General Information of Drug (ID: DM6C4YJ)

Drug Name
Chlorphenamine
Synonyms
Chloropheniramine; Chlorophenylpyridamine; Chloropiril; Chloroprophenpyridamine; Chlorphenamin; Chlorphenamine; Chlorphenaminum; Chlorpheniramine maleate; Chlorpheniramine polistirex; Chlorpheniraminum; Chlorprophenpyridamine; Clorfenamina; Clorfeniramina; Clorfeniramina [Italian]; Cloropiril; Aller-Chlor; Allergican; Allergisan; Antagonate; Chlor-trimeton; Haynon; Histadur; Kloromin; Phenetron; Polaramine; Polaronil; Telachlor; Teldrin; chlorpheniramine; 132-22-9; 4-Chloropheniramine
Indication
Disease Entry ICD 11 Status REF
Allergic rhinitis CA08.0 Approved [1]
Common cold CA00 Approved [2]
Seasonal allergic rhinitis CA08.01 Approved [3]
Urticaria EB00-EB05 Approved [4]
Vasomotor/allergic rhinitis CA08 Approved [5]
Pruritus EC90 Investigative [6]
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Affected Organisms
Humans and other mammals
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 274.79
Logarithm of the Partition Coefficient (xlogp) 3.4
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Absorption
The drug is well absorbed from the gastrointestinal tract []
Half-life
The concentration or amount of drug in body reduced by one-half in 21 - 27 hours [7]
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C16H19ClN2
IUPAC Name
3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
Canonical SMILES
CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2
InChI
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-/m1/s1
InChIKey
SOYKEARSMXGVTM-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2725
ChEBI ID
CHEMBL505
CAS Number
132-22-9
UNII
3U6IO1965U
DrugBank ID
DB01114
INTEDE ID
DR0303
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Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [8]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [9]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [8]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Azelastine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential. Drugs. 1989 Nov;38(5):778-800.
2 Symptomatic treatment of the common cold with a fixed-dose combination of paracetamol, chlorphenamine and phenylephrine: a randomized, placebo-controlled trial. BMC Infect Dis. 2013 Nov 22;13:556.
3 Efficacy and central nervous system impairment of newer-generation prescription antihistamines in seasonal allergic rhinitis. South Med J. 2006 Jun;99(6):593-9.
4 Chlorpheniramine, an Old Drug with New Potential Clinical Applications: A Comprehensive Review of the Literature. Curr Rev Clin Exp Pharmacol. 2024;19(2):137-145.
5 A standard database for drug repositioning. Sci Data. 2017 Mar 14;4:170029.
6 Psychogenic Itch Management. Curr Probl Dermatol. 2016;50:124-32.
7 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
8 Drug Interactions Flockhart Table
9 The roles of CYP2D6 and stereoselectivity in the clinical pharmacokinetics of chlorpheniramine. Br J Clin Pharmacol. 2002 May;53(5):519-25.