Chloral hydrate

Identification

Summary

Chloral hydrate is a mild hypnotic used for experimental purposes that was previously used for the treatment of insomnia.

Brand Names
Nortec
Generic Name
Chloral hydrate
DrugBank Accession Number
DB01563
Background

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.

Type
Small Molecule
Groups
Approved, Illicit, Investigational, Vet approved
Structure
Weight
Average: 165.403
Monoisotopic: 163.919862461
Chemical Formula
C2H3Cl3O2
Synonyms
  • 1,1,1-trichloro-2,2-dihydroxyethane
  • 1,1,1-trichloro-2,2-ethanediol
  • 2,2,2-trichloro-1,1-ethanediol
  • Chloral hydrate
  • chloral monohydrate
  • Chloralhydrat
  • Trichloracetaldehyd-hydrat
  • trichloroacetaldehyde hydrate
External IDs
  • NSC-3210

Pharmacology

Indication

Mainly used as a hypnotic 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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofAlcohol withdrawal••••••••••••
Adjunct therapy in treatment ofPost-operative pain••••••••••••
Symptomatic treatment ofBarbiturate withdrawal••••••••••••
Symptomatic treatment ofOpiate withdrawal••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Chloral hydrate is combined with 1,2-Benzodiazepine.
AbacavirAbacavir may decrease the excretion rate of Chloral hydrate which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Chloral hydrate which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Chloral hydrate which could result in a higher serum level.
AcenocoumarolThe protein binding of Acenocoumarol can be decreased when combined with Chloral hydrate.
Food Interactions
  • Avoid alcohol. Ingesting alcohol may cause a disulfiram-like-reaction (flushing, dizziness, tachycardia).
  • Take after a meal. If chloral hydrate is being used for sedation, it should be taken after meals. Otherwise, it can be taken with or without food.

Products

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International/Other Brands
Aquachloral Supprettes (Amerifit Pharma)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Chloral Hydrate Capsules 500mgCapsule500 mg / capOralD.C. Labs Limited1968-12-312003-07-11Canada flag
Chloral Hydrate Syrup OdanSyrup500 mg / 5 mLOralOdan Laboratories Ltd2003-08-06Not applicableCanada flag
SomnoteCapsule500 mg/1OralBreckenridge Pharmaceutical, Inc.2001-01-012014-08-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-chloral Hydrate SyrupSyrup100 mg / mLOralApotex CorporationNot applicableNot applicableCanada flag
Novo-chlorhydrate Cap 500mgCapsule500 mg / capOralNovopharm Limited1967-12-312005-08-10Canada flag
PMS-chloral Hydrate Capsules 500mgCapsule500 mgOralPharmascience Inc1996-10-102020-07-20Canada flag
PMS-chloral Hydrate Syrup 100mg/mlSyrup500 mg / 5 mLOralPharmascience Inc1990-12-312021-10-20Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Analgesic BalmChloral hydrate (1 g / 100 g) + Levomenthol (10 g / 100 g) + Methyl salicylate (15 g / 100 g)OintmentTopicalD.C. Labs Limited1966-12-312003-07-11Canada flag
Calmitol Itching Relief OntChloral hydrate (.496 %) + Camphor (.62 %) + Hyoscyamine (.0001 %) + Levomenthol (.58 %) + Zinc oxide (12.5 %)OintmentTopicalPfizer Canada Inc., Consumer Healthcare Division1964-12-311996-09-09Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
SomnoteChloral hydrate (500 mg/1)CapsuleOralBreckenridge Pharmaceutical, Inc.2001-01-012014-08-31US flag

Categories

ATC Codes
N05CC01 — Chloral hydrate
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Alkyl chloride / Alkyl halide / Carbonyl hydrate / Chlorohydrin / Hydrocarbon derivative / Organic oxygen compound / Organochloride / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organochlorine compound, aldehyde hydrate, ethanediol (CHEBI:28142) / a small molecule (CPD0-1476)
Affected organisms
Not Available

Chemical Identifiers

UNII
418M5916WG
CAS number
302-17-0
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

References

General References
Not Available
Human Metabolome Database
HMDB0060451
KEGG Drug
D00265
KEGG Compound
C06899
PubChem Compound
2707
PubChem Substance
46507155
ChemSpider
2606
RxNav
2344
ChEBI
28142
ChEMBL
CHEMBL455917
ZINC
ZINC000003872049
PharmGKB
PA448925
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Chloral_hydrate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableAdministration Related Reaction / Chloral Hydrate Adverse Reaction / Failed Moderate Sedation During Procedure1
4CompletedTreatmentCardiovascular Disease (CVD)1
4CompletedTreatmentSedation1
4RecruitingTreatmentChloral Hydrate / Insomnia / Insomnia Chronic1
3CompletedDiagnosticChildren / Electroencephalogram / Epilepsy / Sedation1

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
OintmentTopical
SyrupOral100 mg / mL
CapsuleOral500 mg / cap
SolutionOral100 mg
CapsuleOral500 mg
SyrupOral500 mg / 5 mL
SyrupOral500 mg/5ml
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-MSsplash10-00kb-9800000000-173349d19f15699bc4e2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-f6aa76a44c9ce6824f19
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-20dbd5a6bff2ac9e0a07
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-f9d77ca618403d77b5cf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-1875640a85e2cae348ee
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-7900000000-e3d9de235bca5cfe0fa4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-7900000000-5ab916d24cb123fe2af5
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-103.0593402
predicted
DarkChem Lite v0.1.0
[M-H]-124.30949
predicted
DeepCCS 1.0 (2019)
[M+H]+103.9501402
predicted
DarkChem Lite v0.1.0
[M+H]+126.84767
predicted
DeepCCS 1.0 (2019)
[M+Na]+103.2764402
predicted
DarkChem Lite v0.1.0
[M+Na]+135.44743
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:10 / Updated at March 18, 2024 16:48