β-lactam

L-lysine lactam is a building block.1,2It has been used in the synthesis of lysine sulfonamide HIV protease inhibitors, as well as bengamide derivatives within vitroanticancer activity.

L-Ornithine lactam is a synthetic intermediate. It has been used in the synthesis of dipeptidyl peptidase 4 (DPP-4) inhibitors, as well as signaling peptides.

Olanzapine lactam impurity is a potential impurity found in commercial preparations of olanzapine.1It is a degradation product formed by exposure to thermal or oxidative stress. 1.Baertschi, S.W., Brunner, H., Bunnell, C.A., et al.Isolation, identification, and synthesis of two oxidative degradation products of olanzapine (LY170053) in solid oral formulationsJ. Pharm. Sci.97(2)883-892(2008)

D-Ornithine lactam is a building block. It has been used in the synthesis of hepatitis C virus non-structural protein 5B inhibitors, as well as αVβ3 integrin receptor antagonists.

N-Methyl lactam (Compound 3b), an analogue of peramiue, exhibits feeding-deterrent activity in adult weevils [1].

D-Lysine lactam is a chiral building block.1,2It has been used in the synthesis of a chiral antibiotic synthetic intermediate, as well as in the stereoselective synthesis of neurokinin (NK) receptor antagonists. 1.Kumar, A., Bhashkar, B., Bhavsar, J., et al.Catalytic reduction: Efficient synthesis of chiral key intermediate of besifloxacin hydrochlorideDer Pharma Chemica7(9)297-3000(2015) 2.Gerspacher, M., Lewis, C., Ball, H.A., et al.Stereoselective preparation of N-[(R,R)-(E)-1-(3,4-dichlorobenzyl)-3- (2-oxoazepan-3-yl)carbamoyl]allyl-N-methyl-3,5-bis(trifluoromethyl)benzamide, a potent and orally active dual neurokinin NK(1)/NK(2) receptor antagonistJ. Med. Chem.46(16)3508-3513(2003)

Methicillin sodium salt is the sodium salt form of methicillin, a semisynthetic beta-lactam penicillin antibiotic with beta-lactamase resistant activity.

Cefsulodin sodium (Sulcephalosporin) hydrate is a β lactam antibiotic.

Avibactam sodium (NXL-104) is a non-β-lactam β-lactamase inhibitor that inhibits TEM-1, P99, and KPC-2 β-lactamases (IC50=8 80 38 nM) covalently and reversibly. Avibactam sodium has antimicrobial activity and can be used to treat urinary tract infections.

Amoxicillin Sodium (Clavulanate) is a moderate- spectrum, bacteriolytic, β-lactam antibiotic.

Aztreonam (SQ-26,776), a monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum, possesses bactericidal activity.

Ceftazidime (GR20263) is a beta-lactam, cephalosporin antibiotic with bactericidal activity.

Ceftibuten dihydrate (Sch-39720 dihydrate) is the dihydrate form of ceftibuten, and is a third-generation cephalosporin with antibacterial activity.

Ampicillin (Aminobenzylpenicillin) is a semi-synthetic penicillin belonging to the β-lactam group of antibiotics. Ampicillin has bactericidal activity against a wide range of Gram-positive and Gram-negative bacteria.

Sulbactam (CP45899) is a semi-synthetic beta-lactamase inhibitor. The beta-lactam ring of sulbactam irreversibly binds to beta-lactamase at or near its active site, thereby blocking enzyme activity and preventing metabolism of other beta-lactam antibiotics by the enzyme. Combining this agent with a beta-lactamase susceptible antibiotic, such as penicillins or a cephalosporin, to treat infections caused by beta-lactamase producing organisms, results in a decreased turnover rate of the beta-lactamase sensitive antibiotic and enhances its antibacterial activity.

Ampicillin Trihydrate (NCI-C56086), a broad-spectrum semisynthetic derivative of aminopenicillin, is a β-lactam antibiotic.

Cephalothin is a beta-lactam antibiotic, inhibits class C β-lactamase AmpC (Ki: 0.32 μM).

Ceftriaxone Sodium is a broad-spectrum β-lactam tertiary cephalosporin antibiotic with anti-inflammatory, antitumor, antibacterial, and antioxidant activities.Ceftriaxone Sodium is a covalent GSK3β and Aurora B inhibitor used in the study of sepsis and infective endocarditis.

Penicillin G Procaine is a β-lactam antibiotic and is a crystalline complex produced by chemically combining penicillin G with procaine.

Dicloxacillin Sodium hydrate is a narrow-spectrum β-Lactam antibiotic of the penicillin class, used to treat infections caused by susceptible Gram-positive bacteria.

Clavulanate lithium (Clavulanic acid lithium) is an inhibitor of β-lactamase.

MAC-545496 is a glycopeptide-resistance-associated protein R (GraR) inhibitor, is an antivirulence agent.

NF-1819 is a potent and selective irreversible MGL (β-lactam-based monoacylglycerol lipase) inhibitor. NF-1819 alleviates symptoms in a MS model in vivo and exhibits analgesic effects in an acute inflammatory pain model in vivo. NF-1819 displays high membrane permeability and brain penetrant.

Faropenem daloxate (Faropenem medoxil) is useful for penem and antibiotics. Faropenem medoxomil has excellent in vitro activity against Streptococcus pneumoniae, Haemophilus influenzae and other key pathogens implicated in acute bacterial rhinosinusitis.Faropenem daloxate is the first oral penem in a new class of beta-lactam antibiotics.

Cefoselis Sulfate is a widely used beta-lactam antibiotic.

Mezlocillin Sodium (Baycipen) is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms.

TunR2 is an antibiotic and derivative of tunicamycin .1It is active againstB. subtilis(MIC = 0.3 μg/ml) and increases the efficacy of the β-lactam antibiotics oxacillin , methicillin , and penicillin G againstB. subtiliswhen used at a concentration of 0.4 μg/ml. Unlike tunicamycin, TunR2 is non-toxic toS. cerevisiae(MIC = >10 μg/ml) and does not inhibit glycosylation in a protein N-glycosylation assay. TunR2 also has reduced antiproliferative activity against MDA-MB-231 and CHO cells compared with tunicamycin. 1.Price, N.P., Hartman, T.M., Li, J., et al.Modified tunicamycins with reduced eukaryotic toxicity that enhance the antibacterial activity of β-lactamsJ. Antibiot. (Tokyo)70(11)1070-1077(2017)

A1-226 is a cephalosporin of the class of β-lactam antibiotics, it is originally derived from the fungus Acremonium.

Avibactam sodium hydrate (NXL-104 hydrate) is a covalent and reversible inhibitor of β-lactamase that does not contain a β-lactam core. Avibactam sodium hydrate inhibits β-lactamase CTX-M-15 and TEM-1 with IC 50 s of 5 nM and 8 nM, respectively.

Cefsulodin is a β-lactam antibiotic that lyses actively-growingE. coliby binding specifically to the intermembrane proteins, penicillin-binding proteins 1a and b, whose transglycosylase and transpeptidase activities are involved in cell elongation and septation.1Cefsulodin has been used in combination with other β-lactam antibiotics, such as cefazolin as a strategy to circumvent drug resistance.2

Nacubactam (OP0595 free acid) is a potent non-β-lactam β-lactamase inhibitor, effective against class A and class C β-lactamases.

ANT3310 is an inhibitor of broad-spectrum covalent Serine β-Lactamase with IC50s ranging from 1 nM to 175 nM for AmpC, CTX-M-15, TEM-1, OXA-48, OXA-23, and KPC-2. ANT3310 can be used in studies about bacterial infection.

1-Palmitoyl lysophosphatidic acid (1-Palmitoyl LPA) is a LPA analog containing palmitic acid at the sn-1 position. LPA binds to one of five different G protein-coupled receptors (GPCRs) to mediate a variety of biological responses including cell proliferation, smooth muscle contraction, platelet aggregation, neurite retraction, and cell motility. In addition to playing a role in the aforementioned biological responses, 1-palmitoyl LPA enhances the action of β-lactam antibiotics (ampicillin, piperacillin, and ceftazidime) on various strains of Pseudomonas aeruginosa, a pathogen associated with pulmonary disease and pneumonia, via binding both Ca2+ and Mg2+.

BMS-262084 is a potent selective β-lactam trypsin inhibitor with therapeutic potential in the treatment of asthma.

KPC-2-IN-1, a boronic acid derivative, serves as an effective KPC-2 inhibitor with a K i of 0.032 μM, augmenting cefotaxime's efficacy against KPC-2 expressing E. coli. It demonstrates good tolerance in human HEK-293 cells, rendering it valuable for researching E. coli's resistance to β-lactam antibiotics [1] [2].

Avibactam sodium (NXL-104) dihydrate inhibits CTX-M-15 and β-lactamase TEM-1 with IC50 values of 5 nM and 8 nM, respectively, and is a reversible covalent inhibitor of non-β-lactam β-lactamase [1].

Clavicoronic acid is a β-lactam drug that functions as a mechanism-based β-lactamase inhibitor. While not effective by itself as an antibiotic, when combined with penicillin-group antibiotics, it can overcome antibiotic resistance in bacteria that secrete β-lactamase, which otherwise inactivates most penicillins.

Azidocillin, a semi-synthetic Penicillin and orally active β-lactam antibiotic, features an azide functionality and maintains on-target antibacterial activity. It is utilized in studying osteitis resulting from dental surgery, otitis media, enterococcal septicemia, and various bacterial infections [1] [2] [3].

L-(+)-Ampicillin is an isomer of Ampicillin. Ampicillin is a β-lactam antibiotic used for treating bacterial infections.

Cefmetazole is a second-generation semi-synthetic β-lactam cephalosporin antibiotic with antimicrobial activity.

TunR1 is an antibiotic and derivative of tunicamycin .1It is active againstB. subtilis(MIC = 0.3 μg/ml) and increases the efficacy of the β-lactam antibiotics oxacillin , methicillin , and penicillin G againstB. subtiliswhen used at a concentration of 0.4 μg/ml. TunR1 (5 μg/ml) is cytotoxic to MDA-MB-231 breast cancer cells and non-cancerous CHO cells. Unlike tunicamycin, TunR1 does not inhibit glycosylation in a protein N-glycosylation assay. 1.Price, N.P., Hartman, T.M., Li, J., et al.Modified tunicamycins with reduced eukaryotic toxicity that enhance the antibacterial activity of β-lactamsJ. Antibiot. (Tokyo)70(11)1070-1077(2017)

Ceftobiprole (Ro 63-9141) is a β-lactam antibacterial agent that exhibits potent bactericidal activity by binding to PBPs, inhibiting transpeptidation and formation of bacterial cell walls, leading to cell lysis and death, with a MIC90 value of 2 μg mL against methicillin-resistant Staphylococcus aureus.

Sulfazecin is a β-Lactam antibiotic.

FXIa-IN-1 is a potent β-lactam covalent heparin-derived factor XIa (fXIa) inhibitor.

D-4-Hydroxyphenylglycine (D-(-)-4-Hydroxyphenylglycine) is a vital raw material in the synthesis of semisynthetic β-lactam antibiotics, such as Amoxicillin and Cefadroxil.

Penicillinase, a beta-lactamase enzyme, inactivates beta-lactam antibiotics by hydrolyzing the peptide bond of the characteristic four-membered beta-lactam ring, rendering the antibiotic ineffective [1].

Imipenem monohydrate (Imipenem) is a carbapenem antibiotic isolated from the microorganism Streptomyces cattleya, and is a β lactam antibiotic. Imipenem monohydrate acts on the bacterial cell wall, and is a broadly effective inhibitor of a wide range of Gram-positive and negative bacteria.

O-Benzylhydroxylamine is a building block.1,2It has been used in the synthesis of β-lactam inhibitor precursors and fluoroquinolone derivatives with antibiotic activity. 1.Bellettini, J.R., and Miller, M.J.A short synthesis of an important precursor to a new class of bicyclic β-lactamase inhibitorsTetrahedron Lett.38(2)167-168(1997) 2.Asadipour, A., Moshafi, M.H., Khosravani, L., et al.N-substituted piperazinyl sarafloxacin derivatives: synthesis and in vitro antibacterial evaluationDaru.26(2)199-207(2018)

Novel cyclic peptide that disrupts interaction between GluR6 and PSD-95