Np mrd loader

Showing NP-Card for Cefapirin (NP0333821)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-09 20:41:38 UTC
Updated at2024-09-09 20:41:38 UTC
NP-MRD IDNP0333821
Secondary Accession NumbersNone
Natural Product Identification
Common NameCefapirin
DescriptionActive against gram-positive and -negative bacteria (vet. Use). FDA approved for use in food producing animals, especies dairy cattle. It is used for the treatment of mastitis in cows Cefapirin (INN, also spelled cephapirin) is an injectable, first-generation cephalosporin antibiotic. It is marketed under the trade name Cefadyl. Production for use in humans has been discontinued in the United States.; Cephapirin is a first-generation cephalosporin that has a wide spectrum of activity against gram-positive and gram-negative organisms. Cephapirin is more resistant to beta-lactamases than are the penicillins and so is effective against staphylococci, with the exception of methicillin-resistant staphylococci.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0333821 (Cefapirin)


  Mrv2104 05242323132D          

 28 30  0  0  0  0            999 V2000
    4.5483   -1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2753    2.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2649    3.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8587    3.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    4.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8339    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982    2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4784    3.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5148    2.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049   -0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6451    4.2907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2821    2.3843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905    0.9760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2628   -0.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283    1.3739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2821    0.3926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8339   -0.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8950    2.5407    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049    2.2135    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  4  1  0  0  0  0
  2 11  2  0  0  0  0
  3  5  2  0  0  0  0
  3 11  1  0  0  0  0
  4 18  2  0  0  0  0
  5 18  1  0  0  0  0
  6 10  1  0  0  0  0
  6 26  1  0  0  0  0
  7 10  1  0  0  0  0
  7 28  1  0  0  0  0
  8 12  1  0  0  0  0
  8 27  1  0  0  0  0
  9 21  2  0  0  0  0
  9 26  1  0  0  0  0
 10 14  2  0  0  0  0
 11 27  1  0  0  0  0
 12 19  2  0  0  0  0
 12 22  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 14 20  1  0  0  0  0
 15 20  1  0  0  0  0
 15 23  2  0  0  0  0
 16 20  1  0  0  0  0
 16 28  1  0  0  0  0
 17 24  2  0  0  0  0
 17 25  1  0  0  0  0
M  END
Download

3D MOL for NP0333821 (Cefapirin)

Download
3D SDF for NP0333821 (Cefapirin)

  Mrv2104 05242323132D          

 28 30  0  0  0  0            999 V2000
    4.5483   -1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2753    2.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2649    3.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8587    3.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    4.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8339    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982    2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4784    3.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5148    2.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049    0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049   -0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6451    4.2907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2821    2.3843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905    0.9760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2628   -0.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283    1.3739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2821    0.3926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8339   -0.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8950    2.5407    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049    2.2135    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  4  1  0  0  0  0
  2 11  2  0  0  0  0
  3  5  2  0  0  0  0
  3 11  1  0  0  0  0
  4 18  2  0  0  0  0
  5 18  1  0  0  0  0
  6 10  1  0  0  0  0
  6 26  1  0  0  0  0
  7 10  1  0  0  0  0
  7 28  1  0  0  0  0
  8 12  1  0  0  0  0
  8 27  1  0  0  0  0
  9 21  2  0  0  0  0
  9 26  1  0  0  0  0
 10 14  2  0  0  0  0
 11 27  1  0  0  0  0
 12 19  2  0  0  0  0
 12 22  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 14 20  1  0  0  0  0
 15 20  1  0  0  0  0
 15 23  2  0  0  0  0
 16 20  1  0  0  0  0
 16 28  1  0  0  0  0
 17 24  2  0  0  0  0
 17 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=C(N2C(SC1)C(\N=C(/O)CSC1=CC=NC=C1)C2=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)

> <INCHI_KEY>
UQLLWWBDSUHNEB-UHFFFAOYNA-N

> <FORMULA>
C17H17N3O6S2

> <MOLECULAR_WEIGHT>
423.46

> <EXACT_MASS>
423.055877627

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
40.25204269873893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(acetyloxy)methyl]-7-[(Z)-[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <JCHEM_LOGP>
-1.397107728908594

