GSK1016790A

GSK1016790A
Identifiers
	IUPAC name N-[(1S)-1-[[4-[(2S)-2-[[(2,4-Dichlorophenyl)sulfonyl]amino]-3-hydroxy-1-oxopropyl]-1-piperazinyl]carbonyl]-3-methylbutyl]benzo[b]thiophene-2-carboxamide;
CAS Number	942206-85-1;
PubChem CID	23630211;
ChemSpider	29310491;
ChEBI	CHEBI:140524;
CompTox Dashboard (EPA)	DTXSID30635248 ;
Chemical and physical data
Formula	C28H32Cl2N4O6S2
Molar mass	655.61 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)C[C@H](NC(C1=CC2=CC=CC=C2S1)=O)C(N3CCN(CC3)C([C@H](CO)NS(=O)(C4=C(Cl)C=C(Cl)C=C4)=O)=O)=O;
	InChI InChI=1S/C28H32Cl2N4O6S2/c1-17(2)13-21(31-26(36)24-14-18-5-3-4-6-23(18)41-24)27(37)33-9-11-34(12-10-33)28(38)22(16-35)32-42(39,40)25-8-7-19(29)15-20(25)30/h3-8,14-15,17,21-22,32,35H,9-13,16H2,1-2H3,(H,31,36)/t21-,22-/m0/s1; Key:IVYQPSHHYIAUFO-VXKWHMMOSA-N;

GSK1016790A (aka GSK101) is a drug developed by GlaxoSmithKline which acts as a potent and selective agonist for the TRPV4 receptor. It has been used to study the role of TRPV4 receptors in the function of smooth muscle tissue, particularly that lining blood vessels, lymphatic system, and the bladder.^[1]^[2]^[3]^[4]^[5]

References

^ Thorneloe KS, Sulpizio AC, Lin Z, Figueroa DJ, Clouse AK, McCafferty GP, et al. (August 2008). "N-((1S)-1-{[4-((2S)-2-{[(2,4-dichlorophenyl)sulfonyl]amino}-3-hydroxypropanoyl)-1-piperazinyl]carbonyl}-3-methylbutyl)-1-benzothiophene-2-carboxamide (GSK1016790A), a novel and potent transient receptor potential vanilloid 4 channel agonist induces urinary bladder contraction and hyperactivity: Part I". The Journal of Pharmacology and Experimental Therapeutics. 326 (2): 432–42. doi:10.1124/jpet.108.139295. PMID 18499743. S2CID 517735.
^ Vincent F, Duncton MA (2011). "TRPV4 agonists and antagonists". Current Topics in Medicinal Chemistry. 11 (17): 2216–26. doi:10.2174/156802611796904861. PMID 21671873.
^ Xu S (May 2020). "Therapeutic potential of blood flow mimetic compounds in preventing endothelial dysfunction and atherosclerosis". Pharmacological Research. 155: 104737. doi:10.1016/j.phrs.2020.104737. PMID 32126273. S2CID 212406213.
^ Thapak P, Vaidya B, Joshi HC, Singh JN, Sharma SS (September 2020). "Therapeutic potential of pharmacological agents targeting TRP channels in CNS disorders". Pharmacological Research. 159: 105026. doi:10.1016/j.phrs.2020.105026. PMID 32562815. S2CID 219959586.
^ Solari E, Marcozzi C, Bistoletti M, Baj A, Giaroni C, Negrini D, Moriondo A (August 2020). "TRPV4 channels' dominant role in the temperature modulation of intrinsic contractility and lymph flow of rat diaphragmatic lymphatics". American Journal of Physiology. Heart and Circulatory Physiology. 319 (2): H507–H518. doi:10.1152/ajpheart.00175.2020. hdl:11383/2096014. PMID 32706268. S2CID 220731478.

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[1] Thorneloe KS, Sulpizio AC, Lin Z, Figueroa DJ, Clouse AK, McCafferty GP, et al. (August 2008). "N-((1S)-1-{[4-((2S)-2-{[(2,4-dichlorophenyl)sulfonyl]amino}-3-hydroxypropanoyl)-1-piperazinyl]carbonyl}-3-methylbutyl)-1-benzothiophene-2-carboxamide (GSK1016790A), a novel and potent transient receptor potential vanilloid 4 channel agonist induces urinary bladder contraction and hyperactivity: Part I". The Journal of Pharmacology and Experimental Therapeutics. 326 (2): 432–42. doi:10.1124/jpet.108.139295. PMID 18499743. S2CID 517735.

[2] Vincent F, Duncton MA (2011). "TRPV4 agonists and antagonists". Current Topics in Medicinal Chemistry. 11 (17): 2216–26. doi:10.2174/156802611796904861. PMID 21671873.

[3] Xu S (May 2020). "Therapeutic potential of blood flow mimetic compounds in preventing endothelial dysfunction and atherosclerosis". Pharmacological Research. 155: 104737. doi:10.1016/j.phrs.2020.104737. PMID 32126273. S2CID 212406213.

[4] Thapak P, Vaidya B, Joshi HC, Singh JN, Sharma SS (September 2020). "Therapeutic potential of pharmacological agents targeting TRP channels in CNS disorders". Pharmacological Research. 159: 105026. doi:10.1016/j.phrs.2020.105026. PMID 32562815. S2CID 219959586.

[5] Solari E, Marcozzi C, Bistoletti M, Baj A, Giaroni C, Negrini D, Moriondo A (August 2020). "TRPV4 channels' dominant role in the temperature modulation of intrinsic contractility and lymph flow of rat diaphragmatic lymphatics". American Journal of Physiology. Heart and Circulatory Physiology. 319 (2): H507–H518. doi:10.1152/ajpheart.00175.2020. hdl:11383/2096014. PMID 32706268. S2CID 220731478.

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Identifiers

IUPAC name N-[(1S)-1-[[4-[(2S)-2-[[(2,4-Dichlorophenyl)sulfonyl]amino]-3-hydroxy-1-oxopropyl]-1-piperazinyl]carbonyl]-3-methylbutyl]benzo[b]thiophene-2-carboxamide
CAS Number	942206-85-1
PubChem CID	23630211
ChemSpider	29310491
ChEBI	CHEBI:140524
CompTox Dashboard (EPA)	DTXSID30635248
Chemical and physical data
Formula	C₂₈H₃₂Cl₂N₄O₆S₂
Molar mass	655.61 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)C[C@H](NC(C1=CC2=CC=CC=C2S1)=O)C(N3CCN(CC3)C([C@H](CO)NS(=O)(C4=C(Cl)C=C(Cl)C=C4)=O)=O)=O
InChI InChI=1S/C28H32Cl2N4O6S2/c1-17(2)13-21(31-26(36)24-14-18-5-3-4-6-23(18)41-24)27(37)33-9-11-34(12-10-33)28(38)22(16-35)32-42(39,40)25-8-7-19(29)15-20(25)30/h3-8,14-15,17,21-22,32,35H,9-13,16H2,1-2H3,(H,31,36)/t21-,22-/m0/s1 Key:IVYQPSHHYIAUFO-VXKWHMMOSA-N