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608-73-1 molecular structure
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1,2,3,4,5,6-hexachlorocyclohexane

ChemBase ID: 314
Molecular Formular: C6H6Cl6
Molecular Mass: 290.82984
Monoisotopic Mass: 287.86006627
SMILES and InChIs

SMILES:
ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl
Canonical SMILES:
ClC1C(Cl)C(Cl)C(C(C1Cl)Cl)Cl
InChI:
InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H
InChIKey:
JLYXXMFPNIAWKQ-UHFFFAOYSA-N

Cite this record

CBID:314 http://www.chembase.cn/molecule-314.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1,2,3,4,5,6-hexachlorocyclohexane
IUPAC Traditional name
hexachlorocyclohexane
lindane
Brand Name
Aalindan
Aficide
Agrocide
Agrocide III
Agrocide WP
Ameisenmittel merck
Ameisentod
Aparasin
Aphtiria
Aplidal
Arbitex
Atlas steward
BBH
Ben-Hex
Bentox 10
Benzene hexachloride
Bexol
Celanex
Chloresene
Codechine
DBH
Detmol-Extrakt
Devoran
Dol Granule
Drilltox-Spezial Aglukon
Entomoxan
Esoderm
Fumite lindane
Gamacid
Gamene
Gamma-BHC dust
Gamma-Col
Gamma-HCH dust
Gammalin
Gammalin 20
Gammasan
Gammaterr
Gammexane
Gexane
HCCH
HCH
HGI
Heclotox
Hexa
Hexachloran
Hexachlorane
Hexachlorocyclohexane
Hexatox
Hexaverm
Hexicide
Hexit
Hexyclan
Hortex
Indane
Isotox
Jacutin
Kokotine
Kwell
Lendine
Lentox
Lidenal
Lindafor
Lindatox
Lindex
Lindosep
Lintox
Linvur
Lorexane
Milbol 49
Mszycol
Murfume grain store smoke
Neo-Scabicidol
New kotol
Nexen FB
Nexit
Nexit-Stark
Nexol-E
Nicochloran
Omnitox
Ovadziak
Owadziak
PMS Lindane
Pedraczak
Pflanzol
Quellada
Sang-«
gamma»
Scabene
Scabene lotion
Spritz-Rapidin
Spruehpflanzol
Streunex
TAP 85
Thionex
Tri-6
Viton
beta-BHC
beta-Hexachlorocyclohexane
beta-Lindane
Synonyms
Lindane
HCH
HCH
BHC (mixture of hexachlorocyclohexanes)
BENZENE HEXACHLORIDE
六六六
六六六
六六六(六氯环己烷的混合物)
CAS Number
608-73-1
58-89-9
EC Number
206-270-8
200-401-2
MDL Number
MFCD00003825
PubChem SID
24862770
160963777
PubChem CID
727

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 4.3455415  LogD (pH = 7.4) 4.3455415 
Log P 4.3455415  Molar Refractivity 54.081 cm3
Polarizability 22.464584 Å3 Polar Surface Area 0.0 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 3.94  LOG S -4.73 
Solubility (Water) 5.47e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
7.3 mg/L expand Show data source
Density
1.85 g/ml expand Show data source
Hydrophobicity(logP)
3.8 expand Show data source
RTECS
GV3500000 expand Show data source
GV4900000 expand Show data source
European Hazard Symbols
Nature polluting Nature polluting (N) expand Show data source
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
3 expand Show data source
Risk Statements
20/21-25-40-48/22-50/53-64 expand Show data source
21-25-40-50/53 expand Show data source
R:23/24/25-36/38-50/53 expand Show data source
Safety Statements
22-36/37-45-60-61 expand Show data source
36/37-45-61 expand Show data source
S:13-45-60-61 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H312-H351-H362-H373-H410 expand Show data source
H301-H312-H351-H410 expand Show data source
GHS Precautionary statements
P263-P273-P280-P301 + P310-P501 expand Show data source
P273-P280-P301 + P310-P501 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 2 expand Show data source
UN 2811 6.1/PG 3 expand Show data source
Grade
analytical standard expand Show data source
PESTANAL®, analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source
Packaging
ampule of 500 mg expand Show data source
Empirical Formula (Hill Notation)
C6H6Cl6 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05204985 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB00431 external link
Item Information
Drug Groups approved
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.
Indication For the treatment of patients infested with Sarcoptes scabiei or pediculosis capitis who have either failed to respond to adequate doses, or are intolerant of other approved therapies.
Pharmacology Scabies is a common, highly pruritic infestation of the skin caused by Sarcoptes scabiei (lice). It is a very contagious condition with specific lesions, such as burrows, and nonspecific lesions, such as papules, vesicles and excoriations. The typical areas of the body it affects are finger webs, scalp (hair), wrists, axillary folds, abdomen, buttocks, inframammary folds and genitalia (males). It is characterized by intense night-time itching. Scabies is spread through close personal contact (relatives, sexual partners, schoolchildren, chronically ill patients and crowded communities). Scabies infestations and the corresponding symptoms can be eliminated by killing the scabies with topical insecticides or scabicides. Lindane is a scabicide that is essentially an organochloride insecticide.
Toxicity Lindane is a moderately toxic compound via oral exposure, with a reported oral LD50 of 88 to 190 mg/kg in rats. Gamma-HCH (which constitutes 99% of lindane) is generally considered to be the most acutely toxic of the isomers following single administration. It is moderately toxic via the dermal route as well, with reported dermal LD50 values of 500 to 1000 mg/kg in rats, 300 mg/kg in mice, 400 mg/kg in guinea pigs, and 300 mg/kg in rabbits. Acute exposure to lindane may lead to central nervous system stimulation (usually developing within 1 hour), mental/motor impairment, excitation, clonic (intermittent) and tonic (continuous) convulsion. Other adverse reactions include central nervous system toxicity, as well as skin and gastrointestinal changes.
Affected Organisms
Scabies (Sarcoptes scabei) and other insects
Biotransformation Primarily hepatic through dechlorination leading to 2-chlorophenol, 0-chlorophenol, chlorocyclohexane, chlorocyclohexanol.
Absorption Lindane is absorbed significantly through the skin. A mean peak blood concentration of 28 nanograms per mL occurred in infants and children 6 hours after total body application of lindane lotion for scabies.
Half Life 18 hours
Protein Binding 91%
References
Brown VJ: Life after lindane in California. Environ Health Perspect. 2008 Mar;116(3):A128. [Pubmed]
Strong M, Johnstone PW: Interventions for treating scabies. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000320. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - 36756 external link
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Strong M, Johnstone PW: Interventions for treating scabies. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000320. Pubmed
  • • Brown VJ: Life after lindane in California. Environ Health Perspect. 2008 Mar;116(3):A128. Pubmed
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PATENTS

PATENTS

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