Razupenem

Chemical compound

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 dataFormulaC₁₈H₂₁N₃O₄S₂Molar mass407.50 g·mol⁻¹3D 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.

Antibacterials active on the cell wall and envelope (J01C-J01D)

Beta-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡
β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Glycopeptides Lipoglycopeptides	Inhibit PG chain elongation: Vancomycin^# (Oritavancin Telavancin) Teicoplanin (Dalbavancin) Ristocetin^‡ Avoparcin Inhibit autolysin: Corbomycin (not approved)
Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Polymyxins	Bind to LPS in the outer bacterial membrane, acting in detergent-like fashion: Colistin Polymyxin B
Other	Inhibits PG elongation and crosslinking: Ramoplanin^§