NP-MRD: Showing NP-Card for 1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium (NP0315489)

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Record Information

Version

2.0

Created at

2022-09-11 14:08:50 UTC

Updated at

2022-09-11 14:08:51 UTC

NP-MRD ID

NP0315489

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium

Description

Ceftazidime, also known as CAZ or ceptaz, belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid moiety or a derivative thereof. Ceftazidime is a drug which is used for the treatment of patients with infections caused by susceptible strains of organisms in the following diseases: Lower respiratory tract infections,skin and skin structure infections, urinary tract infections, bacterial septicemia, bone and joint infections, gynecologic infections, intra abdominal infections (including peritonitis), and central nervous system infections (including meningitis). Ceftazidime is a strong basic compound (based on its pKa). 1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium is found in Apis cerana. 1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium was first documented in 1992 (PMID: 1384868). A third-generation cephalosporin antibiotic bearing pyridinium-1-ylmethyl and {imino}acetamido groups at positions 3 and 7, respectively, of the cephem skeleton (PMID: 11252323) (PMID: 11284241) (PMID: 11591698) (PMID: 11605815) (PMID: 11815759) (PMID: 12048030).

Structure

MOL 3D MOL SDF PDB SMILES InChI

438
  Mrv0541 02231214412D          

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M  CHG  2   4  -1  12   1
M  END

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M  CHG  2  17  -1  20   1
M  END

438
  Mrv0541 02231214412D          

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 14 37  2  0  0  0  0
 15 37  1  0  0  0  0
 16 17  1  0  0  0  0
 16 38  1  6  0  0  0
 17 18  1  0  0  0  0
 19 20  2  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 24 25  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 27 30  2  0  0  0  0
 28 33  2  0  0  0  0
 29 31  2  0  0  0  0
 30 31  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 32 36  1  0  0  0  0
M  CHG  2   4  -1  12   1
M  END
> <DATABASE_ID>
NP0315489

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[O-]C(=O)C1=C(CS[C@]2([H])[C@H](NC(=O)C(=N/OC(C)(C)C(O)=O)\C3=CSC(N)=N3)C(=O)N12)C[N+]1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22N6O7S2/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27/h3-7,10,14,18H,8-9H2,1-2H3,(H4-,23,24,25,29,31,32,33,34)/b26-13-/t14-,18-/m1/s1

> <INCHI_KEY>
ORFOPKXBNMVMKC-DWVKKRMSSA-N

> <FORMULA>
C22H22N6O7S2

> <MOLECULAR_WEIGHT>
546.576

> <EXACT_MASS>
546.099138468

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
51.05687027305248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium

> <ALOGPS_LOGP>
-1.21

> <JCHEM_LOGP>
-4.1217156526121475

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.159095320990166

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.768974344324722

> <JCHEM_PKA_STRONGEST_BASIC>
4.260694570217112

> <JCHEM_POLAR_SURFACE_AREA>
191.22

> <JCHEM_REFRACTIVITY>
143.8809

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ceftazidime

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 438                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       9.748   1.251   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      20.273   0.488   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      13.721   4.658   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.415   6.641   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0      11.082   6.641   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      15.611   2.806   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      14.407  -1.655   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      14.690  -5.719   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      12.115  -5.023   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      11.082   3.561   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      13.721   0.923   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       5.747   3.561   0.000  0.00  0.00           N+1
HETATM   13  N   UNK     0      15.895  -1.259   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      18.340   2.060   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      20.849   3.171   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      11.082   2.021   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.635   2.015   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.635   3.567   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748   4.331   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   3.561   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415   2.021   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.081   4.331   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748   5.871   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.210   1.319   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.297   0.228   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.747   2.021   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.414   4.331   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.785   0.623   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.414   1.251   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.080   3.561   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.080   2.021   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.005  -3.141   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.980  -0.348   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.518  -2.740   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.492  -3.543   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.603  -4.628   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      19.878   1.976   0.000  0.00  0.00           C+0
HETATM   38  H   UNK     0      11.398   0.830   0.000  0.00  0.00           H+0
CONECT    1   16   21                                                       
CONECT    2   33   37                                                       
CONECT    3   18                                                            
CONECT    4   23                                                            
CONECT    5   23                                                            
CONECT    6   24                                                            
CONECT    7   13   32                                                       
CONECT    8   36                                                            
CONECT    9   36                                                            
CONECT   10   16   18   19                                                  
CONECT   11   17   24                                                       
CONECT   12   22   26   27                                                  
CONECT   13    7   25                                                       
CONECT   14   28   37                                                       
CONECT   15   37                                                            
CONECT   16    1   10   17   38                                             
CONECT   17   11   16   18                                                  
CONECT   18    3   10   17                                                  
CONECT   19   10   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21    1   20                                                       
CONECT   22   12   20                                                       
CONECT   23    4    5   19                                                  
CONECT   24    6   11   25                                                  
CONECT   25   13   24   28                                                  
CONECT   26   12   29                                                       
CONECT   27   12   30                                                       
CONECT   28   14   25   33                                                  
CONECT   29   26   31                                                       
CONECT   30   27   31                                                       
CONECT   31   29   30                                                       
CONECT   32    7   34   35   36                                             
CONECT   33    2   28                                                       
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36    8    9   32                                                  
CONECT   37    2   14   15                                                  
CONECT   38   16                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	ChEBI
CAZ	ChEBI
Ceftazidima	ChEBI
Ceftazidime anhydrous	ChEBI
Ceftazidimum	ChEBI
Ceptaz	Kegg
Fortaz	Kegg
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	Generator
Pentahydrate, ceftazidime	HMDB
Fortum	HMDB
Anhydrous, ceftazidime	HMDB
Ceftazidime pentahydrate	HMDB
Tazidime	HMDB

Chemical Formula

C₂₂H₂₂N₆O₇S₂

Average Mass

546.5760 Da

Monoisotopic Mass

546.09914 Da

IUPAC Name

1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium

Traditional Name

ceftazidime

CAS Registry Number

Not Available

SMILES

[O-]C(=O)C1=C(CS[C@]2([H])[C@H](NC(=O)C(=N/OC(C)(C)C(O)=O)\C3=CSC(N)=N3)C(=O)N12)C[N+]1=CC=CC=C1

InChI Identifier

InChI=1S/C22H22N6O7S2/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27/h3-7,10,14,18H,8-9H2,1-2H3,(H4-,23,24,25,29,31,32,33,34)/b26-13-/t14-,18-/m1/s1

InChI Key

ORFOPKXBNMVMKC-DWVKKRMSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporins

Alternative Parents

Substituents

Cephalosporin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
2,4-disubstituted 1,3-thiazole
Meta-thiazine
Dicarboxylic acid or derivatives
1,3-thiazol-2-amine
Pyridine
Pyridinium
Azole
Heteroaromatic compound
Tertiary carboxylic acid amide
Thiazole
Amino acid or derivatives
Azetidine
Carboxamide group
Carboxylic acid salt
Amino acid
Secondary carboxylic acid amide
Thioether
Hemithioaminal
Dialkylthioether
Azacycle
Carboxylic acid derivative
Carboxylic acid
Primary amine
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Organic salt
Organonitrogen compound
Organic zwitterion
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cephalosporin (CHEBI:3508 )
oxime O-ether (CHEBI:3508 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.2	ALOGPS
logP	-4.1	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	2.77	ChemAxon
pKa (Strongest Basic)	4.26	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	191.22 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	143.88 m³·mol⁻¹	ChemAxon
Polarizability	51.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0014582

