NP-MRD: Showing NP-Card for 1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium (NP0289599)

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Record Information

Version

2.0

Created at

2022-09-09 19:52:11 UTC

Updated at

2022-09-09 19:52:11 UTC

NP-MRD ID

NP0289599

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Cefepime, also known as CFPM or cefepimum, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Cefepime is a drug which is used for the treatment of pneumonia (moderate to severe) caused by streptococcus pneumoniae, including cases associated with concurrent bacteremia, pseudomonas aeruginosa, klebsiella pneumoniae, or enterobacter species. Also for empiric treatment of febrile neutropenic patients and uncomplicated and complicated urinary tract infections (including pyelonephritis) caused by escherichia coli or klebsiella pneumoniae, when the infection is severe, or caused by escherichia coli, klebsiella pneumoniae, or proteus mirabilis, when the infection is mild to moderate, including cases associated with concurrent bacteremia with these microorganisms. Also for the treatment of uncomplicated skin and skin structure infections caused by staphylococcus aureus (methicillin-susceptible strains only) or streptococcus pyogenes and complicated intra-abdominal infections (used in combination with metronidazole) caused by escherichia coli, viridans group streptococci, pseudomonas aeruginosa, klebsiella pneumoniae, enterobacter species, or bacteroides fragilis. Cefepime is a strong basic compound (based on its pKa). 1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium is found in Apis cerana. 1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium was first documented in 1999 (PMID: 11084674). A cephalosporin bearing (1-methylpyrrolidinium-1-yl)methyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton (PMID: 14720024) (PMID: 11179650) (PMID: 11191931) (PMID: 11260566).

Structure

MOL 3D MOL SDF PDB SMILES InChI

1413
  Mrv0541 02231215282D          

 33 36  0  0  1  0            999 V2000
    4.6868   -0.2673    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.3250   -0.6762    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8152    1.5582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4012    2.6203    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.9722    2.6203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8278    0.5655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1823   -1.8238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5433    0.9702    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.4012    0.9702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8152   -0.4428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9796   -1.6119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2894    0.1661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6337    0.7612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7363    0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577    1.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4037   -0.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6126   -0.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1947   -0.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9921   -0.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6322   -1.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1132    0.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9671   -2.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5707   -0.4926    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  1 24  1  0  0  0  0
  2 30  1  0  0  0  0
  2 31  1  0  0  0  0
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 21 33  1  6  0  0  0
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 23 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  CHG  2   4  -1   8   1
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
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    3.4969    0.7136   -0.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4880   -0.1793   -0.3348 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4547   -1.3712   -0.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2198   -1.9134   -1.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7847   -1.9828   -1.8611 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0145   -1.0305   -2.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7810   -0.5665   -1.6840 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5998    0.4856   -1.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2594    1.3875   -2.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0544    2.2853   -1.9356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262    1.1745   -3.5174 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.8280    0.6215    0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5796    1.8116    0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8457    1.4829    1.2302 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.4114    0.2343    0.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8257    1.4645    2.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2761    1.5596    3.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9108    2.2882    1.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8056    2.5765    1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3026   -0.2608    1.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0066   -1.3807    0.6905 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549   -1.8059   -1.0183 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7261   -2.1749   -0.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4830   -3.8146   -0.9437 S   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8235   -1.6407   -0.3061 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9657    2.1946    1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7522   -0.1675   -0.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4520    0.3702    0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4841   -0.4803    1.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400    2.3906    3.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3480    0.5573    3.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7255    0.5955    3.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3782    2.2014    4.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3687    3.2537    2.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6896    1.7064    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1471    2.5845   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2805    3.5133    1.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1569   -0.8453    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9450    0.3759    2.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518   -2.6261   -1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2866   -1.3206    1.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0854   -2.1946   -0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
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  7  8  1  0
  8  9  1  0
  9 10  2  0
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 26 25  1  0
 25 24  1  0
 24 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
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 21 22  1  0
 22 23  1  0
 16 12  2  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
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 29 30  1  0
 30 31  1  0
 30 32  2  0
 26  8  1  0
 23 18  1  0
 32 27  1  0
 12 11  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  7 36  1  0
  8 37  1  6
 26 53  1  1
 24 51  1  0
 24 52  1  0
 17 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 28 54  1  0
 31 55  1  0
 31 56  1  0
M  CHG  2  15  -1  18   1
M  END

