NAV

Ulimorelin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Ulimorelin
DrugBank Accession Number
DB12128
Background

Ulimorelin is a novel small molecule ghrelin agonist being developed by Tranzyme Pharma as a first-in-class treatment for both POI and diabetic gastroparesis, serious medical conditions in which motility of the GI tract is severely impaired.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 538.664
Monoisotopic: 538.295533915
Chemical Formula
C30H39FN4O4
Synonyms
  • Ulimorelin
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Data gathered thus far demonstrate that Ulimorelin induces a dose-dependent increase of gastric emptying that effectively reverses the delay caused by surgically induced postoperative ileus (POI). Treatment levels as low as 30µg/kg have been shown to be effective in stimulating GI transit in this model. Furthermore, Ulimorelin significantly stimulates gastric emptying in naïve rats with 100-fold greater potency than metoclopramide, a compound currently marketed as a prokinetic treatment for gastroparesis.

Mechanism of action

Postoperative ileus (POI) is a major cause of postoperative complications and prolonged hospitalization. Ghrelin, which is the endogenous ligand for the growth hormone secretagogue receptor, has been found to stimulate gastric motility and accelerate gastric emptying. Ulimorelin is a synthetic ghrelin-receptor agonist, and has been shown to improve gastrointestinal transit in rats with POI.

TargetActionsOrganism
UGrowth hormone secretagogue receptor type 1Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ulimorelin Hydrochloride662MCS79XH951326-02-6ZWIXEQBDJMFCMN-DHHNQDMHSA-N

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Macrolactams / Alpha amino acids and derivatives / Fluorobenzenes / Alkyl aryl ethers / Aryl fluorides / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Lactams / Oxacyclic compounds / Dialkylamines
show 5 more
Substituents
Alkyl aryl ether / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
LGI67MCW2S
CAS number
842131-33-3
InChI Key
WGYPAJVJMXQXTR-ABNZCKJZSA-N
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
IUPAC Name
(2R,5S,8R,11R)-5-cyclopropyl-11-[(4-fluorophenyl)methyl]-2,7,8-trimethyl-3,4,5,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-2H-1,4,7,10,13-benzoxatetrazacyclooctadecine-6,9,12-trione
SMILES
C[C@@H]1CN[C@@H](C2CC2)C(=O)N(C)[C@H](C)C(=O)N[C@H](CC2=CC=C(F)C=C2)C(=O)NCCCC2=CC=CC=C2O1

References

General References
  1. Venkova K, Fraser G, Hoveyda HR, Greenwood-Van Meerveld B: Prokinetic effects of a new ghrelin receptor agonist TZP-101 in a rat model of postoperative ileus. Dig Dis Sci. 2007 Sep;52(9):2241-8. Epub 2007 Apr 10. [Article]
PubChem Compound
11526696
PubChem Substance
347828427
ChemSpider
9701482
BindingDB
50359256
ChEMBL
CHEMBL1963249
Wikipedia
Ulimorelin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentGastrointestinal Dysmotility2
3CompletedTreatmentPostoperative paralytic ileus1
2CompletedTreatmentDiabetes Mellitus / Gastroparesis1
2CompletedTreatmentEnteral Feeding Intolerance (EFI)1
2CompletedTreatmentPostoperative paralytic ileus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00834 mg/mLALOGPS
logP2.86ALOGPS
logP3.19Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)11.14Chemaxon
pKa (Strongest Basic)6.27Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area99.77 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity146.39 m3·mol-1Chemaxon
Polarizability58.53 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0000090000-7eca581534efa602094f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0000090000-d92f929e7e22575ff228
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0000090000-dcb9cf63e83f635d025d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0000090000-3419f36181b063b53624
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kf-9600120000-b3076028e7f8cc3d8177
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fri-6309840000-749e50b6216a4a21d27f
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-227.07114
predicted
DeepCCS 1.0 (2019)
[M+H]+228.96654
predicted
DeepCCS 1.0 (2019)
[M+Na]+234.74487
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Growth hormone secretagogue receptor type 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Peptide hormone binding
Specific Function
Receptor for ghrelin, coupled to G-alpha-11 proteins. Stimulates growth hormone secretion. Binds also other growth hormone releasing peptides (GHRP) (e.g. Met-enkephalin and GHRP-6) as well as non-...
Gene Name
GHSR
Uniprot ID
Q92847
Uniprot Name
Growth hormone secretagogue receptor type 1
Molecular Weight
41328.045 Da
References
  1. Venkova K, Fraser G, Hoveyda HR, Greenwood-Van Meerveld B: Prokinetic effects of a new ghrelin receptor agonist TZP-101 in a rat model of postoperative ileus. Dig Dis Sci. 2007 Sep;52(9):2241-8. Epub 2007 Apr 10. [Article]

Drug created at October 20, 2016 21:24 / Updated at February 21, 2021 18:53