Identification

Name
CR665
Accession Number
DB05155
Type
Small Molecule
Groups
Investigational
Description

CR665 is the lead clinical development candidate from a series of highly selective peripheral kappa opioid receptor agonists. In preclinical studies, CR665 was highly selective for the peripheral kappa opioid receptor. Preclinical animal studies suggest that CR665 is a potent analgesic compound. In addition, unlike currently marketed opioids, CR665 does not produce inhibition of intestinal transit (ileus), induce respiratory depression, or elicit signs of euphoria or addiction in animal models. Preclinical studies also indicate that CR665 possesses anti-inflammatory activities.

Structure
Thumb
Synonyms
Not Available
External IDs
CR 665 / FE 200665
Categories
UNII
3BX9UG06GG
CAS number
Not Available
Weight
Average: 671.847
Monoisotopic: 671.390751094
Chemical Formula
C36H49N9O4
InChI Key
DBOGGOVKHSCMNB-OMRVPHBLSA-N
InChI
InChI=1S/C36H49N9O4/c1-2-3-15-30(34(48)43-29(16-10-19-41-36(38)39)33(47)42-24-27-17-20-40-21-18-27)44-35(49)31(23-26-13-8-5-9-14-26)45-32(46)28(37)22-25-11-6-4-7-12-25/h4-9,11-14,17-18,20-21,28-31H,2-3,10,15-16,19,22-24,37H2,1H3,(H,42,47)(H,43,48)(H,44,49)(H,45,46)(H4,38,39,41)/t28-,29-,30-,31-/m1/s1
IUPAC Name
(2R)-2-[(2R)-2-[(2R)-2-amino-3-phenylpropanamido]-3-phenylpropanamido]-N-[(1R)-4-carbamimidamido-1-{[(pyridin-4-yl)methyl]carbamoyl}butyl]hexanamide
SMILES
CCCC[[email protected]@H](NC(=O)[[email protected]@H](CC1=CC=CC=C1)NC(=O)[[email protected]](N)CC1=CC=CC=C1)C(=O)N[[email protected]](CCCNC(N)=N)C(=O)NCC1=CC=NC=C1

Pharmacology

Indication

Investigated for use/treatment in pain (acute or chronic).

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action

CR665 was highly selective for the peripheral kappa opioid receptor. It is intrinsically poor at penetrating the blood-brain barrier, which decreases the likelihood of CNS-mediated side effects. By acting with unprecedented selectivity at pain relieving receptors on peripheral nerves, and avoiding receptors in the central nervous system and gastrointestinal tract, CR665 has the potential to provide pain relief with minimal side effects.

TargetActionsOrganism
UKappa-type opioid receptorNot AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
25030387
PubChem Substance
347827714
ChemSpider
32702094

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.00349 mg/mLALOGPS
logP1.41ALOGPS
logP1.12ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)12.18ChemAxon
pKa (Strongest Basic)11.69ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area217.21 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity197.95 m3·mol-1ChemAxon
Polarizability74 Å3ChemAxon
Number of Rings3ChemAxon
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 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
Phenylalanine and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Amphetamines and derivatives / Aralkylamines / Pyridines and derivatives / N-acyl amines / Heteroaromatic compounds / Secondary carboxylic acid amides / Guanidines
show 7 more
Substituents
Alpha-oligopeptide / Phenylalanine or derivatives / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Amphetamine or derivatives / Aralkylamine / Fatty amide / N-acyl-amine
show 25 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da

Drug created on October 21, 2007 16:23 / Updated on December 01, 2017 15:35