Supply lowest price Eletriptan in China CAS NO.143322-58-1

Supply lowest price Eletriptan in China

Eletriptan, the seventh member of the triptan class of antimigraine drugs was launched in Switzerland for the acute treatment of migraine. The 5-step synthesis of this conformationally restricted analog of sumatriptan involves the deprotonation of 5- bromoindole with Grignard reagent at the position C3 followed by a condensation with NCbz- D-proline acid chloride to afford the key Cbz-D-prolyl intermediate. After reduction with LiAIH4, the sulfone moiety was introduced in postion 5 by a palladium cross-coupling Heck reaction using the phenylvinyl sulfone. Eletriptan is a 5-HT receptor agonist that binds to 5-HT_1B, 5HT_1D and 5HT_1F receptors with high potency. Activation of these receptors causes constriction of extracerebral intracranial vessels, abolition of the dural extravasation and neurogenic inflammation, and inhibition of trigeminal neuronal discharge. Eletriptan was found to be the most potent agonist at the 5-HT_1D receptor compared to the other triptans with pEC₅₀ value of 9.2. In thousands of participants in clinical trials, eletriptan has acted more effectively and more rapidly than sumatriptan to relieve pain from mild to severe attacks of migraine. Eletriptan also reduced time lost for ordinary activity to patients with migraine attacks when compared to placebo and when compared to sumatriptan. Eletriptan was also superior to sumatriptan in terms of relieving functional disability, nausea, photophobia and phonophobia. Unlike other compounds of its class, eletriptan has a positive logD value, that could underlie its rapid and complete oral absorption and may be suggestive of a good brain penetration. The oral biovailability of Eletriptan is approximately 50% (14% for Sumatriptan) with a half life of 5.7h (2h for Sumatriptan). Eletriptan was well tolerated with mild to moderate adverse events including asthenia, somnolence, dizziness and nausea. Eletriptan is a new potent and fast-acting triptan for the treatment of migraine attacks.

Eletriptan-d3 is a indole-pyrolidine conjugate that is labeled with deuterium at the N-methyl group of the pyrolidine moiety. This compound has shown 5-HTIB/ID receptor agonism that is slightly less potent, but comparable to sumatriptan (sc-204314). Eletriptan, like 5-HT and sumatriptan potently contracted saphenous vein (pEC50: 6.3, 6.9 and 6.1, respectively) and basilar artery (pEC50 7.2, 7.5 and 6.8, respectively).

Eletriptan is an agonist of the serotonin (5-HT) receptor types 5-HT_1B and 5-HT_1D. It inhibits forskolin-induced cAMP accumulation in and induces vasoconstriction of isolated rabbit common carotid artery rings (pD₂s = 7.6 and 4.9, respectively), an effect that can be blocked by the 5-HT_1B antagonist SB216641 but not the 5-HT_1D antagonist BRL15572. Eletriptan preferentially induces constriction of isolated human cerebral over coronary arteries (EC₅₀s = 15.8 and 1,995 nM, respectively). Formulations containing eletriptan have been used in the treatment of migraine headache

Name

Eletriptan

Synonyms

3-[(1-Methylpyrrolidin-2-yl)methyl]-5-(2-phenylsulfonylethyl)-1H-indole

Molecular Structure

Molecular Formula

C22H26N2O2S

Molecular Weight

382.52

CAS Number(Or Watson Number for Non-CAS Products)

143322-58-1

EINECS

Assay, Purity or Standard

98% min

Identification

HNMR/IR