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

Identification

Name
Rivoglitazone
Accession Number
DB09200
Type
Small Molecule
Groups
Experimental, Investigational
Description

Rivoglitazone (INN) is a thiazolidinedione undergoing research for use in the treatment of type 2 diabetes. It is being developed by Daiichi Sankyo Co.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
3A3N0634Q6
CAS number
185428-18-6
Weight
Average: 397.45
Monoisotopic: 397.109627278
Chemical Formula
C20H19N3O4S
InChI Key
XMSXOLDPMGMWTH-UHFFFAOYSA-N
InChI
InChI=1S/C20H19N3O4S/c1-23-16-10-14(26-2)7-8-15(16)21-18(23)11-27-13-5-3-12(4-6-13)9-17-19(24)22-20(25)28-17/h3-8,10,17H,9,11H2,1-2H3,(H,22,24,25)
IUPAC Name
5-({4-[(6-methoxy-1-methyl-1H-1,3-benzodiazol-2-yl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
SMILES
COC1=CC=C2N=C(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)N(C)C2=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
DrugInteraction
(R)-warfarinThe metabolism of Rivoglitazone can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Rivoglitazone.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Rivoglitazone is combined with 2,4-thiazolidinedione.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Rivoglitazone.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Rivoglitazone.
5-(2-methylpiperazine-1-sulfonyl)isoquinolineThe therapeutic efficacy of Rivoglitazone can be increased when used in combination with 5-(2-methylpiperazine-1-sulfonyl)isoquinoline.
5-androstenedioneThe metabolism of Rivoglitazone can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Rivoglitazone can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Rivoglitazone.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Rivoglitazone.
Food Interactions
Not Available

References

General References
  1. Kong AP, Yamasaki A, Ozaki R, Saito H, Asami T, Ohwada S, Ko GT, Wong CK, Leung GT, Lee KF, Yeung CY, Chan JC: A randomized-controlled trial to investigate the effects of rivoglitazone, a novel PPAR gamma agonist on glucose-lipid control in type 2 diabetes. Diabetes Obes Metab. 2011 Sep;13(9):806-13. doi: 10.1111/j.1463-1326.2011.01411.x. [PubMed:21492364]
  2. Schimke K, Davis TM: Drug evaluation: rivoglitazone, a new oral therapy for the treatment of type 2 diabetes. Curr Opin Investig Drugs. 2007 Apr;8(4):338-44. [PubMed:17458185]
External Links
PubChem Compound
3055168
PubChem Substance
310265108
ChemSpider
2316729
ChEMBL
CHEMBL2104753
HET
7VA
Wikipedia
Rivoglitazone
PDB Entries
5u5l

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3CompletedTreatmentType 2 Diabetes Mellitus1

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 Solubility0.0388 mg/mLALOGPS
logP3.13ALOGPS
logP2.81ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)6.62ChemAxon
pKa (Strongest Basic)4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.45 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity105.33 m3·mol-1ChemAxon
Polarizability41.96 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Not Available
Direct Parent
Benzimidazoles
Alternative Parents
Phenoxy compounds / Anisoles / Thiazolidinediones / Alkyl aryl ethers / N-substituted imidazoles / Heteroaromatic compounds / Dicarboximides / Thiocarbamic acid derivatives / Organic carbonic acids and derivatives / Azacyclic compounds
show 5 more
Substituents
Benzimidazole / Phenoxy compound / Anisole / Phenol ether / Alkyl aryl ether / Thiazolidinedione / Monocyclic benzene moiety / Benzenoid / N-substituted imidazole / Azole
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
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. Jaakkola T, Backman JT, Neuvonen M, Neuvonen PJ: Effects of gemfibrozil, itraconazole, and their combination on the pharmacokinetics of pioglitazone. Clin Pharmacol Ther. 2005 May;77(5):404-14. doi: 10.1016/j.clpt.2004.12.266. [PubMed:15900286]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Jaakkola T, Backman JT, Neuvonen M, Neuvonen PJ: Effects of gemfibrozil, itraconazole, and their combination on the pharmacokinetics of pioglitazone. Clin Pharmacol Ther. 2005 May;77(5):404-14. doi: 10.1016/j.clpt.2004.12.266. [PubMed:15900286]

Drug created on October 16, 2015 16:18 / Updated on November 02, 2018 07:00