DEXCHLORPHENIRAMINE MALEATE

US Approved OTC

First approved in 1958

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

Structure Search

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	C16H19ClN2
Molecular Weight	274.788
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://www.medsafe.govt.nz/profs/Datasheet/p/Polaraminetabreptabsyrup.pdf

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

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: http://www.auburn.edu/~deruija/hist_antihis.pdf \| http://www.medsafe.govt.nz/profs/Datasheet/p/Polaraminetabreptabsyrup.pdf	Antagonist 2849
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL2094109 Sources: http://www.auburn.edu/~deruija/hist_antihis.pdf	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergy 44 Sources: http://www.medsafe.govt.nz/profs/Datasheet/p/Polaraminetabreptabsyrup.pdf	Primary		Approved 8583	POLARAMINE Approved Use POLARAMINE is indicated for symptomatic treatment of perennial and seasonal allergic rhinitis, vasomotor rhinitis, allergic conjunctivitis, mild uncomplicated allergic skin manifestations of urticaria and angioedema. Polaramine may relieve itching due to skin conditions such as allergic eczema, pruritus ani, pruritus vulvae, atopic dermatitis, contact dermatitis, insect bites, dermographism and drug reactions, including serum sickness. Launch Date 1981

C_max

Value	Dose	Co-administered	Analyte	Population
2.5 ng/mL EXPERIMENT http://en.cnki.com.cn/Article_en/CJFDTotal-BSDZ200803014.htm	1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	DEXCHLORPHENIRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
67.58 ng × h/mL EXPERIMENT http://en.cnki.com.cn/Article_en/CJFDTotal-BSDZ200803014.htm	1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	DEXCHLORPHENIRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
19.66 h EXPERIMENT http://en.cnki.com.cn/Article_en/CJFDTotal-BSDZ200803014.htm	1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	DEXCHLORPHENIRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
28% EXPERIMENT http://en.cnki.com.cn/Article_en/CJFDTotal-BSDZ200803014.htm	1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	DEXCHLORPHENIRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
6 mg 2 times / day steady, oral Recommended Dose: 6 mg, 2 times / day Route: oral Route: steady Dose: 6 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16390354/	healthy, 22 - 45 years Health Status: healthy Age Group: 22 - 45 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16390354/	Other AEs: Sedation... Other AEs: Sedation (4 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/16390354/
6 mg single, oral Recommended Dose: 6 mg Route: oral Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2972549/	healthy, mean 27 years Health Status: healthy Age Group: mean 27 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/2972549/	Other AEs: Depressive symptom... Other AEs: Depressive symptom (10 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/2972549/

AEs

AE	Significance	Dose	Population
Sedation	4 patients	6 mg 2 times / day steady, oral Recommended Dose: 6 mg, 2 times / day Route: oral Route: steady Dose: 6 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16390354/	healthy, 22 - 45 years Health Status: healthy Age Group: 22 - 45 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16390354/
Depressive symptom	10 patients	6 mg single, oral Recommended Dose: 6 mg Route: oral Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2972549/	healthy, mean 27 years Health Status: healthy Age Group: mean 27 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/2972549/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP2E1 1060 CYP2A6 879 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/589038#sid=104234352	inconclusive
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625245#sid=104234352	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625246#sid=104234352	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625247#sid=104234352	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625248#sid=104234352	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625248#sid=104234352	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625251#sid=104234352	no [IC50 >10 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/625171#sid=104234352

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4464	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4464
eMolecules	8791345	https://www.emolecules.com/cgi-bin/more?vid=8791345
ZINC	ZINC000000113404	http://zinc15.docking.org/substances/ZINC000000113404

