Lindane

Lindane
Ball-and-stick model of the lindane molecule (chair conformation)
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa682651
Pregnancy
category
  • C
Routes of
administration		Topical
ATC code
Legal status
Legal status
  • US: WARNING[1]
  • Production and agricultural use is banned[2] in the 182 countries that are Parties to the Stockholm Convention, but pharmaceutical use is allowed as a second-line treatment for scabies and lice[2]
Pharmacokinetic data
Protein binding91%
MetabolismHepatic cytochrome P-450 oxygenase system
Elimination half-life18 hours
Identifiers
  • (1r,2R,3S,4r,5R,6S)-1,2,3,4,5,6-hexachlorocyclohexane
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.365 Edit this at Wikidata
Chemical and physical data
FormulaC6H6Cl6
Molar mass290.81 g·mol−1
3D model (JSmol)
  • Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl
  • InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4+,5+,6+ checkY
  • Key:JLYXXMFPNIAWKQ-GNIYUCBRSA-N checkY
  (verify)

Lindane, also known as gamma-hexachlorocyclohexane (γ-HCH), gammaxene, Gammallin and benzene hexachloride (BHC),[3] is an organochlorine chemical and an isomer of hexachlorocyclohexane that has been used both as an agricultural insecticide and as a pharmaceutical treatment for lice and scabies.[4][5]

Lindane is a neurotoxin that interferes with GABA neurotransmitter function by interacting with the GABAA receptor-chloride channel complex at the picrotoxin binding site. In humans, lindane affects the nervous system, liver, and kidneys, and may well be a carcinogen.[6][7] Whether lindane is an endocrine disruptor is unclear.[8][9][10]

The World Health Organization classifies lindane as "moderately hazardous", and its international trade is restricted and regulated under the Rotterdam Convention on Prior Informed Consent.[11] In 2009, the production and agricultural use of lindane was banned under the Stockholm Convention on persistent organic pollutants.[2][12] A specific exemption to that ban allows it to continue to be used as a second-line pharmaceutical treatment for lice and scabies.[13]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ a b c "Listing of POPs in the Stockholm Convention". Stockholm Convention.
  3. ^ Brandenberger H, Maes RA (1997). Analytical toxicology: for clinical, forensic, and pharmaceutical chemists. Berlin: Walter de Gruyter. p. 243. ISBN 978-3-11-010731-9. Retrieved 2009-05-10.
  4. ^ "Professional Drug Information: Lindane". Archived from the original on 2018-08-20. Retrieved 2020-02-28.
  5. ^ "The North American Regional Action Plan (NARAP) on Lindane and Other Hexachlorocyclohexane (HCH) Isomers" (PDF). Commission for Environmental Cooperation. 2013. Retrieved 2020-02-28.
  6. ^ "Toxicologic profile for alpha-, beta, gamma- and delta-hexachlorocyclohenxane" (PDF). Agency for Toxic Substances and Disease Registry. U.S. Department of Health and Human Services. August 2005.
  7. ^ "Lindane Voluntary Cancellation and RED Addendum Fact Sheet". US EPA. July 2006. Archived from the original on 2006-10-06.
  8. ^ "Evaluation of the Carcinogenic Potential of Lindane, PC. Code: 009001" (PDF). U.S. EPA. 2001. Archived from the original (PDF) on 2007-09-28.
  9. ^ "Summaries & Evaluations: HEXACHLOROCYCLOHEXANES (Group 2B)". International Agency for Research on Cancer (IARC). 1998-03-02.
  10. ^ World Health Organization (WHO) (2004). "Lindane in Drinking Water: Background Document for Development of WHO Guidelines for Drinking-Water Quality" (PDF). Retrieved 2020-02-28.
  11. ^ World Health Organization, The WHO Recommended Classification of Pesticides by Hazard, 2005.
  12. ^ Press Release - COP4 - Geneva, 8 May 2009: Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty
  13. ^ Eliane Engeler, "UN: Treaty expanded by 9 more dangerous chemicals", Associated Press 2009-05-09