Eletriptan HBr

Names

[ Name ]:
Eletriptan HBr

[Synonym ]:
1H-indole, 3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-, monohydrobromide
Relert
(R)-3-((1-Methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole monohydrobromide
ELETRIPTAN HBR
(R)-3-((1-methylpyrrolidin-2-yl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole hydrobromide
3-{[(2R)-1-méthylpyrrolidin-2-yl]méthyl}-5-[2-(phénylsulfonyl)éthyl]-1H-indole bromhydrate
(R)-3-[(1-methyl-2-pyrrolidinyl)methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-indole hydrobromide salt
3-{[(2R)-1-Methylpyrrolidin-2-yl]methyl}-5-[2-(phenylsulfonyl)ethyl]-1H-indolhydrobromid
1H-Indole,3-(((2R)-1-methyl-2-pyrrolidinyl))methyl)-5-(2-(phenylsulfonyl)ethyl)-,monohydrobromide
3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(phenylsulfonyl)ethyl]-1H-indole hydrobromide
3-{[(2R)-1-Methylpyrrolidin-2-yl]methyl}-5-[2-(phenylsulfonyl)ethyl]-1H-indole hydrobromide (1:1)
(R)-5-[2-(Benzenesulfonyl)ethyl]-3-[(N-Methylpyrrolidin-2-yl)Methyl]-1H-indole hydrobroMide
3-{[(2R)-1-Methyl-2-pyrrolidinyl]methyl}-5-[2-(phenylsulfonyl)ethyl]-1H-indole hydrobromide (1:1)
3-{[(2R)-1-Methylpyrrolidin-2-yl]methyl}-5-[2-(phenylsulfonyl)ethyl]-1H-indolhydrobromid(1:1)
3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(phenylsulfonyl) ethyl]-1H-indole hydrobromide
(S)-3-((1-Methylpyrrolidin-2-yl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole
3-(((2r)-1-methyl-2-pyrrolidinyl))methyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole hydrobromide
1H-Indole, 3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-, hydrobromide (1:1)
Eletriptan Base
(R)-5-[2-(phenylsulfonyl)ethyl]-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole hydrobromide
Eletriptan hydrobromide
(R)-5-(phenylsulfonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole hydrobromide

Biological Activity

[Description]:

Eletriptan HBr is a selective 5-HT1B and 5-HT1D receptor agonist with Ki of 0.92 nM and 3.14 nM, respectively.IC50 value: 0.82 nM/3.14 nM (5-HT1B/5-HT1D, Ki) [1]Target: 5-HT1B/5-HT1D in vitro: [3H]Eletriptan has a total number of binding sites (Bmax) of 2478 fmol/mg and 1576 fmol/mg for 5-HT1B and 5-HT1D, respectively. [3H]Eletriptan has a significantly faster association rate (K(on) 0.249/min/nM) than [3H]sumatriptan (K(on) 0.024/min/nM) and a significantly slower off-rate (K(off) 0.027/min compared to 0.037/min for [3H]sumatriptan) [1]. Eletriptan induces concentration-dependent contractions of meningeal artery, coronary artery, and saphenous vein. The potency of Eletriptan is higher in meningeal artery than in coronary artery (86-fold) or saphenous vein (66-fold). The predicted contraction by Eletriptan (40 mg and 80 mg) and sumatriptan (100 mg) at free C(max) observed in clinical trials is similar in meningeal artery [2].in vivo: Eletriptan (<1000 mg/kg, i.v.) produces a dose-dependent reduction of carotid arterial blood flow in the anaesthetised dog. Eletriptan reduces coronary artery diameter with ED50 value of 63 mg/kg in the anaesthetised dog. Eletriptan (<300 mg/kg, i.v.) administered prior to electrical stimulation of the trigeminal ganglion produces a dose-related and complete inhibition of plasma protein extravasation in the dura mater rats. Eletriptan (100 mg/kg, i.v.) produces a complete inhibition of plasma protein extravasation in rat dura mater [3]. Iontophoretic ejection (50 nA) of Eletriptan suppresses the response in 75% of cells and causes an average suppression of cell firing of 42% in cats [4].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

Research Areas >> Neurological Disease

[References]

[1]. Napier C, et al. Characterisation of the 5-HT receptor binding profile of eletriptan and kinetics of [3H]eletriptan binding at human 5-HT1B and 5-HT1D receptors. Eur J Pharmacol, 1999, 368(2-3), 259-268.

[2]. MaassenVanDenBrink A, et al. Craniovascular selectivity of eletriptan and sumatriptan in human isolated blood vessels. Neurology, 2000, 55(10), 1524-1530.

[3]. Gupta P, et al. The in vivo pharmacological profile of eletriptan (UK-116,044): a potent and novel 5-HT(1B/1D) receptor agonist. Eur J Pharmacol, 2000, 398(1), 73-81.

[4]. Hoskin KL, et al. The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat. Brain Res, 2004, 998(1), 91-99.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
633.9ºC at 760 mmHg

[ Melting Point ]:
169-171ºC

[ Molecular Formula ]:
C₂₂H₂₇BrN₂O₂S

[ Molecular Weight ]:
463.43

[ Flash Point ]:
337.2ºC

[ PSA ]:
61.55000

[ LogP ]:
4.83970

[ Vapour Pressure ]:
1.58E-16mmHg at 25°C

[ Storage condition ]:
Desiccate at RT

[ Water Solubility ]:
DMSO: >10mg/mL

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds

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