LINDANE

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Search structure


Trade Names	GAMENE KWELL LINDANE SCABENE
Synonyms	Benzene hexachloride gamma Benzene hexachloride, gamma Esoderm Gamene Gamma Benzene HCl Gamma benzene hexachloride Gammahexachlorcyclohexane Gammallin Gammaxene Gexane Hexachlorane Hexicide Kwell Lindane Lindanum Lorexane Lorexane no 3 NSC-755895 Quellada Scabene gamma-Hexachlorocyclohexane
Status
Molecule Category	UNKNOWN
ATC	P03AB02
UNII	59NEE7PCAB
EPA CompTox	DTXSID2020686


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	JLYXXMFPNIAWKQ-GNIYUCBRSA-N
Smiles	Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl
InChI	InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4+,5+,6+

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C6H6Cl6
Molecular Weight	290.83
AlogP	3.64
Hydrogen Bond Acceptor	0.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	0.0
Polar Surface Area	0.0
Molecular species	None
Aromatic Rings	0.0
Heavy Atoms	12.0

Bioactivity

Mechanism of Action	Action	Reference
GABA-A receptor negative allosteric modulator	NEGATIVE ALLOSTERIC MODULATOR	PubMed Wikipedia

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Ligand-gated ion channel GABA-A receptor	-	1	-	-	-
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4	-	40738	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	80

Assay Description	Organism	Bioactivity	Reference
Antifeedant activity against L6 larvae of Spodoptera littoralis in Solanum tuberosum by choice test	Spodoptera littoralis	16.8 nmol/cm2
Antifeedant activity against adult of Leptinotarsa decemlineata in Capsicum annuum by choice test	Leptinotarsa decemlineata	0.1 nmol/cm2
Inhibition of recombinant Homo sapiens (human) GABA receptor	Homo sapiens	306.0 nM
Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA rho1 receptor	Homo sapiens	91.0 nM
Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha1beta1 receptor	Homo sapiens	112.0 nM
Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha1beta1gamma2 receptor	Homo sapiens	67.0 nM
Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha1beta3gamma2 receptor	Homo sapiens	21.0 nM
Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha1beta3 receptor	Homo sapiens	12.0 nM
Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha6beta3gamma2 receptor	Homo sapiens	4.9 nM
Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA alpha6beta3 receptor	Homo sapiens	1.3 nM
Displacement of [3H]EBOB from recombinant Homo sapiens (human) GABA beta3 receptor	Homo sapiens	0.9 nM
Inhibition of Musca domestica (house fly) GABA receptor	Musca domestica	11.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	79.82 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	90.09 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	95.19 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	9.788 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.02 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.02 %

Cross References

Resources	Reference
ChEBI	32888
ChEMBL	CHEMBL15891
DrugBank	DB00431
DrugCentral	1583
FDA SRS	59NEE7PCAB
Human Metabolome Database	HMDB0014575
KEGG	C07075
SureChEMBL	SCHEMBL25895
ZINC	ZINC00001621

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).