1413
  Mrv0541 02231215282D          

 33 36  0  0  1  0            999 V2000
    4.6868   -0.2673    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.3250   -0.6762    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8152    1.5582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4012    2.6203    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.9722    2.6203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8278    0.5655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1823   -1.8238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5433    0.9702    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.4012    0.9702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8152   -0.4428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   10.6337    0.7612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1947   -0.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9671   -2.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5707   -0.4926    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  1 24  1  0  0  0  0
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 14 17  1  0  0  0  0
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 16 20  1  0  0  0  0
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 20 23  2  0  0  0  0
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 21 22  1  0  0  0  0
 21 33  1  6  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  CHG  2   4  -1   8   1
M  END
> <DATABASE_ID>
NP0289599

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO\N=C(/C(=O)N[C@@H]1C(=O)N2[C@]1([H])SCC(C[N+]1(C)CCCC1)=C2C([O-])=O)C1=CSC(N)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N6O5S2/c1-25(5-3-4-6-25)7-10-8-31-17-13(16(27)24(17)14(10)18(28)29)22-15(26)12(23-30-2)11-9-32-19(20)21-11/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29)/b23-12-/t13-,17-/m1/s1

> <INCHI_KEY>
HVFLCNVBZFFHBT-ZKDACBOMSA-N

> <FORMULA>
C19H24N6O5S2

> <MOLECULAR_WEIGHT>
480.561

> <EXACT_MASS>
480.124959288

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
47.52971043634327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.37

> <JCHEM_LOGP>
-4.287587759974695

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.150420782470349

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2528262967041304

> <JCHEM_PKA_STRONGEST_BASIC>
4.061872878874441

> <JCHEM_POLAR_SURFACE_AREA>
150.04

> <JCHEM_REFRACTIVITY>
141.97529999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cefepime

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1413                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       8.749  -0.499   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      19.273  -1.262   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      12.722   2.909   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.082   4.891   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0       7.415   4.891   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      14.612   1.056   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.407  -3.404   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       4.747   1.811   0.000  0.00  0.00           N+1
HETATM    9  N   UNK     0      10.082   1.811   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      12.722  -0.827   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      14.895  -3.009   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      17.340   0.310   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      19.850   1.421   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.517   0.477   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.241   1.491   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.081   2.581   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.487  -0.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080  -0.041   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.427   3.318   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.415   1.811   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.082   0.271   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.635   0.265   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.749   2.581   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.415   0.271   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.635   1.818   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.749   4.121   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.210  -0.431   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.297  -1.522   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.785  -1.127   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.980  -2.098   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.878   0.226   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.005  -4.891   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      10.399  -0.920   0.000  0.00  0.00           H+0
CONECT    1   21   24                                                       
CONECT    2   30   31                                                       
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5   26                                                            
CONECT    6   27                                                            
CONECT    7   11   32                                                       
CONECT    8   14   15   16   19                                             
CONECT    9   21   23   25                                                  
CONECT   10   22   27                                                       
CONECT   11    7   28                                                       
CONECT   12   29   31                                                       
CONECT   13   31                                                            
CONECT   14    8   17                                                       
CONECT   15    8   18                                                       
CONECT   16    8   20                                                       
CONECT   17   14   18                                                       
CONECT   18   15   17                                                       
CONECT   19    8                                                            
CONECT   20   16   23   24                                                  
CONECT   21    1    9   22   33                                             
CONECT   22   10   21   25                                                  
CONECT   23    9   20   26                                                  
CONECT   24    1   20                                                       
CONECT   25    3    9   22                                                  
CONECT   26    4    5   23                                                  
CONECT   27    6   10   28                                                  
CONECT   28   11   27   29                                                  
CONECT   29   12   28   30                                                  
CONECT   30    2   29                                                       
CONECT   31    2   12   13                                                  
CONECT   32    7                                                            
CONECT   33   21                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(1-methylpyrrolidinium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	ChEBI
Cefepima	ChEBI
Cefepimum	ChEBI
CFPM	ChEBI
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(1-methylpyrrolidinium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	Generator
Bristol-myers brand OF cefepime dihydrochloride	HMDB
Elan brand OF cefepime dihydrochloride	HMDB
Cefepim	HMDB
Cefepime hydrochloride	HMDB
Axépim	HMDB
Bristol-myers squibb brand OF cefepime dihydrochloride	HMDB
Maxipime	HMDB
Quadrocef	HMDB

