMAD3201

Name: uHTS identification of cystic fibrosis induced NFkb Inhibitors in a fluoresence assay
Source: Burnham Center for Chemical Genomics
Target: cystic fibrosis transmembrane conductance regulator [Homo sapiens]
External Id: SBCCG-A764-CF-PAF-Primary-Assay

Name: Fluorescence-based cell-based primary high throughput screening assay to identify ant...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_ANT_FLUO8_1536_1X%INH PRUN

Name: qHTS for Inhibitors of TGF-b
Source: NCGC
Target: Smad3 [Homo sapiens]
External Id: SMAD3101

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Iopanoic acid

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