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Chemistry

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Also known as: 130-26-7, 5-chloro-7-iodoquinolin-8-ol, Iodochlorhydroxyquin, Chinoform, Chloroiodoquin, 5-chloro-7-iodo-8-quinolinol
Molecular Formula
C9H5ClINO
Molecular Weight
305.50  g/mol
InChI Key
QCDFBFJGMNKBDO-UHFFFAOYSA-N
FDA UNII
7BHQ856EJ5

Clioquinol
A potentially neurotoxic 8-hydroxyquinoline derivative long used as a topical anti-infective, intestinal antiamebic, and vaginal trichomonacide. The oral preparation has been shown to cause subacute myelo-optic neuropathy and has been banned worldwide.
Clioquinol is a Standardized Chemical Allergen. The physiologic effect of clioquinol is by means of Increased Histamine Release, and Cell-mediated Immunity.
1 2D Structure

Clioquinol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-chloro-7-iodoquinolin-8-ol
2.1.2 InChI
InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
2.1.3 InChI Key
QCDFBFJGMNKBDO-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC2=C(C(=C(C=C2Cl)I)O)N=C1
2.2 Other Identifiers
2.2.1 UNII
7BHQ856EJ5
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5 Chloro 7 Iodo 8 Quinolinol

2. 5-chloro-7-iodo-8-quinolinol

3. Chinoform

4. Chloroiodoquine

5. Entero Septol

6. Entero Vioform

7. Entero-septol

8. Entero-vioform

9. Enteroquinol

10. Enteroseptol

11. Enterovioform

12. Iodochlorhydroxyquin

13. Iodochloroxyquinoline

14. Vioform

2.3.2 Depositor-Supplied Synonyms

1. 130-26-7

2. 5-chloro-7-iodoquinolin-8-ol

3. Iodochlorhydroxyquin

4. Chinoform

5. Chloroiodoquin

6. 5-chloro-7-iodo-8-quinolinol

7. Chloroiodoquine

8. 5-chloro-8-hydroxy-7-iodoquinoline

9. Vioform

10. Iodochloroxyquinoline

11. Cliquinol

12. Iodochlorohydroxyquinoline

13. Chlorojodochin

14. Enteroquinol

15. Iodochloroquine

16. Iodochloroxine

17. Iodoenterol

18. 7-iodo-5-chloroxine

19. Entero-vioform

20. Iodochlorhydroxyquinoline

21. 5-chloro-7-iodo-8-hydroxyquinoline

22. Iodoxyquinoline

23. Alchloquin

24. Barquinol

25. Budoform

26. Cifoform

27. Dermaform

28. Dioquinol

29. Domeform

30. Eczecidin

31. Enteroseptol

32. Enterozol

33. Enterseptol

34. Entrokin

35. Iodenterol

36. Lekosept

37. Mycoquin

38. Quinambicide

39. Quinoform

40. Rheaform

41. Amebil

42. Amoenol

43. Bactol

44. Emaform

45. Nioform

46. Rometin

47. Entero-bioform

48. Iodochlorohydroxyquin

49. Hi-enterol

50. Iodochlorhydroxyquinol

51. Hydriodide-enterol

52. Quin-o-creme

53. Entero-septol

54. Enterum Locorten

55. 5-chloro-7-iodo-quinolin-8-ol

56. Domeform-hc

57. 8-quinolinol, 5-chloro-7-iodo-

58. 7-iodo-5-chloro-8-hydroxyquinoline

59. Clioquinolum

60. Chloro-8-hydroxyiodoquinoline

61. Quinoform (antiseptic)

62. Vioform N.n.r.

63. Quinoline, Chloro-8-hydroxyiodo-

64. 5-chlor-7-jod-8-hydroxy-chinolin

65. Rheaform Boluses

66. Iodochlorhydroxyquinolone

67. Nsc-3531

68. Chinoformum

69. Cliochinolum

70. 7bhq856ej5

71. Enterovalodon

72. Alioform

73. Enteritan

74. Jodchloroxychinolinum

75. Oralcer

76. Chebi:74460

77. Corque

78. Cortin

79. Iodochloroxychinolinum

80. Cremo-quin

81. Entero-bio Form

82. Entero-vioformio

83. Ala-quin

84. Uad Lotion

85. Nsc-74938

86. Ncgc00016391-05

87. Cliochinolo

88. Cas-130-26-7

89. Cliochinolo [dcit]

90. Tg2-36-2

91. Caswell No. 193

92. Dsstox_cid_2837

93. Formtone-hc

94. Dsstox_rid_76751

95. Pbt-1

96. Dsstox_gsid_22837

97. Quinoform (van)

98. Clioquinolum [inn-latin]

99. Loquinol

100. Vioformio

101. Hi-eneterol

102. Iodochlorhydroxyquin Cream

103. Vioform-hydrocortisone Mild

104. 22112-03-4

105. Smr000058282

106. Rheaform Boluses (veterinary)

107. Ccris 6050

108. Hsdb 6843

109. 5-chlor-7-jod-8-hydroxy-chinolin [german]

