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
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+
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/1701516Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1701516
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
Sources: https://www.drugs.com/pro/lindane.html
Curator's Comment: Repeaded administration of lindane may cause CNS-related toxicity.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364024 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1701516 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | KWELL Approved UseLindane 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 Date1975 |
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Curative | KWELL LOTION Approved UseLindane 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 Date1974 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse events |
---|---|---|
1 % multiple, topical Recommended Dose: 1 % Route: topical Route: multiple Dose: 1 % Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Seizures... Other AEs: Seizures Sources: |
1 % single, topical Recommended Dose: 1 % Route: topical Route: single Dose: 1 % Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Seizures... Other AEs: Seizures (rare) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Seizures | 1 % multiple, topical Recommended Dose: 1 % Route: topical Route: multiple Dose: 1 % Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Seizures | rare | 1 % single, topical Recommended Dose: 1 % Route: topical Route: single Dose: 1 % Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/20035023/ |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20035023/ |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20035023/ |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20035023/ |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20035023/ |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20035023/ |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20035023/ |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20035023/ |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20035023/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20035023/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20035023/ |
yes |
PubMed
Title | Date | PubMed |
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Effect of lindane and phenobarbital on cyclooxygenase-2 expression and prostanoid synthesis by Kupffer cells. | 1999 Aug |
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PCB biodegradation in aged contaminated soil: interactions between exogenous Phanerochaete chrysosporium and indigenous microorganisms. | 2001 |
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Distribution of organochlorine pesticides in sediments from Kyeonggi Bay and nearby areas, Korea. | 2001 |
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Investigation of hexabromocyclododecane thermal degradation pathways by gas chromatography/mass spectrometry. | 2001 |
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Organochlorine pesticides and PCBs in a southern Atlantic coastal lagoon watershed, Argentina. | 2001 Apr |
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Understanding enantioselective processes: a laboratory rat model for alpha-hexachlorocyclohexane accumulation. | 2001 Apr 15 |
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A HEXA polymorphism (V436I) common to African-Americans and Ethiopian Jews. | 2001 Feb |
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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 |
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Aural abscesses in wild-caught box turtles (Terapene carolina): possible role of organochlorine-induced hypovitaminosis A. | 2001 Jan |
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Effects of gamma-HCH and delta-HCH on human recombinant GABA(A) receptors: dependence on GABA(A) receptor subunit combination. | 2001 Jan |
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Bioaccumulation of persistent organic pollutants in lichen-caribou-wolf food chains of Canada's Central and Western Arctic. | 2001 Jan 15 |
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Subchronic oral toxicity of a combination of insecticide (HCH) and herbicide (ISP) in male rats. | 2001 Jan-Feb |
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Persistent organochlorine pesticides detected in blood and tissue samples of vultures from different localities in South Africa. | 2001 Jul |
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Permeability of the peptidic GH secretagogues hexarelin and EP 51389, across rat jejunum. | 2001 Jul |
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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 |
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Effect of lindane on testicular antioxidant system and steroidogenic enzymes in adult rats. | 2001 Jun |
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[Organochlorine residues in eggs of night heron breeding in Yuantouzhu, Wuxi and their functions as bioindicator]. | 2001 Mar |
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Contamination by persistent organochlorines and butyltin compounds in the west coast of Sri Lanka. | 2001 Mar |
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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 |
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Dietary diversification/modification strategies to enhance micronutrient content and bioavailability of diets in developing countries. | 2001 May |
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Organochlorine pesticide residues in archived UK soil. | 2001 May 15 |
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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 |
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Sperm quality and reproductive traits in male offspring of female rabbits exposed to lindane (gamma-HCH) during pregnancy and lactation. | 2001 May-Jun |
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Atmospheric movements of lindane (gamma-hexachlorocyclohexane) from canola fields planted with treated seed. | 2001 May-Jun |
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Dioxin exposure and public health in Chapaevsk, Russia. | 2001 May-Jun |
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Levels of hexachlorobenzene and other organochlorine compounds in cord blood: exposure across placenta. | 2001 May-Jun |
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Halogenated environmental contaminants in fish from Estonian coastal areas. | 2001 May-Jun |
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MCPA permeation through protective gloves. | 2001 Oct |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1701516
[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
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Record UNII |
59NEE7PCAB
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Record Status |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QP53AB52
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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) | ||
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WHO-ATC |
P03AB02
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WHO-VATC |
QS02QA51
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WHO-VATC |
QS02QA01
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DB00431
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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. | ||
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200-401-2
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C44397
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755895
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Lindane
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m6826
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PRIMARY | Merck Index | ||
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DTXSID2020686
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D001556
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LINDANE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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