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Chloral hydrate
Identification
- Name
- Chloral hydrate
- Accession Number
- DB01563
- 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.
- Type
- Small Molecule
- Groups
- Approved, Illicit, Investigational, Vet approved
- Structure
Structure for Chloral hydrate (DB01563)
- 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 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.
- Associated Conditions
- Associated Therapies
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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.
Drug Interaction Unlock Additional DataAbacavir Abacavir may decrease the excretion rate of Chloral hydrate which could result in a higher serum level. Acarbose Acarbose may decrease the excretion rate of Chloral hydrate which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Chloral hydrate which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Chloral hydrate which could result in a higher serum level. Acenocoumarol The protein binding of Acenocoumarol can be decreased when combined with Chloral hydrate. Acetaminophen Acetaminophen may decrease the excretion rate of Chloral hydrate which could result in a higher serum level. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Chloral hydrate. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Chloral hydrate. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Chloral hydrate which could result in a higher serum level. Aclidinium Chloral hydrate may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- 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
- International/Other Brands
- Aquachloral Supprettes (Amerifit Pharma)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataChloral Hydrate Capsules 500mg Capsule Oral D.C. Labs Limited 1968-12-31 2003-07-11 Canada 
Chloral Hydrate Syrup Odan Syrup Oral Odan Laboratories Ltd 2003-08-06 Not applicable Canada Somnote Capsule 500 mg/1 Oral Breckenridge Pharmaceutical, Inc. 2001-01-01 2014-08-31 US 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataApo-chloral Hydrate Syrup Syrup Oral Apotex Corporation Not applicable Not applicable Canada Novo-chlorhydrate Cap 500mg Capsule Oral Novopharm Limited 1967-12-31 2005-08-10 Canada PMS-chloral Hydrate Capsules 500mg Capsule Oral Pharmascience Inc 1996-10-10 2020-07-20 Canada PMS-chloral Hydrate Syrup 100mg/ml Syrup Oral Pharmascience Inc 1990-12-31 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Analgesic Balm Chloral hydrate (1 g) + Levomenthol (10 g) + Methyl salicylate (15 g) Ointment Topical D.C. Labs Limited 1966-12-31 2003-07-11 Canada Calmitol Itching Relief Ont Chloral hydrate (.496 %) + Camphor (.62 %) + Hyoscyamine (.0001 %) + Levomenthol (.58 %) + Zinc oxide (12.5 %) Ointment Topical Pfizer Canada Inc., Consumer Healthcare Division 1964-12-31 1996-09-09 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Somnote Chloral hydrate (500 mg/1) Capsule Oral Breckenridge Pharmaceutical, Inc. 2001-01-01 2014-08-31 US
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)
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
- External Links
- Human Metabolome Database
- HMDB0060451
- KEGG Drug
- D00265
- KEGG Compound
- C06899
- PubChem Compound
- 2707
- PubChem Substance
- 46507155
- ChemSpider
- 2606
- 2344
- ChEBI
- 28142
- ChEMBL
- CHEMBL455917
- ZINC
- ZINC000003872049
- PharmGKB
- PA448925
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Chloral_hydrate
- AHFS Codes
- 28:24.92 — Miscellaneous Anxiolytics Sedatives and Hypnotics
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Administration Related Reaction / Chloral Hydrate Adverse Reaction / Failed Moderate Sedation During Procedure 1 4 Completed Treatment Heart Diseases 1 4 Completed Treatment Sedation 1 3 Completed Diagnostic Children / Electroencephalogram / Epilepsies / Sedation 1 3 Completed Treatment Other Conditions of Brain 1 3 Terminated Treatment Anxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenia 1 2 Completed Not Available Auditory Brainstem Response in Children / Sedation With Chloral Hydrate 1 2 Withdrawn Diagnostic Computerized tomography / Procedural Sedation / Traumatic Brain Injury (TBI) 1 2 Withdrawn Treatment Procedural Sedation 1 1, 2 Completed Basic Science Healthy Volunteers 1
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
Form Route Strength Ointment Topical Syrup Oral Capsule Oral Capsule Oral 500 mg/1 - Prices
Unit description Cost Unit Pms-Chloral Hydrate 100 mg/ml Syrup 0.05USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 57 °C PhysProp boiling point (°C) 98 °C PhysProp water solubility 7.93E+005 mg/L (at 25 °C) YALKOWSKY,SH & HE,Y (2003) logP 0.99 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 43.4 mg/mL ALOGPS logP 0.88 ALOGPS logP 0.69 ChemAxon logS -0.58 ALOGPS pKa (Strongest Acidic) 9.51 ChemAxon pKa (Strongest Basic) -5.1 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 40.46 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 29.25 m3·mol-1 ChemAxon Polarizability 11.88 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9591 Blood Brain Barrier + 0.9555 Caco-2 permeable - 0.5795 P-glycoprotein substrate Non-substrate 0.8757 P-glycoprotein inhibitor I Non-inhibitor 0.9923 P-glycoprotein inhibitor II Non-inhibitor 0.9794 Renal organic cation transporter Non-inhibitor 0.9454 CYP450 2C9 substrate Non-substrate 0.7898 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7558 CYP450 1A2 substrate Non-inhibitor 0.7969 CYP450 2C9 inhibitor Non-inhibitor 0.8017 CYP450 2D6 inhibitor Non-inhibitor 0.9417 CYP450 2C19 inhibitor Non-inhibitor 0.847 CYP450 3A4 inhibitor Non-inhibitor 0.9446 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9778 Ames test AMES toxic 0.6454 Carcinogenicity Carcinogens 0.616 Biodegradation Not ready biodegradable 0.8453 Rat acute toxicity 2.5068 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9837 hERG inhibition (predictor II) Non-inhibitor 0.9558
Spectra
- Mass Spec (NIST)
- Download (8.88 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created on July 31, 2007 07:10 / Updated on August 10, 2020 08:11
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