| Revision as of 19:34, 21 September 2011 editPotatoBot (talk | contribs)Bots51,239 editsm Stub sorting and placement of stub template(s): systemic-hormonal-drug-stub. See approval. Report errors and suggestions at User talk:PotatoBot.← Previous edit |
Latest revision as of 08:52, 9 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,129 edits removed Category:Chloroarenes; added Category:2-Chlorophenyl compounds using HotCat |
| (33 intermediate revisions by 20 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Watchedfields = changed |
|
| verifiedrevid = 299420967 |
|
| verifiedrevid = 451727532 |
|
| IUPAC_name = (+)-(3''S'')-3-(2-chlorophenyl)-1--3-hydroxo-2-oxo-4-(trifluoromethyl)indoline-6-carboxamide |
|
| IUPAC_name = (+)-(3''S'')-3-(2-chlorophenyl)-1--3-hydroxo-2-oxo-4-(trifluoromethyl)indoline-6-carboxamide |
|
| image = SM-130,686_structure.svg |
|
| image = SM-130,686 skeletal.svg |
|
|
|
|
|
<!--Clinical data--> |
|
<!--Clinical data--> |
|
| tradename = |
|
| tradename = |
|
| pregnancy_AU = |
|
| pregnancy_AU = |
|
| pregnancy_US = |
|
| pregnancy_US = |
|
| legal_AU = |
|
| legal_AU = |
|
| legal_UK = |
|
| legal_UK = |
|
| legal_US = |
|
| legal_US = |
|
| routes_of_administration = |
|
| routes_of_administration = |
|
|
|
|
|
<!--Pharmacokinetic data--> |
|
<!--Pharmacokinetic data--> |
|
| bioavailability = |
|
| bioavailability = |
|
| protein_bound = |
|
| protein_bound = |
|
| metabolism = |
|
| metabolism = |
|
| elimination_half-life = |
|
| elimination_half-life = |
|
| excretion = |
|
| excretion = |
|
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
|
| CAS_number_Ref = {{cascite|correct|CAS}} |
|
| CAS_number = |
|
| CAS_number = 259666-71-2 |
|
| ATC_prefix = |
|
|
| ATC_suffix = |
|
| ATC_prefix = none |
|
| ATC_supplemental = |
|
| ATC_suffix = |
|
|
| ATC_supplemental = |
|
| PubChem = 9890863 |
|
| PubChem = 9890863 |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank = |
|
| DrugBank = |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = |
|
| ChemSpiderID = 7980503 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = 1GH34I6261 |
|
|
|
|
|
<!--Chemical data--> |
|
<!--Chemical data--> |
|
| C=22 | H=23 | Cl=1 | F=3 | N=3 | O=3 |
|
| C=22 | H=23 | Cl=1 | F=3 | N=3 | O=3 |
|
| molecular_weight = 469.884 g/mol |
|
|
| smiles = FC(F)(F)c3c1c(cc(c3)C(N)=O)N(CCN(CC)CC)C(=O)C1(O)c2ccccc2Cl |
|
| smiles = FC(F)(F)c3c1c(cc(c3)C(N)=O)N(CCN(CC)CC)C(=O)C1(O)c2ccccc2Cl |
|
|
| StdInChI=1S/C22H23ClF3N3O3/c1-3-28(4-2)9-10-29-17-12-13(19(27)30)11-15(22(24,25)26)18(17)21(32,20(29)31)14-7-5-6-8-16(14)23/h5-8,11-12,32H,3-4,9-10H2,1-2H3,(H2,27,30)/t21-/m1/s1 |
|
|
| StdInChIKey = YSSPGXCFFITNCE-OAQYLSRUSA-N |
|
}} |
|
}} |
|
|
|
|
|
'''SM-130,686''' is a drug which acts as a potent, orally active ] secretagogue,<ref>Tokunaga T, Hume WE, Nagamine J, Kawamura T, Taiji M, Nagata R. Structure-activity relationships of the oxindole growth hormone secretagogues. ''Bioorganic and Medicinal Chemistry Letters''. 2005 Apr 1;15(7):1789-92. PMID 15780607</ref> with around half the potency of the endogenous agonist ] as a stimulator of growth hormone release.<ref>Nagamine J, Nagata R, Seki H, Nomura-Akimaru N, Ueki Y, Kumagai K, Taiji M, Noguchi H. Pharmacological profile of a new orally active growth hormone secretagogue, SM-130686. ''Journal of Endocrinology''. 2001 Dec;171(3):481-9. PMID 11739014</ref><ref>Tokunaga T, Hume WE, Umezome T, Okazaki K, Ueki Y, Kumagai K, Hourai S, Nagamine J, Seki H, Taiji M, Noguchi H, Nagata R. Oxindole derivatives as orally active potent growth hormone secretagogues. ''Journal of Medicinal Chemistry''. 2001 Dec 20;44(26):4641-9. PMID 11741481</ref> It produces dose-dependent increases in muscle mass and decrease in body fat, and is under investigation for the treatment of growth hormone deficiency and other medical conditions.