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Identification
Name Lindane
Accession Number DB00431 (APRD01072)
Type small molecule
Groups approved
Description

An 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Benzene hexachloride
gamma-BHC
gamma-HCH
gamma-Hexachlorocyclohexane
Lindan
γ-benzene hexachloride
γ-BHC
γ-HCH
γ-hexachlorocyclohexane
γ-Hexachlorzyklohexan
γ-lindane
First Prev Next Last
Salts Not Available
Brand names
Name Company
Aalindan
Aficide
Agrocide
Agrocide III
Agrocide WP
Ameisentod
Aparasin
Aphtiria
Aplidal
Arbitex
Atlas steward
Ben-Hex
Bentox 10
Bexol
Celanex
Chloresene
Codechine
Devoran
Entomoxan
Esoderm
Gamacid
Gamene
Gammalin
Gammalin 20
Gammasan
Gammaterr
Gammexane
Gexane
Heclotox
Hexa
Hexatox
Hexaverm
Hexicide
Hexit
Hexyclan
Hortex
Indane
Isotox
Jacutin
Kokotine
Kwell
Lendine
Lentox
Lidenal
Lindafor
Lindatox
Lindex
Lindosep
Lintox
Linvur
Lorexane
Milbol 49
Mszycol
Neo-Scabicidol
New kotol
Nexen FB
Nexit
Nexit-Stark
Nexol-E
Nicochloran
Omnitox
Ovadziak
Owadziak
Pedraczak
Pflanzol
Quellada
Scabene
Scabene lotion
Spritz-Rapidin
Spruehpflanzol
Streunex
Thionex
Tri-6
Viton
First Prev Next Last
Brand mixtures
Brand Name Ingredients
Dermadex CRM Benzoic Acid + Benzyl Benzoate + Lindane + Salicylic Acid + Zinc Oxide + Zinc Undecylenate
Categories
  • Antiscabies Agent
  • Scabicide
  • Insecticides
CAS number 58-89-9
Weight Average: 290.83
Monoisotopic: 287.860066434
Chemical Formula C6H6Cl6
InChI Key InChIKey=JLYXXMFPNIAWKQ-GNIYUCBRSA-N
InChI
InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4+,5+,6+
Plain Text
IUPAC Name
(1R,2S,3r,4R,5S,6r)-1,2,3,4,5,6-hexachlorocyclohexane
SMILES
Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl
Plain Text
Mass Spec show (11.7 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the treatment of patients infested with Sarcoptes scabiei or pediculosis capitis who have either failed to respond to adequate doses, or are intolerant of other approved therapies.
Pharmacodynamics Scabies is a common, highly pruritic infestation of the skin caused by Sarcoptes scabiei (lice). It is a very contagious condition with specific lesions, such as burrows, and nonspecific lesions, such as papules, vesicles and excoriations. The typical areas of the body it affects are finger webs, scalp (hair), wrists, axillary folds, abdomen, buttocks, inframammary folds and genitalia (males). It is characterized by intense night-time itching. Scabies is spread through close personal contact (relatives, sexual partners, schoolchildren, chronically ill patients and crowded communities). Scabies infestations and the corresponding symptoms can be eliminated by killing the scabies with topical insecticides or scabicides. Lindane is a scabicide that is essentially an organochloride insecticide.
Mechanism of action Lindane is an organochloride insecticide that has similar neurotoxic protperties to DDT. It exerts its parasiticidal action by being directly absorbed through the parasite's exoskeleton (primarily lice, or scabies) and their ova. The gamma-aminobutyric acid (GABA(1)) receptor/chloride ionophore complex is the primary site of action for lindane, and other insecticides such as endosulfan, and fipronil. Blockage of the GABA-gated chloride channel reduces neuronal inhibition, which leads to hyperexcitation of the central nervous system. This results in paralysis, convulsions, and death. Lindane has very low ovicidal activity.
Absorption Lindane is absorbed significantly through the skin. A mean peak blood concentration of 28 nanograms per mL occurred in infants and children 6 hours after total body application of lindane lotion for scabies.
Volume of distribution Not Available
Protein binding 91%
Metabolism Primarily hepatic through dechlorination leading to 2-chlorophenol, 0-chlorophenol, chlorocyclohexane, chlorocyclohexanol.
Route of elimination Not Available
Half life 18 hours
Clearance Not Available
Toxicity Lindane is a moderately toxic compound via oral exposure, with a reported oral LD50 of 88 to 190 mg/kg in rats. Gamma-HCH (which constitutes 99% of lindane) is generally considered to be the most acutely toxic of the isomers following single administration. It is moderately toxic via the dermal route as well, with reported dermal LD50 values of 500 to 1000 mg/kg in rats, 300 mg/kg in mice, 400 mg/kg in guinea pigs, and 300 mg/kg in rabbits. Acute exposure to lindane may lead to central nervous system stimulation (usually developing within 1 hour), mental/motor impairment, excitation, clonic (intermittent) and tonic (continuous) convulsion. Other adverse reactions include central nervous system toxicity, as well as skin and gastrointestinal changes.
Affected organisms
  • Scabies (Sarcoptes scabei) and other insects
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Reed and carnrick pharmaceuticals div block drug co inc
  • Sola barnes hind
  • Olta pharmaceuticals corp
  • Wockhardt eu operations (swiss) ag
  • Stiefel laboratories inc
Packagers
Dosage forms
Form Route Strength
Emulsion Topical
Lotion Topical
Shampoo Topical
Prices
Unit description Cost Unit
Lindane 1% Lotion 60ml Bottle 142.33 USD bottle
Lindane 1% Shampoo 60ml Bottle 142.33 USD bottle
Lindane 1% lotion 5.16 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State liquid
Experimental Properties
Property Value Source
melting point 112.5 °C PhysProp
boiling point 323.4 °C PhysProp
water solubility 7.3 mg/L (at 25 °C) RICHARDSON,LT & MILLER,DM (1960)
logP 3.72 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 5.47e-03 g/l ALOGPS
logP 3.94 ALOGPS
logP 4.35 ChemAxon
logS -4.7 ALOGPS
physiological charge 0 ChemAxon
hydrogen acceptor count 0 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 0 ChemAxon
rotatable bond count 0 ChemAxon
refractivity 54.08 ChemAxon
polarizability 23.08 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Brown VJ: Life after lindane in California. Environ Health Perspect. 2008 Mar;116(3):A128. Pubmed
  2. Strong M, Johnstone PW: Interventions for treating scabies. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000320. Pubmed
External Links
Resource Link
KEGG Drug D00360 Link_out
KEGG Compound C07075 Link_out
ChEBI 32888 Link_out
ChEMBL 32888 Link_out
Therapeutic Targets Database DAP001036 Link_out
PharmGKB PA164754914 Link_out
Drug Product Database 703605 Link_out
RxList http://www.rxlist.com/cgi/generic2/lindane.htm Link_out
Drugs.com http://www.drugs.com/cdi/lindane-lotion.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Lindane Link_out
ATC Codes
  • P03AB02
  • D08AE01
AHFS Codes
  • 84:04.92
  • 84:04.12
PDB Entries Not Available
FDA label Not Available
MSDS show (54.1 KB)
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions Not Available
Targets

