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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19ClN2
Molecular Weight 274.789
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])(c1ccc(cc1)Cl)c2ccccn2

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 274.789
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

3.63916788E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.5 ng/mL
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ACETAMINOPHEN
DEXCHLORPHENIRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
67.58 ng × h/mL
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ACETAMINOPHEN
DEXCHLORPHENIRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
19.66 h
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ACETAMINOPHEN
DEXCHLORPHENIRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
28%
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ACETAMINOPHEN
DEXCHLORPHENIRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse 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:
healthy, 22 - 45 years
n = 4
Health Status: healthy
Age Group: 22 - 45 years
Sex: M+F
Population Size: 4
Sources:
Other AEs: Sedation...
Other AEs:
Sedation (4 patients)
Sources:
6 mg single, oral
Recommended
Dose: 6 mg
Route: oral
Route: single
Dose: 6 mg
Sources:
healthy, mean 27 years
n = 12
Health Status: healthy
Age Group: mean 27 years
Sex: F
Population Size: 12
Sources:
Other AEs: Depressive symptom...
Other AEs:
Depressive symptom (10 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
healthy, 22 - 45 years
n = 4
Health Status: healthy
Age Group: 22 - 45 years
Sex: M+F
Population Size: 4
Sources:
Depressive symptom 10 patients
6 mg single, oral
Recommended
Dose: 6 mg
Route: oral
Route: single
Dose: 6 mg
Sources:
healthy, mean 27 years
n = 12
Health Status: healthy
Age Group: mean 27 years
Sex: F
Population Size: 12
Sources:
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
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.
2001 Apr
Determination of active ingredients in cough-cold preparations by micellar liquid chromatography.
2001 May 30
Neuroimaging of histamine H1-receptor occupancy in human brain by positron emission tomography (PET): a comparative study of ebastine, a second-generation antihistamine, and (+)-chlorpheniramine, a classical antihistamine.
2001 Nov
Comparison of intra-accumbens injection of histamine with histamine H1-receptor antagonist chlorpheniramine in effects on reinforcement and memory parameters.
2001 Oct 15
The effects of a sedative antihistamine, d-chlorpheniramine, on visuomotor spatial discrimination and regional brain activity as measured by positron emission tomography (PET).
2002 Dec
Histamine regulation of interleukin-18-initiating cytokine cascade is associated with down-regulation of intercellular adhesion molecule-1 expression in human peripheral blood mononuclear cells.
2002 Jan
Development of a validated capillary electrophoresis method for enantiomeric purity testing of dexchlorpheniramine maleate.
2002 Jun 7
Histamine inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production in an intercellular adhesion molecule-1- and B7.1-dependent manner.
2003 Feb
[Roles of histamine receptors in pain perception: a study using receptors gene knockout mice].
2003 Nov
[Ring chromosome 20, hypersensitivity to valproate and hyperammonemic encephalopathy].
2003 Oct 16-31
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
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
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
Role of histaminergic neurons in hypnotic modulation of brain processing of visceral perception.
2007 Oct
[Description of an outbreak of lepidopterism (dermatitis associated with contact with moths) among sailors in Salvador, State of Bahia].
2007 Sep-Oct
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
[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
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
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

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 Sat Jun 26 03:12:58 UTC 2021
Edited
by admin
on Sat Jun 26 03:12:58 UTC 2021
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 Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
WHO-VATC QR06AB02
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
WHO-ATC R06AB52
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
WHO-ATC R06AB02
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
WHO-VATC QR06AB52
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1201353
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
FDA UNII
3Q9Q0B929N
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
RXCUI
22697
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY RxNorm
MESH
C018904
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
INN
955
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
PUBCHEM
33036
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
EPA CompTox
25523-97-1
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
NCI_THESAURUS
C61707
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
EVMPD
SUB07022MIG
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
ECHA (EC/EINECS)
247-073-7
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
LACTMED
Dexchlorpheniramine
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
WIKIPEDIA
DEXCHLORPHENIRAMINE
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
DRUG BANK
DB13679
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
MERCK INDEX
M3456
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY Merck Index
HSDB
3054
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
EVMPD
SUB75896
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
CAS
25523-97-1
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
DRUG CENTRAL
4411
Created by admin on Sat Jun 26 03:12:58 UTC 2021 , Edited by admin on Sat Jun 26 03:12:58 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
RACEMATE -> ENANTIOMER
Related Record Type Details
ACTIVE MOIETY