Paraldehyde

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	EPIMERIC
Molecular Formula	C6H12O3
Molecular Weight	132.1577
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1OC(C)O[C@@H](C)O1

InChI

InChIKey=SQYNKIJPMDEDEG-UHFFFAOYSA-N

InChI=1S/C6H12O3/c1-4-7-5(2)9-6(3)8-4/h4-6H,1-3H3

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB09117
Curator's Comment: Description was created based on several sources, including http://drugs.healthgrove.com/l/1199/Paraldehyde and http://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0011591/?report=details

Paraldehyde is the cyclic trimer of acetaldehyde molecules. It was introduced into clinical practice in the UK by the Italian physician Vincenzo Cervello in 1882. It is a central nervous system depressant and was soon found to be an effective anticonvulsant, hypnotic and sedative. It was included in some cough medicines as an expectorant (though there is no known mechanism for this function beyond the placebo effect). Paraldehyde also has been used in the treatment of alcoholism and in the treatment of nervous and mental conditions to calm or relax patients who are nervous or tense and to produce sleep. However, this medicine has generally been replaced by safer and more effective medicines for the treatment of alcoholism and in the treatment of nervous and mental conditions.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Convulsions 72 Sources: https://www.drugs.com/cons/paraldehyde-oral-injection-rectal.html	Primary	Approved 8583	Paraldehyde Injection Approved Use Paraldehyde is used to treat certain convulsive disorders. It also has been used in the treatment of alcoholism and in the treatment of nervous and mental conditions to calm or relax patients who are nervous or tense and to produce sleep. However, paraldehyde has generally been replaced by safer and more effective medicines for the treatment of alcoholism and in the treatment of nervous and mental conditions. Launch Date 2009
Anxiety 275 Sources: https://www.drugs.com/cons/paraldehyde-oral-injection-rectal.html	Primary	Approved 8583	Paraldehyde Injection Approved Use Paraldehyde is used to treat certain convulsive disorders. It also has been used in the treatment of alcoholism and in the treatment of nervous and mental conditions to calm or relax patients who are nervous or tense and to produce sleep. However, paraldehyde has generally been replaced by safer and more effective medicines for the treatment of alcoholism and in the treatment of nervous and mental conditions. Launch Date 2009
Delirium tremens due to alcohol withdrawal 1 Sources: https://www.ebs.tga.gov.au/servlet/xmlmillr6?dbid=ebs/PublicHTML/pdfStore.nsf&docid=160612&agid=(PrintDetailsPublic)&actionid=1	Primary	Approved 8583	Paraldehyde Injection Approved Use Paraldehyde has been used as a sedative and hypnotic. It may also be used in the treatment of convulsive episodes arising from tetanus, status epilepticus and poisoning by convulsive drugs. Paraldehyde may be effective in reducing the anxiety associated with withdrawal from drugs such as narcotics or barbiturates, as well as in the management of acute agitation or delirium tremens due to alcohol withdrawal. Launch Date 2009

C_max

Value	Dose	Co-administered	Analyte	Population
247 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6694030	150 mg/kg/h other, intravenous dose: 150 mg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:		PARALDEHYDE plasma	Homo sapiens population: UNHEALTHY age: NEWBORN sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6694030	150 mg/kg/h other, intravenous dose: 150 mg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:		PARALDEHYDE plasma	Homo sapiens population: UNHEALTHY age: NEWBORN sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
360 mL 1 times / day multiple, oral Dose: 360 mL, 1 times / day Route: oral Route: multiple Dose: 360 mL, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13487613	unhealthy, 38 years Health Status: unhealthy Age Group: 38 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13487613	Disc. AE: Metabolic acidosis... AEs leading to discontinuation/dose reduction: Metabolic acidosis (severe, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/13487613
200 mg/kg single, intravenous Dose: 200 mg/kg Route: intravenous Route: single Dose: 200 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/11785507	unhealthy, 40.1 weeks Health Status: unhealthy Age Group: 40.1 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/11785507	Sources: https://pubmed.ncbi.nlm.nih.gov/11785507
120 mL 1 times / day multiple, oral Dose: 120 mL, 1 times / day Route: oral Route: multiple Dose: 120 mL, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13487613	unhealthy, 43 years Health Status: unhealthy Age Group: 43 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13487613	Disc. AE: Metabolic acidosis... AEs leading to discontinuation/dose reduction: Metabolic acidosis (severe, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/13487613
5 \|5 \| 3\| 5\| 5 mL 1 times / 15 min multiple, intramuscular\|intramuscular\|intravenous\|intravenous\|intravenous Dose: 5 \|5 \| 3\| 5\| 5 mL, 1 times / 15 min Route: intramuscular\|intramuscular\|intravenous\|intravenous\|intravenous Route: multiple Dose: 5 \|5 \| 3\| 5\| 5 mL, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/7105866	unhealthy, 65 years Health Status: unhealthy Age Group: 65 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/7105866	Other AEs: Pulmonary edema... Other AEs: Pulmonary edema Sources: https://pubmed.ncbi.nlm.nih.gov/7105866
10 mL 1 times / 30 min multiple, rectal Dose: 10 mL, 1 times / 30 min Route: rectal Route: multiple Dose: 10 mL, 1 times / 30 min Sources: https://pubmed.ncbi.nlm.nih.gov/1090222	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/1090222	Disc. AE: Apnea... Other AEs: Fever, Tachypnea... AEs leading to discontinuation/dose reduction: Apnea (grade 5, 2 patients) Other AEs: Fever (9 patients) Tachypnea (9 patients) Tachycardia (9 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/1090222
120 mL single, oral Dose: 120 mL Route: oral Route: single Dose: 120 mL Sources: https://pubmed.ncbi.nlm.nih.gov/7105866	unknown Health Status: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/7105866	Other AEs: Pulmonary edema, Congestion pulmonary... Other AEs: Pulmonary edema (grade 5) Congestion pulmonary (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/7105866

AEs

AE	Significance	Dose	Population
Metabolic acidosis	severe, 1 patient Disc. AE	360 mL 1 times / day multiple, oral Dose: 360 mL, 1 times / day Route: oral Route: multiple Dose: 360 mL, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13487613	unhealthy, 38 years Health Status: unhealthy Age Group: 38 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13487613
Metabolic acidosis	severe, 1 patient Disc. AE	120 mL 1 times / day multiple, oral Dose: 120 mL, 1 times / day Route: oral Route: multiple Dose: 120 mL, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13487613	unhealthy, 43 years Health Status: unhealthy Age Group: 43 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13487613
Pulmonary edema		5 \|5 \| 3\| 5\| 5 mL 1 times / 15 min multiple, intramuscular\|intramuscular\|intravenous\|intravenous\|intravenous Dose: 5 \|5 \| 3\| 5\| 5 mL, 1 times / 15 min Route: intramuscular\|intramuscular\|intravenous\|intravenous\|intravenous Route: multiple Dose: 5 \|5 \| 3\| 5\| 5 mL, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/7105866	unhealthy, 65 years Health Status: unhealthy Age Group: 65 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/7105866
Fever	9 patients	10 mL 1 times / 30 min multiple, rectal Dose: 10 mL, 1 times / 30 min Route: rectal Route: multiple Dose: 10 mL, 1 times / 30 min Sources: https://pubmed.ncbi.nlm.nih.gov/1090222	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/1090222
Tachycardia	9 patients	10 mL 1 times / 30 min multiple, rectal Dose: 10 mL, 1 times / 30 min Route: rectal Route: multiple Dose: 10 mL, 1 times / 30 min Sources: https://pubmed.ncbi.nlm.nih.gov/1090222	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/1090222
Tachypnea	9 patients	10 mL 1 times / 30 min multiple, rectal Dose: 10 mL, 1 times / 30 min Route: rectal Route: multiple Dose: 10 mL, 1 times / 30 min Sources: https://pubmed.ncbi.nlm.nih.gov/1090222	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/1090222
Apnea	grade 5, 2 patients Disc. AE	10 mL 1 times / 30 min multiple, rectal Dose: 10 mL, 1 times / 30 min Route: rectal Route: multiple Dose: 10 mL, 1 times / 30 min Sources: https://pubmed.ncbi.nlm.nih.gov/1090222	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/1090222
Congestion pulmonary	grade 5	120 mL single, oral Dose: 120 mL Route: oral Route: single Dose: 120 mL Sources: https://pubmed.ncbi.nlm.nih.gov/7105866	unknown Health Status: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/7105866
Pulmonary edema	grade 5	120 mL single, oral Dose: 120 mL Route: oral Route: single Dose: 120 mL Sources: https://pubmed.ncbi.nlm.nih.gov/7105866	unknown Health Status: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/7105866

