Aztreonam

Structural formula
General
Non-proprietary name	Aztreonam
other names	( Z ) -2 - [({(2-Amino-4-thiazolyl) [(2 S , 3 S ) -2-methyl-4-oxo-1-sulfo-3-azetidinyl] carbamoyl} methylenamino) oxy] - 2-methylpropionic acid
Molecular formula	C 13 H 17 N 5 O 8 S 2 (aztreonam) ; C 13 H 17 N 5 Na 2 O 8 S 2 (aztreonam disodium salt ) ;
Brief description	colorless, odorless, crystalline powder
External identifiers / databases
EC number	278-839-9
ECHA InfoCard	100,071,652
PubChem	5742832
ChemSpider	4674940
DrugBank	DB00355
Wikidata	Q418546
Drug information
ATC code	J01 DF01
Drug class	Monobactams
properties
Molar mass	435.43 g · mol -1
Physical state	firmly
Melting point	227 ° C (decomposition)
solubility	easily soluble in DMF and DMSO ; very poor in ethanol , poor in methanol , practically insoluble in toluene , chloroform and ethyl acetate ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	3300 mg kg −1 ( LD 50 , mouse , iv , aztreonam disodium salt) ; 6600 mg kg −1 ( LD 50 , rat , ip , aztreonam disodium salt) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Aztreonam is a drug selected from the group of the monobactam - antibiotics , in the treatment of infections with gram-negative , aerobic bacteria is used.

application areas

Infections of the kidneys, the lower urinary tract, the lower respiratory tract (including pneumonia and bronchitis), also with cystic fibrosis (as a lysinate inhalation solution Cayston ), meningitis, infections of the bones and joints, of skin and soft tissue, of the abdominal cavity, in gynecology, Aztreonam is used for sepsis and gonorrhea.

Adverse effects (side effects)

Occasionally gastro-intestinal symptoms, rarely headache, dizziness, confusion, changes in the blood count, coagulation disorders and kidney dysfunction, very rarely pseudomembranous colitis, jaundice and tinnitus.

Contraindications and warnings

The contraindication is hypersensitivity to aztreonam. Attention should be paid to the risk of cross-allergy in ceftazidime allergy caused by identical side chains. In addition, it must be used carefully if the patient is allergic to reaction.

Chemical structure

Aztreonam with the β-lactam ring marked blue .

Aztreonam contains - like penicillins and cephalosporins - a β- lactam ring . This is, however - unlike the penicillins and cephalosporins - not to a five- or six-membered heterocyclic ring fused .

Trade names

Monopreparations : Azactam (A, CH, D), Cayston (A, D)

Web links

Entries in the NIH study registry
Public Assessment Report (EPAR) of the European Medicines Agency (EMA) for: Aztreonam

Individual evidence

↑ ^a ^b ^c ^d ^e ^f The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 156, ISBN 978-0-911910-00-1 .
↑ ^a ^b Data sheet Aztreonam, ≥98% (HPLC) from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).
↑ Summary of the European Public Assessment Report (EPAR) for Cayston (PDF; 131 kB) published by the European Medicines Agency . P. 3. Retrieved August 30, 2010.
↑ ROTE LISTE 2008 , Verlag Rote Liste Service GmbH, Frankfurt am Main, ISBN 978-3-939192-20-6 .
^ Marianne Abele-Horn: Antimicrobial Therapy. Decision support for the treatment and prophylaxis of infectious diseases. With the collaboration of Werner Heinz, Hartwig Klinker, Johann Schurz and August Stich, 2nd, revised and expanded edition. Peter Wiehl, Marburg 2009, ISBN 978-3-927219-14-4 , p. 339.
↑ Marianne Abele-Horn (2009), p. 339.

[MERCK_Index-1] ↑ ^a ^b ^c ^d ^e ^f The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 156, ISBN 978-0-911910-00-1 .

[Sigma-2] Data sheet Aztreonam, ≥98% (HPLC) from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).

[ema-3] Summary of the European Public Assessment Report (EPAR) for Cayston (PDF; 131 kB) published by the European Medicines Agency . P. 3. Retrieved August 30, 2010.

[ROTE_LISTE-4] ROTE LISTE 2008 , Verlag Rote Liste Service GmbH, Frankfurt am Main, ISBN 978-3-939192-20-6 .

[5] Marianne Abele-Horn: Antimicrobial Therapy. Decision support for the treatment and prophylaxis of infectious diseases. With the collaboration of Werner Heinz, Hartwig Klinker, Johann Schurz and August Stich, 2nd, revised and expanded edition. Peter Wiehl, Marburg 2009, ISBN 978-3-927219-14-4 , p. 339.

[6] Marianne Abele-Horn (2009), p. 339.