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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Chloral hydrate (DB01563)

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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

Name	Kind	UNII	CAS	InChI Key
Trichloroacetaldehyde	unknown	FLI06WS32H	75-87-6	HFFLGKNGCAIQMO-UHFFFAOYSA-N

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Chloral Hydrate Capsules 500mg	Capsule	500 mg	Oral	D.C. Labs Limited	1968-12-31	2003-07-11
Chloral Hydrate Syrup Odan	Syrup	500 mg	Oral	Odan Laboratories Ltd	2003-08-06	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-chloral Hydrate Syrup	Syrup	100 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Novo-chlorhydrate Cap 500mg	Capsule	500 mg	Oral	Novopharm Limited	1967-12-31	2005-08-10
PMS-chloral Hydrate Capsules 500mg	Capsule	500 mg	Oral	Pharmascience Inc	1996-10-10	Not applicable
PMS-chloral Hydrate Syrup 100mg/ml	Syrup	500 mg	Oral	Pharmascience Inc	1990-12-31	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Somnote	Chloral hydrate (500 mg/1)	Capsule	Oral	Breckenridge Pharmaceutical, Inc.	2001-01-01	2014-08-31

International/Other Brands

Aquachloral Supprettes (Amerifit Pharma) / Somnote (Breckenridge)

Categories

• Alcohols
• Central Nervous System Agents
• Central Nervous System Depressants
• Ethylene Glycols
• Glycols
• Hypnotics and Sedatives
• Miscellaneous Anxiolytics Sedatives and Hypnotics
• Nervous System
• Psycholeptics

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

• Alcohol Withdrawal Syndrome(AWS)
• Opiate withdrawal symptoms
• Post-Operative Pain
• Barbiturate withdrawal

Associated Therapies

• Sedative therapy therapy

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

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
(R)-warfarin	The protein binding of (R)-warfarin can be decreased when combined with Chloral hydrate.
(S)-Warfarin	The protein binding of (S)-Warfarin can be decreased when combined with Chloral hydrate.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when Chloral hydrate is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-Methylenedioxyamphetamine	The risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Chloral hydrate.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Chloral hydrate.
4-hydroxycoumarin	The protein binding of 4-hydroxycoumarin can be decreased when combined with Chloral hydrate.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Chloral hydrate.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of adverse effects can be increased when Chloral hydrate is combined with 5-methoxy-N,N-dimethyltryptamine.
7-Nitroindazole	The risk or severity of adverse effects can be increased when Chloral hydrate is combined with 7-Nitroindazole.
Abacavir	Abacavir 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

• N05CC — Aldehydes and derivatives
• N05C — HYPNOTICS AND SEDATIVES
• N05 — PSYCHOLEPTICS
• N — NERVOUS SYSTEM

AHFS Codes

• 28:24.92 — Miscellaneous Anxiolytics Sedatives and Hypnotics

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
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
3	Completed	Diagnostic	Children / Electroencephalogram / Epilepsies / Sedation therapy	1
3	Completed	Treatment	Other Conditions of Brain	1
3	Terminated	Treatment	Anxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders	1
4	Completed	Treatment	Heart Diseases	1
4	Completed	Treatment	Sedation therapy	1
Not Available	Completed	Not Available	Pediatric	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
Syrup	Oral	100 mg
Capsule	Oral	500 mg
Syrup	Oral	500 mg
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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

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 December 14, 2018 05:37