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DSSTox_CID_3155

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Also known as: 83-73-8, Diiodohydroxyquinoline, 5,7-diiodoquinolin-8-ol, 5,7-diiodo-8-hydroxyquinoline, 5,7-diiodo-8-quinolinol, Diiodoquin

Molecular Formula

C₉H₅I₂NO

Molecular Weight

396.95 g/mol

InChI Key

UXZFQZANDVDGMM-UHFFFAOYSA-N

FDA UNII

63W7IE88K8

One of the halogenated 8-quinolinols widely used as an intestinal antiseptic, especially as an antiamebic agent. It is also used topically in other infections and may cause CNS and eye damage. It is known by very many similar trade names world-wide.

1 2D Structure

DSSTox_CID_3155

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5,7-diiodoquinolin-8-ol

2.1.2 InChI

InChI=1S/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

2.1.3 InChI Key

UXZFQZANDVDGMM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC2=C(C(=C(C=C2I)I)O)N=C1

2.2 Other Identifiers

2.2.1 UNII

63W7IE88K8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Diiodohydroxyquin

2. Diiodohydroxyquinoline

3. Diiodoquin

4. Diodoquin

5. Diodoxyquinoline

6. Diquinol

7. Entero Diyod

8. Entero-diyod

9. Enterodiyod

10. Entodiba

11. Sebaquin

12. Yodoxin

2.3.2 Depositor-Supplied Synonyms

1. 83-73-8

2. Diiodohydroxyquinoline

3. 5,7-diiodoquinolin-8-ol

4. 5,7-diiodo-8-hydroxyquinoline

5. 5,7-diiodo-8-quinolinol

6. Diiodoquin

7. Diodoquin

8. Yodoxin

9. Diiodohydroxyquin

10. Lanodoxin

11. Searlequin

12. Zoaquin

13. Ioquin

14. Quinadome

15. Sebaquin

16. 8-quinolinol, 5,7-diiodo-

17. Diodohydroxyquin

18. Dijodoxichinoline

19. Enterodiamoebin

20. Diamoebin

21. Dinoleine

22. Diodoquine

23. Diodoxylin

24. Direxiode

25. Disoquin

26. Embequin

27. Enterosept

28. Floraquin

29. Fluoraquin

30. Moebiquin

31. Dyodin

32. Di-quinol

33. Stanquinate

34. Rafamebin

35. 5,7-diiodo-oxine

36. Ioquin Suspension

37. Dijodoxichinolinum

38. 8-hydroxy-5,7-diiodoquinoline

39. 5,7-diodo-8-quinolinol

40. Diodoxyquinoleine

41. Diiodoidrossichinolina

42. Panaquin

43. Diiodohidroxiquinoleina

44. Diiodohydroxyquinoleine

45. Diiodohydroxyquinolinum

46. Ss 578

47. Enterodiamoebine

48. Nsc 8704

49. Nsc-8704

50. 5,7-diiod-8-chinolinol [iupac]

51. Diiodohydroxyquinoline [inn]

52. Mls000069404

53. Chebi:5950

54. 63w7ie88k8

55. Mmv002817

56. Ss-578

57. Ncgc00018098-04

58. Smr000059090

59. Dsstox_cid_3155

60. Dsstox_rid_76894

61. Diiodohydroxyquinoline (inn)

62. Dsstox_gsid_23155

63. Iodoquinol [usan]

64. Caswell No. 354

65. Iodoquinol;5,7-diiodo-8-hydroxyquinoline;5,7-diiodo-8-quinolinol

66. Cas-83-73-8

67. Diiodoidrossichinolina [dcit]

68. Hsdb 3224

69. Sr-01000002969

70. Diiodohydroxyquinolinum [inn-latin]

71. Iodoquinol [usan:usp]

72. Diiodohydroxyquinoleine [inn-french]

73. Einecs 201-497-9

74. 5,7-diiod-8-chinolinol

75. Diiodohidroxiquinoleina [inn-spanish]

76. Epa Pesticide Chemical Code 024003

77. Brn 0153639

78. Searlewuin

79. Meobiquin

80. Unii-63w7ie88k8

81. Ai3-16443

82. 5,7-diiodooxine

83. Component Of Vytone

84. Iodoquinol (usp)

85. Yodoxin (tn)

86. Mfcd00006789

87. Spectrum_000943

88. Iodoquinol [mi]

89. 8-quinolinol,7-diiodo-

90. Spectrum2_001041

91. Spectrum3_000470

92. Spectrum4_000020

93. Spectrum5_000872

94. Iodoquinol [hsdb]

95. 4,7-diiodo-8-quinolinol

96. Bmse000836

97. Ec 201-497-9

98. Cid_3728

99. Schembl3460

100. Iodoquinol [usp-rs]

101. Bspbio_002180

102. Cbdive_011080

103. Kbiogr_000399

104. Kbioss_001423

105. Ksc-8-193

106. Chembl86754

107. Divk1c_000119

108. Spectrum1500353

109. Spbio_000962

110. Di-iodohydroxy Quinoline

111. Dtxsid6023155

112. 5,7-bis(iodanyl)quinolin-8-ol

113. Bdbm66035

114. Hms500f21

115. Kbio1_000119

116. Kbio2_001423

117. Kbio2_003991

118. Kbio2_006559

119. Kbio3_001400

120. Uxzfqzandvdgmm-uhfffaoysa-

121. Iodoquinol [usp Impurity]

122. Nsc8704

123. Ninds_000119

124. Wln: T66 Bnj Gi Ii Jq

125. Hms1920h05

126. Hms2091n15

127. Hms2230g24

128. Hms3369c20

129. Iodoquinol [usp Monograph]

130. Kuc105860n

131. Pharmakon1600-01500353

132. Hy-b1400

133. Zinc3830942

134. Tox21_110823

135. Ccg-40132

136. Nsc757077

137. S4565

138. Stk070581

139. Diiodohydroxyquinoline [mart.]

140. Akos000120804

141. Tox21_110823_1

142. 5,7-diiodo-8-hydroxyquinoline, 97%

143. Cs-4910

144. Db09115

145. Diiodohydroxyquinoline [who-dd]

146. Iodoquinol (5,7-diiodoquinolin-8-ol)

147. Nsc-757077

148. Idi1_000119

149. Ncgc00018098-01

150. Ncgc00018098-02

151. Ncgc00018098-03

152. Ncgc00018098-05

153. Ncgc00018098-07

154. Ncgc00018098-08

155. Ncgc00021685-03

156. Ncgc00021685-04

157. Ds-17759

158. Sbi-0051417.p003

159. Db-056739

160. Am20061527

161. D1736

162. Ft-0619847

163. C07636

164. D00581

165. F12461

166. Ab00052024_12

167. An-329/13210059

168. Q5276473

169. Sr-01000002969-2

170. Sr-01000002969-5

171. Brd-k75855670-001-06-8

172. F3034-0058

173. Iodoquinol, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₅I₂NO
Molecular Weight	396.95 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	396.84606 g/mol
Monoisotopic Mass	396.84606 g/mol
Topological Polar Surface Area	33.1 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	191
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Amebicides; Anti-Infective Agents, Local

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

...MAY BE USED IN LOCAL & SYSTEMIC TREATMENT OF TRICHOMONAS VAGINALIS VAGINITIS & INFECTIONS CAUSED BY TRICHOMONAS HOMINIS (INTESTINALIS). IT IS USED IN TOPICAL TREATMENT OF CERTAIN FUNGAL CUTANEOUS INFECTIONS & IN ECZEMA IN WHICH FUNGAL INFECTION IS COMPLICATION.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1159

...HAVE BEEN USED FOR TREATMENT OF VARIOUS DERMATOLOGICAL DISORDERS, & LARGE DOSES HAVE BEEN EMPLOYED ORALLY IN TREATMENT OF ACRODERMATITIS ENTEROPATHICA, RARE, POTENTIALLY FATAL PEDIATRIC CONDITION.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1074

