Orvepitant - CAS 579475-18-6
Catalog number:
579475-18-6
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C31H35F7N4O2
Molecular Weight:
628.63
COA:
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Targets:
Neurokinin 1 Receptor
Description:
Orvepitant is a potent and selective Neurokinin-1 (NK1) antagonist. It may be potential therapeutic for the treatment of patients with major depressive disorder (MDD), anxiety and insomnia. It was developed by GlaxoSmithKline and is in clinical phase 2 trials.
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Purity:
95%
Appearance:
Solid powder
Synonyms:
(2R,4S)-4-[(8aS)-6-oxo-1,3,4,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-N-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-(4-fluoro-2-methylphenyl)-N-methylpiperidine-1-carboxamide;GW-823296;GW823296
Solubility:
Soluble in DMSO, not in water
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
Orvepitant may be potential therapeutic for the treatment of patients with major depressive disorder (MDD), anxiety and insomnia.
Quality Standard:
In-house standard
Quantity:
Milligrams-Grams
Boiling Point:
627.5±55.0 °C | Condition: Press: 760 Torr
Density:
1.37±0.1 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
XWNBGDJPEXZSQM-VZOBGQTKSA-N
InChI:
InChI=1S/C31H35F7N4O2/c1-18-12-23(32)4-6-26(18)27-16-24(40-10-11-41-25(17-40)5-7-28(41)43)8-9-42(27)29(44)39(3)19(2)20-13-21(30(33,34)35)15-22(14-20)31(36,37)38/h4,6,12-15,19,24-25,27H,5,7-11,16-17H2,1-3H3/t19-,24+,25+,27-/m1/s1
Canonical SMILES:
CC1=C(C=CC(=C1)F)C2CC(CCN2C(=O)N(C)C(C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4CCN5C(C4)CCC5=O
Current Developer:
Orvepitant was developed by GlaxoSmithKline and is in clinical phase 2 trials.
1.Full central neurokinin-1 receptor blockade is required for efficacy in depression: evidence from orvepitant clinical studies.
Ratti E1, Bettica P, Alexander R, Archer G, Carpenter D, Evoniuk G, Gomeni R, Lawson E, Lopez M, Millns H, Rabiner EA, Trist D, Trower M, Zamuner S, Krishnan R, Fava M. J Psychopharmacol. 2013 May;27(5):424-34. doi: 10.1177/0269881113480990. Epub 2013 Mar 28.
Full, persistent blockade of central neurokinin-1 (NK1) receptors may be a potential antidepressant mechanism. The selective NK1 antagonist orvepitant (GW823296) was used to test this hypothesis. A preliminary positron emission tomography study in eight male volunteers drove dose selection for two randomized six week studies in patients with major depressive disorder (MDD). Displacement of central [(11)C]GR205171 binding indicated that oral orvepitant doses of 30-60 mg/day provided >99% receptor occupancy for ≥24 h. Studies 733 and 833 randomized patients with MDD and 17-item Hamilton Depression Rating Scale (HAM-D)≥22 to double-blind treatment with orvepitant 30 mg/day, orvepitant 60 mg/day or placebo (1:1:1). Primary outcome measure was change from baseline in 17-item HAM-D total score at Week 6 analyzed using mixed models repeated measures. Study 733 (n=328) demonstrated efficacy on the primary endpoint (estimated drug-placebo differences of 30 mg: -2.
2.Neurokinin-1 receptor antagonist orvepitant is an effective inhibitor of itch-associated response in a Mongolian gerbil model of scratching behaviour.
Trower MK1, Fisher A, Upton N, Ratti E. Exp Dermatol. 2014 Nov;23(11):858-60. doi: 10.1111/exd.12528.
Data suggest that substance P could play an important role in pruritus, and therefore, blockade of the neurokinin (NK)-1 receptor might be antipruritic. Thus, we explored in the Mongolian gerbil the effect on scratching behaviour, induced by intra-dermal injection of the NK-1 receptor-specific agonist GR73632, of oral administration of the NK-1 receptor antagonist orvepitant. Orvepitant at all doses tested (0.1-10 mg/kg p.o.) produced a profound inhibition of GR73632 (30 nmol i.d.) induced hindlimb scratching; the minimum effective dose of orvepitant in this model was identified as ≤0.1 mg/kg. The data generated supported the proposition that the antipruritic potential of orvepitant should be evaluated in clinical trials.
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CAS 579475-18-6 Orvepitant

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