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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H45N5O3.2ClH.3H2O
Molecular Weight 686.71
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LANEPITANT DIHYDROCHLORIDE TRIHYDRATE

SMILES

O.O.O.Cl.Cl.COC1=C(CN(C[C@@H](CC2=CNC3=C2C=CC=C3)NC(=O)CN4CCC(CC4)N5CCCCC5)C(C)=O)C=CC=C1

InChI

InChIKey=MMXNJDDJYCKAES-BQPUMDETSA-N
InChI=1S/C33H45N5O3.2ClH.3H2O/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);2*1H;3*1H2/t28-;;;;;/m1...../s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Study of the analgesic effect of lanepitant in patients with osteoarthritis pain.
2000 Apr
Dose-response study of the analgesic effect of lanepitant in patients with painful diabetic neuropathy.
2001 Jan-Feb
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 15:57:16 GMT 2023
Edited
by admin
on Fri Dec 15 15:57:16 GMT 2023
Record UNII
2Q5BV72CQE
Record Status Validated (UNII)
Record Version
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Name Type Language
LANEPITANT DIHYDROCHLORIDE TRIHYDRATE
Common Name English
(1,4'-BIPIPERIDINE)-1'-ACETAMIDE, N-((1R)-2-(ACETYL((2-METHOXYPHENYL)METHYL)AMINO)-1-(1H-INDOL-3-YLMETHYL)ETHYL)-, DIHYDROCHLORIDE, TRIHYDRATE
Systematic Name English
Code System Code Type Description
FDA UNII
2Q5BV72CQE
Created by admin on Fri Dec 15 15:57:16 GMT 2023 , Edited by admin on Fri Dec 15 15:57:16 GMT 2023
PRIMARY
PUBCHEM
9853000
Created by admin on Fri Dec 15 15:57:16 GMT 2023 , Edited by admin on Fri Dec 15 15:57:16 GMT 2023
PRIMARY
CAS
167678-33-3
Created by admin on Fri Dec 15 15:57:16 GMT 2023 , Edited by admin on Fri Dec 15 15:57:16 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE