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96-83-3

96-83-3 structure
96-83-3 structure
Name 2-[(3-amino-2,4,6-triiodophenyl)methyl]butanoic acid
Synonyms Choladine
iopanoic acid
Iopagnost
Polognost
MFCD00038687
EINECS 202-539-9
Iodopanoic acid
Telepaque
Cholevid
Jopanoic acid
Bilijodon
Description Iopanoic acid is an inhibitor of 5'-Deiodinase and also an iodinated contrast medium.
Related Catalog
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

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
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
16623-25-9 structure

16623-25-9

~%

96-83-3 structure

96-83-3

Literature: Journal of the American Chemical Society, , vol. 71, p. 3753
5253-02-1 structure

5253-02-1

~%

96-83-3 structure

96-83-3

Literature: Journal of the American Chemical Society, , vol. 71, p. 3753
Precursor  2

DownStream  1

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%

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