U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H6Cl6
Molecular Weight 290.83
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LINDANE

SMILES

Cl[C@H]1[C@H](Cl)[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@@H]1Cl

InChI

InChIKey=JLYXXMFPNIAWKQ-GNIYUCBRSA-N
InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4+,5+,6+

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/006309lotionlbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/006309shampoolbl.pdf

Lindane is an isomer of hexachlorocyclohexane that has been used both as an agricultural insecticide and as a pharmaceutical. As a shampoo, lindane is used for treamtment lice infestation. Lindane lotion is used for treatment of scabies. Due to toxicities, associated with lindane, it is used only in patients who cannot tolerate or have failed first-line treatment with safer medication. Lindane exerts its parasiticidal action by being directly absorbed into the parasites and their ova, where it interferes with GABA neurotransmitter function by interacting with the GABAA channel complex at the picrotoxin binding site.

CNS Activity

Curator's Comment: Repeaded administration of lindane may cause CNS-related toxicity.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
KWELL

Approved Use

Lindane Shampoo is indicated for the treatment of head lice (infestations of Pediculus humanus capitis), crab lice (infestations of Pthirus pubis), and their ova only in patients who cannot tolerate other approved therapies, or have failed treatment with other approved therapies. Lindane Shampoo should be used in the context of an overall lice management program that includes: Visual inspection to ensure that the patient is currently infested with live lice (empty egg casings or its can remain on hair shaft long after true infestation). Manual removal of nits using a comb designed for this purpose and/or individual removal with tweezers followed by close examination of the hair and scalp. Evaluation and treatment of sexual contacts simultaneously. Sexual contacts should be prescribed Lindane Shampoo only if they either have failed to respond to adequate doses of other approved therapies or are intolerant of other approved therapies. All recently worn clothing, underwear, pajamas, used sheets, pillowcases, and towels should be washed in very hot water or dry-cleaned. Caregivers applying this product to patients should wear gloves less permeable to Lindane such as nitrile, latex with neoprene or sheer vinyl, and thoroughly clean hands after application. Natural latex gloves should be avoided because they are more permeable to Lindane. Lindane Shampoo does not prevent infestation or reinfestation and should not be used to ward off a possible infestation.

Launch Date

1975
Curative
KWELL LOTION

Approved Use

Lindane Lotion, USP 1%, is an ectoparasiticide and ovicide. Lindane Lotion, USP 1%, is an ectoparasiticide and ovicide effective against Sarcoptes scabiei (scabies). Lindane exerts its parasiticidal action by being directly absorbed into the parasites and their ova. Lindane Lotion is indicated for the treatment of scabies (infestations of Sarcoptes scabei) only in patients who: 1. cannot tolerate other approved therapies, or 2. have failed treatment with other approved therapies.

Launch Date

1974
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
28 ng/mL
1 % single, topical
dose: 1 %
route of administration: Topical
experiment type: SINGLE
co-administered:
LINDANE blood
Homo sapiens
population: UNKNOWN
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
18 h
1 % single, topical
dose: 1 %
route of administration: Topical
experiment type: SINGLE
co-administered:
LINDANE blood
Homo sapiens
population: UNKNOWN
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 % multiple, topical
Recommended
Dose: 1 %
Route: topical
Route: multiple
Dose: 1 %
Sources:
unhealthy
Other AEs: Seizures...
1 % single, topical
Recommended
Dose: 1 %
Route: topical
Route: single
Dose: 1 %
Sources:
unhealthy
Other AEs: Seizures...
AEs

AEs

AESignificanceDosePopulation
Seizures
1 % multiple, topical
Recommended
Dose: 1 %
Route: topical
Route: multiple
Dose: 1 %
Sources:
unhealthy
Seizures rare
1 % single, topical
Recommended
Dose: 1 %
Route: topical
Route: single
Dose: 1 %
Sources:
unhealthy
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Spatial differences in persistent organochlorine pollutant concentrations between the Bering and Chukchi Seas (1993).
2001-10-17
Organochlorine compounds and aliphatic hydrocarbons in Pacific walrus blubber.
2001-10-17
Multiresidue determination of organochlorine pesticides and polychlorinated biphenyls in milk by gas chromatography with electron-capture detection after extraction by matrix solid-phase dispersion.
2001-10-17
Sperm quality and reproductive traits in male offspring of female rabbits exposed to lindane (gamma-HCH) during pregnancy and lactation.
2001-10-11
MCPA permeation through protective gloves.
2001-10
Disposition and depuration of lindane (gamma-HCH) and polychlorinated biphenyl-110 (2,3,3'4'6-pentachlorobiphenyl) in cod (Gadus morhua) and bullrout (Myoxocephalus scorpius) after single oral exposures.
2001-10
Gridded usage inventories of technical hexachlorocyclohexane and lindane for China with 1/6 degrees latitude by 1/4 degrees longitude resolution.
2001-10
Persistent organic pollutants in agricultural soils of central Germany.
2001-09-28
Retrovirus-mediated transfer and expression of beta-hexosaminidase alpha-chain cDNA in human fibroblasts from G(M2)-gangliosidosis B1 variant.
2001-09-20
Comparison of an individual congener standard and a technical mixture for the quantification of toxaphene in environmental matrices by HRGC/ECNI-HRMS.
2001-09-01
Effect of lindane on antioxidant enzymes in epididymis and epididymal sperm of adult rats.
2001-09
Disruption of gap junctional intercellular communication by lindane is associated with aberrant localization of connexin43 and zonula occludens-1 in 42GPA9 Sertoli cells.
2001-09
Stimulation of DNA synthesis and c-fos mRNA expression in primary rat hepatocytes by estrogens.
2001-09
Early childhood determinants of organochlorine concentrations in school-aged children.
2001-09
Determination of organochlorine pesticides and chlorobenzenes in strawberries by using accelerated solvent extraction combined with sorptive enrichment and gas chromatography/mass spectrometry.
2001-08-15
In vitro study of the photocytotoxicity of some hypericin analogs on different cell lines.
2001-08
Deposition of semi-volatile organochlorine compounds in the free troposphere of the eastern North Atlantic Ocean.
2001-08
Seasonal dependence of the chiral composition of alpha-HCH in coastal deposition at the North Sea.
2001-08
Anthropogenic and natural organohalogen compounds in blubber of dolphins and dugongs (Dugong dugon) from northeastern Australia.
2001-08
Organochlorine pollutants in remote mountain lake waters.
2001-07-31
[Genotoxic effect of the insecticides pentachlorophenol and lindane on human nasal mucosal epithelium].
2001-07-27
GABA receptor subunit composition relative to insecticide potency and selectivity.
2001-07-06
Levels of certain metals, organochlorine pesticides and dioxins in cord blood, maternal blood, human milk and some commonly used nutrients in the surroundings of the Aral Sea (Karakalpakstan, Republic of Uzbekistan).