Chemical Formula

C₁₉H₂₄N₆O₅S₂

Average Mass

480.5610 Da

Monoisotopic Mass

480.12496 Da

IUPAC Name

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

Traditional Name

cefepime

CAS Registry Number

Not Available

SMILES

CO\N=C(/C(=O)N[C@@H]1C(=O)N2[C@]1([H])SCC(C[N+]1(C)CCCC1)=C2C([O-])=O)C1=CSC(N)=N1

InChI Identifier

InChI=1S/C19H24N6O5S2/c1-25(5-3-4-6-25)7-10-8-31-17-13(16(27)24(17)14(10)18(28)29)22-15(26)12(23-30-2)11-9-32-19(20)21-11/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29)/b23-12-/t13-,17-/m1/s1

InChI Key

HVFLCNVBZFFHBT-ZKDACBOMSA-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 xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
6-oxopurine
Purinone
Alkaloid or derivatives
Pyrimidone
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dimethylxanthine (CHEBI:28946 )
Purine alkaloids (C07480 )
a small molecule (3-7-DIMETHYLXANTHINE )

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	-0.37	ALOGPS
logP	-4.3	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.25	ChemAxon
pKa (Strongest Basic)	4.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	150.04 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	141.98 m³·mol⁻¹	ChemAxon
Polarizability	47.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0015483

DrugBank ID

DB01413

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4586395

KEGG Compound ID

C08111

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cefepime

METLIN ID

Not Available

PubChem Compound

5479537

PDB ID

Not Available

ChEBI ID

478164

Good Scents ID

Not Available

References

General References

Chapman TM, Perry CM: Cefepime: a review of its use in the management of hospitalized patients with pneumonia. Am J Respir Med. 2003;2(1):75-107. doi: 10.1007/BF03256641. [PubMed:14720024 ]
Sader HS, Cerbara EF, Luz D, Hashimoto A: Evaluation of the Cephalosporins, Cefepime, Cefpirome and Ceftazidime, against Clinical Isolates of Imipenem-Resistant Pseudomonas aeruginosa. Braz J Infect Dis. 1999 Dec;3(6):231-237. [PubMed:11084674 ]
Barnaud G, Labia R, Raskine L, Sanson-Le Pors MJ, Philippon A, Arlet G: Extension of resistance to cefepime and cefpirome associated to a six amino acid deletion in the H-10 helix of the cephalosporinase of an Enterobacter cloacae clinical isolate. FEMS Microbiol Lett. 2001 Feb 20;195(2):185-90. doi: 10.1111/j.1574-6968.2001.tb10519.x. [PubMed:11179650 ]
Jallon P, Fankhauser L, Du Pasquier R, Coeytaux A, Picard F, Hefft S, Assal F: Severe but reversible encephalopathy associated with cefepime. Neurophysiol Clin. 2000 Dec;30(6):383-6. doi: 10.1016/s0987-7053(00)00234-3. [PubMed:11191931 ]
Kebudi R, Gorgun O, Ayan I, Gurler N, Akici F, Toreci K: Randomized comparison of cefepime versus ceftazidime monotherapy for fever and neutropenia in children with solid tumors. Med Pediatr Oncol. 2001 Apr;36(4):434-41. doi: 10.1002/mpo.1107. [PubMed:11260566 ]
LOTUS database [Link]

Showing NP-Card for 1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium (NP0289599)

MOL for NP0289599 (1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium)

3D MOL for NP0289599 (1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium)

3D SDF for NP0289599 (1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium)

3D-SDF for NP0289599 (1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium)

PDB for NP0289599 (1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium)

3D PDB for NP0289599 (1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium)

SMILES for NP0289599 (1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium)

INCHI for NP0289599 (1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium)

Structure for NP0289599 (1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium)

3D Structure for NP0289599 (1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-3h-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium)