Structure via PubChem · Public domain (PubChem)
azlocillin
Sign in to saveAlso known as (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 2,2-dimethyl-6beta-[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetamido]penam-3alpha-carboxylic acid, Azlocilina, Azlocilline, Azlocillinum
Azlocillin is an acyl ampicillin antibiotic with an extended spectrum of activity and greater in vitro potency than the carboxy penicillins. Azlocillin is similar to mezlocillin and piperacillin. It demonstrates antibacterial activity against a broad spectrum of bacteria, including Pseudomonas aeruginosa, and, in contrast to most cephalosporins, exhibits activity against enterococci.
In the Vinony graph
Vinony's link graph records 193 inbound references to azlocillin, and connects out to antibiotic, Pseudomonas aeruginosa and ceftolozane/tazobactam.
It sits within the topics Drugs with no legal status, ECHA InfoCard ID from Wikidata and Enantiopure drugs.
Vinony links it to 17 Wikipedia language editions.
Chemical data
- Formula
- C20H23N5O6S
- Molecular weight
- 461.5 g/mol
- IUPAC name
- (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)O)C
- InChIKey
- JTWOMNBEOCYFNV-NFFDBFGFSA-N
- XLogP
- 0.1
- Polar surface area
- 173 Ų
- H-bond donors
- 4
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1982
- Admin. routes
- parenteral
- Indications
- bacterial disease
via ChEMBL · EBI
Research
775 papers- Azlocillin.Drug and therapeutics bulletin · 1981
- Azlocillin, mezlocillin, and piperacillin: new broad-spectrum penicillins.Annals of internal medicine · 1982
- [Azlocillin pharmacokinetics].Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic] · 1988
- The acylampicillins: mezlocillin, piperacillin, and azlocillin.Reviews of infectious diseases · 1984
- Population pharmacokinetics and dosing optimization of azlocillin in neonates with early-onset sepsis: a real-world study.The Journal of antimicrobial chemotherapy · 2021
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 461.136904
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₀H₂₃N₅O₆S
- Commons category
- Azlocillin
- World Health Organisation international non-proprietary name
- azlocillin
- isomeric SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)O)C
- canonical SMILES
- CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)O)C
- defined daily dose
- 12
- subject has role
- bactericide
- medical condition treated
- bacterial infectious disease
Sources (6)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Spectrum of bacterial susceptibility
- Synthesis
- See also
- References
Azlocillin is an acyl ampicillin antibiotic with an extended spectrum of activity and greater in vitro potency than the carboxy penicillins. Azlocillin is similar to mezlocillin and piperacillin. It demonstrates antibacterial activity against a broad spectrum of bacteria, including Pseudomonas aeruginosa, and, in contrast to most cephalosporins, exhibits activity against enterococci.
== Spectrum of bacterial susceptibility == Azlocillin is considered a broad spectrum antibiotic and can be used against a number of Gram positive and Gram negative bacteria. The following represents MIC susceptibility data for a few medically significant organisms. Escherichia coli 1 μg/mL – 32 μg/mL Haemophilus spp. 0.03 μg/mL – 2 μg/mL Pseudomonas aeruginosa 4 μg/mL – 6.25 μg/mL
Excerpted from Wikipedia’s “azlocillin” article, available under the CC BY-SA 4.0 licence.