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SR-144,528

April 10, 2024

SR144528 is a drug that acts as a potent and highly selective CB2 receptor inverse agonist, with a Ki of 0.6 nM at CB2 and 400 nM at the related CB1 receptor.[1][2] It is used in scientific research for investigating the function of the CB2 receptor,[3][4][5][6] as well as for studying the effects of CB1 receptors in isolation, as few CB1 agonists that do not also show significant activity as CB2 agonists are available.[7][8][9] It has also been found to be an inhibitor of sterol O-acyltransferase, an effect that appears to be independent from its action on CB2 receptors.[10]

SR-144,528
Clinical data
ATC code
  • none
Identifiers
  • 5-(4-Chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-N-[(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl]-1H-pyrazole-3-carboxamide
CAS Number
  • 192703-06-3 Y
PubChem CID
  • 3081355
IUPHAR/BPS
  • 751
ChemSpider
  • 2338975 N
ChEBI
  • CHEBI:146245
ChEMBL
  • ChEMBL381791 N
CompTox Dashboard (EPA)
  • DTXSID50940947
Chemical and physical data
FormulaC29H34ClN3O
Molar mass476.06 g·mol−1
3D model (JSmol)
  • Interactive image
  • CC1=CC=C(C=C1)CN2C(=CC(=N2)C(=O)N[C@H]3[C@]4(CC[C@H](C4)C3(C)C)C)C5=CC(=C(C=C5)Cl)C
  • InChI=1S/C29H34ClN3O/c1-18-6-8-20(9-7-18)17-33-25(21-10-11-23(30)19(2)14-21)15-24(32-33)26(34)31-27-28(3,4)22-12-13-29(27,5)16-22/h6-11,14-15,22,27H,12-13,16-17H2,1-5H3,(H,31,34)/t22-,27-,29+/m1/s1 N
  • Key:SUGVYNSRNKFXQM-XRHWURSXSA-N N
 NY (what is this?)  (verify)

See also edit

References edit

  1. ^ Rinaldi-Carmona M, Barth F, Millan J, Derocq JM, Casellas P, Congy C, et al. (February 1998). "SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor". The Journal of Pharmacology and Experimental Therapeutics. 284 (2): 644–50. PMID 9454810.
  2. ^ Portier M, Rinaldi-Carmona M, Pecceu F, Combes T, Poinot-Chazel C, Calandra B, et al. (February 1999). "SR 144528, an antagonist for the peripheral cannabinoid receptor that behaves as an inverse agonist". The Journal of Pharmacology and Experimental Therapeutics. 288 (2): 582–9. PMID 9918562.
  3. ^ Gouldson P, Calandra B, Legoux P, Kernéis A, Rinaldi-Carmona M, Barth F, et al. (July 2000). "Mutational analysis and molecular modelling of the antagonist SR 144528 binding site on the human cannabinoid CB(2) receptor". European Journal of Pharmacology. 401 (1): 17–25. doi:10.1016/S0014-2999(00)00439-8. PMID 10915832.
  4. ^ Nackley AG, Makriyannis A, Hohmann AG (4 July 2003). "Selective activation of cannabinoid CB(2) receptors suppresses spinal fos protein expression and pain behavior in a rat model of inflammation". Neuroscience. 119 (3): 747–57. doi:10.1016/S0306-4522(03)00126-X. PMID 12809695. S2CID 6447695.
  5. ^ Páldy E, Bereczki E, Sántha M, Wenger T, Borsodi A, Zimmer A, Benyhe S (December 2008). "CB(2) cannabinoid receptor antagonist SR144528 decreases mu-opioid receptor expression and activation in mouse brainstem: role of CB(2) receptor in pain". Neurochemistry International. 53 (6–8): 309–16. doi:10.1016/j.neuint.2008.08.005. PMID 18804501. S2CID 22671432.
  6. ^ Saroz Y, Kho DT, Glass M, Graham ES, Grimsey NL (2019-10-19). "Cannabinoid Receptor 2 (CB 2 ) Signals via G-alpha-s and Induces IL-6 and IL-10 Cytokine Secretion in Human Primary Leukocytes". ACS Pharmacology & Translational Science. 2 (6): 414–428. doi:10.1021/acsptsci.9b00049. ISSN 2575-9108. PMC 7088898. PMID 32259074.
  7. ^ Lay L, Angus JA, Wright CE (March 2000). "Pharmacological characterisation of cannabinoid CB(1) receptors in the rat and mouse". European Journal of Pharmacology. 391 (1–2): 151–61. doi:10.1016/S0014-2999(00)00062-5. PMID 10720647.
  8. ^ Germanò MP, D'Angelo V, Mondello MR, Pergolizzi S, Capasso F, Capasso R, et al. (February 2001). "Cannabinoid CB1-mediated inhibition of stress-induced gastric ulcers in rats". Naunyn-Schmiedeberg's Archives of Pharmacology. 363 (2): 241–4. doi:10.1007/s002100000360. PMID 11218077. S2CID 2655432.
  9. ^ Abalo R, Cabezos PA, Vera G, Fernández-Pujol R, Martín MI (June 2010). "The cannabinoid antagonist SR144528 enhances the acute effect of WIN 55,212-2 on gastrointestinal motility in the rat". Neurogastroenterology and Motility. 22 (6): 694–e206. doi:10.1111/j.1365-2982.2009.01466.x. PMID 20132133. S2CID 10520671.
  10. ^ Thewke D, Freeman-Anderson N, Pickle T, Netherland C, Chilton C (April 2009). "AM-251 and SR144528 are acyl CoA:cholesterol acyltransferase inhibitors". Biochemical and Biophysical Research Communications. 381 (2): 181–6. doi:10.1016/j.bbrc.2009.02.020. PMC 2665256. PMID 19338772.
 

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April 10, 2024
sr144528, drug, that, acts, potent, highly, selective, receptor, inverse, agonist, with, related, receptor, used, scientific, research, investigating, function, receptor, well, studying, effects, receptors, isolation, agonists, that, also, show, significant, a. SR144528 is a drug that acts as a potent and highly selective CB2 receptor inverse agonist with a Ki of 0 6 nM at CB2 and 400 nM at the related CB1 receptor 1 2 It is used in scientific research for investigating the function of the CB2 receptor 3 4 5 6 as well as for studying the effects of CB1 receptors in isolation as few CB1 agonists that do not also show significant activity as CB2 agonists are available 7 8 9 It has also been found to be an inhibitor of sterol O acyltransferase an effect that appears to be independent from its action on CB2 receptors 10 SR 144 528Clinical dataATC codenoneIdentifiersIUPAC name 5 4 Chloro 3 methylphenyl 1 4 methylphenyl methyl N 1S 2S 4R 1 3 3 trimethylbicyclo 2 2 1 heptan 2 yl 1H pyrazole 3 carboxamideCAS Number192703 06 3 YPubChem CID3081355IUPHAR BPS751ChemSpider2338975 NChEBICHEBI 146245ChEMBLChEMBL381791 NCompTox Dashboard EPA DTXSID50940947Chemical and physical dataFormulaC 29H 34Cl N 3OMolar mass476 06 g mol 13D model JSmol Interactive imageSMILES CC1 CC C C C1 CN2C CC N2 C O N C H 3 C 4 CC C H C4 C3 C C C C5 CC C C C5 Cl CInChI InChI 1S C29H34ClN3O c1 18 6 8 20 9 7 18 17 33 25 21 10 11 23 30 19 2 14 21 15 24 32 33 26 34 31 27 28 3 4 22 12 13 29 27 5 16 22 h6 11 14 15 22 27H 12 13 16 17H2 1 5H3 H 31 34 t22 27 29 m1 s1 NKey SUGVYNSRNKFXQM XRHWURSXSA N N N Y what is this verify See also editNESS 040C5 Rimonabant MN 25References edit Rinaldi Carmona M Barth F Millan J Derocq JM Casellas P Congy C et al February 1998 SR 144528 the first potent and selective antagonist of the CB2 cannabinoid receptor The Journal of Pharmacology and Experimental Therapeutics 284 2 644 50 PMID 9454810 Portier M Rinaldi Carmona M Pecceu F Combes T Poinot Chazel C Calandra B et al February 1999 SR 144528 an antagonist for the peripheral cannabinoid receptor that behaves as an inverse agonist The Journal of Pharmacology and Experimental Therapeutics 288 2 582 9 PMID 9918562 Gouldson P Calandra B Legoux P Kerneis A Rinaldi Carmona M Barth F et al July 2000 Mutational analysis and molecular modelling of the antagonist SR 144528 binding site on the human cannabinoid CB 2 receptor European Journal of Pharmacology 401 1 17 25 doi 10 1016 S0014 2999 00 00439 8 PMID 10915832 Nackley AG Makriyannis A Hohmann AG 4 July 2003 Selective activation of cannabinoid CB 2 receptors suppresses spinal fos protein expression and pain behavior in a rat model of inflammation Neuroscience 119 3 747 57 doi 10 1016 S0306 4522 03 00126 X PMID 12809695 S2CID 6447695 Paldy E Bereczki E Santha M Wenger T Borsodi A Zimmer A Benyhe S December 2008 CB 2 cannabinoid receptor antagonist SR144528 decreases mu opioid receptor expression and activation in mouse brainstem role of CB 2 receptor in pain Neurochemistry International 53 6 8 309 16 doi 10 1016 j neuint 2008 08 005 PMID 18804501 S2CID 22671432 Saroz Y Kho DT Glass M Graham ES Grimsey NL 2019 10 19 Cannabinoid Receptor 2 CB 2 Signals via G alpha s and Induces IL 6 and IL 10 Cytokine Secretion in Human Primary Leukocytes ACS Pharmacology amp Translational Science 2 6 414 428 doi 10 1021 acsptsci 9b00049 ISSN 2575 9108 PMC 7088898 PMID 32259074 Lay L Angus JA Wright CE March 2000 Pharmacological characterisation of cannabinoid CB 1 receptors in the rat and mouse European Journal of Pharmacology 391 1 2 151 61 doi 10 1016 S0014 2999 00 00062 5 PMID 10720647 Germano MP D Angelo V Mondello MR Pergolizzi S Capasso F Capasso R et al February 2001 Cannabinoid CB1 mediated inhibition of stress induced gastric ulcers in rats Naunyn Schmiedeberg s Archives of Pharmacology 363 2 241 4 doi 10 1007 s002100000360 PMID 11218077 S2CID 2655432 Abalo R Cabezos PA Vera G Fernandez Pujol R Martin MI June 2010 The cannabinoid antagonist SR144528 enhances the acute effect of WIN 55 212 2 on gastrointestinal motility in the rat Neurogastroenterology and Motility 22 6 694 e206 doi 10 1111 j 1365 2982 2009 01466 x PMID 20132133 S2CID 10520671 Thewke D Freeman Anderson N Pickle T Netherland C Chilton C April 2009 AM 251 and SR144528 are acyl CoA cholesterol acyltransferase inhibitors Biochemical and Biophysical Research Communications 381 2 181 6 doi 10 1016 j bbrc 2009 02 020 PMC 2665256 PMID 19338772 nbsp This cannabinoid related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title SR 144 528 amp oldid 1191992658, wikipedia, wiki, book, books, library,

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