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

Details

Stereochemistry ACHIRAL
Molecular Formula C6H6Cl6
Molecular Weight 290.8297
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LINDANE

SMILES

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

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

1.59580799E11
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

1.56556804E11
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: scabies
Sources: Page: p.1
Other AEs: Seizures...
1 % single, topical
Recommended
Dose: 1 %
Route: topical
Route: single
Dose: 1 %
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: scabies
Sources: Page: p.1
Other AEs: Seizures...
AEs

AEs

AESignificanceDosePopulation
Seizures
1 % multiple, topical
Recommended
Dose: 1 %
Route: topical
Route: multiple
Dose: 1 %
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: scabies
Sources: Page: p.1
Seizures rare
1 % single, topical
Recommended
Dose: 1 %
Route: topical
Route: single
Dose: 1 %
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: scabies
Sources: Page: p.1
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Polychlorinated biphenyl congeners and organochlorine insecticides in the water column and sediments of Daya Bay, China.
2001
Investigation of hexabromocyclododecane thermal degradation pathways by gas chromatography/mass spectrometry.
2001
Trends in organochlorine residue concentrations and burdens in grey seals (Halichoerus grypus) from Sable Is., NS, Canada, between 1974 and 1994.
2001
Assessment of organochlorine pesticide residue levels in dairy milk and buffalo milk from Jaipur City, Rajasthan, India.
2001 Apr
Mixtures of four organochlorines enhance human breast cancer cell proliferation.
2001 Apr
Organochlorine pesticides in carcinoma of the gallbladder: a case-control study.
2001 Apr
Effects of the two-component system comprising GacA and GacS of Erwinia carotovora subsp. carotovora on the production of global regulatory rsmB RNA, extracellular enzymes, and harpinEcc.
2001 Apr
Induction of brain-derived neurotrophic factor by convulsant drugs in the rat brain: involvement of region-specific voltage-dependent calcium channels.
2001 Apr
An historical record of toxaphene and its congeners in a remote lake in western Europe.
2001 Apr 1
In vitro study of the photocytotoxicity of some hypericin analogs on different cell lines.
2001 Aug
Seasonal dependence of the chiral composition of alpha-HCH in coastal deposition at the North Sea.
2001 Aug
Anthropogenic and natural organohalogen compounds in blubber of dolphins and dugongs (Dugong dugon) from northeastern Australia.
2001 Aug
Hexosaminidase-altered aberrant crypts, carrying decreased hexosaminidase alpha and beta subunit mRNAs, in colon of 1,2-dimethylhydrazine-treated rats.
2001 Feb
Automated sampler for the measurement of non-methane organic compounds.
2001 Feb 1
Characterization of hyaluronidase isolated from Agkistrodon contortrix contortrix (Southern Copperhead) venom.
2001 Feb 15
Combined strong anion-exchange HPLC and PAGE approach for the purification of heparan sulphate oligosaccharides.
2001 Feb 15
The mechanism for lindane-induced inhibition of steroidogenesis in cultured rat Leydig cells.
2001 Feb 21
The effect of polychlorinated biphenyls on the high affinity uptake of the neurotransmitters, dopamine, serotonin, glutamate and GABA, into rat brain synaptosomes.
2001 Feb 21
Relationships between plasma levels of organochlorines, retinol and thyroid hormones from polar bears (Ursus maritimus) at Svalbard.
2001 Feb 23
Hepatoprotective and antioxidant property of Andrographis paniculata (Nees) in BHC induced liver damage in mice.
2001 Jan
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
Spatial differences in persistent organochlorine pollutant concentrations between the Bering and Chukchi Seas (1993).
2001 Jan-Jun
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 Jul
Isolation and characterization of Desulfitobacterium sp. strain Y51 capable of efficient dehalogenation of tetrachloroethene and polychloroethanes.
2001 Jul
Permeability of the peptidic GH secretagogues hexarelin and EP 51389, across rat jejunum.
2001 Jul
[Genotoxic effect of the insecticides pentachlorophenol and lindane on human nasal mucosal epithelium].
2001 Jul 27
Effect of lindane on testicular antioxidant system and steroidogenic enzymes in adult rats.
2001 Jun
Effects of nutrient loading and planktivory on the accumulation of organochlorine pesticides in aquatic food chains.
2001 Jun
Degradation of hexachlorocyclohexane isomers by two strains of alcaligenes faecalis isolated from a contaminated site.
2001 Jun
Stimulation of DNA synthesis by tumor promoters in primary rat hepatocytes is not mediated by arachidonic acid metabolites.
2001 Jun
Sudden infant death syndrome: neonatal hypodynamia (reduced exercise level).
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
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
PCBs and organochlorine pesticide residues in eggs of Audouin's gull (Larus audouinii) in the north-eastern Mediterranean.
2001 May
Whole blood concentrations of organochlorines as a dose metric for studies of the glaucous gull (Larus hyperboreus).
2001 May
A novel HEXA mutation [1393G>A (D465N)] in a Mexican Tay-Sachs disease patient.
2001 May
Role of human GABA(A) receptor beta3 subunit in insecticide toxicity.
2001 May 1
Hexachlorocyclohexane (HCH) isomers and chiral signatures of alpha-HCH in the Arctic marine food web of the Northwater Polynya.
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
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
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 Oct
Disruption of gap junctional intercellular communication by lindane is associated with aberrant localization of connexin43 and zonula occludens-1 in 42GPA9 Sertoli cells.
2001 Sep
Early childhood determinants of organochlorine concentrations in school-aged children.
2001 Sep
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
LINDANE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official 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
LINDANE [USP]
Common Name English
.GAMMA.-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
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
LINDANE [WHO-DD]
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 [MART.]
Common Name English
BENZENE HEXACHLORIDE, GAMMA
Common Name English
Classification Tree Code System Code
WHO-VATC QP53AB52
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
NCI_THESAURUS C45410
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
EPA PESTICIDE CODE 9001
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
WHO-VATC QP53AB02
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
IARC Lindane (see also Hexachlorocyclohexanes)
WHO-ATC P03AB02
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
WHO-VATC QS02QA51
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
WHO-VATC QS02QA01
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
Code System Code Type Description
FDA UNII
59NEE7PCAB
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
RXCUI
1388
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY RxNorm
INN
4901
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
HSDB
646
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
CAS
58-89-9
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
ChEMBL
CHEMBL15891
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
DRUG BANK
DB00431
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
LINDANE
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
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 Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
NCI_THESAURUS
C44397
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
EVMPD
SUB08518MIG
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
USP_CATALOG
1367504
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY USP-RS
LACTMED
Lindane
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
MERCK INDEX
M6826
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY Merck Index
EPA CompTox
58-89-9
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
DRUG CENTRAL
1583
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
MESH
D001556
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY
WIKIPEDIA
LINDANE
Created by admin on Fri Jun 25 21:02:28 UTC 2021 , Edited by admin on Fri Jun 25 21:02:28 UTC 2021
PRIMARY