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{{Short description|Organic compound, experimental pharmaceuticum}}
{{Drugbox {{Drugbox
⚫ | verifiedrevid = 477856488
| Watchedfields = changed
⚫ | IUPAC_name = N-methyl}imidazothiazol-6-yl)phenyl]naphthalene-2-carboxamide
⚫ | verifiedrevid = 451167855
⚫ | IUPAC_name = N-methyl}imidazothiazol-6-yl)phenyl]naphthalene-2-carboxamide
| image = SRT2183 skeletal.svg | image = SRT2183 skeletal.svg


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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = Investigational | legal_status = Investigational
| routes_of_administration = | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = | CAS_number = 1001908-89-9
| ATC_prefix = None | ATC_prefix = None
| ATC_suffix = | ATC_suffix =
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 403308
| PubChem = 24180126 | PubChem = 24180126
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6FKU9G9CX6
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
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<!--Chemical data--> <!--Chemical data-->
| C=27 | H=24 | N=4 | O=2 | S=1 | C=27 | H=24 | N=4 | O=2 | S=1
| molecular_weight = 468.570 g/mol
| smiles = c1ccc2cc(ccc2c1)C(=O)Nc3ccccc3c4cn5c(csc5n4)CN6CC(C6)O | smiles = c1ccc2cc(ccc2c1)C(=O)Nc3ccccc3c4cn5c(csc5n4)CN6CC(C6)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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}} }}


'''SRT2183''' is a drug in development by ] intended as a ] ] of the ] subtype ]. It has similar activity in the body to another SIRT1 activator ], but is closer in potency to ]. In animal studies it was found to improve ] and lower ] levels in fat, muscle and liver tissue, and increased ] and ].<ref name="pmid18046409">{{cite journal | author = Milne JC, Lambert PD, Schenk S, Carney DP, Smith JJ, Gagne DJ, Jin L, Boss O, Perni RB, Vu CB, Bemis JE, Xie R, Disch JS, Ng PY, Nunes JJ, Lynch AV, Yang H, Galonek H, Israelian K, Choy W, Iffland A, Lavu S, Medvedik O, Sinclair DA, Olefsky JM, Jirousek MR, Elliott PJ, Westphal CH | title = Small molecule activators of SIRT1 as therapeutics for the treatment of type 2 diabetes | journal = Nature | volume = 450 | issue = 7170 | pages = 712–6 | year = 2007 | month = November | pmid = 18046409 | pmc = 2753457 | doi = 10.1038/nature06261 | url = | issn = }}</ref> '''SRT-2183''' is a drug in development by ] intended as a ] ] of the ] subtype ]. It has similar activity in animal studies to another SIRT1 activator ], but is closer in potency to ]. In animal studies it was found to improve ] and lower ] levels in fat, muscle and liver tissue, and increased ] and ].<ref name="pmid18046409">{{cite journal | vauthors = Milne JC, Lambert PD, Schenk S, Carney DP, Smith JJ, Gagne DJ, Jin L, Boss O, Perni RB, Vu CB, Bemis JE, Xie R, Disch JS, Ng PY, Nunes JJ, Lynch AV, Yang H, Galonek H, Israelian K, Choy W, Iffland A, Lavu S, Medvedik O, Sinclair DA, Olefsky JM, Jirousek MR, Elliott PJ, Westphal CH | display-authors = 6 | title = Small molecule activators of SIRT1 as therapeutics for the treatment of type 2 diabetes | journal = Nature | volume = 450 | issue = 7170 | pages = 712–6 | date = November 2007 | pmid = 18046409 | pmc = 2753457 | doi = 10.1038/nature06261 | bibcode = 2007Natur.450..712M }}</ref>
However, the claim that SRT2183 is a SIRT1 activator has been questioned<ref name="pmid20061378">{{cite journal | author = Pacholec M, Chrunyk BA, Cunningham D, Flynn D, Griffith DA, Griffor M, Loulakis P, Pabst B, Qiu X, Stockman B, Thanabal V, Varghese A, Ward J, Withka J, Ahn K | title = SRT1720, SRT2183, SRT1460, and resveratrol are not direct activators of SIRT1 | journal = J Biol Chem | volume = 285| issue = 11| pages = 8340–8351| year = 2010 | month = January | pmid = 20061378 | doi = 10.1074/jbc.M109.088682 | url = | issn = | pmc=2832984}}</ref> and further defended.<ref name="pmid20702418">{{cite journal | author = Dai H, Kustigian L, Carney D, Case A, Considine T, Hubbard BP, Perni RB, Riera TV, Szczepankiewicz B, Vlasuk GP, Stein RL | title = SIRT1 activation by small molecules - kinetic and biophysical evidence for direct interaction of enzyme and activator | journal = J Biol Chem | volume = 285| issue = 43| pages = 32695–32703| year = 2010 | month = August | pmid = 20702418 | doi = 10.1074/jbc.M110.133892 | url = | issn = | pmc = 2963390 }}</ref> However, the claim that SRT-2183 is a SIRT1 activator has been questioned<ref name="pmid20061378">{{cite journal | vauthors = Pacholec M, Bleasdale JE, Chrunyk B, Cunningham D, Flynn D, Garofalo RS, Griffith D, Griffor M, Loulakis P, Pabst B, Qiu X, Stockman B, Thanabal V, Varghese A, Ward J, Withka J, Ahn K | display-authors = 6 | title = SRT1720, SRT2183, SRT1460, and resveratrol are not direct activators of SIRT1 | journal = The Journal of Biological Chemistry | volume = 285 | issue = 11 | pages = 8340–51 | date = March 2010 | pmid = 20061378 | pmc = 2832984 | doi = 10.1074/jbc.M109.088682 | doi-access = free }}</ref> and further defended.<ref name="pmid20702418">{{cite journal | vauthors = Dai H, Kustigian L, Carney D, Case A, Considine T, Hubbard BP, Perni RB, Riera TV, Szczepankiewicz B, Vlasuk GP, Stein RL | display-authors = 6 | title = SIRT1 activation by small molecules: kinetic and biophysical evidence for direct interaction of enzyme and activator | journal = The Journal of Biological Chemistry | volume = 285 | issue = 43 | pages = 32695–703 | date = October 2010 | pmid = 20702418 | pmc = 2963390 | doi = 10.1074/jbc.M110.133892 | doi-access = free }}</ref>


==See also== == See also ==
*] *]


==References== == References ==
{{Reflist}} {{Reflist}}


] ]
]



{{gastrointestinal-drug-stub}} {{gastrointestinal-drug-stub}}

Latest revision as of 11:16, 25 May 2023

Organic compound, experimental pharmaceuticum Pharmaceutical compound
SRT-2183
Clinical data
ATC code
  • None
Legal status
Legal status
  • Investigational
Identifiers
IUPAC name
  • N-methyl}imidazothiazol-6-yl)phenyl]naphthalene-2-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H24N4O2S
Molar mass468.58 g·mol
3D model (JSmol)
SMILES
  • c1ccc2cc(ccc2c1)C(=O)Nc3ccccc3c4cn5c(csc5n4)CN6CC(C6)O
InChI
  • InChI=1S/C27H24N4O2S/c32-22-11-12-30(15-22)14-21-17-34-27-29-25(16-31(21)27)23-7-3-4-8-24(23)28-26(33)20-10-9-18-5-1-2-6-19(18)13-20/h1-10,13,16-17,22,32H,11-12,14-15H2,(H,28,33)/t22-/m1/s1
  • Key:MUFSINOSQBMSLE-JOCHJYFZSA-N
  (verify)

SRT-2183 is a drug in development by Sirtris Pharmaceuticals intended as a small-molecule activator of the sirtuin subtype SIRT1. It has similar activity in animal studies to another SIRT1 activator SRT-1720, but is closer in potency to resveratrol. In animal studies it was found to improve insulin sensitivity and lower plasma glucose levels in fat, muscle and liver tissue, and increased mitochondrial and metabolic function. However, the claim that SRT-2183 is a SIRT1 activator has been questioned and further defended.

See also

References

  1. Milne JC, Lambert PD, Schenk S, Carney DP, Smith JJ, Gagne DJ, et al. (November 2007). "Small molecule activators of SIRT1 as therapeutics for the treatment of type 2 diabetes". Nature. 450 (7170): 712–6. Bibcode:2007Natur.450..712M. doi:10.1038/nature06261. PMC 2753457. PMID 18046409.
  2. Pacholec M, Bleasdale JE, Chrunyk B, Cunningham D, Flynn D, Garofalo RS, et al. (March 2010). "SRT1720, SRT2183, SRT1460, and resveratrol are not direct activators of SIRT1". The Journal of Biological Chemistry. 285 (11): 8340–51. doi:10.1074/jbc.M109.088682. PMC 2832984. PMID 20061378.
  3. Dai H, Kustigian L, Carney D, Case A, Considine T, Hubbard BP, et al. (October 2010). "SIRT1 activation by small molecules: kinetic and biophysical evidence for direct interaction of enzyme and activator". The Journal of Biological Chemistry. 285 (43): 32695–703. doi:10.1074/jbc.M110.133892. PMC 2963390. PMID 20702418.
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