Nacubactam

Nacubactam
Identifiers
	IUPAC name [(2S,5R)-2-(2-aminoethoxycarbamoyl)-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate;
CAS Number	1452458-86-4;
PubChem CID	73386748;
DrugBank	DB15353;
ChemSpider	58827979;
UNII	832O37V7MZ;
KEGG	D11329;
ChEMBL	ChEMBL3989959;
Chemical and physical data
Formula	C9H16N4O7S
Molar mass	324.31 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1C[C@H](N2C[C@@H]1N(C2=O)OS(=O)(=O)O)C(=O)NOCCN;
	InChI InChI=InChI=1S/C9H16N4O7S/c10-3-4-19-11-8(14)7-2-1-6-5-12(7)9(15)13(6)20-21(16,17)18/h6-7H,1-5,10H2,(H,11,14)(H,16,17,18)/t6-,7+/m1/s1; Key:RSBPYSTVZQAADE-RQJHMYQMSA-N;

Nacubactam is an investigational β-lactamase inhibitor being developed for the treatment of infections caused by carbapenem-resistant Enterobacteriaceae (CRE). It belongs to the diazabicyclooctane (DBO) class of compounds and exhibits a dual mechanism of action. Nacubactam inhibits serine β-lactamases, including classes A and C and some class D enzymes, while also directly inhibiting penicillin-binding protein 2 (PBP2) in Enterobacteriaceae.^[1]^[2] This unique profile allows nacubactam to both protect partner β-lactam antibiotics from degradation and exert direct antibacterial effects. As of 2024, nacubactam is undergoing clinical trials in combination with other β-lactam antibiotics such as meropenem, cefepime, and aztreonam for the treatment of complicated urinary tract infections and other serious bacterial infections caused by multidrug-resistant pathogens.^[3]^[4]

References

^ Mallalieu NL, Winter E, Fettner S, Patel K, Zwanziger E, Attley G, et al. (April 2020). "Safety and Pharmacokinetic Characterization of Nacubactam, a Novel β-Lactamase Inhibitor, Alone and in Combination with Meropenem, in Healthy Volunteers". Antimicrobial Agents and Chemotherapy. 64 (5). doi:10.1128/AAC.02229-19. PMC 7179653. PMID 32041717.
^ Igarashi Y, Takemura W, Liu X, Kojima N, Morita T, Chuang VT, et al. (April 2023). "Development of an optimized and practical pharmacokinetics/pharmacodynamics analysis method for aztreonam/nacubactam against carbapenemase-producing K. pneumoniae". The Journal of Antimicrobial Chemotherapy. 78 (4): 991–999. doi:10.1093/jac/dkad033. PMC 10068424. PMID 36775998.
^ "Nacubactam". DrugBank.
^ Hagihara M, Kato H, Sugano T, Okade H, Sato N, Shibata Y, et al. (September 2021). "In Vivo Pharmacodynamics of β-Lactams/Nacubactam against Carbapenem-Resistant and/or Carbapenemase-Producing Enterobacter cloacae and Klebsiella pneumoniae in Murine Pneumonia Model". Antibiotics. 10 (10). Basel, Switzerland: 1179. doi:10.3390/antibiotics10101179. PMC 8532682. PMID 34680760.

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[Mallalieu_2020-1] Mallalieu NL, Winter E, Fettner S, Patel K, Zwanziger E, Attley G, et al. (April 2020). "Safety and Pharmacokinetic Characterization of Nacubactam, a Novel β-Lactamase Inhibitor, Alone and in Combination with Meropenem, in Healthy Volunteers". Antimicrobial Agents and Chemotherapy. 64 (5). doi:10.1128/AAC.02229-19. PMC 7179653. PMID 32041717.

[Igarashi_2023-2] Igarashi Y, Takemura W, Liu X, Kojima N, Morita T, Chuang VT, et al. (April 2023). "Development of an optimized and practical pharmacokinetics/pharmacodynamics analysis method for aztreonam/nacubactam against carbapenemase-producing K. pneumoniae". The Journal of Antimicrobial Chemotherapy. 78 (4): 991–999. doi:10.1093/jac/dkad033. PMC 10068424. PMID 36775998.

[DrugBank-3] "Nacubactam". DrugBank.

[Hagihara_2021-4] Hagihara M, Kato H, Sugano T, Okade H, Sato N, Shibata Y, et al. (September 2021). "In Vivo Pharmacodynamics of β-Lactams/Nacubactam against Carbapenem-Resistant and/or Carbapenemase-Producing Enterobacter cloacae and Klebsiella pneumoniae in Murine Pneumonia Model". Antibiotics. 10 (10). Basel, Switzerland: 1179. doi:10.3390/antibiotics10101179. PMC 8532682. PMID 34680760.

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Identifiers

IUPAC name [(2S,5R)-2-(2-aminoethoxycarbamoyl)-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
CAS Number	1452458-86-4
PubChem CID	73386748
DrugBank	DB15353
ChemSpider	58827979
UNII	832O37V7MZ
KEGG	D11329
ChEMBL	ChEMBL3989959
Chemical and physical data
Formula	C₉H₁₆N₄O₇S
Molar mass	324.31 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1C[C@H](N2C[C@@H]1N(C2=O)OS(=O)(=O)O)C(=O)NOCCN
InChI InChI=InChI=1S/C9H16N4O7S/c10-3-4-19-11-8(14)7-2-1-6-5-12(7)9(15)13(6)20-21(16,17)18/h6-7H,1-5,10H2,(H,11,14)(H,16,17,18)/t6-,7+/m1/s1 Key:RSBPYSTVZQAADE-RQJHMYQMSA-N