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;
CAS Number	426253-04-5 ;
ChemSpider	9168406 ;
UNII	26020H3Q1L;
KEGG	D09658;
CompTox Dashboard (EPA)	DTXSID801045429 ;
Chemical and physical data
Formula	C18H21N3O4S2
Molar mass	407.50 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 DM, Mushtaq S, Warner M (August 2009). "Activity of the anti-MRSA carbapenem razupenem (PTZ601) against Enterobacteriaceae with defined resistance mechanisms". The Journal of Antimicrobial Chemotherapy. 64 (2): 330–5. doi:10.1093/jac/dkp187. PMID 19497942.
^ Tran CM, Tanaka K, Yamagishi Y, Goto T, Mikamo H, Watanabe K (May 2011). "In vitro antimicrobial activity of razupenem (SMP-601, PTZ601) against anaerobic bacteria". Antimicrobial Agents and Chemotherapy. 55 (5): 2398–402. doi:10.1128/AAC.01038-10. PMC 3088197. PMID 21343447.

[1] Livermore DM, Mushtaq S, Warner M (August 2009). "Activity of the anti-MRSA carbapenem razupenem (PTZ601) against Enterobacteriaceae with defined resistance mechanisms". The Journal of Antimicrobial Chemotherapy. 64 (2): 330–5. doi:10.1093/jac/dkp187. PMID 19497942.

[2] Tran CM, Tanaka K, Yamagishi Y, Goto T, Mikamo H, Watanabe K (May 2011). "In vitro antimicrobial activity of razupenem (SMP-601, PTZ601) against anaerobic bacteria". Antimicrobial Agents and Chemotherapy. 55 (5): 2398–402. doi:10.1128/AAC.01038-10. PMC 3088197. PMID 21343447.

[1]

[2]

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
CAS Number	426253-04-5^Y
ChemSpider	9168406^Y
UNII	26020H3Q1L
KEGG	D09658
CompTox Dashboard (EPA)	DTXSID801045429
Chemical and physical data
Formula	C₁₈H₂₁N₃O₄S₂
Molar mass	407.50 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