U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H17N5O4S
Molecular Weight 375.402
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AZIDOCILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)C(O)=O

InChI

InChIKey=ODFHGIPNGIAMDK-NJBDSQKTSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6894241 | https://www.ncbi.nlm.nih.gov/pubmed/6971244 | https://www.ncbi.nlm.nih.gov/pubmed/6894819 | https://www.ncbi.nlm.nih.gov/pubmed/6895200

Azidocillin is a narrow-spectrum, semisynthetic penicillin derivative with antibacterial activity towards Grain-positive and Gram-negative microorganisms, including Haemophilus influenze, against which it is as effective as ampicillin. Azidocillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis. Azidocillin can be applied in the treatment of inflammation of upper airways, middle ear, sinuses, throat, larynx and palatine tonsils. The substance is excreted with urine in 50-70% in the unchan¬ged form. It binds to the blood plasma proteins in 84%, and its half-life period is 30 min. The side effects are similar as those of benzylpenicillin but occur less frequently.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Globacillin

Approved Use

Unknown
Curative
Globacillin

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Methods for the assessment of quality and stability of azidocillin.
2003 Mar-Apr
Alveolar osteitis: a comprehensive review of concepts and controversies.
2010
Patents

Patents

Sample Use Guides

Healthy volunteers were treated with Azidocillin as single doses of 375 mg, 750 mg, 1500 mg as tablets, 750 mg as a suspension, i.m. and i.v. injections of 799 mg, and a course of 750 mg tablets twice daily for 14 days.
Route of Administration: Other
In Vitro Use Guide
One hundred and eighty strains of viridans Streptococci (Str. mitis, Str. salivarius, Str. MG, Str. SBE, Str. bovis, Str. equinus and Str. uberis) were isolated from mouth and upper respiratory tract secretions of humans at random in different parts of Poland. These strains were tested for susceptibility to Azidocillin.
Name Type Language
AZIDOCILLIN
INN   MI   WHO-DD  
INN  
Official Name English
Azidocillin [WHO-DD]
Common Name English
D-(-)-(.ALPHA.-AZIDOBENZYL)PENICILLIN
Common Name English
BRL-2534
Code English
BRL 2534
Code English
SPC-297-D
Code English
azidocillin [INN]
Common Name English
AZIDOCILLIN [MI]
Common Name English
SPC 297 D
Code English
(2S,5R,6R)-6-((R)-2-AZIDO-2-PHENYLACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTAN-2-CARBOXYLIC ACID
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
WHO-VATC QJ01CE04
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WHO-ATC J01CE04
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Code System Code Type Description
WIKIPEDIA
AZIDOCILLIN
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DRUG BANK
DB08795
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NCI_THESAURUS
C76853
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RXCUI
18609
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SMS_ID
100000086103
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MESH
C100243
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PUBCHEM
15574941
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FDA UNII
R8XDP7L3SL
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ChEMBL
CHEMBL2105907
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CAS
17243-38-8
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DRUG CENTRAL
273
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EPA CompTox
DTXSID20938154
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CHEBI
51758
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ECHA (EC/EINECS)
241-278-5
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INN
2458
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EVMPD
SUB05655MIG
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MERCK INDEX
m2172
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PRIMARY Merck Index