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Identification
NameChlorhexadol
Accession NumberDB01534
TypeSmall Molecule
GroupsExperimental, Illicit
Description

Chlorhexadol is a sedative and hypnotic which is regulated in the United States as a Schedule III controlled substance. It is a derivative of chloral hydrate.

Structure
Thumb
Synonyms
SynonymLanguageCode
2-methyl-4-(2,2,2-trichloro-1-hydroxy-ethoxy)pentan-2-olNot AvailableNot Available
2-Methyl-4-(2,2,2-trichloro-1-hydroxyethoxy)-2-pentanolNot AvailableNot Available
2-methyl-4-(2,2,2-trichloro-1-hydroxyethoxy)pentan-2-olNot AvailableNot Available
2-PentanolNot AvailableNot Available
CloralodolNot AvailableNot Available
LoraNot AvailableNot Available
MecoralNot AvailableNot Available
MedodormNot AvailableNot Available
MerchloralNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number3563-58-4
WeightAverage: 265.562
Monoisotopic: 264.008677467
Chemical FormulaC8H15Cl3O3
InChI KeyQVFWZNCVPCJQOP-UHFFFAOYSA-N
InChI
InChI=1S/C8H15Cl3O3/c1-5(4-7(2,3)13)14-6(12)8(9,10)11/h5-6,12-13H,4H2,1-3H3
IUPAC Name
2-methyl-4-(2,2,2-trichloro-1-hydroxyethoxy)pentan-2-ol
SMILES
CC(CC(C)(C)O)OC(O)C(Cl)(Cl)Cl
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassAlcohols and Polyols
SubclassTertiary Alcohols
Direct parentTertiary Alcohols
Alternative parentsHemiacetals; Chlorohydrins; Polyamines; Organochlorides; Alkyl Chlorides
Substituentschlorohydrin; halohydrin; hemiacetal; ether; polyamine; organohalogen; organochloride; alkyl halide; alkyl chloride
Classification descriptionThis compound belongs to the tertiary alcohols. These are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
Pharmacology
IndicationNot Available
PharmacodynamicsChloral hydrate has sedative/hypnotic activity which has been shown to extend the sleep of normal made adults via a dose-response relationship. [1]
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9867
Blood Brain Barrier + 0.9769
Caco-2 permeable - 0.5191
P-glycoprotein substrate Non-substrate 0.6485
P-glycoprotein inhibitor I Non-inhibitor 0.8956
P-glycoprotein inhibitor II Non-inhibitor 0.8033
Renal organic cation transporter Non-inhibitor 0.956
CYP450 2C9 substrate Non-substrate 0.8184
CYP450 2D6 substrate Non-substrate 0.8683
CYP450 3A4 substrate Substrate 0.5052
CYP450 1A2 substrate Non-inhibitor 0.9172
CYP450 2C9 substrate Non-inhibitor 0.8425
CYP450 2D6 substrate Non-inhibitor 0.9166
CYP450 2C19 substrate Non-inhibitor 0.5114
CYP450 3A4 substrate Non-inhibitor 0.8803
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7975
Ames test Non AMES toxic 0.7245
Carcinogenicity Carcinogens 0.6919
Biodegradation Not ready biodegradable 0.9906
Rat acute toxicity 2.7114 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9798
hERG inhibition (predictor II) Non-inhibitor 0.9061
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point103 °CPhysProp
boiling point304.7°Cat760mmHgNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.24ALOGPS
logP2.34ALOGPS
logP1.82ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.63 m3·mol-1ChemAxon
Polarizability24.4 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference

1. Condouris, George A., and Desmond D. Bonnycastle. “A pharmacological investigation of the hypnotic action of a new derivative of chloral hydrate, chlorhexadol.” The American Journal of the Medical Sciences 242.5 (1961): 574-578.

External Links
ResourceLink
KEGG DrugD07325
PubChem Compound19094
PubChem Substance46508125
ChemSpider18027
WikipediaChloralodol
ATC CodesN05CC02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15