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
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
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 |
|||
Target ID: CHEMBL2094109 Sources: http://www.auburn.edu/~deruija/hist_antihis.pdf |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | POLARAMINE Approved UsePOLARAMINE 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 Date3.63916788E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
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: |
healthy, 22 - 45 years n = 4 Health Status: healthy Age Group: 22 - 45 years Sex: M+F Population Size: 4 Sources: |
Other AEs: Sedation... |
6 mg single, oral Recommended |
healthy, mean 27 years n = 12 Health Status: healthy Age Group: mean 27 years Sex: F Population Size: 12 Sources: |
Other AEs: Depressive symptom... |
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: |
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 |
healthy, mean 27 years n = 12 Health Status: healthy Age Group: mean 27 years Sex: F Population Size: 12 Sources: |
PubMed
Title | Date | PubMed |
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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 |
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Determination of active ingredients in cough-cold preparations by micellar liquid chromatography. | 2001 May 30 |
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A case of probable codeine poisoning in a young infant after the use of a proprietary cough and cold medicine. | 2004 Aug |
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[Herpes gestationis]. | 2004 Jan-Feb |
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Drug interaction between methamphetamine and antihistamines: behavioral changes and tissue concentrations of methamphetamine in rats. | 2004 Nov 28 |
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Allergy to dexchlorpheniramine. Study of a case. | 2004 Sep-Oct |
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An unusual adverse drug reaction? | 2005 Jul-Aug |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Severe anaphylactic reaction after intracameral antibiotic administration during cataract surgery. | 2005 Mar |
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Enhanced antinociception by intracerebroventricularly administered orexin A in histamine H1 or H2 receptor gene knockout mice. | 2005 Nov |
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Derivative ultraviolet spectrophotometric determination of dexchlorpheniramine maleate in tablets in presence of coloring agents. | 2005 Nov-Dec |
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Histamine H1 antagonists block M-currents in dissociated rat cortical neurons. | 2005 Sep 28 |
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Angioedema from angiotensin-converting enzyme (ACE) inhibitor treated with complement 1 (C1) inhibitor concentrate. | 2006 Jan |
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Repeated-dose effects of mequitazine, cetirizine and dexchlorpheniramine on driving and psychomotor performance. | 2006 Jan |
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Localized expression of histamine H1 receptors in syncytiotrophoblast cells of human placenta. | 2006 Nov |
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Interventions for pityriasis rosea. | 2007 Apr 18 |
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Modification of formalin-induced nociception by different histamine receptor agonists and antagonists. | 2007 Jan 15 |
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Anaphylactic reaction to ranitidine and dexchlorpheniramine. | 2007 Mar-Apr |
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Anastrozole quantification in human plasma by high-performance liquid chromatography coupled to photospray tandem mass spectrometry applied to pharmacokinetic studies. | 2007 May 1 |
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Role of histaminergic neurons in hypnotic modulation of brain processing of visceral perception. | 2007 Oct |
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[Description of an outbreak of lepidopterism (dermatitis associated with contact with moths) among sailors in Salvador, State of Bahia]. | 2007 Sep-Oct |
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Anaphylaxis to oral iron salts. desensitization protocol for tolerance induction. | 2008 |
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Analysis of disease-dependent sedative profiles of H(1)-antihistamines by large-scale surveillance using the visual analog scale. | 2008 Apr |
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Uniformly sized molecularly imprinted polymers for d-chlorpheniramine: influence of a porogen on their morphology and enantioselectivity. | 2008 Apr 14 |
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Histamine H1-receptor blockade in humans affects psychomotor performance but not memory. | 2008 Aug |
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[Efficacy of premedication with intravenous corticosteroids and antihistaminics in preventing infusion reactions to infliximab]. | 2008 Dec |
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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 |
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Intrathecal high-dose histamine induces spinally-mediated nociceptive behavioral responses through a polyamine site of NMDA receptors. | 2008 Feb 26 |
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The potential utility of B cell-directed biologic therapy in autoimmune diseases. | 2008 Jan |
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Anaphylaxis induced by Anisakis. | 2008 Jan-Feb |
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Cocaine-like neurochemical effects of antihistaminic medications. | 2008 Jul |
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Progress in allergy signal research on mast cells: up-regulation of histamine signal-related gene expression in allergy model rats. | 2008 Mar |
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Effects of a sedative antihistamine, D-chlorpheniramine, on regional cerebral perfusion and performance during simulated car driving. | 2008 Mar |
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'Renal hypersensitivity' to inulin and IgA nephropathy. | 2008 Oct |
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Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS). | 2008 Sep |
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Fexofenadine hydrochloride in the treatment of allergic disease: a review. | 2008 Sep 19 |
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Anaphylactic reaction to hydroxyzine in an anesthetized patient. | 2009 Aug |
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Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines. | 2009 Aug 31 |
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Psychoactive medication and traffic safety. | 2009 Mar |
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Urticaria due to etanercept in a patient with psoriatic arthritis. | 2009 Mar |
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Histamine H1 receptor blockade predominantly impairs sensory processes in human sensorimotor performance. | 2009 May |
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Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
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Memory in humans is unaffected by central H1-antagonism, while objectively and subjectively measured sedation is increased. | 2010 Apr |
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Treatment of congestion in upper respiratory diseases. | 2010 Apr 8 |
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[A case of IgG4-positive multi-organ lymphoproliferative syndrome associated with Kimura disease]. | 2010 Jul |
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Determination of chlorpheniramine in human plasma by HPLC-ESI-MS/MS: application to a dexchlorpheniramine comparative bioavailability study. | 2010 Jul |
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Network-based relating pharmacological and genomic spaces for drug target identification. | 2010 Jul 26 |
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[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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7748542
dexchlorpheniramine (< 0.62 uM) altered the growth kinetics of RPMI 8866 (B-cell line)
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CFR |
21 CFR 341.12
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NCI_THESAURUS |
C29578
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219-450-6
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DB09555
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5281070
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B10YD955QW
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2438-32-6
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C47478
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100000092786
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m3456
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1179005
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54828
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B10YD955QW
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CHEMBL1201353
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759156
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD