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Identification
NameChloral hydrate
Accession NumberDB01563
TypeSmall Molecule
GroupsExperimental, Illicit
Description

A hypnotic and sedative used in the treatment of insomnia. The safety margin is too narrow for chloral hydrate to be used as a general anesthetic in humans, but it is commonly used for that purpose in animal experiments. It is no longer considered useful as an anti-anxiety medication. [PubChem]

Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
Aquachloral SupprettesAmerifit Pharma
SomnoteBreckenridge
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number302-17-0
WeightAverage: 165.403
Monoisotopic: 163.919862461
Chemical FormulaC2H3Cl3O2
InChI KeyRNFNDJAIBTYOQL-UHFFFAOYSA-N
InChI
InChI=1S/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H
IUPAC Name
2,2,2-trichloroethane-1,1-diol
SMILES
OC(O)C(Cl)(Cl)Cl
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassHalohydrins
Sub ClassChlorohydrins
Direct ParentChlorohydrins
Alternative Parents
Substituents
  • Chlorohydrin
  • 1,1-diol
  • Carbonyl hydrate
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationMainly used as a hyponotic in the treatment of insomnia; however, it is only effective as a hypnotic for short-term use. May be used as a routine sedative preoperatively to decrease anxiety and cause sedation and/or sleep with respiration depression or cough reflex.
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionRapidly absorbed in the GI tract following oral or rectal administration. Chloral hydrate and its active metabolite, trichloroethanol, have been detected in CSF, umbilical cord blood, fetal blood, and amniotic fluid.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Metabolized by the liver and erythrocytes to form trichloroethanol, an active metabolite. This reaction is catalyzed by alcohol dehydrogenase and other enzymes. Oxidation of chloral hydrate and trichloroethanol to trichloroacetic acid in the liver and kidneys also occurs to a lesser extent. Trichloroethanol also undergoes glucuronidation to produce an inactive metabolism.

Route of eliminationTrichloroethanol, trichloroethanol glucuronide, and trichloroacetic acid are excreted in the urine. Some trichloroethanol glucuronide may be secreted into bile and excreted in the feces.
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+0.9591
Blood Brain Barrier+0.9555
Caco-2 permeable-0.5795
P-glycoprotein substrateNon-substrate0.8757
P-glycoprotein inhibitor INon-inhibitor0.9923
P-glycoprotein inhibitor IINon-inhibitor0.9794
Renal organic cation transporterNon-inhibitor0.9454
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateNon-inhibitor0.7969
CYP450 2C9 substrateNon-inhibitor0.8017
CYP450 2D6 substrateNon-inhibitor0.9417
CYP450 2C19 substrateNon-inhibitor0.847
CYP450 3A4 substrateNon-inhibitor0.9446
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9778
Ames testAMES toxic0.6454
CarcinogenicityCarcinogens 0.616
BiodegradationNot ready biodegradable0.8453
Rat acute toxicity2.5068 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9837
hERG inhibition (predictor II)Non-inhibitor0.9558
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Pms-Chloral Hydrate 100 mg/ml Syrup0.05USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point57 °CPhysProp
boiling point98 °CPhysProp
water solubility7.93E+005 mg/L (at 25 °C)YALKOWSKY,SH & HE,Y (2003)
logP0.99HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility43.4 mg/mLALOGPS
logP0.88ALOGPS
logP0.69ChemAxon
logS-0.58ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.25 m3·mol-1ChemAxon
Polarizability11.88 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.88 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 28:24.92
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolMay increase the serum concentration of Vitamin K Antagonists.
FurosemideFurosemide may enhance the adverse/toxic effect of Chloral Hydrate.
Food InteractionsNot Available
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Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15