PubMed

Title	Date	PubMed
Urticaria due to aloe vera: a new sensitizer?	2010-11	21055672
Network-based relating pharmacological and genomic spaces for drug target identification.	2010-07-26	20668676
[A case of IgG4-positive multi-organ lymphoproliferative syndrome associated with Kimura disease].	2010-07	20684218
Determination of chlorpheniramine in human plasma by HPLC-ESI-MS/MS: application to a dexchlorpheniramine comparative bioavailability study.	2010-07	19924675
Treatment of congestion in upper respiratory diseases.	2010-04-08	20463825
Memory in humans is unaffected by central H1-antagonism, while objectively and subjectively measured sedation is increased.	2010-04	20083393
[Systemic mastocytosis and perioperative management: a report of 2 cases].	2010-03	20422858
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009-10-02	19798416
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.	2009-08-31	21437146
Anaphylactic reaction to hydroxyzine in an anesthetized patient.	2009-08	19877565
Histamine H1 receptor blockade predominantly impairs sensory processes in human sensorimotor performance.	2009-05	19220286
[Protocol for inducing infliximab tolerance in a patient with psoriatic spondylarthritis].	2009-03-04	20304368
Psychoactive medication and traffic safety.	2009-03	19440432
Urticaria due to etanercept in a patient with psoriatic arthritis.	2009-03	19204628
[Efficacy of premedication with intravenous corticosteroids and antihistaminics in preventing infusion reactions to infliximab].	2008-12	19174078
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.	2008-12	19075512
'Renal hypersensitivity' to inulin and IgA nephropathy.	2008-10	18535847
Fexofenadine hydrochloride in the treatment of allergic disease: a review.	2008-09-19	21436982
Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS).	2008-09	18566547
Histamine H1-receptor blockade in humans affects psychomotor performance but not memory.	2008-08	18208925
Cocaine-like neurochemical effects of antihistaminic medications.	2008-07	18363822
Uniformly sized molecularly imprinted polymers for d-chlorpheniramine: influence of a porogen on their morphology and enantioselectivity.	2008-04-14	17644298
Analysis of disease-dependent sedative profiles of H(1)-antihistamines by large-scale surveillance using the visual analog scale.	2008-04	18597008
Progress in allergy signal research on mast cells: up-regulation of histamine signal-related gene expression in allergy model rats.	2008-03	18360087
Effects of a sedative antihistamine, D-chlorpheniramine, on regional cerebral perfusion and performance during simulated car driving.	2008-03	18181241
Intrathecal high-dose histamine induces spinally-mediated nociceptive behavioral responses through a polyamine site of NMDA receptors.	2008-02-26	18155693
Anaphylaxis induced by Anisakis.	2008-02-12	18261432
The potential utility of B cell-directed biologic therapy in autoimmune diseases.	2008-01	17957371
Anaphylaxis to oral iron salts. desensitization protocol for tolerance induction.	2008	18714540
Role of histaminergic neurons in hypnotic modulation of brain processing of visceral perception.	2007-10	17883434
Anastrozole quantification in human plasma by high-performance liquid chromatography coupled to photospray tandem mass spectrometry applied to pharmacokinetic studies.	2007-05-01	17240203
Interventions for pityriasis rosea.	2007-04-18	17443568
[Description of an outbreak of lepidopterism (dermatitis associated with contact with moths) among sailors in Salvador, State of Bahia].	2007-04-09	17992420
Anaphylactic reaction to ranitidine and dexchlorpheniramine.	2007-03-06	17337410
Modification of formalin-induced nociception by different histamine receptor agonists and antagonists.	2007-01-15	16631358
Localized expression of histamine H1 receptors in syncytiotrophoblast cells of human placenta.	2006-11	17099293
Angioedema from angiotensin-converting enzyme (ACE) inhibitor treated with complement 1 (C1) inhibitor concentrate.	2006-01	16451161
Repeated-dose effects of mequitazine, cetirizine and dexchlorpheniramine on driving and psychomotor performance.	2006-01	16390354
Enhanced antinociception by intracerebroventricularly administered orexin A in histamine H1 or H2 receptor gene knockout mice.	2005-11	16202530
Histamine H1 antagonists block M-currents in dissociated rat cortical neurons.	2005-09-28	16125149
An unusual adverse drug reaction?	2005-07-28	16045865
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Severe anaphylactic reaction after intracameral antibiotic administration during cataract surgery.	2005-03	15811754
Derivative ultraviolet spectrophotometric determination of dexchlorpheniramine maleate in tablets in presence of coloring agents.	2005-02-28	16226263
[Herpes gestationis].	2005-01-08	15636736
Drug interaction between methamphetamine and antihistamines: behavioral changes and tissue concentrations of methamphetamine in rats.	2004-11-28	15556146
Allergy to dexchlorpheniramine. Study of a case.	2004-10-01	15456628
A case of probable codeine poisoning in a young infant after the use of a proprietary cough and cold medicine.	2004-08	15299176
Determination of active ingredients in cough-cold preparations by micellar liquid chromatography.	2001-05-30	18968285
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.	1994-09-01	7925364

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 `Mon Mar 31 17:36:52 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:52 GMT 2025`
Record UNII	B10YD955QW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHLORPHENIRAMINE D-FORM MALEATE

Preferred Name

English

DEXCHLORPHENIRAMINE MALEATE

Common Name

English

POLARAMINE

Brand Name

English

DEXCHLORPHENIRAMINE MALEATE [VANDF]

Common Name

English

CHLORPHENIRAMINE D-FORM MALEATE [MI]

Common Name

English

DEXCHLORPHENIRAMINE MALEATE [EP IMPURITY]

Common Name

English

NSC-759156

Code

English

DEXCHLORPHENIRAMINE MALEATE [USP MONOGRAPH]

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

Common Name

English

DEXCHLORPHENIRAMINE MALEATE [USP-RS]

Common Name

English

D-CHLORPHENIRAMINE MALEATE [JAN]

Common Name

English

Dexchlorpheniramine maleate [WHO-DD]

Common Name

English

DEXCHLORPHENIRAMINE MALEATE [EP MONOGRAPH]

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