Razupenem

Razupenem
Clinical data
Trade names	PTZ-601
Routes of; administration	IV
Legal status
Legal status	US: Investigational New Drug ;
Identifiers
	IUPAC name (4R,5S,6S)-6-((R)-1-hydroxyethyl)-4-methyl-3-((4-((S)-5-methyl-2,5-dihydro-1H-pyrrol-3-yl)thiazol-2-yl)thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;
ChemSpider	9168406 ;
KEGG	D09658;
Chemical and physical data
Formula	C18H21N3O4S2
Molar mass	407.51 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [H][C@]12N(C(C(O)=O)=C(SC3=NC(C4=C[C@H](C)NC4)=CS3)[C@@H]2C)C([C@@]1([C@H](O)C)[H])=O;
	InChI InChI=1S/C18H21N3O4S2/c1-7-4-10(5-19-7)11-6-26-18(20-11)27-15-8(2)13-12(9(3)22)16(23)21(13)14(15)17(24)25/h4,6-9,12-13,19,22H,5H2,1-3H3,(H,24,25)/t7-,8+,9+,12+,13+/m0/s1; Key:XFGOMLIRJYURLQ-GOKYHWASSA-N;

Razupenem (PTZ-601) is a broad spectrum injectable antibiotic, from the carbapenem subgroup of beta-lactam antibiotics. It was developed as a replacement drug to combat bacteria that had acquired antibiotic resistance to commonly used antibiotics.[1] Razupenem performed well against a variety of bacterial strains,[2] but further development is in doubt due to a high rate of side effects in Phase II clinical trials.

References

Livermore, D. M.; Mushtaq, S.; Warner, M. (2009). "Activity of the anti-MRSA carbapenem razupenem (PTZ601) against Enterobacteriaceae with defined resistance mechanisms". Journal of Antimicrobial Chemotherapy. 64 (2): 330–335. doi:10.1093/jac/dkp187. PMID 19497942.
Tran, C. M.; Tanaka, K.; Yamagishi, Y.; Goto, T.; Mikamo, H.; Watanabe, K. (2011). "In Vitro Antimicrobial Activity of Razupenem (SMP-601, PTZ601) against Anaerobic Bacteria". Antimicrobial Agents and Chemotherapy. 55 (5): 2398–2402. doi:10.1128/AAC.01038-10. PMC 3088197. PMID 21343447.

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[1] Livermore, D. M.; Mushtaq, S.; Warner, M. (2009). "Activity of the anti-MRSA carbapenem razupenem (PTZ601) against Enterobacteriaceae with defined resistance mechanisms". Journal of Antimicrobial Chemotherapy. 64 (2): 330–335. doi:10.1093/jac/dkp187. PMID 19497942.

[2] Tran, C. M.; Tanaka, K.; Yamagishi, Y.; Goto, T.; Mikamo, H.; Watanabe, K. (2011). "In Vitro Antimicrobial Activity of Razupenem (SMP-601, PTZ601) against Anaerobic Bacteria". Antimicrobial Agents and Chemotherapy. 55 (5): 2398–2402. doi:10.1128/AAC.01038-10. PMC 3088197. PMID 21343447.