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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tertiary alcohols. These are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassTertiary alcohols
Direct ParentTertiary alcohols
Alternative Parents
Substituents
  • Tertiary alcohol
  • Hemiacetal
  • Halohydrin
  • Chlorohydrin
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9867
Blood Brain Barrier+0.9769
Caco-2 permeable-0.5191
P-glycoprotein substrateNon-substrate0.6485
P-glycoprotein inhibitor INon-inhibitor0.8956
P-glycoprotein inhibitor IINon-inhibitor0.8033
Renal organic cation transporterNon-inhibitor0.956
CYP450 2C9 substrateNon-substrate0.8184
CYP450 2D6 substrateNon-substrate0.8683
CYP450 3A4 substrateSubstrate0.5052
CYP450 1A2 substrateNon-inhibitor0.9172
CYP450 2C9 substrateNon-inhibitor0.8425
CYP450 2D6 substrateNon-inhibitor0.9166
CYP450 2C19 substrateNon-inhibitor0.5114
CYP450 3A4 substrateNon-inhibitor0.8803
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7975
Ames testNon AMES toxic0.7245
CarcinogenicityCarcinogens 0.6919
BiodegradationNot ready biodegradable0.9906
Rat acute toxicity2.7114 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9798
hERG inhibition (predictor II)Non-inhibitor0.9061
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 Solubility1.24 mg/mLALOGPS
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesNot Available
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