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
Structure for Ulimorelin (DB12128)
- Weight
- Average: 538.664
Monoisotopic: 538.295533915 - Chemical Formula
- C30H39FN4O4
- Synonyms
- Ulimorelin
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism UGrowth hormone secretagogue receptor type 1 Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Ulimorelin Hydrochloride 662MCS79XH 951326-02-6 ZWIXEQBDJMFCMN-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
- 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]
- External Links
- PubChem Compound
- 11526696
- PubChem Substance
- 347828427
- ChemSpider
- 9701482
- BindingDB
- 50359256
- ChEMBL
- CHEMBL1963249
- Wikipedia
- Ulimorelin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Gastrointestinal Dysmotility 2 3 Completed Treatment Postoperative paralytic ileus 1 2 Completed Treatment Diabetes Mellitus / Gastroparesis 1 2 Completed Treatment Enteral Feeding Intolerance (EFI) 1 2 Completed Treatment Postoperative paralytic ileus 1 1 Completed Diagnostic Digestive System Disorders 1 1 Completed Treatment Diabetes Mellitus / Gastroparesis 1 1 Completed Treatment Digestive System Disorders 1 1 Completed Treatment Healthy Subjects (HS) 1 1 Completed Treatment Postoperative paralytic ileus 1
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
Property Value Source Water Solubility 0.00834 mg/mL ALOGPS logP 2.86 ALOGPS logP 3.19 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 11.14 Chemaxon pKa (Strongest Basic) 6.27 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 99.77 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 146.39 m3·mol-1 Chemaxon Polarizability 58.53 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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