110. Sr-01000002987

111. Nsc 3531

112. Einecs 204-984-4

113. Epa Pesticide Chemical Code 024001

114. Brn 0153637

115. Unii-7bhq856ej5

116. Linolasept

117. Clioquinol [usp:inn:ban]

118. Cloquinol

119. Ai3-16451

120. Clioquinol (cq)

121. Component Of Hyquin

122. Mfcd00006787

123. Nsc 74938

124. Nystaform (salt/mix)

125. Clioquinol (usp/inn)

126. Clioquinol [inn]

127. Component Of Formtone-hc

128. Component Of Heb-cort V

129. Prestwick0_000886

130. Prestwick1_000886

131. Prestwick2_000886

132. Prestwick3_000886

133. Clioquinol [hsdb]

134. Formtone-hc (salt/mix)

135. Clioquinol [vandf]

136. Chembl497

137. Ec 204-984-4

138. Cid_2788

139. Clioquinol [mart.]

140. Schembl3967

141. Clioquinol [usp-rs]

142. Clioquinol [who-dd]

143. Nciopen2_009062

144. Oprea1_438281

145. Bspbio_000672

146. Bspbio_002466

147. 5-21-03-00294 (beilstein Handbook Reference)

148. Ksc-8-192

149. Mls000069389

150. Mls002454410

151. Spectrum1505114

152. Spbio_002891

153. Bpbio1_000740

154. Clioquinol [orange Book]

155. Component Of Hyquin (salt/mix)

156. Dtxsid7022837

157. Bdbm32188

158. Iodochlorhydroxyquin [mi]

159. Clioquinol [ep Monograph]

160. Nsc3531

161. Wln: T66 Bnj Gg Ii Jq

162. Clioquinol [usp Monograph]

163. Hms1570b14

164. Hms1648j07

165. Hms2093i12

166. Hms2097b14

167. Hms2230i20

168. Hms3372j20

169. Hms3714b14

170. Kuc105859n

171. Pharmakon1600-01505114

172. Albb-031653

173. Component Of Cort-quin (salt/mix)

174. Zinc6409735

175. Tox21_110416

176. Tox21_200291

177. Nsc759822

178. Nystaform Component Clioquinol

179. S4601

180. Stk399761

181. 5-chloro-8-hydroxy-7-iodo-quinoline

182. Component Of Heb-cort V (salt/mix)

183. Akos000120779

184. Tox21_110416_1

185. Ac-6792

186. Ccg-213339

187. Db04815

188. Fd10468

189. Nsc-759822

190. Clioquinol Component Of Nystaform

191. Smp1_000073

192. Iodochlorhydroxyquin [green Book]

193. Ncgc00016391-01

194. Ncgc00016391-02

195. Ncgc00016391-03

196. Ncgc00016391-04

197. Ncgc00016391-06

198. Ncgc00016391-07

199. Ncgc00016391-08

200. Ncgc00016391-09

201. Ncgc00016391-10

202. Ncgc00016391-13

203. Ncgc00021665-03

204. Ncgc00021665-04

205. Ncgc00021665-05

206. Ncgc00257845-01

207. S4601 5-chloro-8-hydroxy-7-iodoquin

208. As-14597

209. Bc167259

210. Hy-14603

211. Sbi-0206782.p001

212. Db-041956

213. Ab00384254

214. Ft-0603209

215. 4-stearylamino-phenyl-trimethylam. Metilsulf.

