Chloral hydrate

Identification

Name
Chloral hydrate
Accession Number
DB01563
Type
Small Molecule
Groups
Approved, Illicit, Investigational, Vet approved
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.

Structure
Thumb
Synonyms
  • 1,1,1-trichloro-2,2-dihydroxyethane
  • 1,1,1-trichloro-2,2-ethanediol
  • 2,2,2-trichloro-1,1-ethanediol
  • chloral monohydrate
  • Chloralhydrat
  • Trichloracetaldehyd-hydrat
  • trichloroacetaldehyde hydrate
External IDs
NSC-3210
Active Moieties
NameKindUNIICASInChI Key
TrichloroacetaldehydeunknownFLI06WS32H75-87-6HFFLGKNGCAIQMO-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Chloral Hydrate Capsules 500mgCapsule500 mgOralD.C. Labs Limited1968-12-312003-07-11Canada
Chloral Hydrate Syrup OdanSyrup500 mgOralOdan Laboratories Ltd2003-08-06Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-chloral Hydrate SyrupSyrup100 mgOralApotex CorporationNot applicableNot applicableCanada
Novo-chlorhydrate Cap 500mgCapsule500 mgOralNovopharm Limited1967-12-312005-08-10Canada
PMS-chloral Hydrate Capsules 500mgCapsule500 mgOralPharmascience Inc1996-10-10Not applicableCanada
PMS-chloral Hydrate Syrup 100mg/mlSyrup500 mgOralPharmascience Inc1990-12-31Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Analgesic BalmChloral hydrate (1 g) + Menthol (10 g) + Methyl salicylate (15 g)OintmentTopicalD.C. Labs Limited1966-12-312003-07-11Canada
Calmitol Itching Relief OntChloral hydrate (.496 %) + Camphor (.62 %) + Hyoscyamine (.0001 %) + Menthol (.58 %) + Zinc oxide (12.5 %)OintmentTopicalPfizer Canada Inc., Consumer Healthcare Division1964-12-311996-09-09Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
SomnoteChloral hydrate (500 mg/1)CapsuleOralBreckenridge Pharmaceutical, Inc.2001-01-012014-08-31Us
International/Other Brands
Aquachloral Supprettes (Amerifit Pharma) / Somnote (Breckenridge)
Categories
UNII
418M5916WG
CAS number
302-17-0
Weight
Average: 165.403
Monoisotopic: 163.919862461
Chemical Formula
C2H3Cl3O2
InChI Key
RNFNDJAIBTYOQL-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

Pharmacology

Indication

Mainly 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.

Associated Conditions
Associated Therapies
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption

Rapidly 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 distribution
Not Available
Protein binding
Not 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 elimination

Trichloroethanol, trichloroethanol glucuronide, and trichloroacetic acid are excreted in the urine. Some trichloroethanol glucuronide may be secreted into bile and excreted in the feces.

Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe protein binding of (R)-warfarin can be decreased when combined with Chloral hydrate.
(S)-WarfarinThe protein binding of (S)-Warfarin can be decreased when combined with Chloral hydrate.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Chloral hydrate is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Chloral hydrate.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Chloral hydrate.
4-hydroxycoumarinThe protein binding of 4-hydroxycoumarin can be decreased when combined with Chloral hydrate.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Chloral hydrate.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Chloral hydrate is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Chloral hydrate is combined with 7-Nitroindazole.
AbacavirAbacavir may decrease the excretion rate of Chloral hydrate which could result in a higher serum level.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0060451
KEGG Drug
D00265
KEGG Compound
C06899
PubChem Compound
2707
PubChem Substance
46507155
ChemSpider
2606
ChEBI
28142
ChEMBL
CHEMBL455917
PharmGKB
PA448925
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Chloral_hydrate
ATC Codes
N05CC01 — Chloral hydrate
AHFS Codes
  • 28:24.92 — Miscellaneous Anxiolytics Sedatives and Hypnotics

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedNot AvailableAuditory Brainstem Response in Children / Sedation With Chloral Hydrate1
2WithdrawnDiagnosticComputerized tomography / Procedural Sedation / Traumatic Brain Injury (TBI)1
2WithdrawnTreatmentProcedural Sedation1
3CompletedDiagnosticChildren / Electroencephalogram / Epilepsies / Sedation therapy1
3CompletedTreatmentOther Conditions of Brain1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
4CompletedTreatmentHeart Diseases1
4CompletedTreatmentSedation therapy1
Not AvailableCompletedNot AvailablePediatric1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Amerifit Inc.
  • Bio Pharm Inc.
  • Breckenridge Pharmaceuticals
  • Dispensing Solutions
  • G & W Labs
  • G Pohl Boskamp GmbH and Co. KG
  • International Laboratories Inc.
  • Letco Medical Inc.
  • Major Pharmaceuticals
  • Pharmaceutical Association
  • Pharmascience Inc.
  • Physicians Total Care Inc.
  • Qualitest
  • United Research Laboratories Inc.
  • Vintage Pharmaceuticals Inc.
Dosage forms
FormRouteStrength
SyrupOral100 mg
OintmentTopical
CapsuleOral500 mg
SyrupOral500 mg
CapsuleOral500 mg/1
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)57 °CPhysProp
boiling point (°C)98 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.8017
CYP450 2D6 inhibitorNon-inhibitor0.9417
CYP450 2C19 inhibitorNon-inhibitor0.847
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.88 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organohalogen compounds
Class
Halohydrins
Sub Class
Chlorohydrins
Direct Parent
Chlorohydrins
Alternative Parents
Carbonyl hydrates / Organochlorides / Hydrocarbon derivatives / Alkyl chlorides
Substituents
Chlorohydrin / Carbonyl hydrate / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Organochloride / Alkyl halide / Alkyl chloride / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organochlorine compound, aldehyde hydrate, ethanediol (CHEBI:28142) / a small molecule (CPD0-1476)

Drug created on July 31, 2007 07:10 / Updated on November 17, 2018 07:19