Drug (ID: DG00425) and It's Reported Resistant Information
Name
Cephalosporin C
Synonyms
Cephalosporin C; 7-(5-Amino-5-carboxyvaleramido)cephalosporanic acid; 61-24-5; UNII-3XIY7HJT5L; CHEBI:15776; EINECS 200-501-6; 3XIY7HJT5L; BRN 0065348; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-((5-amino-5-carboxy-1-oxopentyl)amino)-8-oxo-, (6R-(6alpha,7beta(R*)))-; (6R,7R)-3-[(acetyloxy)methyl]-7-{[(5R)-5-amino-5-carboxypentanoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(5-amino-5-carboxyvaleramid
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Indication
In total 1 Indication(s)
Discovery agent [ICD-11: N.A.]
Investigative
[1]
Structure
Drug Resistance Disease(s)
Disease(s) with Clinically Reported Resistance for This Drug (2 diseases)
Peritonitis [ICD-11: DC50]
[2]
Sepsis with septic shock [ICD-11: 1G41]
[3]
Disease(s) with Resistance Information Validated by in-vivo Model for This Drug (1 diseases)
Bacterial infection [ICD-11: 1A00-1C4Z]
[1]
Target Bacterial DD-carboxypeptidase (Bact vanYB) VANY_ENTFA [1]
Bacterial Penicillin binding protein 3 (Bact mrcA) FTSI_ECOLI [1]
Bacterial Penicillin-binding protein 1B (Bact mrcB) PBPB_ECOLI [1]
Click to Show/Hide the Molecular Information and External Link(s) of This Drug
Formula
C16H21N3O8S
IsoSMILES
CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CCC[C@H](C(=O)O)N)SC1)C(=O)O
InChI
1S/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/t9-,11-,14-/m1/s1
InChIKey
HOKIDJSKDBPKTQ-GLXFQSAKSA-N
PubChem CID
65536
ChEBI ID
CHEBI:15776
TTD Drug ID
D0O4TL
DrugBank ID
DB03313
Type(s) of Resistant Mechanism of This Drug
  DISM: Drug Inactivation by Structure Modification
Drug Resistance Data Categorized by Their Corresponding Diseases
ICD-01: Infectious/parasitic diseases
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Bacterial infection [ICD-11: 1A00-1C4Z]
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Drug Resistance Data Categorized by Their Corresponding Mechanisms
       Drug Inactivation by Structure Modification (DISM) Click to Show/Hide
Key Molecule: Beta-lactamase (BLA) [1]
Molecule Alteration Expression
Inherence
Resistant Disease Rhodobacter sphaeroides infection [ICD-11: 1A00-1C4Z]
Experimental Note Discovered Using In-vivo Testing Model
In Vitro Model Rhodopseudomonas sphaeroides strain DSM 160(Y) 1063
Rhodopseudomonas sphaeroides strain DSM158 1063
Rhodopseudomonas sphaeroides strain DSM159 1063
Experiment for
Molecule Alteration
Sodium dodecyl sulfate-PAGE assay
Experiment for
Drug Resistance
MIC assay
Mechanism Description Thirteen strains of the gram-negative, facultative phototrophic bacterium Rhodobacter sphaeroides were examined fro susceptibility to beta-lactam antibiotics. All strains were sensitive to the semisynthetic penicillins ampicillin, carbenicillin, oxacillin, cloxacillin, and methicillin, but 10 of the 13 strains were resistant to penicillin G, as well as a number of cephalosporins, such as cephalothin, cephapirin, and cephalosporin C. A beta-lactamase (EC 3.5.2.6) with strong cephalosporinase activity was detected in all of the resistant strains of R. sphaeroides. With strain Y-1 as a model, it was shown that the beta-lactamase was inducible by penicillin G, cephalosporin C, cephalothin, and to some minor extent, cephapirin.
References
Ref 1 Susceptibility of Rhodobacter sphaeroides to beta-lactam antibiotics: isolation and characterization of a periplasmic beta-lactamase (cephalosporinase). J Bacteriol. 1989 Jan;171(1):308-13. doi: 10.1128/jb.171.1.308-313.1989.
Ref 2 Cocoon-like fibroadhesive tuberculous peritonitis in a peritoneal dialysis patient .Chin J Physiol. 2012 Oct 31;55(5):361-5. doi: 10.4077/CJP.2012.BAA060. 10.4077/CJP.2012.BAA060
Ref 3 Antimicrobial resistance patterns, clinical features, and risk factors for septic shock and death of nosocomial E coli bacteremia in adult patients with hematological disease: A monocenter retrospective study in China .Medicine (Baltimore). 2017 May;96(21):e6959. doi: 10.1097/MD.0000000000006959. 10.1097/MD.0000000000006959

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