216. A16461

217. Clioquinol, Vetranal(tm), Analytical Standard

218. Component Of Vioform-hydrocortisone (salt/mix)

219. D03538

220. Ab00384254_17

221. 5-chloro-7-iodo-8-quinolinol, >=95.0% (hplc)

222. Cu-01000000767-2

223. Q-200875

224. Q5134338

225. Sr-01000002987-2

226. Sr-01000002987-3

227. Sr-01000002987-4

228. Brd-k09255212-001-04-2

229. Z2768770393

230. Clioquinol, British Pharmacopoeia (bp) Reference Standard

231. Clioquinol, European Pharmacopoeia (ep) Reference Standard

232. Clindamycin Phosphate, Antibiotic For Culture Media Use Only

233. Clioquinol, United States Pharmacopeia (usp) Reference Standard

234. Cql

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 305.50 g/mol
Molecular Formula C9H5ClINO
XLogP33.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass304.91044 g/mol
Monoisotopic Mass304.91044 g/mol
Topological Polar Surface Area33.1 Ų
Heavy Atom Count13
Formal Charge0
Complexity193
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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)


Clioquinol is used topically in the treatment of tinea pedis, tinea cruris, and other skin infections caused by dermatophytic fungi (ringworm).

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 2178


MEDICATION (VET): has been used as an intestinal anti-infective.

Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 796


Topical anti-infective; anti-amebic

Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 796


For more Therapeutic Uses (Complete) data for CLIOQUINOL (7 total), please visit the HSDB record page.


4.2 Drug Warning

Although clioquinol previously was used in the treatment of diaper rash (diaper dermatitis), use of the drug in children currently is not recommended, and use in those younger than 2 years of age is contraindicated.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 2178


Clioquinol generally appears to be well tolerated following topical application to the skin. Local irritation, rash, and sensitivity reactions have been reported occasionally. If any of these effects occurs, the drug should be discontinued and a physician consulted. Cross sensitivity with other hydroxyquinoline and quinoline derivatives (eg, certain antimalarials) and, occasionally, to iodides can occur. Clioquinol can stain the skin, and discoloration of the hair and nails has been reported rarely. Prolonged use of the drug can result in overgrowth of nonsusceptible organisms, which may require appropriate therapy. When clioquinol is used topically in fixed combination with hydrocortisone, the usual precautions associated with topical corticosteroid therapy should be observed.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 2178


Because of an association between oculotoxic/neurotoxic effects (eg, optic neuritis, optic atrophy, subacute myelo-optic neuropathy) and oral clioquinol therapy (usually at high dosages for prolonged periods) and the availability of effective alternative topical antifungals, use of clioquinol in children is not recommended, and use in those younger than 2 years of age is contraindicated.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 2178


Percutaneously absorbed clioquinol, which contains iodine, may interfere with certain thyroid function tests (eg, protein-bound iodine); therefore, the manufacturer recommends that at least 1 month elapse between discontinuance of topical therapy with the drug and performance of these tests. Clioquinol also may produce false positive results in the ferric chloride test for phenylketonuria when the drug is present in urine or the diaper.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 2178


For more Drug Warnings (Complete) data for CLIOQUINOL (8 total), please visit the HSDB record page.


4.3 Drug Indication

Used as a topical antifungal treatment.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Clioquinol is a broad-spectrum antibacterial with antifungal properties. Application of clioquinol to extensive or eroded areas of the skin may lead to increased protein-bound iodine (PBI) levels within 1 week. In addition, elevated PBI levels may occur when relatively small areas of the skin are treated with clioquinol for more than 1 week.


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
CLIOQUINOL
5.2.2 FDA UNII
7BHQ856EJ5
5.2.3 Pharmacological Classes
Chemical Structure [CS] - Allergens
5.3 ATC Code

D - Dermatologicals

D08 - Antiseptics and disinfectants

D08A - Antiseptics and disinfectants

D08AH - Quinoline derivatives

D08AH30 - Clioquinol


D - Dermatologicals

D09 - Medicated dressings

D09A - Medicated dressings

D09AA - Medicated dressings with antiinfectives

D09AA10 - Clioquinol


G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AC - Quinoline derivatives

G01AC02 - Clioquinol


P - Antiparasitic products, insecticides and repellents

P01 - Antiprotozoals

P01A - Agents against amoebiasis and other protozoal diseases

P01AA - Hydroxyquinoline derivatives

P01AA02 - Clioquinol


S - Sensory organs

S02 - Otologicals

S02A - Antiinfectives

S02AA - Antiinfectives

S02AA05 - Clioquinol


5.4 Absorption, Distribution and Excretion

Absorption

Topical absorption is rapid and extensive, especially when the skin is covered with an occlusive dressing or if the medication is applied to extensive or eroded areas of the skin. Clioquinol is absorbed through the skin in sufficient amounts to affect thyroid function tests.


