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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19ClN2.C4H4O4
Molecular Weight 390.861
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DEXCHLORPHENIRAMINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C2=CC=CC=N2

InChI

InChIKey=DBAKFASWICGISY-DASCVMRKSA-N
InChI=1S/C16H19ClN2.C4H4O4/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-9,11,15H,10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t15-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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

Chlorpheniramine is an antihistamine. Chlorpheniramine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine. Chlorpheniramine is used for relieving symptoms of sinus congestion, sinus pressure, runny nose, watery eyes, itching of the nose and throat, and sneezing due to upper respiratory infections (eg, colds), allergies, and hay fever. In addition to being a histamine H1 receptor (HRH1) antagonist, chlorphenamine has been shown to work as a serotonin-norepinephrine reuptake inhibitor or SNRI.

CNS Activity

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Chlor-Trimeton
PubMed

PubMed

TitleDatePubMed
Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity.
1975 Feb
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule.
1978 Oct 7
The I antigen as an immune complex receptor in a case of haemolytic anaemia induced by an antihistaminic agent.
1981 Sep
Enhancement of morphine-induced hyperactivity by antihistaminic drugs in mice.
1986 Dec
Antagonism of drug-induced yawning and penile erections in rats.
1986 Mar 18
Antihistaminics enhance morphine-, but not amphetamine- and scopolamine-induced hyperactivity in mice.
1987
Treatment of lethal pertussis vaccine reaction with histamine H1 antagonists.
1987 Jun
Histamine and hepatic glutathione in the mouse.
1987 May 25
Multicenter, double-blind, multiple-dose, parallel-groups efficacy and safety trial of azelastine, chlorpheniramine, and placebo in the treatment of spring allergic rhinitis.
1988 Nov
A comparison of acrivastine versus chlorpheniramine in the treatment of chronic idiopathic urticaria.
1989
Drug-induced acute pulmonary edema--sequential changes in CT images.
1991 Nov-Dec
Proconvulsant effect of ketotifen, a histamine H1 antagonist, confirmed by the use of d-chlorpheniramine with monitoring electroencephalography.
1993 Apr
Role of cysteinyl-leukotrienes and histamine in mediating intrinsic tone in isolated human bronchi.
1994 Jan
Benefit/risk ratio of the antihistamines (H1-receptor antagonists) terfenadine and chlorpheniramine in children.
1994 Jun
In vivo and in vitro interaction of the novel selective histamine H1 receptor antagonist mizolastine with H1 receptors in the rodent.
1995 May
Combining event rates from clinical trials: comparison of Bayesian and classical methods.
1996 May
The role of histaminergic-noradrenergic axis in naloxone-induced withdrawal symptoms in mice.
1996 Sep
[Dexchlorpheniramine-induced acute hepatitis: a case with positive rechallenge].
1998 Oct
Central nervous system effects of H1-receptor antagonists in the elderly.
1999 Feb
A new model of allergic rhinitis in rats by topical sensitization and evaluation of H(1)-receptor antagonists.
2000 Jun
The specificity of a chlorphenamine-imprinted polymer and its application.
2001 Aug 3
Synergistic antiallergic activity of combined histamine H1- and cysteinyl leukotriene1-receptor blockade in human bronchus.
2001 May 11
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Simple and sensitive method for the determination of chlorpheniramine maleate in human plasma using liquid chromatography-mass spectrometry.
2002 Sep 5
Aseptic meningitis associated with intravenous administration of dexchlorpheniramine.
2003 May
[Roles of histamine receptors in pain perception: a study using receptors gene knockout mice].
2003 Nov
2-O-(2-hydroxybutyl)-beta-cyclodextrin as a chiral selector for the capillary electrophoretic separation of chiral drugs.
2005 Aug
Chlorphenamine.
2005 Aug 9-15
Differentiating midazolam over-sedation from neurological damage in the intensive care unit.
2005 Feb
Carrier mediated transport of chlorpheniramine and chlorcyclizine across bovine olfactory mucosa: implications on nose-to-brain transport.
2005 Mar
Enhanced antinociception by intracerebroventricularly administered orexin A in histamine H1 or H2 receptor gene knockout mice.
2005 Nov
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro.
2005 Nov
Phase II study of gemcitabine, doxorubicin and paclitaxel (GAT) as first-line chemotherapy for metastatic breast cancer: a translational research experience.
2006 Mar 21
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
Progress in allergy signal research on mast cells: up-regulation of histamine signal-related gene expression in allergy model rats.
2008 Mar
Rare case of "red man" syndrome in a female patient treated with oral vancomycin for Clostridium difficile diarrhoea.
2009
Investigation of enantiomeric separation of basic drugs by capillary electrophoresis using clindamycin phosphate as a novel chiral selector.
2009 Aug
Suspected anaphylactic reactions associated with anaesthesia.
2009 Feb
A computational approach to studying monomer selectivity towards the template in an imprinted polymer.
2009 Jul
Block of HERG k channel by classic histamine h(1) receptor antagonist chlorpheniramine.
2009 Jun
Extended weekly dose-dense paclitaxel/carboplatin is feasible and active in heavily pre-treated platinum-resistant recurrent ovarian cancer.
2009 Mar 10
Dextromethorphan, chlorphenamine and serotonin toxicity: case report and systematic literature review.
2010 Dec
Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting.
2010 Dec
The discovery of phthalazinone-based human H1 and H3 single-ligand antagonists suitable for intranasal administration for the treatment of allergic rhinitis.
2011 Apr 14
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Sample Use Guides

In Vivo Use Guide
Tablets or syrup: 4 mg orally every 4 to 6 hours. Sustained-release: 8 to 16 mg orally every 8 to 12 hours as needed or 16 mg orally once a day as needed. Maximum dose 32 mg/day.
Route of Administration: Oral
In Vitro Use Guide
Chlorpheniramine inhibits the [3H]mepyramine binding to the histamine H1 receptor in guinea pig cortex with IC50 of 8.8 nM.
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
B10YD955QW
Record Status Validated (UNII)
Record Version
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Name Type Language
DEXCHLORPHENIRAMINE MALEATE
EP   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
DEXCHLORPHENIRAMINE MALEATE [USP]
Common Name English
POLARAMINE
Brand Name English
DEXCHLORPHENIRAMINE MALEATE [EP]
Common Name English
CHLORPHENIRAMINE D-FORM MALEATE
MI  
Common Name English
DEXCHLORPHENIRAMINE MALEATE [VANDF]
Common Name English
CHLORPHENIRAMINE D-FORM MALEATE [MI]
Common Name English
(+)-2-(P-CHLORO-.ALPHA.-(2-(DIMETHYLAMINO)ETHYL)BENZYL)PYRIDINE MALEATE (1:1)
Common Name English
CHLORPHENIRAMINE MALEATE, (S)-
Common Name English
D-CHLORPHENIRAMINE MALEATE
JAN  
Common Name English
DEXCHLORPHENIRAMINE MALEATE [USP-RS]
Common Name English
D-CHLORPHENIRAMINE MALEATE [JAN]
Common Name English
DEXCHLORPHENIRAMINE MALEATE [MART.]
Common Name English
DEXCHLORPHENIRAMINE MALEATE [WHO-DD]
Common Name English
DEXCHLORPHENIRAMINE MALEATE [ORANGE BOOK]
Common Name English
2-PYRIDINEPROPANAMINE, .GAMMA.-(4-CHLOROPHENYL)-N,N-DIMETHYL-, (S)-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 341.12
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
Code System Code Type Description
ECHA (EC/EINECS)
219-450-6
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
5281070
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
SUB01628MIG
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
2438-32-6
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
C47478
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
RXCUI
54828
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
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
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
RACEMATE -> ENANTIOMER
Related Record Type Details
ACTIVE MOIETY