Azidocillin

Azidocillin
Clinical data

Routes of administration	Oral, IV, IM
ATC code	J01CE04 (WHO)
Pharmacokinetic data
Bioavailability	57–64%
Elimination half-life	0.6-1.1 hrs
Excretion	37–50% active substance in urine
Identifiers
IUPAC name 6-[(2-azido-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number	17243-38-8^Y
PubChem CID	71886
DrugBank	DB08795^Y
ChemSpider	16735689^Y
UNII	R8XDP7L3SL
KEGG	D07235^Y
ChEBI	CHEBI:51758^Y
ChEMBL	ChEMBL2105907^N
CompTox Dashboard (EPA)	DTXSID20938154
ECHA InfoCard	100.037.510
Chemical and physical data
Formula	C₁₆H₁₇N₅O₄S
Molar mass	375.40 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@H](\N=[N+]=[N-])c1ccccc1)[C@H]3SC2(C)C
InChI InChI=1S/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1^Y Key:ODFHGIPNGIAMDK-NJBDSQKTSA-N^Y
^NY (what is this?) (verify)

Azidocillin is a type of penicillin.^[1]^[2]

References

^ Axelsson A, Jensen C, Melin O, Singer F, von Sydow C (1981). "Treatment of acute maxillary sinusitis. V. Amoxicillin azidocillin, phenylpropanolamine and pivampicillin". Acta Oto-Laryngologica. 91 (3–4): 313–8. doi:10.3109/00016488109138513. PMID 6894819.
^ Bergan T, Sørensen G (1980). "Pharmacokinetics of azidocillin in healthy adults". Arzneimittel-Forschung. 30 (12): 2185–91. PMID 6894241.

Antibacterials active on the cell wall and envelope (J01C-J01D)

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡
β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin^§

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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