Human Metabolome Database Version 3.5

Showing metabocard for Lindane (HMDB14575)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:49 -0600
Update Date 2013-02-08 11:42:51 -0700
HMDB ID HMDB14575
Secondary Accession Numbers None
Metabolite Identification
Common Name Lindane
Description An organochlorine insecticide that has been used as a pediculicide and a scabicide. Lindane has been banned in California, United Kingdom, Australia, and many western countries due to concerns about neurotoxicity and adverse effects on the environment. In Canada, Lindane is not recommmended as a first-line therapy due to reports of resistance, neurotoxicity, and bone marrow suppression, but has been approved by the FDA as a second-line therapy for topical treatment of pediculosis capitis (head lice), pediculosis pubis (pubic lice), or scabies in patients greater than two years of age who cannot tolerate or have failed first-line treatment.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Benzene hexachloride
  2. gamma-Benzene hexachloride
  3. gamma-BHC
  4. gamma-HCH
  5. gamma-Hexachlorocyclohexane
  6. gamma-Hexachlorzyklohexan
  7. gamma-Lindane
  8. Lindan
Chemical Formula C6H6Cl6
Average Molecular Weight 290.83
Monoisotopic Molecular Weight 287.860066434
IUPAC Name (1R,2S,3r,4R,5S,6r)-1,2,3,4,5,6-hexachlorocyclohexane
Traditional IUPAC Name lindane
CAS Registry Number 58-89-9
SMILES Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl
InChI Identifier InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4+,5+,6+
InChI Key JLYXXMFPNIAWKQ-GNIYUCBRSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Homomonocyclic Compounds
Class Cycloalkanes
Sub Class N/A
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Alkyl Chlorides
  • Organochlorine insecticides(KEGG)
  • cyclodiene organochlorine insecticide(ChEBI)
  • hexachlorocyclohexane(ChEBI)
Substituents
  • N/A
Direct Parent Cycloalkanes
Ontology
Status Detected and Quantified
Origin
  • Drug
Biofunction
  • Antiscabies Agent
  • Insecticides
  • Scabicide
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point 112.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 5.47e-03 g/L Not Available
LogP 3.8 Not Available
Predicted Properties
Property Value Source
LogP 3.94 ALOGPS
LogP 4.35 ChemAxon
LogS -4.73 ALOGPS
Hydrogen Acceptor Count 0 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 0 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 54.08 ChemAxon
Polarizability 23.08 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.00105(0.00037-0.00179) uM Adult (>18 years old) Both Normal
  • Report on Hu...
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00431
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00431
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00431 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 10481896 Link_out
KEGG Compound ID C07075 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Lindane Link_out
NuGOwiki Link HMDB14575 Link_out
Metagene Link HMDB14575 Link_out
METLIN ID Not Available
PubChem Compound Not Available
PDB ID Not Available
ChEBI ID 32888 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Strong M, Johnstone P: Interventions for treating scabies. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000320. Pubmed: 17636630 Link_out
  2. Brown VJ: Life after lindane in California. Environ Health Perspect. 2008 Mar;116(3):A128. Pubmed: 18335087 Link_out
  3. REES BE, RALEY TG, DAVIS ED: Prehatiching treatment of irrigated lands with DDT, dichlorodiphenyl dichloroethane, and gammabenzene hexachloride for control of flood water mosquitoes. J Econ Entomol. 1949 Aug;42(4):586-90. Pubmed: 18138195 Link_out
  4. Lundstedt-Enkel K, Tysklind M, Trygg J, Schuller P, Asplund L, Eriksson U, Haggberg L, Odsjo T, Hjelmberg M, Olsson M, Orberg J: A statistical resampling method to calculate biomagnification factors exemplified with organochlorine data from herring (Clupea harengus) muscle and guillemot (Uria aalge) egg from the Baltic sea. Environ Sci Technol. 2005 Nov 1;39(21):8395-402. Pubmed: 16294879 Link_out
  5. Alm H, Torner H, Tiemann U, Kanitz W: Influence of organochlorine pesticides on maturation and postfertilization development of bovine oocytes in vitro. Reprod Toxicol. 1998 Sep-Oct;12(5):559-63. Pubmed: 9763248 Link_out
  6. Tiemann U, Pohland R, Kuchenmeister U, Viergutz T: Influence of organochlorine pesticides on transmembrane potential, oxidative activity, and ATP-induced calcium release in cultured bovine oviductal cells. Reprod Toxicol. 1998 Sep-Oct;12(5):551-7. Pubmed: 9763247 Link_out
  7. Belpomme D, Irigaray P, Ossondo M, Vacque D, Martin M: Prostate cancer as an environmental disease: an ecological study in the French Caribbean islands, Martinique and Guadeloupe. Int J Oncol. 2009 Apr;34(4):1037-44. Pubmed: 19287960 Link_out
  8. Tiemann U, Pohland R: Inhibitory effects of organochlorine pesticides on intercellular transfer of Lucifer Yellow in cultured bovine oviductal cells. Reprod Toxicol. 1999 Mar-Apr;13(2):123-30. Pubmed: 10213519 Link_out
  9. Tiemann U, Pohland R, Schneider F: Influence of organochlorine pesticides on physiological potency of cultured granulosa cells from bovine preovulatory follicles. Theriogenology. 1996 Jul 15;46(2):253-65. Pubmed: 16727895 Link_out
  10. Katsumata K, Katsumata K: Norwegian scabies in an elderly patient who died after treatment with gammaBHC. Intern Med. 2003 Apr;42(4):367-9. Pubmed: 12729329 Link_out
  11. Storelli MM, Stuffler RG, Marcotrigianoi GO: Polycyclic aromatic hydrocarbons, polychlorinated biphenyls, chlorinated pesticides (DDTs), hexachlorocyclohexane, and hexachlorobenzene residues in smoked seafood. J Food Prot. 2003 Jun;66(6):1095-9. Pubmed: 12801016 Link_out
  12. Corrigan FM, Wienburg CL, Shore RF, Daniel SE, Mann D: Organochlorine insecticides in substantia nigra in Parkinson's disease. J Toxicol Environ Health A. 2000 Feb 25;59(4):229-34. Pubmed: 10706031 Link_out
  13. Luczak J, Sitkiewicz D: [Effect of Tritox (DDT, DMDT, gammaHCH) on physico-chemical properties and indices of microbial pollution of water]. Rocz Panstw Zakl Hig. 1969;20(4):495-501. Pubmed: 4908314 Link_out
  14. Panvelkar V, Chari KV: Gammabenzene hexachloride-induced convulsions in an HIV positive individual. Indian J Dermatol Venereol Leprol. 1996 Sep-Oct;62(5):306-7. Pubmed: 20948097 Link_out

Enzymes
Name: Gamma-aminobutyric acid receptor subunit beta-1
Reactions: Not Available
Gene Name: GABRB1
Uniprot ID: P18505 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycine receptor subunit alpha-1
Reactions: Not Available
Gene Name: GLRA1
Uniprot ID: P23415 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycine receptor subunit alpha-2
Reactions: Not Available
Gene Name: GLRA2
Uniprot ID: P23416 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycine receptor subunit alpha-3
Reactions: Not Available
Gene Name: GLRA3
Uniprot ID: O75311 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycine receptor subunit beta
Reactions: Not Available
Gene Name: GLRB
Uniprot ID: P48167 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA