VGX-1027

VGX-1027
Identifiers
	IUPAC name 2-(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)acetic acid;
CAS Number	6501-72-0 ;
PubChem CID	10798271;
ChemSpider	8973577;
UNII	AKT814N13R;
ChEMBL	ChEMBL1320667;
CompTox Dashboard (EPA)	DTXSID50445023 ;
Chemical and physical data
Formula	C11H11NO3
Molar mass	205.213 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1C(ON=C1C2=CC=CC=C2)CC(=O)O;
	InChI InChI=1S/C11H11NO3/c13-11(14)7-9-6-10(12-15-9)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,14); Key:MUFJHYRCIHHATF-UHFFFAOYSA-N;

VGX-1027 (GIT-27) is a drug which acts as an immunomodulator. It acts by blocking downstream signalling of the Toll-like receptors TLR2, TLR4 and TLR6, and thereby reducing production of various cytokines, including interleukins and TNF-α. In animal studies it has antiinflammatory effects and has been investigated for conditions such as arthritis and lung inflammation.^[1]^[2]^[3]^[4]^[5]^[6]

References

^ Stojanovic I, Cuzzocrea S, Mangano K, Mazzon E, Miljkovic D, Wang M, et al. (June 2007). "In vitro, ex vivo and in vivo immunopharmacological activities of the isoxazoline compound VGX-1027: modulation of cytokine synthesis and prevention of both organ-specific and systemic autoimmune diseases in murine models". Clinical Immunology. 123 (3): 311–23. doi:10.1016/j.clim.2007.03.004. PMID 17449326.
^ Cha JJ, Hyun YY, Lee MH, Kim JE, Nam DH, Song HK, et al. (June 2013). "Renal protective effects of toll-like receptor 4 signaling blockade in type 2 diabetic mice". Endocrinology. 154 (6): 2144–55. doi:10.1210/en.2012-2080. PMID 23568555.
^ Saurus P, Kuusela S, Lehtonen E, Hyvönen ME, Ristola M, Fogarty CL, et al. (May 2015). "Podocyte apoptosis is prevented by blocking the Toll-like receptor pathway". Cell Death & Disease. 6 (5): e1752. doi:10.1038/cddis.2015.125. PMC 4669704. PMID 25950482.
^ Lee JC, Menacherry S, Diehl MC, Giffear MD, White CJ, Juba R, et al. (March 2016). "Safety, bioavailability, and pharmacokinetics of VGX-1027-A novel oral anti-inflammatory drug in healthy human subjects". Clinical Pharmacology in Drug Development. 5 (2): 91–101. doi:10.1002/cpdd.193. PMID 27138022. S2CID 22577185.
^ Xu M, Li F, Wang M, Zhang H, Xu L, Adcock IM, et al. (January 2019). "Protective effects of VGX-1027 in PM_2.5-induced airway inflammation and bronchial hyperresponsiveness". European Journal of Pharmacology. 842: 373–383. doi:10.1016/j.ejphar.2018.11.010. hdl:10044/1/66292. PMID 30419239. S2CID 53292202.
^ Ahmad SF, Nadeem A, Ansari MA, Bakheet SA, Alasmari F, Alasmari AF, et al. (November 2019). "The potent immunomodulatory compound VGX-1027 regulates inflammatory mediators in CD4⁺ T cells, which are concomitant with the prevention of neuroimmune dysregulation in BTBR T⁺ Itpr3^tf/J mice". Life Sciences. 237: 116930. doi:10.1016/j.lfs.2019.116930. PMID 31610190. S2CID 204702143.

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[1] Stojanovic I, Cuzzocrea S, Mangano K, Mazzon E, Miljkovic D, Wang M, et al. (June 2007). "In vitro, ex vivo and in vivo immunopharmacological activities of the isoxazoline compound VGX-1027: modulation of cytokine synthesis and prevention of both organ-specific and systemic autoimmune diseases in murine models". Clinical Immunology. 123 (3): 311–23. doi:10.1016/j.clim.2007.03.004. PMID 17449326.

[2] Cha JJ, Hyun YY, Lee MH, Kim JE, Nam DH, Song HK, et al. (June 2013). "Renal protective effects of toll-like receptor 4 signaling blockade in type 2 diabetic mice". Endocrinology. 154 (6): 2144–55. doi:10.1210/en.2012-2080. PMID 23568555.

[3] Saurus P, Kuusela S, Lehtonen E, Hyvönen ME, Ristola M, Fogarty CL, et al. (May 2015). "Podocyte apoptosis is prevented by blocking the Toll-like receptor pathway". Cell Death & Disease. 6 (5): e1752. doi:10.1038/cddis.2015.125. PMC 4669704. PMID 25950482.

[4] Lee JC, Menacherry S, Diehl MC, Giffear MD, White CJ, Juba R, et al. (March 2016). "Safety, bioavailability, and pharmacokinetics of VGX-1027-A novel oral anti-inflammatory drug in healthy human subjects". Clinical Pharmacology in Drug Development. 5 (2): 91–101. doi:10.1002/cpdd.193. PMID 27138022. S2CID 22577185.

[5] Xu M, Li F, Wang M, Zhang H, Xu L, Adcock IM, et al. (January 2019). "Protective effects of VGX-1027 in PM_2.5-induced airway inflammation and bronchial hyperresponsiveness". European Journal of Pharmacology. 842: 373–383. doi:10.1016/j.ejphar.2018.11.010. hdl:10044/1/66292. PMID 30419239. S2CID 53292202.

[6] Ahmad SF, Nadeem A, Ansari MA, Bakheet SA, Alasmari F, Alasmari AF, et al. (November 2019). "The potent immunomodulatory compound VGX-1027 regulates inflammatory mediators in CD4⁺ T cells, which are concomitant with the prevention of neuroimmune dysregulation in BTBR T⁺ Itpr3^tf/J mice". Life Sciences. 237: 116930. doi:10.1016/j.lfs.2019.116930. PMID 31610190. S2CID 204702143.

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Identifiers

IUPAC name 2-(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)acetic acid
CAS Number	6501-72-0^Y
PubChem CID	10798271
ChemSpider	8973577
UNII	AKT814N13R
ChEMBL	ChEMBL1320667
CompTox Dashboard (EPA)	DTXSID50445023
Chemical and physical data
Formula	C₁₁H₁₁NO₃
Molar mass	205.213 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1C(ON=C1C2=CC=CC=C2)CC(=O)O
InChI InChI=1S/C11H11NO3/c13-11(14)7-9-6-10(12-15-9)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,14) Key:MUFJHYRCIHHATF-UHFFFAOYSA-N