U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19ClN2
Molecular Weight 274.788
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXCHLORPHENIRAMINE

SMILES

CN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C2=CC=CC=N2

InChI

InChIKey=SOYKEARSMXGVTM-HNNXBMFYSA-N
InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H19ClN2
Molecular Weight 274.788
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Dexchlorpheniramine, the d-isomer of the racemic compound chlorpheniramine, is two times more active than chlorpheniramine. Dexchlorpheniramine does not prevent the release of histamine, but rather, competes with free histamine for binding at the H1-receptor sites, and competitively antagonizes the effects of histamine on H1-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Blockade of H1-receptors also suppresses the formation of oedema, flare, and pruritus that result from histaminic activity. Since dexchlorpheniramine binds to central and peripheral H1-receptors, sedative effects are likely to occur. H1-antagonists are structurally similar to anticholinergic agents and therefore possess the potential to exhibit anticholinergic properties of varying degrees. They also have antipruritic effects. Dexchlorpheniramine has high antihistaminic activity, moderate anticholinergic effects and minimal sedative effects. The drug does not possess antiemetic properties.

CNS Activity

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
POLARAMINE
PubMed

PubMed

TitleDatePubMed
Stable expression of human H1-histamine-receptor cDNA in Chinese hamster ovary cells. Pharmacological characterisation of the protein, tissue distribution of messenger RNA and chromosomal localisation of the gene.
1994 Sep 1
Determination of active ingredients in cough-cold preparations by micellar liquid chromatography.
2001 May 30
Comparative study of acute effects of single doses of fexofenadine, olopatadine, d-chlorpheniramine and placebo on psychomotor function in healthy volunteers.
2003 Dec
Anaphylactoid reaction to carboplatin: successful "desensitization".
2003 Nov-Dec
A case of probable codeine poisoning in a young infant after the use of a proprietary cough and cold medicine.
2004 Aug
A dose-ranging study of the effects of mequitazine on actual driving, memory and psychomotor performance as compared to dexchlorpheniramine, cetirizine and placebo.
2004 Feb
[Herpes gestationis].
2004 Jan-Feb
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic.
2004 Mar
Evaluation of in vivo selective binding of [11C]doxepin to histamine H1 receptors in five animal species.
2004 May
Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases.
2004 May 5
Drug interaction between methamphetamine and antihistamines: behavioral changes and tissue concentrations of methamphetamine in rats.
2004 Nov 28
Allergy to dexchlorpheniramine. Study of a case.
2004 Sep-Oct
An unusual adverse drug reaction?
2005 Jul-Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Severe anaphylactic reaction after intracameral antibiotic administration during cataract surgery.
2005 Mar
Enhanced antinociception by intracerebroventricularly administered orexin A in histamine H1 or H2 receptor gene knockout mice.
2005 Nov
Derivative ultraviolet spectrophotometric determination of dexchlorpheniramine maleate in tablets in presence of coloring agents.
2005 Nov-Dec
Histamine H1 antagonists block M-currents in dissociated rat cortical neurons.
2005 Sep 28
Angioedema from angiotensin-converting enzyme (ACE) inhibitor treated with complement 1 (C1) inhibitor concentrate.
2006 Jan
Repeated-dose effects of mequitazine, cetirizine and dexchlorpheniramine on driving and psychomotor performance.
2006 Jan
Localized expression of histamine H1 receptors in syncytiotrophoblast cells of human placenta.
2006 Nov
Modification of formalin-induced nociception by different histamine receptor agonists and antagonists.
2007 Jan 15
Anaphylactic reaction to ranitidine and dexchlorpheniramine.
2007 Mar-Apr
Anastrozole quantification in human plasma by high-performance liquid chromatography coupled to photospray tandem mass spectrometry applied to pharmacokinetic studies.
2007 May 1
Anaphylaxis to oral iron salts. desensitization protocol for tolerance induction.
2008
Analysis of disease-dependent sedative profiles of H(1)-antihistamines by large-scale surveillance using the visual analog scale.
2008 Apr
Histamine H1-receptor blockade in humans affects psychomotor performance but not memory.
2008 Aug
[Efficacy of premedication with intravenous corticosteroids and antihistaminics in preventing infusion reactions to infliximab].
2008 Dec
Repeated pre-treatment with antihistamines suppresses [corrected] transcriptional up-regulations of histamine H(1) receptor and interleukin-4 genes in toluene-2,4-diisocyanate-sensitized rats.
2008 Dec