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.24595932021349

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2798349876259434

> <JCHEM_PKA_STRONGEST_BASIC>
5.170068938696805

> <JCHEM_POLAR_SURFACE_AREA>
129.39000000000001

> <JCHEM_REFRACTIVITY>
102.95239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(acetyloxy)methyl]-7-[(Z)-[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0333821 (Cefapirin)
Download
PDB for NP0333821 (Cefapirin)
HEADER    PROTEIN                                 24-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAY-23         0                                  
HETATM    1  C   UNK     0       8.490  -2.798   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.114   5.433   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.228   7.319   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.203   6.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.317   8.408   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.157   1.052   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.823   3.362   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.050   5.141   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.490  -1.258   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.823   1.822   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.626   5.832   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.961   4.052   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.616   3.362   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.489   1.052   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.616   1.822   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.156   3.362   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.489  -0.488   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -6.804   8.009   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       0.527   4.451   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       3.156   1.822   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       9.824  -0.488   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.360   2.565   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.527   0.733   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.156  -1.258   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.823  -1.258   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.157  -0.488   0.000  0.00  0.00           O+0
HETATM   27  S   UNK     0      -3.537   4.743   0.000  0.00  0.00           S+0
HETATM   28  S   UNK     0       4.489   4.132   0.000  0.00  0.00           S+0
CONECT    1    9                                                            
CONECT    2    4   11                                                       
CONECT    3    5   11                                                       
CONECT    4    2   18                                                       
CONECT    5    3   18                                                       
CONECT    6   10   26                                                       
CONECT    7   10   28                                                       
CONECT    8   12   27                                                       
CONECT    9    1   21   26                                                  
CONECT   10    6    7   14                                                  
CONECT   11    2    3   27                                                  
CONECT   12    8   19   22                                                  
CONECT   13   15   16   19                                                  
CONECT   14   10   17   20                                                  
CONECT   15   13   20   23                                                  
CONECT   16   13   20   28                                                  
CONECT   17   14   24   25                                                  
CONECT   18    4    5                                                       
CONECT   19   12   13                                                       
CONECT   20   14   15   16                                                  
CONECT   21    9                                                            
CONECT   22   12                                                            
CONECT   23   15                                                            
CONECT   24   17                                                            
CONECT   25   17                                                            
CONECT   26    6    9                                                       
CONECT   27    8   11                                                       
CONECT   28    7   16                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

Download
3D PDB for NP0333821 (Cefapirin)
Download
SMILES for NP0333821 (Cefapirin)
CC(=O)OCC1=C(N2C(SC1)C(\N=C(/O)CSC1=CC=NC=C1)C2=O)C(O)=O
Download
INCHI for NP0333821 (Cefapirin)
InChI=1/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC17H17N3O6S2
Average Mass423.4600 Da
Monoisotopic Mass423.05588 Da
IUPAC Name3-[(acetyloxy)methyl]-7-[(Z)-[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Name3-[(acetyloxy)methyl]-7-[(Z)-[1-hydroxy-2-(pyridin-4-ylsulfanyl)ethylidene]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(=O)OCC1=C(N2C(SC1)C(\N=C(/O)CSC1=CC=NC=C1)C2=O)C(O)=O
InChI Identifier
InChI=1/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)
InChI KeyUQLLWWBDSUHNEB-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactams  
Sub ClassBeta lactams  
Direct ParentCephalosporin 3'-esters  
Alternative Parents
Substituents
  • Cephalosporin 3'-ester
    • 

  • N-acyl-alpha amino acid or derivatives
    • 

  • Alpha-amino acid or derivatives
    • 

  • Aryl thioether
    • 

  • Alkylarylthioether
    • 

  • Meta-thiazine
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Pyridine
    • 

  • Heteroaromatic compound
    • 

  • Tertiary carboxylic acid amide
    • 

  • Azetidine
    • 

  • Carboxamide group
    • 

  • Carboxylic acid ester
    • 

  • Secondary carboxylic acid amide
    • 

  • Azacycle
    • 

  • Dialkylthioether
    • 

  • Sulfenyl compound
    • 

  • Hemithioaminal
    • 

  • Thioether
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organosulfur compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.4ChemAxon
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)5.17ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area129.39 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity102.95 m³·mol⁻¹ChemAxon
Polarizability40.25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCefapirin  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hanzen C, Rahab H: Propaedeutic and Therapeutic Practices Used for Retained Fetal Membranes by Rural European Veterinary Practitioners. Animals (Basel). 2024 Mar 29;14(7):1042. doi: 10.3390/ani14071042. [PubMed:38612281  ] 
  2. Menoud V, Holinger M, Graf-Schiller S, Mayer P, Gerber L, Walkenhorst M, Hirsbrunner G: Comparison between intrauterine application of an antibiotic and an herbal product to treat clinical endometritis in dairy cattle - A randomized multicentre field study. Res Vet Sci. 2024 Jun;172:105250. doi: 10.1016/j.rvsc.2024.105250. Epub 2024 Mar  27. [PubMed:38599065  ] 
  3. Scharen-Bannert M, Starke A, Snedec T, Vogel L, Wagner R, Kuhn T, Bittner-Schwerda L: Case report: Teat stenosis in a suckler cow. Front Vet Sci. 2023 Dec 5;10:1199021. doi: 10.3389/fvets.2023.1199021.  eCollection 2023. [PubMed:38116508  ] 
  4. Guironnet A, Wiest L, Vulliet E: Advantages of MS/MS/MS (MRM(3)) vs classic MRM quantification for complex environmental matrices: Analysis of beta-lactams in WWTP sludge. Anal Chim Acta. 2022 May 1;1205:339773. doi: 10.1016/j.aca.2022.339773. Epub 2022  Mar 26. [PubMed:35414382  ] 
  5. Guironnet A, Wiest L, Vulliet E: Improvement of the QuEChERS extraction step by matrix-dispersion effect and application on beta-lactams analysis in wastewater sludge by LC-MS/MS. Talanta. 2022 Jan 15;237:122923. doi: 10.1016/j.talanta.2021.122923. Epub 2021  Oct 2. [PubMed:34736660  ]