...EFFECTIVE FOR INTESTINAL AMEBIASIS &...FOR TREATMENT OF ASYMPTOMATIC PASSERS OF CYSTS. ...USEFUL FOR AMBULATORY & MASS TREATMENT. THEY ARE INEXPENSIVE. ...OF VALUE IN CASES OF LAMBLIASIS RESISTANT TO QUINACRINE THERAPY, IN BALANTIDIAL DYSENTERY, & IN INTESTINAL INFECTIONS DUE TO DIENTAMEBA FRAGILIS. /8-HYDROXYQUINOLINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1074

For more Therapeutic Uses (Complete) data for DIIODOHYDROXYQUIN (8 total), please visit the HSDB record page.

4.2 Drug Warning

WHILE...EFFECTIVE IN CYST-PASSING PT, THEY ARE MUCH LESS EFFECTIVE IN TREATMENT OF ACUTE AMEBIC DYSENTERY.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1073

USE OF THESE AGENTS TO TREAT "TRAVELER'S DIARRHEA" & CHRONIC NONSPECIFIC DIARRHEA IN CHILDREN /PRC: OR ADULTS/ CANNOT BE CONDONED, SINCE SUCH CONDITIONS ARE SELF-LIMITED & ANY POSSIBLE THERAPEUTIC BENEFIT DOES NOT JUSTIFY RISK OF SERIOUS NEUROTOXICITY. /8-HYDROXYQUINOLINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1074

THESE DRUGS ARE CONTRAINDICATED IN PT WITH HEPATIC DAMAGE OR IODINE INTOLERANCE. ...THESE AGENTS INTERFERE WITH CERTAIN THYROID FUNCTION TESTS FOR MO BECAUSE OF THEIR CONTENT OF IODINE. /8-HYDROXYQUINOLINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1074

...IT NOW APPEARS THAT GI-NEUROLOGIC SYNDROME OF OBSCURE ETIOLOGY, COMMON IN REGIONS WHERE DIIODOHYDROXYQUIN IS USED, IS CAUSED BY DRUG... FOR THIS REASON, JAPAN WITHDREW SUCH DRUGS FROM MARKET.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1159

VET: COMMERCIAL PREPN MAY CAUSE YELLOW-BROWN STAINING OF WHITE HAIR. USE MAY ALTER SERUM PROTEIN-BOUND IODINE TEST.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 177

4.3 Minimum/Potential Fatal Human Dose

4(?). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB). ...ITS TOXICITY IS UNPREDICTABLE.

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-234

4.4 Drug Indication

Used in the treatment of amoebiasis.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Amebicides

Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal. (See all compounds classified as Amebicides.)

5.2 ATC Code

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AC - Quinoline derivatives

G01AC01 - Diiodohydroxyquinoline

5.3 Absorption, Distribution and Excretion

AFTER ORAL ADMIN, VARIABLE BUT SIGNIFICANT PORTION OF INGESTED DOSE IS ABSORBED. ... DIIODOHYDROXYQUIN WAS LEAST WELL ABSORBED--ONLY 1/3 AS MUCH AS IODOCHLORHYDROXYQUIN. BULK OF THESE DRUGS IS PASSED IN FECES.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1073

5.4 Mechanism of Action

Unknown.

...IT IS NOT KNOWN IF THEY ARE EFFECTIVE IN INTESTINAL AMEBIASIS SOLELY BY VIRTUE OF THEIR PRESENCE IN LUMEN OF BOWEL OR ALSO IN PART BY THEIR PRESENCE IN CIRCULATION. /8-HYDROXYQUINOLINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1073

...8-HYDROXYQUINOLINES ARE DIRECTLY AMEBICIDAL. THEY ARE ACTIVE AGAINST BOTH MOTILE & CYSTIC FORMS, BUT THEIR EFFICACY IN ELIMINATING CYSTS IS PROBABLY BASED ON THEIR ABILITY TO DESTROY TROPHOZOITES. THEY ACT ONLY ON AMEBAE IN INTESTINAL TRACT & ARE INEFFECTIVE IN AMEBIC ABSCESS & HEPATITIS. /8-HYDROXYQUINOLINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1073