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Structure via PubChem · Public domain (PubChem)
CGS-21680
Sign in to saveAlso known as CGS21680, 4-(2-((6-Amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl)amino)ethyl)benzenepropanoic acid, CGS 21680, 2-(4-(2-Carboxyethyl)phenethylamino)-5'-N-ethylcarboxamidoadenosine, 4-[2-[[6-Amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid
CGS-21680 is a specific adenosine A2A subtype receptor agonist. It is usually presented as an organic hydrochloride salt with a molecular weight of 536.0 g/M. It is soluble up to 3.4 mg/mL in DMSO and 20 mg/mL in 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin.
Chemical data
- Formula
- C23H29N7O6
- Molecular weight
- 499.5 g/mol
- IUPAC name
- 3-[4-[2-[[6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl]amino]ethyl]phenyl]propanoic acid
- SMILES
- CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=C(N=C32)NCCC4=CC=C(C=C4)CCC(=O)O)N)O)O
- InChIKey
- PAOANWZGLPPROA-RQXXJAGISA-N
- XLogP
- 0.5
- Polar surface area
- 198 Ų
- H-bond donors
- 6
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,401 papers- CGS 21680, an agonist of the adenosine (A2A) receptor, reduces progression of murine type II collagen-induced arthritis.The Journal of rheumatology · 2011
- The adenosine A(2A) receptor agonist, CGS 21680, attenuates a probabilistic reversal learning deficit and elevated grooming behavior in BTBR mice.Autism research : official journal of the International Society for Autism Research · 2018
- The adenosine A(2A) receptor agonist CGS 21680 alleviates auditory sensorimotor gating deficits and increases in accumbal CREB in rats neonatally treated with quinpirole.Psychopharmacology · 2020
- The A(2A) receptor agonist CGS 21680 has beneficial and adverse effects on disease development in a humanised mouse model of graft-versus-host disease.International immunopharmacology · 2019
- CGS 21680, an agonist of the adenosine (A2A) receptor, decreases acute lung inflammation.European journal of pharmacology · 2011
via PubMed
Wikidata facts
- Mass
- 499.218
Show 3 more facts
- chemical formula
- C₂₃H₂₉N₇O₆
- canonical SMILES
- CCNC(=O)C1C(C(C(O1)N2C=NC3=C2N=C(N=C3N)NCCC4=CC=C(C=C4)CCC(=O)O)O)O
- isomeric SMILES
- CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C2N=C(N=C3N)NCCC4=CC=C(C=C4)CCC(=O)O)O)O
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 403602802 | ImageFile = CGS21680.png | IUPACName = 3-[4-(2-{[6-Amino-9-(N-ethyl-β-D-ribofuranosyluronamide)-9H-purin-2-yl]amino}ethyl)phenyl]propanoic acid | SystematicName = 3-{4-[2-({6-Amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-9H-purin-2-yl}amino)ethyl]phenyl}propanoic acid | OtherNames = CGS 21680 |Section1= |Section2= |Section3= }}
CGS-21680 is a specific adenosine A2A subtype receptor agonist. It is usually presented as an organic hydrochloride salt with a molecular weight of 536.0 g/M. It is soluble up to 3.4 mg/mL in DMSO and 20 mg/mL in 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin.
Excerpted from Wikipedia’s “CGS-21680” article, available under the CC BY-SA 4.0 licence.