ULIMORELIN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H39FN4O4.ClH.H2O
Molecular Weight	593.13
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.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=C(O1)C=CC=C4

InChI

InChIKey=ZWIXEQBDJMFCMN-DHHNQDMHSA-N

InChI=1S/C30H39FN4O4.ClH.H2O/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;1H2/t19-,20-,25-,27+;;/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	C30H39FN4O4
Molecular Weight	538.6535
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
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

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
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 Dec 22	22106937
The mechanism of enhanced defecation caused by the ghrelin receptor agonist, ulimorelin.	2014 Feb	24304447
Analysis of the ghrelin receptor-independent vascular actions of ulimorelin.	2015 Apr 5	25687251

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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:35:18 GMT 2023` Edited by `admin` on `Fri Dec 15 18:35:18 GMT 2023`
Record UNII	662MCS79XH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ULIMORELIN HYDROCHLORIDE

Official 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 MONOHYDRATE

Systematic Name

English

ULIMORELIN HYDROCHLORIDE MONOHYDRATE

Common Name

English

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

Common Name

English

Ulimorelin hydrochloride monohydrate [WHO-DD]

Common Name

English

ULIMORELIN HYDROCHLORIDE MONOHYDRATE [MI]

Common Name

English

ULIMORELIN HYDROCHLORIDE [USAN]

Common Name

English

TZP-101

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C78276