Substance

ID:314

Names and Identifiers
Brand Name
AgrocideAparasinAplidalArbitexBexolDBHPflanzolQuelladaSpruehpflanzolStreunexTAP 85LindatoxLindosepLorexaneNew kotolOmnitoxPedraczakGamacidGamma-BHC dustGamma-ColHexachloranHexachlorocyclohexaneKwellbeta-LindaneAgrocide IIIAmeisentodCodechineDol GranuleNexitNexit-StarkNexol-ESang-«Vitonbeta-BHCJacutinKokotineLendineLidenalLindexNexen FBEntomoxanGameneGamma-HCH dustGammalin 20HCHHexavermOwadziakScabene lotionSpritz-RapidinChloreseneDevoranLentoxLinvurMurfume grain store smokeNeo-ScabicidolNicochloranOvadziakGexaneHexatoxHexicideHexitHexyclanIsotoxBentox 10Benzene hexachlorideCelanexDrilltox-Spezial AglukonEsodermGammalinAgrocide WPAmeisenmittel merckAphtiriaAtlas stewardBBHBen-HexScabeneThionexTri-6beta-HexachlorocyclohexaneAalindanAficideLindaforLintoxMilbol 49MszycolPMS Lindanegamma»HGIHeclotoxHexaHexachloraneHortexIndaneDetmol-ExtraktFumite lindaneGammasanGammaterrGammexaneHCCH
Synonyms
Lindane
IUPAC Traditional name
hexachlorocyclohexane
IUPAC name
1,2,3,4,5,6-hexachlorocyclohexane
Registration numbers
CAS Number
Properties
Physical Property
Hydrophobicity(logP)
3.8
Solubility
7.3 mg/L
Molecule Details
Drug 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.
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.
Pharmacology
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.
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
Biotransformation
Primarily hepatic through dechlorination leading to 2-chlorophenol, 0-chlorophenol, chlorocyclohexane, chlorocyclohexanol.
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.
Half Life
18 hours
Protein Binding
91%
References
• Brown VJ: Life after lindane in California. Environ Health Perspect. 2008 Mar;116(3):A128. [Pubmed]
• Strong M, Johnstone PW: Interventions for treating scabies. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000320. [Pubmed]
External Links
Molecular Spectra
No Data Available
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References
• Brown VJ: Life after lindane in California. Environ Health Perspect. 2008 Mar;116(3):A128. Pubmed
• Strong M, Johnstone PW: Interventions for treating scabies. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000320. Pubmed