Dexchlorpheniramine

Chlorpheniramine
Clinical data
Trade namesChlor-trimeton
AHFS/Drugs.comMonograph
MedlinePlusa682543
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • AU: S3 (Pharmacist only)
Identifiers
IUPAC name
  • (3S)-3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-3-ylpropan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.042.779
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Chemical and physical data
FormulaC16H19ClN2
Molar mass274.79 g·mol−1
3D model (JSmol)
SMILES
  • Clc1ccc(cc1)[C@@H](c2ncccc2)CCN(C)C
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-/m0/s1 checkY
  • Key:SOYKEARSMXGVTM-HNNXBMFYSA-N checkY
  (verify)

Dexchlorpheniramine (trade name Polaramine) is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria.[1][2] It is the pharmacologically active dextrorotatory isomer of chlorpheniramine.

It came into medical use in 1959 and was patented in 1962.[3]

Pharmacology

Dexchlorpheniramine is an antihistamine, or an antagonist of the histamine H1 receptor. A study found that dexchlorpheniramine had a Ki value of 20 to 30 μM for the muscarinic acetylcholine receptors using rat brain tissue.[4]

References

  1. ↑ Theunissen, E. L.; Vermeeren, A.; Ramaekers, J. G. (2006). "Repeated-dose effects of mequitazine, cetirizine and dexchlorpheniramine on driving and psychomotor performance". British Journal of Clinical Pharmacology. 61 (1): 79–86. doi:10.1111/j.1365-2125.2005.02524.x. PMC 1884990. PMID 16390354.
  2. ↑ Ortíz San Román, L.; Sanavia Morán, E.; Campos Domínguez, M.; Peinador García, M. M. (2013). "Síndrome anticolinérgico por dexclorfeniramina como causa de retención urinaria". Anales de Pediatría. 79 (6): 400–1. doi:10.1016/j.anpedi.2013.02.014. PMID 23680058.
  3. ↑ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 547. ISBN 9783527607495.
  4. ↑ Yamamura HI, Snyder SH (1974). "Muscarinic cholinergic binding in rat brain". Proc. Natl. Acad. Sci. U.S.A. 71 (5): 1725–9. Bibcode:1974PNAS...71.1725Y. doi:10.1073/pnas.71.5.1725. PMC 388311. PMID 4151898.
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