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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

Molecular Formula C6H6Cl6
Molecular Weight 290.83
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Effect of lindane and phenobarbital on cyclooxygenase-2 expression and prostanoid synthesis by Kupffer cells.
1999 Aug
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
Investigation of hexabromocyclododecane thermal degradation pathways by gas chromatography/mass spectrometry.
2001
Organochlorine pesticides and PCBs in a southern Atlantic coastal lagoon watershed, Argentina.
2001 Apr
Understanding enantioselective processes: a laboratory rat model for alpha-hexachlorocyclohexane accumulation.
2001 Apr 15
A HEXA polymorphism (V436I) common to African-Americans and Ethiopian Jews.
2001 Feb
Presence of a no-observed effect level for enhancing effects of development of the alpha-isomer of benzene hexachloride (alpha-BHC) on diethylnitrosamine-initiated hepatic foci in rats.
2001 Feb 26
Aural abscesses in wild-caught box turtles (Terapene carolina): possible role of organochlorine-induced hypovitaminosis A.
2001 Jan
Effects of gamma-HCH and delta-HCH on human recombinant GABA(A) receptors: dependence on GABA(A) receptor subunit combination.
2001 Jan
Bioaccumulation of persistent organic pollutants in lichen-caribou-wolf food chains of Canada's Central and Western Arctic.
2001 Jan 15
Subchronic oral toxicity of a combination of insecticide (HCH) and herbicide (ISP) in male rats.
2001 Jan-Feb
Persistent organochlorine pesticides detected in blood and tissue samples of vultures from different localities in South Africa.
2001 Jul
Permeability of the peptidic GH secretagogues hexarelin and EP 51389, across rat jejunum.
2001 Jul
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 Jul
Effect of lindane on testicular antioxidant system and steroidogenic enzymes in adult rats.
2001 Jun
[Organochlorine residues in eggs of night heron breeding in Yuantouzhu, Wuxi and their functions as bioindicator].
2001 Mar
Contamination by persistent organochlorines and butyltin compounds in the west coast of Sri Lanka.
2001 Mar
Gas-phase reactions of hydrated alkaline earth metal ions, M2+ (H2O)n (M = Mg, Ca, Sr, Ba and n = 4-7), with benzene.
2001 Mar
Dietary diversification/modification strategies to enhance micronutrient content and bioavailability of diets in developing countries.
2001 May
Organochlorine pesticide residues in archived UK soil.
2001 May 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 May 8
Sperm quality and reproductive traits in male offspring of female rabbits exposed to lindane (gamma-HCH) during pregnancy and lactation.
2001 May-Jun
Atmospheric movements of lindane (gamma-hexachlorocyclohexane) from canola fields planted with treated seed.
2001 May-Jun
Dioxin exposure and public health in Chapaevsk, Russia.
2001 May-Jun
Levels of hexachlorobenzene and other organochlorine compounds in cord blood: exposure across placenta.
2001 May-Jun
Halogenated environmental contaminants in fish from Estonian coastal areas.
2001 May-Jun
MCPA permeation through protective gloves.
2001 Oct
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:53:04 GMT 2025
Edited
by admin
on Mon Mar 31 17:53:04 GMT 2025
Record UNII
59NEE7PCAB
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Mon Mar 31 17:53:04 GMT 2025 , Edited by admin on Mon Mar 31 17:53:04 GMT 2025
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
Created by admin on Mon Mar 31 17:53:04 GMT 2025 , Edited by admin on Mon Mar 31 17:53:04 GMT 2025
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
Created by admin on Mon Mar 31 17:53:04 GMT 2025 , Edited by admin on Mon Mar 31 17:53:04 GMT 2025
PRIMARY
WIKIPEDIA
LINDANE
Created by admin on Mon Mar 31 17:53:04 GMT 2025 , Edited by admin on Mon Mar 31 17:53:04 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY