X56

Cefazolin

Created: 2023-10-30
Last modified:  2024-11-13

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Chemical Details

Formal Charge0
Atom Count43
Chiral Atom Count2
Bond Count46
Aromatic Bond Count10
2D diagram of X56
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Chemical Component Summary

NameCefazolin
Systematic Name (OpenEye OEToolkits)(6~{R},7~{R})-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxidanylidene-7-[2-(1,2,3,4-tetrazol-1-yl)ethanoylamino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
FormulaC14 H14 N8 O4 S3
Molecular Weight454.507
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.385Cc1sc(SCC2=C(N3[CH](SC2)[CH](NC(=O)Cn4cnnn4)C3=O)C(O)=O)nn1
SMILESOpenEye OEToolkits2.0.7Cc1nnc(s1)SCC2=C(N3C(C(C3=O)NC(=O)Cn4cnnn4)SC2)C(=O)O
Canonical SMILESCACTVS3.385 Cc1sc(SCC2=C(N3[C@H](SC2)[C@H](NC(=O)Cn4cnnn4)C3=O)C(O)=O)nn1
Canonical SMILESOpenEye OEToolkits2.0.7 Cc1nnc(s1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)Cn4cnnn4)SC2)C(=O)O
InChIInChI1.06 InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
InChIKeyInChI1.06 MLYYVTUWGNIJIB-BXKDBHETSA-N

Drug Info: DrugBank

DrugBank IDDB01327 
NameCefazolin
Groups approved
DescriptionA semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.
Synonyms
  • CEZ
  • Cefazolina
  • Cefazolin sodium
  • Cefazolin
  • (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Brand Names
  • Ancef
  • Ancef Inj Pws 500mg/vial USP
  • Ancef Inj Pws 10gm/vial USP
  • Cefazolin for Injection USP
  • Cefazolin
IndicationMainly used to treat bacterial infections of the skin. It can also be used to treat moderately severe bacterial infections involving the lung, bone, joint, stomach, blood, heart valve, and urinary tract. It is clinically effective against infections caused by staphylococci and streptococci species of Gram positive bacteria. May be used for surgical prophylaxis; if required metronidazole may be added to cover B. fragilis.
Categories
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-CodeJ01DB04
CAS number25953-19-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Penicillin-binding protein 1AMKFVKYFLILAVCCILLGAGSIYGLYRYIEPQLPDVATLKDVRLQIPMQI...unknowninhibitor
Penicillin-binding protein 1BMAGNDREPIGRKGKPTRPVKQKVSRRRYEDDDDYDDYDDYEDEEPMPRKG...unknowninhibitor
Penicillin-binding protein 1CMPRLLTKRGCWITLAAAPFLLFLAAWGADKLWPLPLHEVNPARVVVAQDG...unknowninhibitor
Penicillin-binding protein 2MKLQNSFRDYTAESALFVRRALVAFLGILLLTGVLIANLYNLQIVRFTDY...unknowninhibitor
Peptidoglycan synthase FtsIMKAAAKTQKPKRQEEHANFISWRFALLCGCILLALAFLLGRVAWLQVISP...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1435
PubChem 33255
ChEMBL CHEMBL1435
ChEBI CHEBI:474053