Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H45N5O3 |
Molecular Weight | 559.7421 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(CN(C[C@@H](CC2=CNC3=C2C=CC=C3)NC(=O)CN4CCC(CC4)N5CCCCC5)C(C)=O)C=CC=C1
InChI
InChIKey=CVXJAPZTZWLRBP-MUUNZHRXSA-N
InChI=1S/C33H45N5O3/c1-25(39)38(22-26-10-4-7-13-32(26)41-2)23-28(20-27-21-34-31-12-6-5-11-30(27)31)35-33(40)24-36-18-14-29(15-19-36)37-16-8-3-9-17-37/h4-7,10-13,21,28-29,34H,3,8-9,14-20,22-24H2,1-2H3,(H,35,40)/t28-/m1/s1
Molecular Formula | C33H45N5O3 |
Molecular Weight | 559.7421 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
LANEPITANT is a selective nonpeptide antagonist for the neurokinin-1 receptor. It inhibits neurogenic dural inflammation. LANEPITANT was under development as a potential analgesic drug for the treatment of migraine, arthritis and diabetic neuropathy. However, it failed to show sufficient efficacy to support further development.
Originator
Approval Year
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7473161
Lanepitant (LY303870) bound selectively and with high affinity to human peripheral (Ki = 0.15 nM) and central (Ki = 0.10 nM) neurokinin-1 (NK-1) receptor. LY303870 inhibited [125I]substance P (SP) binding to guinea pig brain homogenates with similar affinity; however, it had approximately 50-fold lesser affinity for rat NK-1 sites. The less active S-enantiomer was 1,000- to 15,000-fold less potent in all the species examined. LY303870 antagonized in vitro NK-1 receptor effects as demonstrated by blockade of SP-stimulated phosphoinositide turnover in UC-11 MG human astrocytoma cells (Ki = 1.5 nM) and interleukin-6 secretion from U-373 MG human astrocytoma cells (Ki = 5 nM). In addition, LY303870 inhibited SP-induced rabbit vena cava contractions (pA2 = 9.4) with high (50,000-fold) selectivity vs. NK-2 or NK-3 receptor-mediated responses.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:04:30 UTC 2023
by
admin
on
Fri Dec 15 16:04:30 UTC 2023
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Record UNII |
17G8FN2E1F
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C267
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CHEMBL42407
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Lanepitant
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7616
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170566-84-4
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100000082573
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17G8FN2E1F
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3086681
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SUB08397MIG
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C79124
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DTXSID80168879
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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