aztreonam

Also known as SO-26776, SQ-26776, (Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulfo-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic acid, Aztréonam, Azactam, Primbactam, 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

Aztreonam, sold under the brand name Azactam among others, is an antibiotic used primarily to treat infections caused by gram-negative bacteria such as Pseudomonas aeruginosa. This may include bone infections, endometritis, intra abdominal infections, pneumonia, urinary tract infections, and sepsis. It is given by intravenous or intramuscular injection or by inhalation.

Key facts

Drug.verifiedrevid: 458976305
Drug.image: Aztreonam skeletal structure.svg
Drug.image_class: skin-invert-image
Drug.width: 250
Drug.image2: Aztreonam ball-and-stick model from xtal 2023 inversion.png
Drug.image_class2: bg-transparent
Drug.width2: 250
Drug.tradename: Azactam, others
Drug.MedlinePlus: a687010
Drug.pregnancy_AU: B1
Drug.routes_of_administration: Intravenous, intramuscular, inhalation
Drug.ATC_prefix: J01
Drug.ATC_suffix: DF01
Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.legal_EU: Rx-only
Drug.bioavailability: 100% (IM) 0.1% (by mouth in rats) Unknown (by mouth in humans)
Drug.protein_bound: 56%

via Wikipedia infobox

Chemical data

Formula: C13H17N5O8S2
Molecular weight: 435.4 g/mol
IUPAC name: (2S,3S)-3-[[(2Z)-2-(2-amino-1,3-thiazol-3-ium-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-2-methyl-4-oxoazetidine-1-sulfonate
SMILES: C[C@H]1[C@@H](C(=O)N1S(=O)(=O)[O-])NC(=O)/C(=N\OC(C)(C)C(=O)O)/C2=CSC(=[NH+]2)N
InChIKey: WZPBZJONDBGPKJ-VEHQQRBSSA-N
XLogP: -0.2
Polar surface area: 242 Å²
H-bond donors: 4
H-bond acceptors: 11
Formal charge: 0

via PubChem

Research

4,742 papers

via PubMed

Wikidata facts

Mass: 435.051855

Show 4 more facts

chemical formula: C₁₃H₁₇N₅O₈S₂
isomeric SMILES: C[C@H]1[C@@H](C(=O)N1S(=O)(=O)O)NC(=O)/C(=N\OC(C)(C)C(=O)O)/C2=CSC(=N2)N
canonical SMILES: CC1C(C(=O)N1S(=O)(=O)O)NC(=O)C(=NOC(C)(C)C(=O)O)C2=CSC(=N2)N
Commons category: Aztreonam

Sources (6)

via Wikidata · CC0

~8 min read

Article

8 sections

Contents

Medical uses
Spectrum of activity
Administration
Contraindications
Side effects
Mechanism of action
Research
References

{{Infobox drug | verifiedrevid = 458976305 | image = Aztreonam skeletal structure.svg | image_class = skin-invert-image | width = 250 | alt = | image2 = Aztreonam ball-and-stick model from xtal 2023 inversion.png | image_class2 = bg-transparent | width2 = 250