Ulimorelin

Ulimorelin (INN, USAN) (developmental code name TZP-101) is a drug with a modified cyclic peptide structure which acts as a selective agonist of the ghrelin/growth hormone secretagogue receptor (GHSR-1a).^[1] Unlike many related drugs, ulimorelin has little or no effect on growth hormone (GH) release in rats.^[2] However, like ghrelin and other ghrelin agonists, ulimorelin does stimulate GH release with concomitant increases in insulin-like growth factor 1 (IGF-1) in humans.^[3] It has been researched for enhancing gastrointestinal motility, especially in gastroparesis^[4] and in aiding recovery of bowel function following gastrointestinal surgery, where opioid analgesic drugs used for post-operative pain relief may worsen existing constipation.^[5][6][7][8] While ulimorelin has been shown to increase both upper and lower gastrointestinal motility in rats,^[8] and showed promising results initially in humans,^[4][6] it failed in pivotal clinical trials in post operative ileus.^[7]

ATC code

• None

CAS Number

• 842131-33-3

PubChem CID

• 11526696

ChemSpider

• 9701482

Quick facts Clinical data, ATC code ...

Ulimorelin

Clinical data
ATC code	None
Identifiers
IUPAC name (7R,10R,13S,16R)-13-cyclopropyl-7-(4-fluorobenzyl)-10,11,16-trimethyl-17-oxa-5,8,11,14-tetrazabicyclo[16.4.0]docosa-1(22),18,20-triene-6,9,12-trione
CAS Number	842131-33-3
PubChem CID	11526696
ChemSpider	9701482
UNII	LGI67MCW2S
KEGG	D09981
CompTox Dashboard (EPA)	DTXSID00233139
Chemical and physical data
Formula	C30H39FN4O4
Molar mass	538.664 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@@H]1CN[C@H](C(=O)N([C@@H](C(=O)N[C@@H](C(=O)NCCCC2=CC=CC=C2O1)CC3=CC=C(C=C3)F)C)C)C4CC4
InChI InChI=1S/C30H39FN4O4/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)/t19-,20-,25-,27+/m1/s1 Key:WGYPAJVJMXQXTR-ABNZCKJZSA-N

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A common side effect of ghrelin is reduced blood pressure. Ulimorelin has been shown to inhibit vasoconstriction of rat arteries in vitro elicited by the α₁-adrenoceptors agonists phenylephrine and methoxamine, and to increase artery tension at high concentrations.^[9] Effects on blood pressure, however, were not observed in human clinical trials.^[4][7]