Aztreonam

Title: Aztreonam
CAS Registry Number: 78110-38-0
CAS Name: [2S-[2a,3b(Z)]]-2-[[[1-(2-Amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid
Additional Names: azthreonam
Manufacturers' Codes: SQ-26776
Trademarks: Azactam (BMS); Primbactam (Menarini)
Molecular Formula: C13H17N5O8S2
Molecular Weight: 435.43
Percent Composition: C 35.86%, H 3.94%, N 16.08%, O 29.40%, S 14.73%
Literature References: The first totally synthetic monocyclic b-lactam (monobactam) antibiotic. It has a high degree of resistance to b-lactamases and shows specific activity vs aerobic gram-negative rods. Prepn: R. B. Sykes et al., NL 8100571 (1981 to Squibb), C.A. 96, 181062x (1982). Fast-atom-bombardment mass spectra: A. I. Cohen et al., J. Pharm. Sci. 71, 1065 (1982). Activity vs gram-negative bacteria: R. B. Sykes et al., Antimicrob. Agents Chemother. 21, 85 (1982). Series of articles on structure-activity, in vitro and in vivo properties, pharmacokinetics: J. Antimicrob. Chemother. 8, Suppl. E, 1-148 (1981). Toxicology: G. R. Keim et al., ibid. 141. Mechanism of action study: A. D. Russell, J. R. Furr, ibid. 9, 329 (1982). Comparative stability to renal dipeptidase: H. Mikami et al., Antimicrob. Agents Chemother. 22, 693 (1982). Human pharmacokinetics: E. A. Swabb et al., ibid. 21, 944 (1982). Clinical evaluation in urinary tract infection: C. Donadio et al., Drugs Exp. Clin. Res. 13, 167 (1987). Clinical efficacy in neonatal sepsis: S. Sklavunu-Tsurutsoglu et al., Rev. Infect. Dis. 13, Suppl. 7, S591 (1991). Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 17, 1-39 (1988).
Properties: White crystalline, odorless powder, dec 227°. Very slightly sol in ethanol, slightly sol in methanol, sol in DMF, DMSO. Practically insol in toluene, chloroform, ethyl acetate.
Derivative Type: Disodium salt
Molecular Formula: C13H15N5Na2O8S2
Molecular Weight: 479.40
Percent Composition: C 32.57%, H 3.15%, N 14.61%, Na 9.59%, O 26.70%, S 13.38%
Properties: LD50 (mg/kg): 3300 i.v. in mice; 6600 i.p. in rats (Keim).
Toxicity data: LD50 (mg/kg): 3300 i.v. in mice; 6600 i.p. in rats (Keim)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Monobactams.
Azulene Azure B Azure C Babbitt Metal Bacampicillin

Aztreonam
Aztreonam structure.svg
Systematic (IUPAC) name
2-({[(1Z)-1-(2-amino-1,3-thiazol-4-yl) -2- {[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino} -2- oxoethylidene]amino}oxy)-2-methylpropanoic acid
Clinical data
Trade names Azactam
AHFS/Drugs.com monograph
Pregnancy cat. B1 (Au), B (U.S.)
Legal status ℞-only (U.S.)
Routes Intravenous, intramuscular, inhalation
Pharmacokinetic data
Bioavailability 100% (IM)
Protein binding 56%
Metabolism hepatic (minor %)
Half-life 1.7 hours
Excretion Renal
Identifiers
CAS number 78110-38-0 YesY
ATC code J01DF01
PubChem CID 54116
DrugBank DB00355
ChemSpider 4674940 YesY
UNII G2B4VE5GH8 YesY
KEGG D00240 YesY
ChEBI CHEBI:161680 YesY
ChEMBL CHEMBL158 YesY
Chemical data
Formula C13H17N5O8S2 
Mol. mass 435.433 g/mol
 YesY (what is this?)  (verify)

Aztreonam (trade names Azactam injection, Cayston inhalation) is a synthetic monocyclic beta-lactam antibiotic (a monobactam), with the nucleus based on a simpler monobactam isolated from Chromobacterium violaceum. It was approved by the U.S. Food and Drug Administration (FDA) in 1986. It is resistant to some beta-lactamases, but is inactivated by extended-spectrum beta-lactamases.