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Clobutinol

Summary

Clobutinol is a cough suppressant formerly distributed by Boehringer Ingelheim and its licensees under the names Lomisat and Silomat, by Bioter as Biotussin, and by Violani-Farmavigor as Pertoxil. It has been withdrawn from the market worldwide.

Clobutinol
Clinical data
Trade namesBiotussin, Lomisat, Pertoxil, Silomat
AHFS/Drugs.comInternational Drug Names
Routes of
administration		oral
ATC code
Legal status
Legal status
  • Withdrawn
(EU)
Identifiers
  • (RS)-1-(4-chlorophenyl)-4-dimethylamino-2,3-dimethyl-butan-2-ol
CAS Number
  • 14860-49-2 checkY
PubChem CID
  • 26937
DrugBank
  • DB09004 ☒N
ChemSpider
  • 25085 checkY
UNII
  • 1NY2IX043A
KEGG
  • D07716 checkY
ChEMBL
  • ChEMBL1474889 ☒N
CompTox Dashboard (EPA)
  • DTXSID2022838 Edit this at Wikidata
ECHA InfoCard100.035.373 Edit this at Wikidata
Chemical and physical data
FormulaC14H22ClNO
Molar mass255.79 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic mixture
  • Clc1ccc(cc1)CC(O)(C)C(C)CN(C)C
  • InChI=1S/C14H22ClNO/c1-11(10-16(3)4)14(2,17)9-12-5-7-13(15)8-6-12/h5-8,11,17H,9-10H2,1-4H3 checkY
  • Key:KVHHQGIIZCJATJ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Side effects and withdrawal edit

Side effects include drowsiness, dizziness, insomnia, nausea, vomiting, and abdominal discomfort.[1] Studies in 2004 had indicated that clobutinol has the potential to prolong the QT interval.[2] Clobutinol was in 2007 determined to cause cardiac arrhythmia in some patients.[3]

Boehringer Ingelheim products containing clobutinol were voluntarily withdrawn from sale in Germany, and the rest of the world, on August 31, 2007.[4]

The approval for Germany and the EU was revoked in 2008.[5]

Prior to withdrawal, it was available throughout Europe and Central America, as well as in South Africa. Trade names include Biotussin, Lomisat (Spain), Pertoxil (Italy), and in most of the world, Silomat.[6]

See also edit

References edit

  1. ^ Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 29. ISBN 0-8103-7177-4.
  2. ^ Bellocq C, Wilders R, Schott JJ, Louérat-Oriou B, Boisseau P, Le Marec H, et al. (November 2004). "A common antitussive drug, clobutinol, precipitates the long QT syndrome 2". Molecular Pharmacology. 66 (5): 1093–102. doi:10.1124/mol.104.001065. PMID 15280442. S2CID 12883606.
  3. ^ "Clobutinol-haltige Arzneimittel: BfArM ordnet Widerruf der Zulassung an". BfArM (German Federal Institute for Drugs and Medical Devices). 2007-08-31. Archived from the original on 2012-04-01. Clobutinol: BfArM orders cancellation of approval
  4. ^ "Boehringer Ingelheim voluntarily withdraws its clobutinol containing medications". Boehringer Ingelheim. 2007-08-31. Archived from the original on 2012-01-27.
  5. ^ "Cancellation of approval" (PDF). BfArM (German Federal Institute for Drugs and Medical Devices). 2008-06-06. Archived from the original (pdf) on 2012-04-01. Die Zulassungen für die o.g. Arzneimittel werden mit sofortiger Wirkung widerrufen.
  6. ^ Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 29. ISBN 0-8103-7177-4.