Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H26N2O3.CH4O3S |
| Molecular Weight | 522.613 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.CC1=C(C(=O)C2=CC=CC3=C2C=CC=C3)C4=C5N1[C@H](CN6CCOCC6)COC5=CC=C4
InChI
InChIKey=FSGCSTPOPBJYSX-VEIFNGETSA-N
InChI=1S/C27H26N2O3.CH4O3S/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;1-5(2,3)4/h2-11,20H,12-17H2,1H3;1H3,(H,2,3,4)/t20-;/m1./s1
| Molecular Formula | CH4O3S |
| Molecular Weight | 96.106 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C27H26N2O3 |
| Molecular Weight | 426.5069 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
WIN 55212-2 is the synthetic cannabimimetic compound. It is a potent aminoalkylindole cannabinoid receptor agonist. WIN 55,212-2 increases expression of anti-oxidant Cu/Zn SOD and is able to prevent inflammation induced by Aβ1-42 in cultured astrocytes. It exerts neuroprotective and anti-inflammatory actions against Aβ damage through both CB₁ and CB₂ receptors. WIN 55212-2 attenuates hyperalgesia and allodynia in a rat model of neuropathic pain. In the clinical trial, it was revealed that WIN 55212-2, applied topically, decreases the intraocular pressure of human glaucoma resistant to conventional therapies within the first 30 min.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL218 |
93.0 nM [Ki] | ||
Target ID: WP195 |
|||
Target ID: CHEMBL253 |
3.3 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The rodent amygdala contributes to the production of cannabinoid-induced antinociception. | 2003 |
|
| Functional tolerance and blockade of long-term depression at synapses in the nucleus accumbens after chronic cannabinoid exposure. | 2003 Jun 15 |
|
| Cannabinoid receptor type 1 modulates excitatory and inhibitory neurotransmission in mouse colon. | 2004 Jan |
|
| R-(+)-[2,3-Dihydro-5-methyl-3-(4-morpholinylmethyl)-pyrrolo-[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphtalenylmethanone (WIN-2) ameliorates experimental autoimmune encephalomyelitis and induces encephalitogenic T cell apoptosis: partial involvement of the CB(2) receptor. | 2006 Dec 15 |
|
| Evaluation of the role of nicotinic acetylcholine receptor subtypes and cannabinoid system in the discriminative stimulus effects of nicotine in rats. | 2006 Jul 1 |
|
| Cannabinoid receptor type 1 located on presynaptic terminals of principal neurons in the forebrain controls glutamatergic synaptic transmission. | 2006 May 24 |
|
| Neuropathic pain and the endocannabinoid system in the dorsal raphe: pharmacological treatment and interactions with the serotonergic system. | 2006 Oct |
|
| Anti-inflammatory property of the cannabinoid agonist WIN-55212-2 in a rodent model of chronic brain inflammation. | 2007 Feb 23 |
|
| Mapping the structural requirements in the CB1 cannabinoid receptor transmembrane helix II for signal transduction. | 2008 Apr |
|
| Subunit-specific modulation of glycine receptors by cannabinoids and N-arachidonyl-glycine. | 2008 Oct 15 |
|
| Gz mediates the long-lasting desensitization of brain CB1 receptors and is essential for cross-tolerance with morphine. | 2009 Mar 10 |
Patents
Sample Use Guides
ChIP assays were performed to evaluate whether R(+)WIN 55,212-2 could affect the binding of the NF-kB subunit, p65, to the ICAM-1 and IL-8 promoters. 1321N1 astrocytoma were pre-treated with or without R(+)WIN 55,212-2 (20 uM) for 1 h prior to stimulation for a further 1 h in the absence or presence of IL-1 (10 ng/ml). p65 was absent at the promoters in unstimulated 1321N1 cells, but after 1-h stimulation with IL-1, p65 was detected at both promoters.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 16:12:04 UTC 2023
by
admin
on
Thu Jul 06 16:12:04 UTC 2023
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| Record UNII |
2J851TP7VJ
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| Record Status |
Validated (UNII)
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| Record Version |
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6604176
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WIN 55-212-2
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DBSALT002620
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2J851TP7VJ
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DTXSID50424974
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131543-23-2
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admin on Thu Jul 06 16:12:04 UTC 2023 , Edited by admin on Thu Jul 06 16:12:04 UTC 2023
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
