| 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 |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
Approval Year
Doses
AEs
Sourcing
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
[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.
