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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2013-02-08 18:42:51 UTC
HMDB IDHMDB14575
Secondary Accession NumbersNone
Metabolite Identification
Common NameLindane
DescriptionAn organochlorine insecticide that has been used as a pediculicide and a scabicide. Lindane has been banned in California, United Kingdom, Australia, and many western countries due to concerns about neurotoxicity and adverse effects on the environment. In Canada, Lindane is not recommmended as a first-line therapy due to reports of resistance, neurotoxicity, and bone marrow suppression, but has been approved by the FDA as a second-line therapy for topical treatment of pediculosis capitis (head lice), pediculosis pubis (pubic lice), or scabies in patients greater than two years of age who cannot tolerate or have failed first-line treatment.
Structure
Thumb
Synonyms
  1. Benzene hexachloride
  2. gamma-Benzene hexachloride
  3. gamma-BHC
  4. gamma-HCH
  5. gamma-Hexachlorocyclohexane
  6. gamma-Hexachlorzyklohexan
  7. gamma-Lindane
  8. Lindan
Chemical FormulaC6H6Cl6
Average Molecular Weight290.83
Monoisotopic Molecular Weight287.860066434
IUPAC Name(1R,2S,3r,4R,5S,6r)-1,2,3,4,5,6-hexachlorocyclohexane
Traditional Namelindane
CAS Registry Number58-89-9
SMILES
Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl
InChI Identifier
InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4+,5+,6+
InChI KeyJLYXXMFPNIAWKQ-GNIYUCBRSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Homomonocyclic Compounds
ClassCycloalkanes
Sub ClassN/A
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Alkyl Chlorides
  • Organochlorine insecticides(KEGG)
  • cyclodiene organochlorine insecticide(ChEBI)
  • hexachlorocyclohexane(ChEBI)
Substituents
  • N/A
Direct ParentCycloalkanes
Ontology
StatusDetected and Quantified
Origin
  • Drug
Biofunction
  • Antiscabies Agent
  • Insecticides
  • Scabicide
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point112.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.47e-03 g/LNot Available
LogP3.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0055 g/LALOGPS
logP3.94ALOGPS
logP4.35ChemAxon
logS-4.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.08ChemAxon
Polarizability23.08ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00105(0.00037-0.00179) uMAdult (>18 years old)BothNormal
    • Report on Human B...
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00431
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00431
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00431
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10481896
KEGG Compound IDC07075
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLindane
NuGOwiki LinkHMDB14575
Metagene LinkHMDB14575
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID32888
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Strong M, Johnstone P: Interventions for treating scabies. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000320. Pubmed: 17636630
  2. Brown VJ: Life after lindane in California. Environ Health Perspect. 2008 Mar;116(3):A128. Pubmed: 18335087
  3. REES BE, RALEY TG, DAVIS ED: Prehatiching treatment of irrigated lands with DDT, dichlorodiphenyl dichloroethane, and gammabenzene hexachloride for control of flood water mosquitoes. J Econ Entomol. 1949 Aug;42(4):586-90. Pubmed: 18138195
  4. Lundstedt-Enkel K, Tysklind M, Trygg J, Schuller P, Asplund L, Eriksson U, Haggberg L, Odsjo T, Hjelmberg M, Olsson M, Orberg J: A statistical resampling method to calculate biomagnification factors exemplified with organochlorine data from herring (Clupea harengus) muscle and guillemot (Uria aalge) egg from the Baltic sea. Environ Sci Technol. 2005 Nov 1;39(21):8395-402. Pubmed: 16294879
  5. Alm H, Torner H, Tiemann U, Kanitz W: Influence of organochlorine pesticides on maturation and postfertilization development of bovine oocytes in vitro. Reprod Toxicol. 1998 Sep-Oct;12(5):559-63. Pubmed: 9763248
  6. Tiemann U, Pohland R, Kuchenmeister U, Viergutz T: Influence of organochlorine pesticides on transmembrane potential, oxidative activity, and ATP-induced calcium release in cultured bovine oviductal cells. Reprod Toxicol. 1998 Sep-Oct;12(5):551-7. Pubmed: 9763247
  7. Belpomme D, Irigaray P, Ossondo M, Vacque D, Martin M: Prostate cancer as an environmental disease: an ecological study in the French Caribbean islands, Martinique and Guadeloupe. Int J Oncol. 2009 Apr;34(4):1037-44. Pubmed: 19287960
  8. Tiemann U, Pohland R: Inhibitory effects of organochlorine pesticides on intercellular transfer of Lucifer Yellow in cultured bovine oviductal cells. Reprod Toxicol. 1999 Mar-Apr;13(2):123-30. Pubmed: 10213519
