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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H16N5O4S.Na
Molecular Weight 397.384
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AZIDOCILLIN SODIUM

SMILES

[Na+].[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=DKUPMJBOYNDXNY-YWUHCJSESA-M
InChI=1S/C16H17N5O4S.Na/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);/q;+1/p-1/t9-,10-,11+,14-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C16H16N5O4S
Molecular Weight 374.394
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 17:13:00 GMT 2023
Edited
by admin
on Fri Dec 15 17:13:00 GMT 2023
Record UNII
0XPT6W6670
Record Status Validated (UNII)
Record Version
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Name Type Language
AZIDOCILLIN SODIUM
MART.   WHO-DD  
Common Name English
AZIDOCILLIN SODIUM [MART.]
Common Name English
SODIUM (2S,5R,6R)-6-)((2R)-AZIDOPHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE
Common Name English
LONGATREN
Common Name English
Azidocillin sodium [WHO-DD]
Common Name English
AZIDOCILLIN SODIUM SALT [MI]
Common Name English
GLOBACILLIN
Brand Name English
AZIDOCILLIN SODIUM SALT
MI  
Common Name English
Code System Code Type Description
CAS
35334-12-4
Created by admin on Fri Dec 15 17:13:00 GMT 2023 , Edited by admin on Fri Dec 15 17:13:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
252-516-2
Created by admin on Fri Dec 15 17:13:00 GMT 2023 , Edited by admin on Fri Dec 15 17:13:00 GMT 2023
PRIMARY
PUBCHEM
15574945
Created by admin on Fri Dec 15 17:13:00 GMT 2023 , Edited by admin on Fri Dec 15 17:13:00 GMT 2023
PRIMARY
RXCUI
236787
Created by admin on Fri Dec 15 17:13:00 GMT 2023 , Edited by admin on Fri Dec 15 17:13:00 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m2172
Created by admin on Fri Dec 15 17:13:00 GMT 2023 , Edited by admin on Fri Dec 15 17:13:00 GMT 2023
PRIMARY Merck Index
FDA UNII
0XPT6W6670
Created by admin on Fri Dec 15 17:13:00 GMT 2023 , Edited by admin on Fri Dec 15 17:13:00 GMT 2023
PRIMARY
EVMPD
SUB00644MIG
Created by admin on Fri Dec 15 17:13:00 GMT 2023 , Edited by admin on Fri Dec 15 17:13:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID70956762
Created by admin on Fri Dec 15 17:13:00 GMT 2023 , Edited by admin on Fri Dec 15 17:13:00 GMT 2023
PRIMARY
CHEBI
51761
Created by admin on Fri Dec 15 17:13:00 GMT 2023 , Edited by admin on Fri Dec 15 17:13:00 GMT 2023
PRIMARY
SMS_ID
100000084987
Created by admin on Fri Dec 15 17:13:00 GMT 2023 , Edited by admin on Fri Dec 15 17:13:00 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY