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

Identification

Name
WIN 55212-2
Accession Number
DB13950
Type
Small Molecule
Groups
Experimental
Description

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.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
WIN 55212-2 mesylate2J851TP7VJ131543-23-2FSGCSTPOPBJYSX-VEIFNGETSA-N
Categories
UNII
5H31GI9502
CAS number
131543-22-1
Weight
Average: 426.516
Monoisotopic: 426.194342705
Chemical Formula
C27H26N2O3
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with WIN 55212-2.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with WIN 55212-2.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when WIN 55212-2 is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of Tachycardia can be increased when WIN 55212-2 is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when WIN 55212-2 is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when WIN 55212-2 is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with WIN 55212-2.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when WIN 55212-2 is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with WIN 55212-2.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when WIN 55212-2 is combined with 4-Methoxyamphetamine.
Food Interactions
Not Available

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. [PubMed:29113897]
External Links
ChemSpider
4470978
BindingDB
21281
ChEBI
73295
ChEMBL
CHEMBL188
Wikipedia
WIN_55,212-2

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 Solubility0.00444 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
Not Available

Taxonomy

Classification
Not classified

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:22039822]

Drug created on January 12, 2018 10:40 / Updated on November 02, 2018 09:13