ULIMORELIN HYDROCHLORIDE ANHYDROUS

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H39FN4O4.ClH
Molecular Weight	575.114
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of ULIMORELIN HYDROCHLORIDE ANHYDROUS

Structure Search

SMILES

Cl.C[C@@H]1CN[C@@H](C2CC2)C(=O)N(C)[C@H](C)C(=O)N[C@H](CC3=CC=C(F)C=C3)C(=O)NCCCC4=CC=CC=C4O1

InChI

InChIKey=WZRLNIOAVAFOOD-UZAUECDSSA-N

InChI=1S/C30H39FN4O4.ClH/c1-19-18-33-27(23-12-13-23)30(38)35(3)20(2)28(36)34-25(17-21-10-14-24(31)15-11-21)29(37)32-16-6-8-22-7-4-5-9-26(22)39-19;/h4-5,7,9-11,14-15,19-20,23,25,27,33H,6,8,12-13,16-18H2,1-3H3,(H,32,37)(H,34,36);1H/t19-,20-,25-,27+;/m1./s1

HIDE SMILES / InChI

Description
Sources: https://adisinsight.springer.com/drugs/800021027 | https://www.ncbi.nlm.nih.gov/pubmed/22106937 | https://www.ncbi.nlm.nih.gov/pubmed/25687251

Ulimorelin (TZP101) is a small molecule, intravenously administered, ghrelin receptor agonist that is being developed by Lyric Pharmaceuticals. Ulimorelin stimulates intestinal motility, but also reduces blood pressure in rodents and humans and dilates blood vessels. It has been proposed as a treatment for intestinal motility disorders. Ulimorelin has progressed to phase III human clinical trials for the treatment of postoperative ileus.

Originator

Approval Year

PubMed

Title	Date	PubMed
Analysis of the ghrelin receptor-independent vascular actions of ulimorelin.	2015-04-05	25687251
The mechanism of enhanced defecation caused by the ghrelin receptor agonist, ulimorelin.	2014-02	24304447
Optimization of the potency and pharmacokinetic properties of a macrocyclic ghrelin receptor agonist (Part I): Development of ulimorelin (TZP-101) from hit to clinic.	2011-12-22	22106937

Patents

Sample Use Guides

In Vivo Use Guide

Partial bowel resection: Thirty-minute intravenous infusions (160 ug/kg, 480 ug/kg ulimorelin, or placebo) once daily were started within 60 minutes after the end of surgery and ended at the first of the following: primary efficacy end point fulfilled (defined below), hospital discharge, or 7 days treatment.

Route of Administration: Intravenous

In Vitro Use Guide

Ulimorelin (0.03-30uM) inhibited phenylephrine-induced contractions of rat saphenous (IC50=0.6uM; Imax=66±5%; n=3-6) and mesenteric arteries (IC50=5uM, Imax=113±16%; n=3-4). In mesenteric arteries, ulimorelin, 1-10uM, caused a surmountable rightward shift in the response to phenylephrine (0.01-1000uM; pA2=5.7; n=3-4). Ulimorelin is an agonist of G-protein coupled receptor (Ki=16 nM, EC50=29 nM).

Name

Type

Language

ULIMORELIN HYDROCHLORIDE ANHYDROUS

Common Name

English

D-PHENYLALANINE, (2S)-N-((2R)-2-(2-(3-AMINOPROPYL)PHENOXY)PROPYL)-2-CYCLOPROPYLGLYCYL-N-METHYL-D-ALANYL-4-FLUORO-, (3->1)-LACTAM, HYDROCHLORIDE (1:1)

Preferred Name

English

Ulimorelin hydrochloride [WHO-DD]

Common Name

English

(2R,5S,8R,11R)-5-CYCLOPROPYL-11-((4-FLUOROPHENYL)METHYL)-2,7,8-TRIMETHYL- 2,3,4,5,7,8,10,11,13,14,15,16-DODECAHYDRO-6H-1,4,7,10,13- BENZOXATETRAAZACYCLOOCTADECINE-6,9,12-TRIONE HYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID20236344