Carumonam - Misplaced Pages

Chemical compound Pharmaceutical compound

Carumonam
Clinical data

Trade names	Amasulin
AHFS/Drugs.com	International Drug Names
ATC code	J01DF02 (WHO)
Identifiers
IUPAC name 2-amino]-2-oxoethylidene]amino]oxyacetic acid
CAS Number	87638-04-8
PubChem CID	6540466
DrugBank	DB13553
ChemSpider	5022832
UNII	486890PI06
ChEBI	CHEBI:55486
ChEMBL	ChEMBL1614658
CompTox Dashboard (EPA)	DTXSID3048312
Chemical and physical data
Formula	C₁₂H₁₄N₆O₁₀S₂
Molar mass	466.40 g·mol
3D model (JSmol)	Interactive image
SMILES C1=C(N=C(S1)N)/C(=N/OCC(=O)O)/C(=O)N2(N(C2=O)S(=O)(=O)O)COC(=O)N
InChI InChI=1S/C12H14N6O10S2/c13-11-15-4(3-29-11)7(17-28-2-6(19)20)9(21)16-8-5(1-27-12(14)23)18(10(8)22)30(24,25)26/h3,5,8H,1-2H2,(H2,13,15)(H2,14,23)(H,16,21)(H,19,20)(H,24,25,26)/b17-7-/t5-,8+/m1/s1 Key:UIMOJFJSJSIGLV-JNHMLNOCSA-N
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Carumonam (INN) is a monobactam antibiotic. It is very resistant to beta-lactamases, which means that it is more difficult for bacteria to break down using β-lactamase enzymes.

References

McNulty CA, Garden GM, Ashby J, Wise R (September 1985). "Pharmacokinetics and tissue penetration of carumonam, a new synthetic monobactam". Antimicrobial Agents and Chemotherapy. 28 (3): 425–7. doi:10.1128/aac.28.3.425. PMC 180266. PMID 4073864.
PubChem. "Carumonam". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-12-08.

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

β-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

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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