NAV

WIN 55212-2

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

Identification

Generic Name
WIN 55212-2
DrugBank Accession Number
DB13950
Background

WIN 55,212-2 is a chemical described as an aminoalkylindole derivative, which produces effects similar to those of cannabinoids such as tetrahydrocannabinol (THC) but has an entirely different chemical structure. It is a potent cannabinoid receptor agonist that has been found to be a potent analgesic in a rat model of neuropathic pain. It activates p42 and p44 MAP kinase via receptor-mediated signaling.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 426.516
Monoisotopic: 426.194342705
Chemical Formula
C27H26N2O3
Synonyms
  • (2,3-Dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl)methanone monomethanesulfonate
External IDs
  • WIN 55212-2
  • WIN-55212-2
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when WIN 55212-2 is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of WIN 55212-2 can be increased when it is combined with Abametapir.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with WIN 55212-2.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with WIN 55212-2.
AcarboseThe risk or severity of hypoglycemia can be increased when WIN 55212-2 is combined with Acarbose.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
WIN 55212-2 mesylate2J851TP7VJ131543-23-2FSGCSTPOPBJYSX-VEIFNGETSA-N

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
5H31GI9502
CAS number
131543-22-1
InChI Key
HQVHOQAKMCMIIM-HXUWFJFHSA-N
InChI
InChI=1S/C27H26N2O3/c1-18-25(27(30)22-9-4-7-19-6-2-3-8-21(19)22)23-10-5-11-24-26(23)29(18)20(17-32-24)16-28-12-14-31-15-13-28/h2-11,20H,12-17H2,1H3/t20-/m1/s1
IUPAC Name
(11R)-2-methyl-11-[(morpholin-4-yl)methyl]-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0^{4,12}]dodeca-2,4(12),5,7-tetraene
SMILES
CC1=C(C(=O)C2=CC=CC3=CC=CC=C23)C2=C3N1[C@H](CN1CCOCC1)COC3=CC=C2

References

General References
  1. Perdikaris P, Tsarouchi M, Fanarioti E, Natsaridis E, Mitsacos A, Giompres P: Long lasting effects of chronic WIN55,212-2 treatment on mesostriatal dopaminergic and cannabinoid systems in the rat brain. Neuropharmacology. 2018 Feb;129:1-15. doi: 10.1016/j.neuropharm.2017.11.005. Epub 2017 Nov 4. [Article]
ChemSpider
4470978
BindingDB
21281
ChEBI
73295
ChEMBL
CHEMBL188
ZINC
ZINC000025783468
PDBe Ligand
WI5
Wikipedia
WIN_55,212-2
PDB Entries
6pt0 / 7mwn

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 Solubility0.00444 mg/mLALOGPS
logP3.85ALOGPS
logP4.47Chemaxon
logS-5ALOGPS
pKa (Strongest Basic)6.35Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area43.7 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity125.47 m3·mol-1Chemaxon
Polarizability46.41 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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/MSsplash10-004i-0000900000-234041043e800de1bc88
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0040900000-2c9593974351f2e9b090
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0402900000-983e1eb587ac9b2963a3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004r-0109400000-bd4aa999fa342a80cd26
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-4906300000-bde7a6ff2f72310d6f79
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0928000000-08789c5a7dc19d09c2c5
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
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. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [Article]

Drug created at January 12, 2018 17:40 / Updated at June 12, 2020 16:53