  9. Tiemann U, Pohland R, Schneider F: Influence of organochlorine pesticides on physiological potency of cultured granulosa cells from bovine preovulatory follicles. Theriogenology. 1996 Jul 15;46(2):253-65. Pubmed: 16727895
  10. Katsumata K, Katsumata K: Norwegian scabies in an elderly patient who died after treatment with gammaBHC. Intern Med. 2003 Apr;42(4):367-9. Pubmed: 12729329
  11. Storelli MM, Stuffler RG, Marcotrigianoi GO: Polycyclic aromatic hydrocarbons, polychlorinated biphenyls, chlorinated pesticides (DDTs), hexachlorocyclohexane, and hexachlorobenzene residues in smoked seafood. J Food Prot. 2003 Jun;66(6):1095-9. Pubmed: 12801016
  12. Corrigan FM, Wienburg CL, Shore RF, Daniel SE, Mann D: Organochlorine insecticides in substantia nigra in Parkinson's disease. J Toxicol Environ Health A. 2000 Feb 25;59(4):229-34. Pubmed: 10706031
  13. Luczak J, Sitkiewicz D: [Effect of Tritox (DDT, DMDT, gammaHCH) on physico-chemical properties and indices of microbial pollution of water]. Rocz Panstw Zakl Hig. 1969;20(4):495-501. Pubmed: 4908314
  14. Panvelkar V, Chari KV: Gammabenzene hexachloride-induced convulsions in an HIV positive individual. Indian J Dermatol Venereol Leprol. 1996 Sep-Oct;62(5):306-7. Pubmed: 20948097

Enzymes

General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRB1
Uniprot ID:
P18505
Molecular weight:
54234.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Cole LM, Roush RT, Casida JE: Drosophila GABA-gated chloride channel: modified [3H]EBOB binding site associated with Ala-->Ser or Gly mutants of Rdl subunit. Life Sci. 1995;56(10):757-65. Pubmed: 7885191
  4. Sauviat MP, Pages N: [Cardiotoxicity of lindane, a gamma isomer of hexachlorocyclohexane] J Soc Biol. 2002;196(4):339-48. Pubmed: 12645305
  5. Anand M, Agrawal AK, Rehmani BN, Gupta GS, Rana MD, Seth PK: Role of GABA receptor complex in low dose lindane (HCH) induced neurotoxicity: neurobehavioural, neurochemical and electrophysiological studies. Drug Chem Toxicol. 1998 Feb;21(1):35-46. Pubmed: 9530529
  6. Joy RM, Walby WF, Stark LG, Albertson TE: Lindane blocks GABAA-mediated inhibition and modulates pyramidal cell excitability in the rat hippocampal slice. Neurotoxicology. 1995 Summer;16(2):217-28. Pubmed: 7566682
  7. Bloomquist JR: Chloride channels as tools for developing selective insecticides. Arch Insect Biochem Physiol. 2003 Dec;54(4):145-56. Pubmed: 14635176
  8. Narahashi T: Neuronal ion channels as the target sites of insecticides. Pharmacol Toxicol. 1996 Jul;79(1):1-14. Pubmed: 8841090
  9. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
  10. Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. Pubmed: 12614680
  11. Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. Epub 2010 Jun 21. Pubmed: 20600211
General function:
Involved in ion transport
Specific function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:
GLRA1
Uniprot ID:
P23415
Molecular weight:
52623.4
References
  1. Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. Pubmed: 12614680
  2. Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. Epub 2010 Jun 21. Pubmed: 20600211
General function:
Involved in ion transport
Specific function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:
GLRA2
Uniprot ID:
P23416
Molecular weight:
52001.6
References
  1. Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. Pubmed: 12614680
  2. Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. Epub 2010 Jun 21. Pubmed: 20600211
General function:
Involved in ion transport
Specific function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:
GLRA3
Uniprot ID:
O75311
Molecular weight:
53799.8
References
  1. Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. Pubmed: 12614680
  2. Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. Epub 2010 Jun 21. Pubmed: 20600211
General function:
Involved in extracellular-glycine-gated chloride channel activity
Specific function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)
Gene Name:
GLRB
Uniprot ID:
P48167
Molecular weight:
56121.6
References
  1. Vale C, Fonfria E, Bujons J, Messeguer A, Rodriguez-Farre E, Sunol C: The organochlorine pesticides gamma-hexachlorocyclohexane (lindane), alpha-endosulfan and dieldrin differentially interact with GABA(A) and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. Pubmed: 12614680
  2. Heusinkveld HJ, Thomas GO, Lamot I, van den Berg M, Kroese AB, Westerink RH: Dual actions of lindane (gamma-hexachlorocyclohexane) on calcium homeostasis and exocytosis in rat PC12 cells. Toxicol Appl Pharmacol. 2010 Oct 1;248(1):12-9. Epub 2010 Jun 21. Pubmed: 20600211