2001-07
Isolation and characterization of Desulfitobacterium sp. strain Y51 capable of efficient dehalogenation of tetrachloroethene and polychloroethanes.
2001-07
Persistent organochlorine pesticides detected in blood and tissue samples of vultures from different localities in South Africa.
2001-07
Perinatal metabolism of dichlorodiphenyldichloroethylene in Nicaraguan mothers.
2001-07
Permeability of the peptidic GH secretagogues hexarelin and EP 51389, across rat jejunum.
2001-07
Monitoring of organochlorine pesticide residues in the Indian marine environment.
2001-07
Organochlorine pesticides, polychlorinated biphenyls, and butyltin compounds in blubber and livers of stranded California sea lions, elephant seals, and harbor seals from coastal California, USA.
2001-07
Atmospheric movements of lindane (gamma-hexachlorocyclohexane) from canola fields planted with treated seed.
2001-06-13
[Home transfer of 2,3,7,8-tetrachlorodibenzo-p-dioxin and beta-hexachlorocyclohexane?].
2001-06
Effect of lindane on testicular antioxidant system and steroidogenic enzymes in adult rats.
2001-06
Effects of nutrient loading and planktivory on the accumulation of organochlorine pesticides in aquatic food chains.
2001-06
Dioxin exposure and public health in Chapaevsk, Russia.
2001-05-25
Organochlorine pesticide residues in archived UK soil.
2001-05-15
Hexachlorocyclohexane (HCH) isomers and chiral signatures of alpha-HCH in the Arctic marine food web of the Northwater Polynya.
2001-05-15
A facile and effective synthesis of alpha-(1-->6)-linked mannose di-, tri-, tetra-, hexa-, octa-, and dodecasaccharides, and beta-(1-->6)-linked glucose di-, tri-, tetra-, hexa-, and octasaccharides using sugar trichloroacetimidates as the donors and unprotected or partially protected glycosides as the acceptors.
2001-05-08
Continuous surveillance of organochlorine compounds in human breast milk from 1972 to 1998 in Osaka, Japan.
2001-05
Dietary diversification/modification strategies to enhance micronutrient content and bioavailability of diets in developing countries.
2001-05
PCBs and organochlorine pesticide residues in eggs of Audouin's gull (Larus audouinii) in the north-eastern Mediterranean.
2001-05
Organochlorine pesticides and PCBs in a southern Atlantic coastal lagoon watershed, Argentina.
2001-04
[Organochlorine residues in eggs of night heron breeding in Yuantouzhu, Wuxi and their functions as bioindicator].
2001-03
Contamination by persistent organochlorines and butyltin compounds in the west coast of Sri Lanka.
2001-03
Accumulation status of persistent organochlorines in albatrosses from the North Pacific and the Southern Ocean.
2001
PCB biodegradation in aged contaminated soil: interactions between exogenous Phanerochaete chrysosporium and indigenous microorganisms.
2001
Distribution of organochlorine pesticides in sediments from Kyeonggi Bay and nearby areas, Korea.
2001
[Organochlorine insecticides of women's milk in Olsztyn in 1976, 1986, 1996].
2001
Contaminant residues in seabird eggs from the Canadian Arctic. Part I. Temporal trends 1975-1998.
2001
Polychlorinated biphenyl congeners and organochlorine insecticides in the water column and sediments of Daya Bay, China.
2001
Biomagnification of organochlorines along a Barents Sea food chain.
2001
Patents