The potential utility of B cell-directed biologic therapy in autoimmune diseases.
2008 Jan
Anaphylaxis induced by Anisakis.
2008 Jan-Feb
Cocaine-like neurochemical effects of antihistaminic medications.
2008 Jul
Progress in allergy signal research on mast cells: up-regulation of histamine signal-related gene expression in allergy model rats.
2008 Mar
'Renal hypersensitivity' to inulin and IgA nephropathy.
2008 Oct
Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS).
2008 Sep
Fexofenadine hydrochloride in the treatment of allergic disease: a review.
2008 Sep 19
Anaphylactic reaction to hydroxyzine in an anesthetized patient.
2009 Aug
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.
2009 Aug 31
Psychoactive medication and traffic safety.
2009 Mar
Urticaria due to etanercept in a patient with psoriatic arthritis.
2009 Mar
Histamine H1 receptor blockade predominantly impairs sensory processes in human sensorimotor performance.
2009 May
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Memory in humans is unaffected by central H1-antagonism, while objectively and subjectively measured sedation is increased.
2010 Apr
Treatment of congestion in upper respiratory diseases.
2010 Apr 8
[A case of IgG4-positive multi-organ lymphoproliferative syndrome associated with Kimura disease].
2010 Jul
Determination of chlorpheniramine in human plasma by HPLC-ESI-MS/MS: application to a dexchlorpheniramine comparative bioavailability study.
2010 Jul
Network-based relating pharmacological and genomic spaces for drug target identification.
2010 Jul 26
[Systemic mastocytosis and perioperative management: a report of 2 cases].
2010 Mar
[Protocol for inducing infliximab tolerance in a patient with psoriatic spondylarthritis].
2010 Mar-Apr
Urticaria due to aloe vera: a new sensitizer?
2010 Nov
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Polaramine (dexchlorpheniramine maleate) Tablets Adults and children over 12 years: One tablet every 6 hours Polaramine Syrup Adults and children over 12 years: 5 mL every 6 hours Children 6 – 12 years: 2 – 4 mL every 6 - 8 hours Children 4 - 6 years: 1.75 – 2 mL every 6 - 8 hours Children 2 – 4 years: 1.25 – 1.75 mL every 6 - 8 hours
Route of Administration: Oral
In Vitro Use Guide
dexchlorpheniramine (< 0.62 uM) altered the growth kinetics of RPMI 8866 (B-cell line)
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:43:27 UTC 2019
Edited
by admin
on Tue Oct 22 00:43:27 UTC 2019
Record UNII
3Q9Q0B929N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXCHLORPHENIRAMINE
HSDB   INN   VANDF   WHO-DD  
INN  
Official Name English
CHLORPHENIRAMINE D-FORM [MI]
Common Name English
DAPRITON
Brand Name English
CHLORPHENIRAMINE, (S)-
Common Name English
DEXCHLORPHENIRAMINE [VANDF]
Common Name English
DEXCHLORPHENIRAMINE [WHO-DD]
Common Name English
CHLORPHENAMINE, (S)-
Common Name English
DEXCHLORPHENIRAMINE [INN]
Common Name English
CHLORPHENIRAMINE, D-
Common Name English
2-PYRIDINEPROPANAMINE, .GAMMA.-(4-CHLOROPHENYL)-N,N-DIMETHYL-, (.GAMMA.S)-
Systematic Name English
DEXCHLORPHENIRAMINE [HSDB]
Common Name English
CHLORPHENIRAMINE D-FORM
MI  
Common Name English
Classification Tree Code System Code
LIVERTOX 289
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
WHO-VATC QR06AB02
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
WHO-ATC R06AB52
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
NCI_THESAURUS C29578
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
WHO-ATC R06AB02
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
WHO-VATC QR06AB52
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL1201353
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
RXCUI
22697
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY RxNorm
MESH
C018904
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
LactMed
25523-97-1
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
INN
955
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
PUBCHEM
33036
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
EPA CompTox
25523-97-1
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
NCI_THESAURUS
C61707
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
EVMPD
SUB07022MIG
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
ECHA (EC/EINECS)
247-073-7
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
WIKIPEDIA
DEXCHLORPHENIRAMINE
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
MERCK INDEX
M3456
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY Merck Index
HSDB
25523-97-1
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
EVMPD
SUB75896
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
CAS
25523-97-1
Created by admin on Tue Oct 22 00:43:27 UTC 2019 , Edited by admin on Tue Oct 22 00:43:27 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
RACEMATE -> ENANTIOMER
Related Record Type Details
ACTIVE MOIETY