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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H28N8O9S2
Molecular Weight 672.689
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIROXICILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)NC3=CNC(NC4=CC=C(C=C4)S(N)(=O)=O)=NC3=O)C5=CC=C(O)C=C5)C(O)=O

InChI

InChIKey=YCDUQXXFNZLWJU-CROMWVBPSA-N
InChI=1S/C27H28N8O9S2/c1-27(2)19(24(40)41)35-22(39)18(23(35)45-27)32-21(38)17(12-3-7-14(36)8-4-12)33-26(42)31-16-11-29-25(34-20(16)37)30-13-5-9-15(10-6-13)46(28,43)44/h3-11,17-19,23,36H,1-2H3,(H,32,38)(H,40,41)(H2,28,43,44)(H2,31,33,42)(H2,29,30,34,37)/t17-,18-,19+,23-/m1/s1

HIDE SMILES / InChI

Molecular Formula C27H28N8O9S2
Molecular Weight 672.689
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Piroxicillin is a broad-spectrum antibiotic. In vitro it is more active than piperacillin, apalcillin and mezlocillin especially against the following strains; E. coli, Ps. aeruginosa, Ps. stutzeri, K. pneumoniae, Eb. cloacae, Ser. marcescens, Proteus, Sh. flexneri, Y. enterocolitica, Cb. freundii, Acb. calcoaceticus, Bacteroides and Sc. faecalis. It shows very low MIC values against clinically important Gram-negative bacteria, primarily Pseudomonas aeruginosa. The action of piroxicillin is bactericidal.

Approval Year

PubMed

PubMed

TitleDatePubMed
[6R-[(R)-2-[3-[2-(p-Aminosulfonyl)anilino-4-hydroxy-5- pyrimidinyl]ureido]-2-(4-hydroxyphenyl)acetamido]-penicillanic acid, sodium salt (VX-VC 43), a new broad-spectrum beta-lactam antibiotic. In vitro and in vivo antibiotic activity].
1985
Synthesis and antibacterial activity of pyrimidinylureidopenicillins.
1985
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:19:45 GMT 2023
Edited
by admin
on Sat Dec 16 16:19:45 GMT 2023
Record UNII
HPI5A94GD9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIROXICILLIN
INN  
INN  
Official Name English
piroxicillin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Sat Dec 16 16:19:45 GMT 2023 , Edited by admin on Sat Dec 16 16:19:45 GMT 2023
Code System Code Type Description
CAS
82509-56-6
Created by admin on Sat Dec 16 16:19:45 GMT 2023 , Edited by admin on Sat Dec 16 16:19:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID00231817
Created by admin on Sat Dec 16 16:19:45 GMT 2023 , Edited by admin on Sat Dec 16 16:19:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103982
Created by admin on Sat Dec 16 16:19:45 GMT 2023 , Edited by admin on Sat Dec 16 16:19:45 GMT 2023
PRIMARY
EVMPD
SUB09937MIG
Created by admin on Sat Dec 16 16:19:45 GMT 2023 , Edited by admin on Sat Dec 16 16:19:45 GMT 2023
PRIMARY
INN
5305
Created by admin on Sat Dec 16 16:19:45 GMT 2023 , Edited by admin on Sat Dec 16 16:19:45 GMT 2023
PRIMARY
SMS_ID
100000081679
Created by admin on Sat Dec 16 16:19:45 GMT 2023 , Edited by admin on Sat Dec 16 16:19:45 GMT 2023
PRIMARY
FDA UNII
HPI5A94GD9
Created by admin on Sat Dec 16 16:19:45 GMT 2023 , Edited by admin on Sat Dec 16 16:19:45 GMT 2023
PRIMARY
PUBCHEM
3047855
Created by admin on Sat Dec 16 16:19:45 GMT 2023 , Edited by admin on Sat Dec 16 16:19:45 GMT 2023
PRIMARY
NCI_THESAURUS
C76857
Created by admin on Sat Dec 16 16:19:45 GMT 2023 , Edited by admin on Sat Dec 16 16:19:45 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY