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Lindane

Catalog No. DB00431 Name DrugBank
CAS Number 58-89-9 Website http://www.ualberta.ca/
M. F. C6H6Cl6 Telephone (780) 492-3111
M. W. 290.82984 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 314

SYNONYMS

IUPAC name
1,2,3,4,5,6-hexachlorocyclohexane
IUPAC Traditional name
hexachlorocyclohexane
Brand Name
Celanex
Lorexane
Heclotox
Dol Granule
HCCH
Ameisenmittel merck
Aphtiria
Arbitex
Ben-Hex
Gamma-HCH dust
Hortex
Lidenal
Lindatox
Nexol-E
Thionex
beta-Lindane
Agrocide
Agrocide WP
Ameisentod
Atlas steward
BBH
Bexol
DBH
Entomoxan
Fumite lindane
Gammalin
Hexicide
Hexyclan
Indane
Isotox
Kokotine
Neo-Scabicidol
Nexen FB
Nicochloran
Sang-«
gamma»
Scabene
TAP 85
Viton
Agrocide III
Aplidal
Benzene hexachloride
Chloresene
Codechine
Detmol-Extrakt
Devoran
Drilltox-Spezial Aglukon
Esoderm
Gamene
Gamma-BHC dust
Gamma-Col
Gammasan
Gammaterr
Gammexane
HCH
HGI
Hexa
Hexachloran
Hexatox
Hexaverm
Jacutin
Kwell
Lendine
Lentox
Lindafor
Lindex
Lindosep
Lintox
Linvur
Milbol 49
Mszycol
Murfume grain store smoke
New kotol
Nexit
Nexit-Stark
Omnitox
Ovadziak
Owadziak
PMS Lindane
Pedraczak
Quellada
Scabene lotion
Spritz-Rapidin
Spruehpflanzol
Streunex
beta-BHC
beta-Hexachlorocyclohexane
Aalindan
Aficide
Aparasin
Bentox 10
Gamacid
Gammalin 20
Gexane
Hexachlorane
Hexachlorocyclohexane
Hexit
Pflanzol
Tri-6

DATABASE IDS

CAS Number 58-89-9

PROPERTIES

Hydrophobicity(logP) 3.8
Solubility 7.3 mg/L

DETAILS

Description (English)
Item Information
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
Wikipedia
RxList
Drugs.com

REFERENCES

  • Strong M, Johnstone PW: Interventions for treating scabies. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000320. Pubmed
  • Brown VJ: Life after lindane in California. Environ Health Perspect. 2008 Mar;116(3):A128. Pubmed