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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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    Average Price (USD/KGS)

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    Total Quantity (KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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