Emricasan

Emricasan
Legal status
Legal status	US: Investigational New Drug ;
Identifiers
	IUPAC name (3S)-3-{[(2S)-2-{[2-(2-tert-butylanilino)-2-oxoacetyl]amino}propanoyl]amino}-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic acid;
CAS Number	254750-02-2 ;
PubChem CID	12000240;
ChemSpider	10172707;
UNII	P0GMS9N47Q;
KEGG	D10004;
Chemical and physical data
Formula	C26H27F4N3O7
Molar mass	569.501 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)COc1c(c(cc(c1F)F)F)F)NC(=O)C(=O)Nc2ccccc2C(C)(C)C;
	InChI InChI=1S/C26H27F4N3O7/c1-12(31-24(38)25(39)32-16-8-6-5-7-13(16)26(2,3)4)23(37)33-17(10-19(35)36)18(34)11-40-22-20(29)14(27)9-15(28)21(22)30/h5-9,12,17H,10-11H2,1-4H3,(H,31,38)(H,32,39)(H,33,37)(H,35,36)/t12-,17-/m0/s1; Key:SCVHJVCATBPIHN-SJCJKPOMSA-N;

Emricasan (IDN-6556, PF-03491390) is a potential drug invented in 1998 by Idun Pharmaceuticals.[1][2] The drug was acquired by Pfizer in 2005[3] and then sold to Conatus Pharmaceuticals in 2010.[1] Conatus in turn licensed emricasan to Novartis in 2017 for exclusive development and commercialization.[4]

The substance acts as a pan-caspase inhibitor and has antiapoptotic and antiinflammatory effects.[4] It was developed for the treatment of liver disease[5] and has been granted fast track designation by the FDA for the treatment of non-alcoholic steatohepatitis cirrhosis[6][7][8] The susbtance is the first pan-caspase inhibitor to advance to broad clinical testing, and its novel mechanism of action has led to research using it for other potential applications.[9][10]

References

McCallister E (Aug 9, 2010). "IDUN IT AGAIN: Conatus Reacquires Idun Assets From Pfizer, Hopes Data Will Attract Investors". BioCentury.
Linton SD, Aja T, Armstrong RA, Bai X, Chen LS, Chen N, et al. (November 2005). "First-in-class pan caspase inhibitor developed for the treatment of liver disease". Journal of Medicinal Chemistry. 48 (22): 6779–82. doi:10.1021/jm050307e. PMID 16250635.
"Pfizer to acquire Idun Pharmaceuticals in cash transaction". Scrip. May 2005.
Taylor P (May 4, 2017). "Novartis adds to NASH pipeline, activating license for Conatus' emricasan". FierceBiotech.
Hoglen NC, Chen LS, Fisher CD, Hirakawa BP, Groessl T, Contreras PC (May 2004). "Characterization of IDN-6556 (3-[2-(2-tert-butyl-phenylaminooxalyl)-amino]-propionylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid): a liver-targeted caspase inhibitor". The Journal of Pharmacology and Experimental Therapeutics. 309 (2): 634–40. doi:10.1124/jpet.103.062034. PMID 14742742.
Marriott N (10 May 2017). "Lonza NEWS Novartis enter agreement with Conatus for NASH treatment". European Pharmaceutical Review.
Haddad JJ (September 2013). "Current opinion on 3-[2-[(2-tert-butyl-phenylaminooxalyl)-amino]-propionylamino]- 4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid, an investigational drug targeting caspases and caspase-like proteases: the clinical trials in sight and recent anti-inflammatory advances". Recent Patents on Inflammation & Allergy Drug Discovery. 7 (3): 229–58. doi:10.2174/1872213X113079990017. PMID 23859695.
Rotman Y, Sanyal AJ (January 2017). "Current and upcoming pharmacotherapy for non-alcoholic fatty liver disease" (PDF). Gut. 66 (1): 180–190. doi:10.1136/gutjnl-2016-312431. PMID 27646933.
Brumatti G, Ma C, Lalaoui N, Nguyen NY, Navarro M, Tanzer MC, et al. (May 2016). "The caspase-8 inhibitor emricasan combines with the SMAC mimetic birinapant to induce necroptosis and treat acute myeloid leukemia". Science Translational Medicine. 8 (339): 339ra69. doi:10.1126/scitranslmed.aad3099. PMID 27194727.
Xu M, Lee EM, Wen Z, Cheng Y, Huang WK, Qian X, et al. (October 2016). "Identification of small-molecule inhibitors of Zika virus infection and induced neural cell death via a drug repurposing screen". Nature Medicine. 22 (10): 1101–1107. doi:10.1038/nm.4184. PMC 5386783. PMID 27571349.

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[BioCentury-1] McCallister E (Aug 9, 2010). "IDUN IT AGAIN: Conatus Reacquires Idun Assets From Pfizer, Hopes Data Will Attract Investors". BioCentury.

[J_med_Chem-2] Linton SD, Aja T, Armstrong RA, Bai X, Chen LS, Chen N, et al. (November 2005). "First-in-class pan caspase inhibitor developed for the treatment of liver disease". Journal of Medicinal Chemistry. 48 (22): 6779–82. doi:10.1021/jm050307e. PMID 16250635.

[3] "Pfizer to acquire Idun Pharmaceuticals in cash transaction". Scrip. May 2005.

[Fierce-4] Taylor P (May 4, 2017). "Novartis adds to NASH pipeline, activating license for Conatus' emricasan". FierceBiotech.

[pmid14742742-5] Hoglen NC, Chen LS, Fisher CD, Hirakawa BP, Groessl T, Contreras PC (May 2004). "Characterization of IDN-6556 (3-[2-(2-tert-butyl-phenylaminooxalyl)-amino]-propionylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid): a liver-targeted caspase inhibitor". The Journal of Pharmacology and Experimental Therapeutics. 309 (2): 634–40. doi:10.1124/jpet.103.062034. PMID 14742742.

[EPR-6] Marriott N (10 May 2017). "Lonza NEWS Novartis enter agreement with Conatus for NASH treatment". European Pharmaceutical Review.

[pmid23859695-7] Haddad JJ (September 2013). "Current opinion on 3-[2-[(2-tert-butyl-phenylaminooxalyl)-amino]-propionylamino]- 4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid, an investigational drug targeting caspases and caspase-like proteases: the clinical trials in sight and recent anti-inflammatory advances". Recent Patents on Inflammation & Allergy Drug Discovery. 7 (3): 229–58. doi:10.2174/1872213X113079990017. PMID 23859695.

[pmid27646933-8] Rotman Y, Sanyal AJ (January 2017). "Current and upcoming pharmacotherapy for non-alcoholic fatty liver disease" (PDF). Gut. 66 (1): 180–190. doi:10.1136/gutjnl-2016-312431. PMID 27646933.

[pmid27194727-9] Brumatti G, Ma C, Lalaoui N, Nguyen NY, Navarro M, Tanzer MC, et al. (May 2016). "The caspase-8 inhibitor emricasan combines with the SMAC mimetic birinapant to induce necroptosis and treat acute myeloid leukemia". Science Translational Medicine. 8 (339): 339ra69. doi:10.1126/scitranslmed.aad3099. PMID 27194727.

[pmid27571349-10] Xu M, Lee EM, Wen Z, Cheng Y, Huang WK, Qian X, et al. (October 2016). "Identification of small-molecule inhibitors of Zika virus infection and induced neural cell death via a drug repurposing screen". Nature Medicine. 22 (10): 1101–1107. doi:10.1038/nm.4184. PMC 5386783. PMID 27571349.