Rupatadine Fumarate

• CAT Number: A000900
• CAS Number: 182349-12-8
• Molecular Formula: C26H26ClN3.C4H4O4
• Molecular Weight: 532.03
• Purity: ≥95%
• Target: Histamine Receptor
• Solubility: >11.75mg/mL in DMSO
• Storage: <label class=
• IUPAC Name: (E)-but-2-enedioic acid;13-chloro-2-[1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene]-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene
• InChI: InChI=1S/C26H26ClN3.C4H4O4/c1-18-13-19(16-28-15-18)17-30-11-8-20(9-12-30)25-24-7-6-23(27)14-22(24)5-4-21-3-2-10-29-26(21)25;5-3(6)1-2-4(7)8/h2-3,6-7,10,13-16H,4-5,8-9,11-12,17H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
• InChIKey: JYBLCDXVHQWMSU-WLHGVMLRSA-N
• SMILES: CC1=CC(=CN=C1)CN2CCC(=C3C4=C(CCC5=C3N=CC=C5)C=C(C=C4)Cl)CC2. C(=CC(=O)O)C(=O)O

Rupatadine Fumarate(CAS 182349-12-8) is an inhibitor of PAFR and histamine (H1) receptor with Ki of 550 nM and 102 nM, respectively.
Rupatadine inhibits both platelet-activating factor (PAF) and histamine (H1) effects through its interaction with specific receptors. Rupatadine competitively inhibits histamine-induced guinea pig ileum contraction (pA2 = 9.29 ± 0.06) without affecting contraction induced by ACh, serotonin or leukotriene D4(LTD4). It also competitively inhibits PAF-induced platelet aggregation in washed rabbit platelets (WRP) (pA2= 6.68 ± 0.08) and in human platelet-rich plasma (HPRP) (IC50 = 0.68 μM), while not affecting ADP- or arachidonic acid-induced platelet aggregation.
Rupatadine blocks histamine- and PAF-induced effects in vivo, such as hypotension in rats (ID50 = 1.4 and 0.44 mg/kg i.v., respectively) and bronchoconstriction in guinea pigs (ID50 = 113 and 9.6 μg/kg i.v.). Moreover, it potently inhibits PAF-induced mortality in mice (ID50 = 0.31 and 3.0 mg/kg i.v. and p.o., respectively) and endotoxin-induced mortality in mice and rats (ID50 = 1.6 and 0.66 mg/kg i.v.). Rupatadine/'s duration of action is long, as assessed by the histamine- and PAF-induced increase in vascular permeability test in dogs (42 and 34% inhibition at 26 h after 1 mg/kg p.o.). Rupatadine at a dose of 100 mg/kg p.o. neither modifies spontaneous motor activity nor prolongs barbiturate-sleeping time in mice, which indicates a lack of sedative effects.

Overview of Clinical Research

Rupatadine Fumarate is a histamine H1 receptor antagonist, which is considered as a platelet activating factor inhibitor. Teikoku Seiyaku and Mitsubishi Tanabe Pharma Corporation launched rupatadine fumarate (Rupafin®) in Japan on November 27, 2017.

Reference

1:Olopatadine hydrochloride and rupatadine fumarate in seasonal allergic rhinitis: A comparative study of efficacy and safety. Maiti R, Jaida J, Rahman J, Gaddam R, Palani A.J Pharmacol Pharmacother. 2011 Oct;2(4):270-6. doi: 10.4103/0976-500X.85958. PMID: 22025856 Free PMC Article
2:Fixed drug eruption against rupatadine fumarate. Fidan V, Fidan T.J Craniofac Surg. 2011 Sep;22(5):1682-3. doi: 10.1097/SCS.0b013e31822e5c76. PMID: 21959412
3:Futura study: evaluation of efficacy and safety of rupatadine fumarate in the treatment of persistent allergic rhinitis. Mion Ode G, Campos RA, Antila M, Rapoport PB, Rosario N, de Mello Junior JF, Guimarães RE, Mocellin M, Di Gesu G, Solé D, Wexler L, de Mello JF, Castro FM, Chavarria ML.Braz J Otorhinolaryngol. 2009 Sep-Oct;75(5):673-9. PMID: 19893935 Free Article