Otenabant

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

Identification

Generic Name
Otenabant
DrugBank Accession Number
DB11745
Background

Otenabant has been investigated for the treatment of Obesity.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 510.42
Monoisotopic: 509.1497639
Chemical Formula
C25H25Cl2N7O
Synonyms
  • Otenabant
External IDs
  • CP-945,598
  • CP-945598
  • CP-945598-01

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Pharmacodynamics

Not Available

Mechanism of action

Pre-clinical and clinical trial data suggest that CB-1 antagonists may have favorable effects on glucose metabolism in patients with type 2 diabetes and may also be an effective therapy for the treatment of obesity.

TargetActionsOrganism
UCannabinoid receptor 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
Adverseeffects
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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
Otenabant hydrochlorideX2166Z319O686347-12-6KPYUQCJBZGQHPL-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Phenylimidazoles / 6-alkylaminopurines / Piperidinecarboxamides / Dialkylarylamines / Aminopiperidines / Aminopyrimidines and derivatives / Chlorobenzenes / N-substituted imidazoles / Imidolactams / Aryl chlorides
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Substituents
1-phenylimidazole / 2-phenylimidazole / 4-aminopiperidine / 6-alkylaminopurine / 6-aminopurine / Alpha-amino acid amide / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Aryl chloride
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
J8211Y53EF
CAS number
686344-29-6
InChI Key
UNAZAADNBYXMIV-UHFFFAOYSA-N
InChI
InChI=1S/C25H25Cl2N7O/c1-2-31-25(24(28)35)11-13-33(14-12-25)22-20-23(30-15-29-22)34(17-9-7-16(26)8-10-17)21(32-20)18-5-3-4-6-19(18)27/h3-10,15,31H,2,11-14H2,1H3,(H2,28,35)
IUPAC Name
1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-(ethylamino)piperidine-4-carboxamide
SMILES
CCNC1(CCN(CC1)C1=C2N=C(N(C2=NC=N1)C1=CC=C(Cl)C=C1)C1=CC=CC=C1Cl)C(N)=O

References

General References
  1. Heimann AS, Gomes I, Dale CS, Pagano RL, Gupta A, de Souza LL, Luchessi AD, Castro LM, Giorgi R, Rioli V, Ferro ES, Devi LA: Hemopressin is an inverse agonist of CB1 cannabinoid receptors. Proc Natl Acad Sci U S A. 2007 Dec 18;104(51):20588-93. Epub 2007 Dec 12. [Article]
  2. Buchweitz JP, Karmaus PW, Williams KJ, Harkema JR, Kaminski NE: Targeted deletion of cannabinoid receptors CB1 and CB2 produced enhanced inflammatory responses to influenza A/PR/8/34 in the absence and presence of Delta9-tetrahydrocannabinol. J Leukoc Biol. 2008 Mar;83(3):785-96. Epub 2007 Dec 11. [Article]
  3. Gerdeman GL, Schechter JB, French ED: Context-specific reversal of cocaine sensitization by the CB1 cannabinoid receptor antagonist rimonabant. Neuropsychopharmacology. 2008 Oct;33(11):2747-59. Epub 2007 Dec 5. [Article]
PubChem Compound
10052040
PubChem Substance
347828103
ChemSpider
8227602
BindingDB
27337
ChEMBL
CHEMBL562668
ZINC
ZINC000003948997
Wikipedia
Otenabant

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentObesity (Disorder)4
2, 3CompletedTreatmentObesity (Disorder)1
1CompletedBasic ScienceNon Alcoholic Steatohepatitis (NASH)1
1CompletedDiagnosticHealthy Subjects (HS)1
1CompletedTreatmentHepatic Insufficiency / Obesity (Disorder)1
1CompletedTreatmentObesity (Disorder)4

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 Solubility0.0107 mg/mLALOGPS
logP3.66ALOGPS
logP4.42ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)15.89ChemAxon
pKa (Strongest Basic)8.97ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area101.96 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity158.88 m3·mol-1ChemAxon
Polarizability53.2 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Drug binding
Specific Function
Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered l...
Gene Name
CNR1
Uniprot ID
P21554
Uniprot Name
Cannabinoid receptor 1
Molecular Weight
52857.365 Da

Drug created on October 20, 2016 20:44 / Updated on February 21, 2021 18:53