Identification
NameCR665
Accession NumberDB05155
TypeSmall Molecule
GroupsInvestigational
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
SynonymsNot Available
External IDs CR 665 / FE 200665
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII3BX9UG06GG
CAS numberNot Available
WeightAverage: 671.847
Monoisotopic: 671.390751094
Chemical FormulaC36H49N9O4
InChI KeyDBOGGOVKHSCMNB-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[C@@H](NC(=O)[C@@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
PharmacodynamicsNot 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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Kappa-type opioid receptorProteinunknownNot AvailableHumanP41145 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 featuresNot Available
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative ParentsPhenylalanine 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
SubstituentsAlpha-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
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot 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 synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates th...
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 June 24, 2017 13:23