Oxymetazoline (hydrochloride)

Oxymetazoline is an agonist of alpha1- and alpha2-adrenergic receptors (alpha1- and alpha2-ARs, Kds = 6, 320, and 390 nM for alpha1A-, alpha1B-, and alpha1D-ARs, respectively, Ki = 15 nM for alpha2-AR). It is also an agonist of the serotonin (5-HT) receptor subtype 5-HT1 (Kds = 4.68, 25.7, and 5.01 nM for 5-HT1A, 5-HT1B, and 5-HT1D, respectively). Oxymetazoline increases intracellular calcium levels in CHO cells transfected with the alpha1A-AR (EC50 = 40.7 nM), but does not increase it measurably in cells transfected with the alpha1B- or alpha1D-AR (EC50s = 79.4 and 240 nM, respectively). It acts as a partial agonist of the alpha2-AR in isolated perfused rat heart (IC50 = 63 nM and EC50 = 13.5 nM for norepinephrine release). Oxymetazoline also acts as an agonist and antagonist of the 5-HT1C receptor in the presence of methiothepin (Kd = 110 nM, Cay-23138) and clonidine (Kd = 257 nM, Cay-15949), respectively. In functional second messenger assays, oxymetazoline inhibits forskolin-stimulated adenylate cyclase activity (EC50s = 18.6, 24.0, and 44.7 nM in tissues expressing high levels of 5-HT1A, 5-HT1B, 5-HT1D receptors, respectively) and accumulation of inositol phosphates (EC50 = 269 nM in pig choroid plexus preparations, which highly express 5-HT1C receptors). Oxymetazoline (0.2 µg/kg) decreases nasal pressure in dogs by 6.9%. Formulations containing oxymetazoline have been used as nasal decongestants.Formal Name: 3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethyl-phenol, monohydrochloride. CAS Number: 2315-02-8. Synonyms: SCH 9384. Molecular Formula: C16H24N2O . HCl. Formula Weight: 296.8. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 20 mg/ml, DMSO: 25 mg/ml, Ethanol: 25 mg/ml, PBS (pH 7.2): 10 mg/ml. SMILES: OC1=C(C)C(CC2=NCCN2)=C(C)C=C1C(C)(C)C.Cl. InChi Code: InChI=1S/C16H24N2O.ClH/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14,/h8,19H,6-7,9H2,1-5H3,(H,17,18),1H. InChi Key: BEEDODBODQVSIM-UHFFFAOYSA-N.