1. Gamma-aminobutyric-acid receptor subunit beta-1

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P18505 Link_out
Gene: GABRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  4. Sauviat MP, Pages N: [Cardiotoxicity of lindane, a gamma isomer of hexachlorocyclohexane] J Soc Biol. 2002;196(4):339-48. Pubmed
  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
  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
  7. Bloomquist JR: Chloride channels as tools for developing selective insecticides. Arch Insect Biochem Physiol. 2003 Dec;54(4):145-56. Pubmed
  8. Narahashi T: Neuronal ion channels as the target sites of insecticides. Pharmacol Toxicol. 1996 Jul;79(1):1-14. Pubmed
  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
  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 and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. Pubmed
  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

2. Glycine receptor subunit alpha-1

Pharmacological action: unknown
Actions: antagonist

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)

Organism class: human
UniProt ID: P23415 Link_out
Gene: GLRA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. Pubmed
  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

3. Glycine receptor subunit alpha-2

Pharmacological action: unknown
Actions: antagonist

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)

Organism class: human
UniProt ID: P23416 Link_out
Gene: GLRA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. Pubmed
  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

4. Glycine receptor subunit alpha-3

Pharmacological action: unknown
Actions: antagonist

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)

Organism class: human
UniProt ID: O75311 Link_out
Gene: GLRA3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. Pubmed
  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

5. Glycine receptor subunit beta

Pharmacological action: unknown
Actions: antagonist

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)

Organism class: human
UniProt ID: P48167 Link_out
Gene: GLRB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 and glycine-gated chloride channels in primary cultures of cerebellar granule cells. Neuroscience. 2003;117(2):397-403. Pubmed
  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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19