OPC-51803

Identification

Generic Name
OPC-51803
DrugBank Accession Number
DB05838
Background

OPC-51803 is the first nonpeptide vasopressin (AVP) V(2)-receptor-selective agonist. It is a V(2)-selective agonist that produces a significant antidiuretic action after single and multiple oral dosing in AVP-deficient and normal AVP states. It is useful therapeutic drug in the treatment of hypothalamic diabetes insipidus, nocturnal enuresis, and some kinds of urinary incontinence.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 454.004
Monoisotopic: 453.21830499
Chemical Formula
C26H32ClN3O2
Synonyms
Not Available

Pharmacology

Indication

Investigated for use/treatment in nocturia (frequent nighttime urination) and urinary incontinence.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UVasopressin V2 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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzazepines
Sub Class
Not Available
Direct Parent
Benzazepines
Alternative Parents
Phenylpyrrolidines / 2-halobenzoic acids and derivatives / Aminobenzoic acids and derivatives / Benzamides / Aniline and substituted anilines / Dialkylarylamines / Benzoyl derivatives / Chlorobenzenes / Azepines / Aryl chlorides
show 11 more
Substituents
1-phenylpyrrolidine / 2-halobenzoic acid or derivatives / Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
1IGV6WTK9I
CAS number
Not Available
InChI Key
INGXCNVWWKKWOO-LJQANCHMSA-N
InChI
InChI=1S/C26H32ClN3O2/c1-18(2)28-25(31)16-19-8-7-15-30(24-10-4-3-9-21(19)24)26(32)22-12-11-20(17-23(22)27)29-13-5-6-14-29/h3-4,9-12,17-19H,5-8,13-16H2,1-2H3,(H,28,31)/t19-/m1/s1
IUPAC Name
2-[(5R)-1-[2-chloro-4-(pyrrolidin-1-yl)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-yl]-N-(propan-2-yl)acetamide
SMILES
CC(C)NC(=O)C[C@H]1CCCN(C(=O)C2=C(Cl)C=C(C=C2)N2CCCC2)C2=CC=CC=C12

References

General References
  1. Nakamura S, Hirano T, Tsujimae K, Aoyama M, Kondo K, Yamamura Y, Mori T, Tominaga M: Antidiuretic effects of a nonpeptide vasopressin V(2)-receptor agonist, OPC-51803, administered orally to rats. J Pharmacol Exp Ther. 2000 Dec;295(3):1005-11. [Article]
PubChem Compound
3038506
PubChem Substance
175427043
ChemSpider
2302070
BindingDB
50117486
ChEMBL
CHEMBL332447
ZINC
ZINC000003828536

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.00385 mg/mLALOGPS
logP5ALOGPS
logP4.58Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)15.21Chemaxon
pKa (Strongest Basic)1.56Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area52.65 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity130.69 m3·mol-1Chemaxon
Polarizability49.92 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.9865
Caco-2 permeable-0.618
P-glycoprotein substrateSubstrate0.724
P-glycoprotein inhibitor IInhibitor0.9486
P-glycoprotein inhibitor IIInhibitor0.9429
Renal organic cation transporterNon-inhibitor0.5286
CYP450 2C9 substrateNon-substrate0.7842
CYP450 2D6 substrateNon-substrate0.7529
CYP450 3A4 substrateSubstrate0.8308
CYP450 1A2 substrateNon-inhibitor0.6018
CYP450 2C9 inhibitorNon-inhibitor0.5163
CYP450 2D6 inhibitorNon-inhibitor0.5909
CYP450 2C19 inhibitorInhibitor0.7924
CYP450 3A4 inhibitorInhibitor0.7408
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9368
Ames testNon AMES toxic0.7837
CarcinogenicityNon-carcinogens0.7224
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5013 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9031
hERG inhibition (predictor II)Inhibitor0.9095
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-0009700000-6b0376c8b4e9872bd8c5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ldi-2019500000-47b337c72181c61a235f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0011900000-dbb5ece26143c647743d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-2933600000-c78a9353cb7c9331c019
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-2019000000-3d8283f560755b957ad2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fdo-4418900000-69d9bd54927e369d408f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.03621
predicted
DeepCCS 1.0 (2019)
[M+H]+207.43175
predicted
DeepCCS 1.0 (2019)
[M+Na]+213.34596
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details
1. Vasopressin V2 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Vasopressin receptor activity
Specific Function
Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate adenylate cyclase. Involved in renal water reabsorption.
Gene Name
AVPR2
Uniprot ID
P30518
Uniprot Name
Vasopressin V2 receptor
Molecular Weight
40278.57 Da

Drug created at November 18, 2007 18:28 / Updated at June 12, 2020 16:52