Sample Use Guides

Administration of shampoo for treatment of lice infestation: Most patients will require only 1 ounce of Lindane Shampoo. Based on the length and density of hair, some patients may require 2 ounces of Lindane Shampoo. Apply shampoo directly to dry hair without adding water. Work thoroughly into the hair and allow to remain in place for 4 minutes only. Special attention should be given to the fine hairs along the neck. After 4 minutes, add small quantities of water to hair until a good lather forms. Immediately rinse all lather away. Avoid unnecessary contact of lather with other body surfaces. Administration of lotion for treatment of scabies: Apply a thin layer of Lindane Lotion over all skin from the neck down. One ounce is sufficient for an average adult. Do not prescribe more than 2 ounces for larger adults. Apply only once. Wash off in 8 to 12 hours.
Route of Administration: Topical
In Vitro Use Guide
[35S]TBPS (t-butylbicyclophosphorothionate) binding was determined in a final volume of 1 ml consisting of 0.3-0.5 ml of tissue suspension (0.3--0.7 mg of protein), 0.1 ml of [35S]TBPS to give a final assay concentration of 2 nM, 0.1 ml of 2 M NaCI, and drug solutions or buffer to 1 ml. Incubations at 25°C were initiated by addition of tissue and lasted 90 min (nonwashed (NW) membranes) or 240 min (washed (W) and extensively washed (EW) membrane preparations). NW membranes were assayed in absence (NW) or presence (NW + B) of 10 uM bicuculline. Bicuculline, a GABA competitive antagonist, is used to block the inhibition of [35S]TBPS binding induced by endogenous GABA. Incubations were terminated by rapid filtration through glass-fiber filter strips, which were rinsed with three 4-ml portions of ice-cold Tris-citrate buffer using a Brandel M24 filtering manifold. Filter-bound radioactivity was quantitated by conventional liquid scintillation techniques. Lindane (0.01-100uM) and bicuculline were added in 10 uL dimethylsulfoxide. IC50 values for lindane inhibition of [35S]TBPS binding obtained for the seven brain areas ranged from 150 to 1675 nM, being smaller as the membrane preparation was more washed.
Name Type Language
Gamma-HCH [ISO]
ISO  
Preferred Name English
LINDANE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
Lindane [WHO-DD]
Common Name English
LINDANE [USAN]
Common Name English
BENZENE HEXACHLORIDE GAMMA
Common Name English
LINDANE [MI]
Common Name English
LINDANUM [WHO-IP LATIN]
Common Name English
NSC-755895
Code English
KWELL
Brand Name English
GAMMAHEXACHLORCYCLOHEXANE [WHO-IP]
Common Name English
LINDANE [WHO-IP]
Common Name English
LINDANE [USP MONOGRAPH]
Common Name English
?-1,2,3,4,5,6-Hexachlorocyclohexane
Common Name English
SCABENE
Brand Name English
LINDANE [ORANGE BOOK]
Common Name English
1.ALPHA.,2.ALPHA.,3.BETA.,4.ALPHA.,5.ALPHA.,6.BETA.-HEXACHLOROCYCLOHEXANE
Common Name English
?-HCH
Common Name English
LINDANE [HSDB]
Common Name English
LINDANE [IARC]
Common Name English
CYCLOHEXANE, 1,2,3,4,5,6-HEXACHLORO-, (1.ALPHA.,2.ALPHA.,3.BETA.,4.ALPHA.,5.ALPHA.,6.BETA.)-
Common Name English
(1.ALPHA.,2.ALPHA.,3.BETA.,4.ALPHA.,5.ALPHA.,6.BETA.)-1,2,3,4,5,6-HEXACHLOROCYCLOHEXANE
Common Name English
GAMENE
Brand Name English
lindane [INN]
Common Name English
GAMMA BENZENE HEXACHLORIDE [WHO-IP]
Common Name English
LINDANE [USP-RS]
Common Name English
(1R,2R,3S,4R,5R,6S)-1,2,3,4,5,6-HEXACHLOROCYCLOHEXANE
Common Name English
LINDANE [USP IMPURITY]
Common Name English
LINDANE [MART.]
Common Name English
BENZENE HEXACHLORIDE, GAMMA
Common Name English
Classification Tree Code System Code
WHO-VATC QP53AB52
Created by admin on Mon Mar 31 17:53:04 GMT 2025 , Edited by admin on Mon Mar 31 17:53:04 GMT 2025
NCI_THESAURUS C45410
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EPA PESTICIDE CODE 9001
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WHO-VATC QP53AB02
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IARC Lindane (see also Hexachlorocyclohexanes)
WHO-ATC P03AB02
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WHO-VATC QS02QA51
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WHO-VATC QS02QA01
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Code System Code Type Description
FDA UNII
59NEE7PCAB
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PRIMARY
RXCUI
1388
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PRIMARY RxNorm
CHEBI
24536
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PRIMARY
INN
4901
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PRIMARY
HSDB
646
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PRIMARY
CHEBI
32888
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PRIMARY
RS_ITEM_NUM
1367504
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PRIMARY
CAS
58-89-9
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PRIMARY
ChEMBL
CHEMBL15891
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PRIMARY
DRUG BANK
DB00431
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
LINDANE
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PRIMARY Description: A white, crystalline powder; odour, slight. Solubility: Practically insoluble in water; soluble in dehydrated ethanol R and ether R. Category: Pediculicide; scabicide. Storage: Lindane should be kept in a well-closed container. Definition: Lindane contains not less than 99.0% and not more than 100.5% of C6H6Cl6, calculated with reference to the anhydrous substance.
ECHA (EC/EINECS)
200-401-2
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PRIMARY
NCI_THESAURUS
C44397
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PRIMARY
EVMPD
SUB08518MIG
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PRIMARY
NSC
755895
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PRIMARY
LACTMED
Lindane
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PRIMARY
MERCK INDEX
m6826
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PRIMARY Merck Index
EPA CompTox
DTXSID2020686
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PRIMARY
DRUG CENTRAL
1583
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PRIMARY
MESH
D001556
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PRIMARY
SMS_ID
100000082316
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PRIMARY
DAILYMED
59NEE7PCAB
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PRIMARY
WIKIPEDIA
LINDANE
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PRIMARY