Eravacycline

Eravacycline
Names
	Preferred IUPAC name (4S,4aS,5aR,12aS)-4-(Dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[2-(pyrrolidin-1-yl)acetamido]-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
	Other names Xerava
Identifiers
CAS Number	1207283-85-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	28495485;
KEGG	D10369; D10421;
PubChem CID	54726192;
UNII	07896928ZC ;
	InChI InChI=1S/C27H31FN4O8/c1-31(2)20-13-8-11-7-12-14(28)9-15(30-16(33)10-32-5-3-4-6-32)21(34)18(12)22(35)17(11)24(37)27(13,40)25(38)19(23(20)36)26(29)39/h9,11,13,20,34,36-37,40H,3-8,10H2,1-2H3,(H2,29,39)(H,30,33)/t11-,13-,20-,27-/m0/s1 Key: HLFSMUUOKPBTSM-ISIOAQNYSA-N;
	SMILES CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=C(C(=C4C(=O)C3=C([C@@]2(C(=O)C(=C1O)C(=O)N)O)O)O)NC(=O)CN5CCCC5)F;
Properties
Chemical formula	C27H31FN4O8
Molar mass	558.555
Pharmacology
ATC code	J01AA13 (WHO)
Legal status	EU: Rx-only;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Eravacycline (TP-434, Xerava) is a synthetic halogenated tetracycline class antibiotic by Tetraphase Pharmaceuticals. It is closely related to tigecycline. It has a broad spectrum of activity including many multi-drug resistant strains of bacteria. Phase III studies in complicated intra-abdominal infections (cIAI)^[2] and complicated urinary tract infections (cUTI)^[3] were recently completed with mixed results. Eravacycline was granted fast track designation by the FDA^[4] and is currently available in USA.

^ "Xerava EPAR". European Medicines Agency. 8 October 2018. Retrieved 29 June 2024.
^ Solomkin J, Evans D, Slepavicius A, Lee P, Marsh A, Tsai L, et al. (16 November 2016). "Assessing the Efficacy and Safety of Eravacycline vs Ertapenem in Complicated Intra-abdominal Infections in the Investigating Gram-Negative Infections Treated With Eravacycline (IGNITE 1) Trial: A Randomized Clinical Trial". JAMA Surgery. 152 (3): 224–232. doi:10.1001/jamasurg.2016.4237. ISSN 2168-6262. PMID 27851857. S2CID 42977246.
^ "Tetraphase Announces Top-Line Results From IGNITE2 Phase 3 Clinical Trial of Eravacycline in cUTI (NASDAQ:TTPH)". ir.tphase.com. Archived from the original on 21 November 2016. Retrieved 20 November 2016.
^ "FDA Grants QIDP Designation to Eravacycline, Tetraphase's Lead Antibiotic Product Candidate | Business Wire". businesswire.com. 15 July 2013. Retrieved 20 November 2016.

[1] "Xerava EPAR". European Medicines Agency. 8 October 2018. Retrieved 29 June 2024.

[:1-2] Solomkin J, Evans D, Slepavicius A, Lee P, Marsh A, Tsai L, et al. (16 November 2016). "Assessing the Efficacy and Safety of Eravacycline vs Ertapenem in Complicated Intra-abdominal Infections in the Investigating Gram-Negative Infections Treated With Eravacycline (IGNITE 1) Trial: A Randomized Clinical Trial". JAMA Surgery. 152 (3): 224–232. doi:10.1001/jamasurg.2016.4237. ISSN 2168-6262. PMID 27851857. S2CID 42977246.

[:2-3] "Tetraphase Announces Top-Line Results From IGNITE2 Phase 3 Clinical Trial of Eravacycline in cUTI (NASDAQ:TTPH)". ir.tphase.com. Archived from the original on 21 November 2016. Retrieved 20 November 2016.

[4] "FDA Grants QIDP Designation to Eravacycline, Tetraphase's Lead Antibiotic Product Candidate | Business Wire". businesswire.com. 15 July 2013. Retrieved 20 November 2016.

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