DrugBank ID

DB00438

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4587145

KEGG Compound ID

C06889

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ceftazidime

METLIN ID

Not Available

PubChem Compound

5481173

PDB ID

Not Available

ChEBI ID

3508

Good Scents ID

Not Available

References

General References

Shimizu T, Souma S, Nagakura N, Masuzawa T, Iwamoto Y, Yanagihara Y: Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity. Int Arch Allergy Immunol. 1992;98(4):392-7. doi: 10.1159/000236216. [PubMed:1384868 ]
Marumo K, Takeda A, Nakamura Y, Nakaya K: Detection of OXA-4 beta-lactamase in Pseudomonas aeruginosa isolates by genetic methods. J Antimicrob Chemother. 1999 Feb;43(2):187-93. doi: 10.1093/jac/43.2.187. [PubMed:11252323 ]
Orrett FA, Shurland SM: Neonatal sepsis and mortality in a regional hospital in Trinidad: aetiology and risk factors. Ann Trop Paediatr. 2001 Mar;21(1):20-5. doi: 10.1080/02724930020028867. [PubMed:11284241 ]
Zhang Z, Yu Y, Musser JM, Palzkill T: Amino acid sequence determinants of extended spectrum cephalosporin hydrolysis by the class C P99 beta-lactamase. J Biol Chem. 2001 Dec 7;276(49):46568-74. doi: 10.1074/jbc.M102757200. Epub 2001 Oct 8. [PubMed:11591698 ]
Huang CH, Jang TN, Liu CY, Fung CP, Yu KW, Wong WW: Characteristics of patients with Burkholderia cepacia bacteremia. J Microbiol Immunol Infect. 2001 Sep;34(3):215-9. [PubMed:11605815 ]
Bruckner LB, Korones DN, Karnauchow T, Hardy DJ, Gigliotti F: High incidence of penicillin resistance among alpha-hemolytic streptococci isolated from the blood of children with cancer. J Pediatr. 2002 Jan;140(1):20-6. doi: 10.1067/mpd.2002.118886. [PubMed:11815759 ]
Di Martino P, Gagniere H, Berry H, Bret L: Antibiotic resistance and virulence properties of Pseudomonas aeruginosa strains from mechanically ventilated patients with pneumonia in intensive care units: comparison with imipenem-resistant extra-respiratory tract isolates from uninfected patients. Microbes Infect. 2002 May;4(6):613-20. doi: 10.1016/s1286-4579(02)01579-4. [PubMed:12048030 ]
Astal Z, El-Manama A, Sharif FA: Antibiotic resistance of bacteria associated with community-acquired urinary tract infections in the southern area of the Gaza Strip. J Chemother. 2002 Jun;14(3):259-64. doi: 10.1179/joc.2002.14.3.259. [PubMed:12120880 ]
Barekzi NA, Felts AG, Poelstra KA, Slunt JB, Grainger DW: Locally delivered polyclonal antibodies potentiate intravenous antibiotic efficacy against gram-negative infections. Pharm Res. 2002 Dec;19(12):1801-7. doi: 10.1023/a:1021481122011. [PubMed:12523657 ]
White NJ: Melioidosis. Lancet. 2003 May 17;361(9370):1715-22. doi: 10.1016/s0140-6736(03)13374-0. [PubMed:12767750 ]
Guerrero C, Cesteros R, Miranda A, Menasalvas A, Blazquez R, Segovia M: [Antimicrobial susceptibility of Pseudomonas aeruginosa clinical isolates in Murcia, Spain]. Rev Esp Quimioter. 2003 Dec;16(4):444-9. [PubMed:14961139 ]
Bret L, Di Martino P: Effect of ceftazidime, amikacin and ciprofloxacin on biofilm formation by some enterobacterial clinical isolates. Chemotherapy. 2004 Nov;50(5):255-9. doi: 10.1159/000081947. Epub 2004 Nov 3. [PubMed:15528892 ]
Araki H, Ogake N, Tsuneda R, Minami S, Watanabe Y, Tamai I, Tsuji A: Muscle distribution of antimicrobial agents after a single intravenous administration to rats. Drug Metab Pharmacokinet. 2002;17(3):237-44. doi: 10.2133/dmpk.17.237. [PubMed:15618675 ]
Perez-Capilla T, Baquero MR, Gomez-Gomez JM, Ionel A, Martin S, Blazquez J: SOS-independent induction of dinB transcription by beta-lactam-mediated inhibition of cell wall synthesis in Escherichia coli. J Bacteriol. 2005 Feb;187(4):1515-8. doi: 10.1128/JB.187.4.1515-1518.2005. [PubMed:15687217 ]
de Jong CE, Jonsson N, Field H, Smith C, Crichton EG, Phillips N, Johnston SD: Collection, seminal characteristics and chilled storage of spermatozoa from three species of free-range flying fox (Pteropus spp.). Theriogenology. 2005 Sep 15;64(5):1072-89. doi: 10.1016/j.theriogenology.2005.02.016. [PubMed:15913752 ]
LOTUS database [Link]

Showing NP-Card for 1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium (NP0315489)

MOL for NP0315489 (1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium)

3D MOL for NP0315489 (1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium)

3D SDF for NP0315489 (1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium)

3D-SDF for NP0315489 (1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium)

PDB for NP0315489 (1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium)

3D PDB for NP0315489 (1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium)

SMILES for NP0315489 (1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium)

INCHI for NP0315489 (1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium)

Structure for NP0315489 (1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium)

3D Structure for NP0315489 (1-{[(6r,7r)-2-carboxy-7-{[(2z)-2-[(1-carboxylato-1-methylethoxy)imino]-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium)