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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
POLARAMINE

Cmax

ValueDoseCo-administeredAnalytePopulation
2.5 ng/mL
1.5 mg single, oral
DEXCHLORPHENIRAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
67.58 ng × h/mL
1.5 mg single, oral
DEXCHLORPHENIRAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
19.66 h
1.5 mg single, oral
DEXCHLORPHENIRAMINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
28%
1.5 mg single, oral
DEXCHLORPHENIRAMINE plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Tox targets

PubMed

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
Record UNII
3Q9Q0B929N
Record Status Validated (UNII)
Record Version