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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
Structure of LANEPITANT

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

HIDE SMILES / InChI

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Pharmacological characterization of LY303870: a novel, potent and selective nonpeptide substance P (neurokinin-1) receptor antagonist.
1995 Nov
Lanepitant, an NK-1 antagonist, in migraine prevention.
2001 Mar
Neurokinin-1 receptor antagonists: a comprehensive patent survey.
2010 Aug
Patents

Patents

Sample Use Guides

In Vitro Use Guide
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 Fri Dec 15 16:04:30 GMT 2023
Edited
by admin
on Fri Dec 15 16:04:30 GMT 2023
Record UNII
17G8FN2E1F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LANEPITANT
INN  
INN  
Official Name English
N-((R)-2-INDOL-3-YL-1-((N-(O-METHOXYBENZYL)ACETAMIDO)METHYL)ETHYL)(1,4'-BIPIPERIDINE)-1'-ACETAMIDE
Common Name English
lanepitant [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Fri Dec 15 16:04:30 GMT 2023 , Edited by admin on Fri Dec 15 16:04:30 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL42407
Created by admin on Fri Dec 15 16:04:30 GMT 2023 , Edited by admin on Fri Dec 15 16:04:30 GMT 2023
PRIMARY
WIKIPEDIA
Lanepitant
Created by admin on Fri Dec 15 16:04:30 GMT 2023 , Edited by admin on Fri Dec 15 16:04:30 GMT 2023
PRIMARY
INN
7616
Created by admin on Fri Dec 15 16:04:30 GMT 2023 , Edited by admin on Fri Dec 15 16:04:30 GMT 2023
PRIMARY
CAS
170566-84-4
Created by admin on Fri Dec 15 16:04:30 GMT 2023 , Edited by admin on Fri Dec 15 16:04:30 GMT 2023
PRIMARY
SMS_ID
100000082573
Created by admin on Fri Dec 15 16:04:30 GMT 2023 , Edited by admin on Fri Dec 15 16:04:30 GMT 2023
PRIMARY
FDA UNII
17G8FN2E1F
Created by admin on Fri Dec 15 16:04:30 GMT 2023 , Edited by admin on Fri Dec 15 16:04:30 GMT 2023
PRIMARY
PUBCHEM
3086681
Created by admin on Fri Dec 15 16:04:30 GMT 2023 , Edited by admin on Fri Dec 15 16:04:30 GMT 2023
PRIMARY
EVMPD
SUB08397MIG
Created by admin on Fri Dec 15 16:04:30 GMT 2023 , Edited by admin on Fri Dec 15 16:04:30 GMT 2023
PRIMARY
NCI_THESAURUS
C79124
Created by admin on Fri Dec 15 16:04:30 GMT 2023 , Edited by admin on Fri Dec 15 16:04:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID80168879
Created by admin on Fri Dec 15 16:04:30 GMT 2023 , Edited by admin on Fri Dec 15 16:04:30 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY