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Compound Detail

CHEMBL15891

LINDANE
💊 Approved Drug
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💊 Approved Drug
Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl

Basic Information

ChEMBL ID CHEMBL15891
Name LINDANE
Phase Approved
Structure Type MOL
InChI Key JLYXXMFPNIAWKQ-GNIYUCBRSA-N
Therapeutic ✓ Yes

Known Names

Benzene hexachloride gamma Benzene hexachloride, gamma Esoderm Gamene Gamma benzene hexachloride Gamma benzene hydrochloride Gamma-hexachlorocyclohexane Gammahexachlorcyclohexane Gammallin Gammaxene Gexane Hexachlorane +10 more
11
Targets
11
Activities
1
Assay Types
0
PK Parameters
20
Publications
22
Known Names
2
Indications
2
Mechanisms

Molecular Properties

290.8
MW (Da)
3.64
ALogP
0
HBA
0
HBD
0.0
PSA (Ų)
0.60
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1974
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Black Box Warning Withdrawn Natural Product
USAN Year 1980

Extended Properties

Molecular Formula C6H6Cl6
MW 290.83
Aromatic Rings 0
Heavy Atoms 12
NP-Likeness 0.18

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
GABA-A receptor negative allosteric modulator NEGATIVE ALLOSTERIC MODULATOR GABA-A receptor
GABA-A receptor negative allosteric modulator NEGATIVE ALLOSTERIC MODULATOR GABA-A receptor

Indications

Ectoparasitic Infestations Lice Infestations

ATC Classification

P03AB02
lindane
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ECTOPARASITICIDES, INCL. SCABICIDES, INSECTICIDES AND REPELLENTS

Drug Warnings

Withdrawn
General Warning
potential to cause toxic effects
Country: Chile; Brazil   Year: 2001
Withdrawn
General Warning
Toxic effects on environment and human health
Country: Chile; Brazil   Year: 2001
Black Box Warning
neurotoxicity
Country: United States

Activity Summary

IC50 11 meas. best 9.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Gamma-aminobutyric acid receptor subunit beta-3
CHEMBL1847
IC50 9.05 9.05 0.9 1
Gamma-aminobutyric acid receptor subunit alpha-6/beta-3
CHEMBL3885578
IC50 8.89 8.89 1.3 1
GABA-A receptor; alpha-6/beta-3/gamma-2
CHEMBL2095190
IC50 8.31 8.31 4.9 1
GABA receptor subunit
CHEMBL3986
IC50 7.96 7.96 11.0 1
GABA-A receptor alpha-1/beta-3
CHEMBL4106151
IC50 7.92 7.92 12.0 1
GABA-A receptor; alpha-1/beta-3/gamma-2
CHEMBL2094121
IC50 7.68 7.68 21.0 1
GABA A receptor alpha-1/beta-1/gamma-2
CHEMBL2111392
IC50 7.17 7.17 67.0 1
Gamma-aminobutyric acid receptor subunit rho-1
CHEMBL3561
IC50 7.04 7.04 91.0 1
Gamma-aminobutyric acid receptor subunit alpha-1/ beta-1
CHEMBL3885570
IC50 6.95 6.95 112.0 1
Unchecked
CHEMBL612545
IC50 6.51 6.51 306.0 1
Androgen receptor
CHEMBL3072
IC50 4.39 4.39 40738.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Gamma-aminobutyric acid receptor subunit beta-3 IC50 = 0.9 nM 9.05 Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA beta3 recept... -
Gamma-aminobutyric acid receptor subunit alpha-6/beta-3 IC50 = 1.3 nM 8.89 Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha6beta3 ... -
GABA-A receptor; alpha-6/beta-3/gamma-2 IC50 = 4.9 nM 8.31 Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha6beta3g... -
GABA receptor subunit IC50 = 11.0 nM 7.96 Inhibition of Musca domestica (house fly) GABA receptor -
GABA-A receptor alpha-1/beta-3 IC50 = 12.0 nM 7.92 Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha1beta3 ... -
GABA-A receptor; alpha-1/beta-3/gamma-2 IC50 = 21.0 nM 7.68 Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha1beta3g... -
GABA A receptor alpha-1/beta-1/gamma-2 IC50 = 67.0 nM 7.17 Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha1beta1g... -
Gamma-aminobutyric acid receptor subunit rho-1 IC50 = 91.0 nM 7.04 Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA rho1 recepto... -
Gamma-aminobutyric acid receptor subunit alpha-1/ beta-1 IC50 = 112.0 nM 6.95 Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha1beta1 ... -
Unchecked IC50 = 306.0 nM 6.51 Inhibition of recombinant Homo sapiens (human) GABA receptor -
Androgen receptor IC50 = 40738.03 nM 4.39 Inhibitory concentration against recombinant rat androgen receptor expressed in ... 16134935

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19642076 10.1002/ps.1818 Ceutorhynchus obstrictus 4
12428955 10.1021/jf025857p Spodoptera littoralis 4
12590481 10.1021/jf025892w Leaf 3
12428955 10.1021/jf025857p Leptinotarsa decemlineata 3
12590481 10.1021/jf025892w Stem 3
12590481 10.1021/jf025892w Root 3
12590481 10.1021/jf025892w Unchecked 3
- 10.1584/jpestics.R07-07 Unchecked 2
20553011 10.1021/tx1000865 Hepatotoxicity 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
12590481 10.1021/jf025892w Fruit 2
12428955 10.1021/jf025857p ADMET 1
12428955 10.1021/jf025857p Rhopalosiphum padi 1
12428955 10.1021/jf025857p CHO 1
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] A 1
16134935 10.1021/jm050403f Androgen receptor 1

Data from ChEMBL 36 via Core Engine