<ref>Nagamine J, Kawamura T, Tokunaga T, Hume WE, Nagata R, Nakagawa T, Taiji M. Synthesis and pharmacological profile of an orally-active growth hormone secretagogue, SM-130686. ''Combinatorial Chemistry and High Throughput Screening''. 2006 Mar;9(3):187-96. PMID 16533152</ref> Concerns about its potential use as a performance-enhancing drug for athletes have led to the development of urine tests for SM-130,686 and other growth hormone secretagogues, even though no drugs from this class have yet progressed to clinical use.<ref>Thevis M, Wilkens F, Geyer H, Schänzer W. Determination of therapeutics with growth-hormone secretagogue activity in human urine for doping control purposes. ''Rapid Communications in Mass Spectrometry''. 2006;20(22):3393-402. PMID 17051614</ref> |
|
'''SM-130686''' is a ] ] which acts as a potent, ] ] of the ] (GHSR) and ],<ref>{{cite journal | vauthors = Tokunaga T, Hume WE, Nagamine J, Kawamura T, Taiji M, Nagata R | title = Structure-activity relationships of the oxindole growth hormone secretagogues | journal = Bioorganic & Medicinal Chemistry Letters | volume = 15 | issue = 7 | pages = 1789–92 | date = April 2005 | pmid = 15780607 | doi = 10.1016/j.bmcl.2005.02.042 }}</ref> with around half the potency of the ] ] ] as a stimulator of ] release.<ref>{{cite journal | vauthors = Nagamine J, Nagata R, Seki H, Nomura-Akimaru N, Ueki Y, Kumagai K, Taiji M, Noguchi H | display-authors = 6 | title = Pharmacological profile of a new orally active growth hormone secretagogue, SM-130686 | journal = The Journal of Endocrinology | volume = 171 | issue = 3 | pages = 481–9 | date = December 2001 | pmid = 11739014 | doi = 10.1677/joe.0.1710481 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Tokunaga T, Hume WE, Umezome T, Okazaki K, Ueki Y, Kumagai K, Hourai S, Nagamine J, Seki H, Taiji M, Noguchi H, Nagata R | display-authors = 6 | title = Oxindole derivatives as orally active potent growth hormone secretagogues | journal = Journal of Medicinal Chemistry | volume = 44 | issue = 26 | pages = 4641–9 | date = December 2001 | pmid = 11741481 | doi = 10.1021/jm0103763 }}</ref> It produces dose-dependent increases in muscle mass and decrease in body fat, and is under investigation for the treatment of ] and other medical conditions.<ref>{{cite journal | vauthors = Nagamine J, Kawamura T, Tokunaga T, Hume WE, Nagata R, Nakagawa T, Taiji M | title = Synthesis and pharmacological profile of an orally-active growth hormone secretagogue, SM-130686 | journal = Combinatorial Chemistry & High Throughput Screening | volume = 9 | issue = 3 | pages = 187–96 | date = March 2006 | pmid = 16533152 | doi = 10.2174/138620706776055548 }}</ref> Concerns about its potential use as a performance-enhancing drug for athletes have led to the development of urine tests for SM-130686 and other GHSR agonists, even though no drugs from this class have yet progressed to clinical use.<ref>{{cite journal | vauthors = Thevis M, Wilkens F, Geyer H, Schänzer W | title = Determination of therapeutics with growth-hormone secretagogue activity in human urine for doping control purposes | journal = Rapid Communications in Mass Spectrometry | volume = 20 | issue = 22 | pages = 3393–402 | pmid = 17051614 | doi = 10.1002/rcm.2758 | year = 2006 | bibcode = 2006RCMS...20.3393T }}</ref> |
|
|
|
|
|
==See also== |
|
== See also == |
|
|
* ] |
|
* ] |
|
|
* ] |
|
|
* ] |
|
|
|
|
|
|
==References== |
|
== References == |
|
|
{{Reflist|2}} |
|
<references/> |
|
|
|
|
|
|
|
{{GH/IGF-1 axis signaling modulators}} |
|
{{Neuropeptide agonists and antagonists}} |
|
|
|
|
|
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
] |
|
] |
|
|
] |
|
|
|
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
|
|
|
{{systemic-hormonal-drug-stub}} |
|
{{systemic-hormonal-drug-stub}} |
|
|
|
|
] |
|