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

Identification

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Name
Mitemcinal
Accession Number
DB06587
Type
Small Molecule
Groups
Investigational
Description

Mitemcinal (GM-611) is a novel erythromycin-derived prokinetic agent that acts as an agonist at the motilin receptor.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Mitemcinal fumarateXU63LQ260J154802-96-7IDLXWTNPDREJQZ-HSOMBQIOSA-N
Categories
UNII
6X5NRJ664L
CAS number
154738-42-8
Weight
Average: 755.987
Monoisotopic: 755.481976666
Chemical Formula
C40H69NO12
InChI Key
BELMMAAWNYFCGF-PZXAHSFZSA-N
InChI
InChI=1S/C40H69NO12/c1-16-28-40(12,47-15)33(43)23(6)31-21(4)18-39(11,53-31)35(52-37-30(42)27(17-22(5)48-37)41(13)20(2)3)24(7)32(25(8)36(45)50-28)51-29-19-38(10,46-14)34(44)26(9)49-29/h20,22-30,32,34-35,37,42,44H,16-19H2,1-15H3/t22-,23+,24+,25-,26+,27+,28-,29+,30-,32+,34+,35-,37+,38-,39-,40-/m1/s1
IUPAC Name
(2S,4R,5R,8R,9S,10S,11R,12R)-5-ethyl-9-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-11-{[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[methyl(propan-2-yl)amino]oxan-2-yl]oxy}-4-methoxy-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-ene-3,7-dione
SMILES
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C(C)C)[C@@]2(C)CC(C)=C(O2)[C@H](C)C(=O)[C@]1(C)OC

Pharmacology

Indication

Investigated for use/treatment in gastroparesis and irritable bowel syndrome (IBS).

Pharmacodynamics
Not Available
Mechanism of action

Mitemcinal, an oral motilin agonist, accelerates gastric emptying.

TargetActionsOrganism
UMotilin receptorNot 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
Toxicity
Not Available
Affected organisms
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.
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Mitemcinal.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Mitemcinal.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Mitemcinal.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Mitemcinal.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Mitemcinal.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Mitemcinal.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Mitemcinal.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Mitemcinal.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Mitemcinal.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with Mitemcinal.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Saitoh R, Miyayama T, Mitsui T, Akiba Y, Higashida A, Takata S, Kawanishi T, Aso Y, Itoh Z, Omura S: Nonlinear intestinal pharmacokinetics of mitemcinal, the first acid-resistant non-peptide motilin receptor agonist, in rats. Xenobiotica. 2007 Dec;37(12):1421-32. [PubMed:17926229]
External Links
ChemSpider
5293473
BindingDB
85390
ChEMBL
CHEMBL2110756
Wikipedia
Mitemcinal

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentGastroparesis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.038 mg/mLALOGPS
logP4.2ALOGPS
logP4.9ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)12.63ChemAxon
pKa (Strongest Basic)9.63ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area151.68 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity197.85 m3·mol-1ChemAxon
Polarizability83.09 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminoglycosides
Alternative Parents
O-glycosyl compounds / Monosaccharides / Oxanes / Dihydrofurans / 1,2-aminoalcohols / Amino acids and derivatives / Carboxylic acid esters / Cyclic ketones / Trialkylamines / Lactones
show 9 more
Substituents
Aminoglycoside core / Glycosyl compound / O-glycosyl compound / Monosaccharide / Oxane / Dihydrofuran / 1,2-aminoalcohol / Amino acid or derivatives / Carboxylic acid ester / Ketone
show 22 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Growth hormone-releasing hormone receptor activity
Specific Function
Receptor for motilin.
Gene Name
MLNR
Uniprot ID
O43193
Uniprot Name
Motilin receptor
Molecular Weight
45343.725 Da
References
  1. Kimura K, Tabo M, Mizoguchi K, Kato A, Suzuki M, Itoh Z, Omura S, Takanashi H: Hemodynamic and electrophysiological effects of mitemcinal (GM-611), a novel prokinetic agent derived from erythromycin in a halothane-anesthetized canine model. J Toxicol Sci. 2007 Aug;32(3):231-9. [PubMed:17785940]
  2. Ozaki K, Monnai M, Onoma M, Muramatsu H, Yogo K, Watanabe T, Oda Y, Katagiri K, Arakawa H, Itoh Z, Omura S, Takanashi H: Effects of mitemcinal (GM-611), an orally active erythromycin-derived prokinetic agent, on delayed gastric emptying and postprandial glucose in a new minipig model of diabetes. J Diabetes Complications. 2008 Sep-Oct;22(5):339-47. doi: 10.1016/j.jdiacomp.2007.03.005. Epub 2008 Apr 16. [PubMed:18413164]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kuper JI, D'Aprile M: Drug-Drug interactions of clinical significance in the treatment of patients with Mycobacterium avium complex disease. Clin Pharmacokinet. 2000 Sep;39(3):203-14. [PubMed:11020135]

Drug created on March 19, 2008 10:38 / Updated on September 02, 2019 22:12