Aztreonam

Aztreonam
Clinical data
Trade names	Azactam, Cayston, others
AHFS/Drugs.com	Monograph
Pregnancy; category	AU: B1; ;
Routes of; administration	Intravenous, intramuscular, inhalation
ATC code	J01DF01 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	100% (IM) 0.1% (by mouth in rats) Unknown (by mouth in humans)
Protein binding	56%
Metabolism	Liver (minor %)
Elimination half-life	1.7 hours
Excretion	Kidney
Identifiers
	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;
CAS Number	78110-38-0 ;
PubChem CID	5742832;
DrugBank	DB00355 ;
ChemSpider	4674940 ;
UNII	G2B4VE5GH8;
KEGG	D00240 ;
ChEBI	CHEBI:161680 ;
ChEMBL	ChEMBL158 ;
CompTox Dashboard (EPA)	DTXSID0022640 ;
ECHA InfoCard	100.071.652
Chemical and physical data
Formula	C13H17N5O8S2
Molar mass	435.43 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	227 °C (441 °F) (dec.)
	SMILES O=S(=O)(O)N2C(=O)[C@@H](NC(=O)C(=N\OC(C(=O)O)(C)C)/c1nc(sc1)N)[C@@H]2C;
	InChI InChI=1S/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/b17-8-/t5-,7-/m0/s1 ; Key:WZPBZJONDBGPKJ-VEHQQRBSSA-N ;
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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.^[1]^[2] This may include bone infections, endometritis, intra abdominal infections, pneumonia, urinary tract infections, and sepsis.^[1] It is given by intravenous or intramuscular injection or by inhalation.^[1]

Common side effects when given by injection include pain at the site of injection, vomiting, and rash.^[1] Common side effects when inhaled include wheezing, cough, and vomiting.^[1] Serious side effects include Clostridium difficile infection and allergic reactions including anaphylaxis.^[1] Those who are allergic to other β-lactam have a low rate of allergy to aztreonam.^[1] Use in pregnancy appears to be safe.^[1] It is in the monobactam family of medications.^[1] Aztreonam inhibits cell wall synthesis by blocking peptidoglycan crosslinking to cause bacterial death.^[1]

Aztreonam was approved for medical use in the United States in 1986.^[1] It was removed from the World Health Organization's List of Essential Medicines in 2019.^[3]^[4] It is available as a generic medication.^[1] It is a manufactured version of a chemical from the bacterium Chromobacterium violaceum.^[5] Aztreonam is available in a combination with avibactam (aztreonam/avibactam).

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l "Aztreonam". The American Society of Health-System Pharmacists. Retrieved 8 December 2017.
^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 381. ISBN 9780857111562.
^ World Health Organization (2019). Executive summary: the selection and use of essential medicines 2019: report of the 22nd WHO Expert Committee on the selection and use of essential medicines. Geneva: World Health Organization. hdl:10665/325773. WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO.
^ World Health Organization (2019). The selection and use of essential medicines: report of the WHO Expert Committee on Selection and Use of Essential Medicines, 2019 (including the 21st WHO Model List of Essential Medicines and the 7th WHO Model List of Essential Medicines for Children). Geneva: World Health Organization. hdl:10665/330668. ISBN 9789241210300. ISSN 0512-3054. WHO technical report series;1021.
^ Yaffe SJ, Aranda JV (2010). Neonatal and Pediatric Pharmacology: Therapeutic Principles in Practice. Lippincott Williams & Wilkins. p. 438. ISBN 9780781795388.