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY41712	https://www.001chemical.com/chem/123-63-7
3B Scientific (Wuhan) Corp	3B4-0820	http://www.3bsc.com/index/pro_info.php?id=18668
3B Scientific (Wuhan) Corp	3B4-3110	http://www.3bsc.com/index/pro_info.php?id=77742
abcr GmbH	AB251765	http://www.abcr.com/shop/en/AB251765
Acadechem	ACDS-036519	http://www.acadechemical.com/product/111218
Aceschem	ACS015401	https://www.aceschem.com/catalog/123-63-7.html
Achemtek	0104-018731	http://www.achemtek.com/123-63-7
Angene	AGN-PC-0JKLU0	http://www.angenechemical.com/productshow/AGN-PC-0JKLU0.html
Anward	ANW-56373	http://www.anward.com/pro_result/42824
BioSynth	J-523868	https://www.biosynth.com/en/products/all-products/products/J-523868.html
ChemMol	49415702	http://www.chemmol.com/chemmol/49415702.html
Chemspace	CSSS00016148904	https://chem-space.com/CSSS00016148904
Clearsynth	CS-EB-01617	https://www.clearsynth.com/en/CSEB01617.html
Clearsynth	CS-ER-01609	https://www.clearsynth.com/en/CSER01609.html
Finetech	FT-0650173	http://www.finetechnology-ind.com/product_detail.shtml?catalogNo=FT-0650173
Glentham Life Sciences	GK9043	http://www.glentham.com/products/product/GK9043/
Hairui	HR147213	http://www.hairuichem.com/en/product/123-63-7.html
iChemical	EBD17268	http://www.ichemical.com/chemicals/cas-123-63-7
LGC Standards	DRE-C15848200	https://www.lgcstandards.com/US/en/p/DRE-C15848200
Molcore	MC41712	https://www.molcore.com/product/123-63-7
Otava	2826861	https://search.otavachemicals.com/#!/search?query=2826861&type=code&base=dbb
Renno Tech	RP19992	http://www.rennotech.com/product_show.asp?id=25742
Sigma-Aldrich	1496959_USP	https://www.sigmaaldrich.com/catalog/product/usp/1496959?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	743844_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/743844?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	76260_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/76260?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	P5520_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/p5520?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S020862	http://www.sinfoobiotech.com/product/1024260
Smolecule	S538626	http://www.smolecule.com/products/s538626
THE BioTek	bt-278780	https://www.thebiotek.com/product/inhibitors/bt-278780
VladaChem	VL166706	https://www.vladachem.com/product.php?products=123-63-7
VladaChem	VL272104-250ML	https://www.vladachem.com/product.php?products=123-63-7
Yuhao Chemical	XJ0507	http://www.chemyuhao.com/123-63-7.html

PubMed

Title	Date	PubMed
Molecular dynamics simulations suggest that electrostatic funnel directs binding of Tamiflu to influenza N1 neuraminidases.	2010-09-23	20885781
Use of biocidal products (insect sprays and electro-vaporizer) in indoor areas--exposure scenarios and exposure modeling.	2009-09	19345645
Game and balance multicast architecture algorithms for sensor grid.	2009	22399992
Energy balanced strategies for maximizing the lifetime of sparsely deployed underwater acoustic sensor networks.	2009	22399970
Autonomous distributed self-organization for mobile wireless sensor networks.	2009	22291548
In silico identification and experimental validation of PmrAB targets in Salmonella typhimurium by regulatory motif detection.	2004	14759259
Elicitin genes expressed in vitro by certain tobacco isolates of Phytophthora parasitica are down regulated during compatible interactions.	2001-03	11277430
Brain-derived neurotrophic factor superinduction parallels anti-epileptic--neuroprotective treatment in the pilocarpine epilepsy model.	2001-03	11259499
Complications following sedation of paediatric oncology patients undergoing radiotherapy.	1999-01-28	9921085
Effects of drugs on the initiation and maintenance of status epilepticus induced by administration of pilocarpine to lithium-pretreated rats.	1987-07	3582562
Dangers of treatment of status epilepticus with diazepam.	1969-01-18	4973764

Patents

Sample Use Guides

In Vivo Use Guide

Usual adult dose: Anticonvulsant Oral, up to 12 mL (diluted to a 10% solution) via gastric tube every four hours as needed; Rectal, 10 to 20 mL; Usual pediatric dose: Anticonvulsant Oral, 0.3 mL per kg of body weight or 12 mL per square meter of body surface; Rectal, 0.3 mL per kg of body weight or 12 mL per square meter of body surface.

Route of Administration: Enteral

In Vitro Use Guide

Paraldehyde (3.8 X 10(-3) M) reduced TEA induced contractures of the chick biventer cervicis muscle

Name

Type

Language

PARAL

Preferred Name

English

Paraldehyde

Common Name

English

PARALDEHYDE [MART.]

Common Name

English

1,3,5-TRIOXANE, 2,4,6-TRIMETHYL-

Systematic Name

English

PARALDEHYDE [VANDF]

Common Name

English

FEMA NO. 4010

Code

English

PARALDEHYDE [EP MONOGRAPH]

Common Name

English

2,4,6-Trimethyl-S-trioxane

Common Name

English

NSC-9799

Code

English

PARALDEHYDE [FHFI]

Brand Name

English

Paraldehyde [WHO-DD]

Common Name

English

PARACETALDEHYDE

Common Name

English

PARALDEHYDE [HSDB]

Common Name

English

PARALDEHYDE [USP MONOGRAPH]

Common Name

English

PARALDEHYDE [MI]

Common Name

English

PARALDEHYDE CIV [USP-RS]

Common Name

English

Classification Tree Code System Code

DEA NO.

2585