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Chemistry

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Also known as: 96-83-3, Iodopanoic acid, Telepaque, Cholevid, Iopagnost, Iopanic acid
Molecular Formula
C11H12I3NO2
Molecular Weight
570.93  g/mol
InChI Key
OIRFJRBSRORBCM-UHFFFAOYSA-N
FDA UNII
FE9794P71J

Iopanoic Acid
Radiopaque medium used as diagnostic aid.
1 2D Structure

Iopanoic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[(3-amino-2,4,6-triiodophenyl)methyl]butanoic acid
2.1.2 InChI
InChI=1S/C11H12I3NO2/c1-2-5(11(16)17)3-6-7(12)4-8(13)10(15)9(6)14/h4-5H,2-3,15H2,1H3,(H,16,17)
2.1.3 InChI Key
OIRFJRBSRORBCM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC(CC1=C(C(=C(C=C1I)I)N)I)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
FE9794P71J
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, Iodopanoic

2. Acid, Iopanoic

3. Cholevid

4. Iodopanoic Acid

5. Iopagnost

6. Polognost

7. Telepaque

2.3.2 Depositor-Supplied Synonyms

1. 96-83-3

2. Iodopanoic Acid

3. Telepaque

4. Cholevid

5. Iopagnost

6. Iopanic Acid

7. Bilijodon

8. Choladine

9. Cistobil

10. Copanoic

11. Jopagnost

12. Polognost

13. Colepax

14. Iopanoicum

15. Jopanoic Acid

16. 2-(3-amino-2,4,6-triiodobenzyl)butyric Acid

17. 2-(3-amino-2,4,6-triiodobenzyl)butanoic Acid

18. Acidum Iopanoicum

19. Teletrast

20. Iodopanic Acid

21. 2-[(3-amino-2,4,6-triiodophenyl)methyl]butanoic Acid

22. Nsc 41706

23. Iopanoate

24. 3-amino-alpha-ethyl-2,4,6-triiodohydrocinnamic Acid

25. Nsc-41706

26. 2-ethyl-3-(3-amino-2,4,6-triiodophenyl)propionic Acid

27. 3-(3-amino-2,4,6-triiodophenyl)-2-ethylpropanoic Acid

28. 3-amino-alpha-ethyl-2,4,6-triiodobenzenepropanoic Acid

29. Chebi:5951

30. Fe9794p71j

31. 2-[(3-amino-2,4,6-triiodo-phenyl)methyl]butanoic Acid

32. Benzenepropanoic Acid, 3-amino-.alpha.-ethyl-2,4,6-triiodo-

33. Dsstox_cid_3159

34. Dsstox_rid_76897

35. Dsstox_gsid_23159

36. 3-amino-.alpha.-ethyl-2,4,6-triiodobenzenepropanoic Acid

37. Hydrocinnamic Acid, 3-amino-.alpha.-ethyl-2,4,6-triiodo-

38. Acido Iopanoico

39. Acide Iopanoique

40. .alpha.-ethyl-.beta.-(3-amino-2,4,6-triiodophenyl)propionic Acid

41. Acide Iopanoique [french]

42. Acide Iopanoique [inn-french]

43. Acido Iopanoico [inn-spanish]

44. Acidum Iopanoicum [inn-latin]

45. Acido Iopanoico [latin,spanish]

46. Hsdb 3345

47. Sr-05000001877

48. Win 2011

49. Einecs 202-539-9

50. Brn 2220381

51. Unii-fe9794p71j

52. Benzenepropanoic Acid, 3-amino-alpha-ethyl-2,4,6-triiodo-

53. Cas-96-83-3

54. Telepaque (tn)

55. Ncgc00016357-01

56. Iopanoic Acid [usp:inn:ban:jan]

57. Hydrocinnamic Acid, 3-amino-alpha-ethyl-2,4,6-triiodo-

58. Spectrum_001576

59. Beta-(3-amino-2,4,6-triiodophenyl)-alpha-ethylpropionic Acid

60. Prestwick0_001052

61. Prestwick1_001052

62. Prestwick2_001052

63. Prestwick3_001052

64. Spectrum2_001206

65. Spectrum4_000879

66. Spectrum5_001681

67. Chembl867

68. Iopanoic Acid [mi]

69. (.+/-.)-iopanoic Acid

70. Iopanoic Acid [inn]

71. Iopanoic Acid [jan]

72. Schembl38976

73. Bspbio_001004

74. Iopanoic Acid [hsdb]

75. Kbiogr_001577

76. Kbioss_002056

77. Mls002154127

78. Divk1c_000902

79. Iopanoic Acid [vandf]

80. Spectrum1503923

81. Spbio_000992

82. Spbio_002932

83. Iopanoic Acid [mart.]

84. Bpbio1_001106

85. Iopanoic Acid (jan/usp/inn)

86. Iopanoic Acid [who-dd]

87. Iopanoic Acid [who-ip]

88. Dtxsid6023159

89. Hms502n04

90. Kbio1_000902

91. Kbio2_002056

92. Kbio2_004624

93. Kbio2_007192

94. Oirfjrbsrorbcm-uhfffaoysa-

95. (pm)-3-amino-alpha-ethyl-2,4,6-triiodohydrocinnamic Acid

96. Hydrocinnamic Acid,4,6-triiodo-

97. Ninds_000902

98. Hms1571c06

99. Hms1922k20

100. Hms2093m03

101. Hms2098c06

102. Hms2231g12

103. Hms3369d07

104. Hms3715c06

105. Iopanoic Acid, Analytical Standard

106. Pharmakon1600-01503923

107. Benzenepropanoic Acid,4,6-triiodo-

108. Hy-b1664

109. Iopanoic Acid [ep Impurity]

110. Iopanoic Acid [orange Book]

111. Nsc41706

112. Tox21_110394

113. Tox21_303477

114. Benzenepropanoic Acid, 3-amino-alpha-ethyl-2,4,6-triiodo-, (+-)-

115. Ccg-39139

116. Iopanoic Acid [ep Monograph]

117. Iopanoic Acid [usp Impurity]

118. Mfcd00038687

119. Nsc758646

120. S5497

121. Akos015854598

122. Tox21_110394_1

123. Cs-8125

124. Db08946

125. Nsc-758646

126. Idi1_000902

127. Wln: Zr Bi Di Fi C1y2 & Vq

128. Acidum Iopanoicum [who-ip Latin]

129. Ncgc00095082-01

130. Ncgc00095082-02

131. Ncgc00095082-03

132. Ncgc00095082-06

133. Ncgc00257386-01

134. As-66216

135. Smr001233434

136. Sbi-0051863.p002

137. 2-(2-carbamimidoylsulfanylethyl)isothiourea

138. 2-(3-amino-2,6-triiodobenzyl)butyric Acid

139. Ab00052387

140. Ft-0631496

141. I0300

142. C08217

143. D01014

144. T73105

145. Ab00052387_07

146. 2-(3-amino-2,4,6-triiodobenzyl)butanoic Acid #

147. A845646

148. Q1672108

149. Sr-05000001877-1

150. Sr-05000001877-3

151. W-100130

152. 2-ethyl-3-(3-amino-2,6-triiodophenyl)propionic Acid

153. 3-(3-amino-2,6-triiodophenyl)-2-ethylpropanoic Acid

154. 3-amino-.alpha.-ethyl-2,6-triiodohydrocinnamic Acid

155. 3-amino-alpha-ethyl-2,4,6-triiodobenzenepropanoicacid

156. Brd-a42628519-001-04-1

157. Brd-a42628519-001-07-4

158. 3-(3-amino-2,4,6-triiodophenyl)-2-ethylpropionic Acid

159. 3-amino-.alpha.-ethyl-2,4,6-triiodohydrocinnamic Acid

160. Iopanoic Acid, European Pharmacopoeia (ep) Reference Standard

161. (pm)-3-amino-.alpha.-ethyl-2,4,6-triiodohydrocinnamic Acid

162. .beta.-(3-amino-2,4,6-triiodophenyl)-.alpha.-ethylpropionic Acid

163. .beta.-(3-amino-2,6-triiodophenyl)-.alpha.-ethylpropionic Acid

164. Benzenepropanoic Acid, 3-amino-.alpha.-ethyl-2,4,6-triiodo-, (.+/-.)-

165. Benzenepropanoic Acid, 3-amino-.alpha.-ethyl-2,4,6-triiodo-, (+/-)-

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 570.93 g/mol
Molecular Formula C11H12I3NO2
XLogP33.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass570.8002 g/mol
Monoisotopic Mass570.8002 g/mol
Topological Polar Surface Area63.3 Ų
Heavy Atom Count17
Formal Charge0
Complexity277
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Contrast Media

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


ORALLY AS A RADIOPAQUE MEDIUM IN CHOLECYSTOGRAPHY. ALTHOUGH NOT THE METHOD OF CHOICE, IT MAY ALSO BE USED FOR ORAL CHOLANGIOGRAPHY.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1213


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.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1214


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.

PARKS R; DOUBLE-BLIND STUDY OF 4 ORAL CHOLECYSTOGRAPHIC PREPARATIONS; RADIOLOGY 112(SEP) 525 (1974)


4.2 Drug Warning

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.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1214


IOPANOIC ACID APPEARS TO COMPETE WITH BILIRUBIN FOR HEPATIC UPTAKE, RESULTING IN TRANSIENT ELEVATIONS OF SERUM BILIRUBIN.

Hansten, P.D. Drug Interactions. 4th ed. Philadelphia: Lea and Febiger, 1979., p. 330


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.

HARKONEN S, KIELLSTRAND C; CONTRAST NEPHROPATHY; AM J NEPHROL 1 (2): 69-77 (1981)


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Contrast Media

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


5.2 ATC Code

V - Various

V08 - Contrast media

V08A - X-ray contrast media, iodinated

V08AC - Watersoluble, hepatotropic x-ray contrast media

V08AC06 - Iopanoic acid


5.3 Absorption, Distribution and Excretion

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

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 802


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.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 75


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.

MOSS AA ET AL; PHARMACOKINETICS OF IOPANOIC ACID IN THE RHESUS MONKEY; BILIARY EXCRETION, PLASMA PROTEIN BINDING AND BIOTRANSFORMATION; INVEST RADIOL 14(2) 171 (1979)


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

LOEB PM ET AL; DEPENDENCE OF THE BILIARY EXCRETION OF IOPANOIC ACID ON BILE SALTS; GASTROENTEROLOGY 72(2) 174 (1978)


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


5.4 Metabolism/Metabolites

...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.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 423


5.5 Mechanism of Action

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

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 5th ed. Chicago: American Medical Association, 1983., p. 1068


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.

LAURBERG P; SECRETION OF DIIODOTHYRONINES FROM THE PERFUSED CANINE THYROID ISOLATED IN SITU; THE INFLUENCE OF RADIOCONTRAST AGENTS; THYROID RES 8 (8) (EIGHT) PROC INT THYROID CONGR 8TH 359-62 (1980)


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.

DEGROOT LJ, RUE PA; ROENTGENOGRAPHIC CONTRAST AGENTS INHIBIT TRIIODOTHYRONINE BINDING TO NUCLEAR RECEPTORS IN VITRO; J CLIN ENDOCRINOL METAB 49 (4): 538-42 (1979)


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.

SUZUKI H ET AL; EFFECTS OF ORAL CHOLECYSTOGRAPHIC AGENTS ON THE PITUITARY-THYROID AXIS. I. CHANGES IN SERUM IODOTHYRONINES AND THYROTROPIN AFTER REPEATED DOSES OF ORAL CHOLECYSTOGRAPHIC AGENTS AND COMPARISON OF THE EFFECTS AMONG SOME IODOCONTRAST AGENTS; SAISHIN IGAKU 35 (1): 194-8 (1980)


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