Clioquinol is absorbed systemically following topical application to the skin. In 2 studies in which clioquinol combined with a corticosteroid was applied topically to the skin as a cream or ointment, it was estimated that about 2-3% of the dose was absorbed systemically. However, in another study in which the drug was applied alone to the skin as a 3% cream and covered with an occlusive wrap for 12 hr, it was estimated that about 40% of the dose was absorbed percutaneously during this period.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 2178


Patients with widespread dermatitis were treated with 15-20 g of 3% clioquinol ointment to 40% of the body area twice daily. The serum concentration increased to 0.8-1.2 ug/ml within 4 hr of application. In one patient, 15-20 mg was excreted in the urine daily mainly in the form of conjugated metabolites. This skin treatment resulted in a urinary excretion somewhat less than is obtained after a daily oral dose of 25 mg (one tablet) of clioquinol. Thus, 3-4% of the applied clioquinol was absorbed. 25% was excreted in the urine.

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 363


5.5 Metabolism/Metabolites

Clioquinol has known human metabolites that include Clioquinol O-glucuronide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.6 Biological Half-Life

11-14 hr

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 363


5.7 Mechanism of Action

Clioquinol is bacteriostatic, however, the precise mechanism of its action is unknown.


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310052, , CHI CHINA","customerAddress":"PLOT 170-172, CHANDRAMOULI,INDUSTR"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724005800,"product":"1-(BENZYLOXY)-2-IODOBENZENE","address":"BIOCON SEZ, BIOCON PARK,PLOT NO.2 3","city":"N\/A","supplier":"COMBI BLOCKS INC","supplierCountry":"UNITED STATES","foreign_port":"STEGER, IL","customer":"SYNGENE INTERNATIONAL LIMITED","customerCountry":"INDIA","quantity":"0.17","actualQuantity":"165","unit":"GMS","unitRateFc":"6.9","totalValueFC":"1165.8","currency":"USD","unitRateINR":"586.7","date":"19-Aug-2024","totalValueINR":"96808","totalValueInUsd":"1165.8","indian_port":"Biocon-SEZ","hs_no":"29420090","bill_no":"1010743","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"STEGER, IL","supplierAddress":"7949 SILVERTON AV SUITE 915 SAN DIEGO CA 92126 U.S.A.","customerAddress":"BIOCON SEZ, BIOCON PARK,PLOT NO.2 3"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724697000,"product":"2-CHLORO-3-IODOPYRIDIN-4-AMINE (CAS: 909036-46-0)","address":"Plot No. 26 & 27, Technocrat Industrial Estate (TIE)","city":"Hyderabad","supplier":"NINGBO SANGER MEDTECH CO.,LTD","supplierCountry":"CHINA","foreign_port":"HONG KONG","customer":"COHANCE LIFESCIENCES","customerCountry":"INDIA","quantity":"70.00","actualQuantity":"70","unit":"KGS","unitRateFc":"1500","totalValueFC":"107285.2","currency":"USD","unitRateINR":"127275","date":"27-Aug-2024","totalValueINR":"8909250","totalValueInUsd":"107285.2","indian_port":"Bombay Air","hs_no":"29333990","bill_no":"5268209","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"HONG KONG","supplierAddress":"7-1-20 NO.666 SANGTIAN ROADNINGBO 315040 CHINA, CHINA","customerAddress":"Plot No. 26 & 27, Technocrat Industrial Estate (TIE)"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724869800,"product":"3-IODOPROPIONICACID-VALUE FOR CUSTOM PURPOSES ONLY","address":"BIOCON SEZ, BIOCON PARK,PLOT NO.2 3","city":"N\/A","supplier":"AMBEED INC","supplierCountry":"CHINA","foreign_port":"LAI CHI KOK","customer":"SYNGENE INTERNATIONAL LIMITED","customerCountry":"INDIA","quantity":"0.03","actualQuantity":"25","unit":"GMS","unitRateFc":"2.5","totalValueFC":"62.6","currency":"USD","unitRateINR":"208","date":"29-Aug-2024","totalValueINR":"5201","totalValueInUsd":"62.6","indian_port":"Biocon-SEZ","hs_no":"29159099","bill_no":"1011260","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"LAI CHI KOK","supplierAddress":"3860 N VENTURA DRARLINGTON HEIGHTS IL 60004SDNF US US","customerAddress":"BIOCON SEZ, BIOCON PARK,PLOT NO.2 3"}]
02-Jan-2021
31-Aug-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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