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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

Molecular Formula C16H17N5O4S
Molecular Weight 375.402
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:29:00 GMT 2023
Edited
by admin
on Fri Dec 15 15:29:00 GMT 2023
Record UNII
R8XDP7L3SL
Record Status Validated (UNII)
Record Version
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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
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-ATC J01CE04
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
Code System Code Type Description
WIKIPEDIA
AZIDOCILLIN
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
DRUG BANK
DB08795
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
NCI_THESAURUS
C76853
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
RXCUI
18609
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY RxNorm
SMS_ID
100000086103
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
MESH
C100243
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
PUBCHEM
15574941
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
FDA UNII
R8XDP7L3SL
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105907
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
CAS
17243-38-8
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
DRUG CENTRAL
273
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PRIMARY
EPA CompTox
DTXSID20938154
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
CHEBI
51758
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
241-278-5
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
INN
2458
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
EVMPD
SUB05655MIG
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY
MERCK INDEX
m2172
Created by admin on Fri Dec 15 15:29:00 GMT 2023 , Edited by admin on Fri Dec 15 15:29:00 GMT 2023
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY