Drug Information

General Information
Drug ID
DR00577
Drug Name
Cefazolin
Synonyms
(6R, 7R)-3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[1H-tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-(((5-Methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(2-(1H-tetrazol-1-yl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; (6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (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; (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R-trans)-3-(((5-Methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(((1H-tetrazol-1-yl)acetyl)-amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-7beta-[(1H-tetrazol-1-ylacetyl)amino]-3,4-didehydrocepham-4-carboxylic acid; 7-(1-(1H-)-Tetrazolylacetamido)-3-(2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl)delta3-cephem-4-carboxylic acid; Ancef (TN); CEZ; Cefacidal (TN); Cefamezin; Cefamezin (TN); Cefamezine; Cefazolin (USP); Cefazolin [USAN:INN]; Cefazolin(usp); Cefazolina; Cefazolina [INN-Spanish]; Cefazoline; Cefazoline [INN-French]; Cefazolinum; Cefazolinum [INN-Latin]; Cefrina (TN); Cephamezine; Cephazolidin; Cephazolin; Cephazolin Sodium; Cephazoline; Elzogram; Elzogram (TN); Faxilen (TN); Gramaxin (TN); Kefazol (TN); Kefol (TN); Kefzol (TN); Kefzolan (TN); Kezolin (TN); Novaporin (TN); Zolicef (TN)
Drug Type
Small molecular drug
Indication Methicillin-susceptible staphylococcus aureus [ICD11:1B74.0] Approved [1]
Therapeutic Class
Antibiotics
Structure
3D MOL 2D MOL
Formula
C14H14N8O4S3
Canonical SMILES
CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
InChI
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
InChIKey
MLYYVTUWGNIJIB-BXKDBHETSA-N
CAS Number
CAS 25953-19-9
Pharmaceutical Properties Molecular Weight 454.5 Topological Polar Surface Area 235
Heavy Atom Count 29 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 12
XLogP
-0.4
PubChem CID
33255
PubChem SID
103510684 ,104133789 ,104231690 ,104315593 ,11335189 ,11360428 ,11362960 ,11365522 ,11368084 ,11371259 ,11373873 ,11376246 ,11461400 ,11466764 ,11467884 ,11484775 ,11486367 ,11488956 ,11490146 ,11492082 ,11493920 ,117600526 ,124766146 ,14833488 ,15008581 ,29215418 ,34675123 ,46506123 ,47193754 ,47290958 ,47440062 ,47440063 ,47440064 ,47810578 ,48110278 ,48259043 ,48334299 ,48415713 ,50051012 ,56314760 ,57311487 ,602960 ,75509242 ,7849358 ,7978873 ,81093146 ,8173059 ,85663279 ,9097 ,92714647
ChEBI ID
CHEBI:474053
TTD Drug ID
D09KDN
DT(s) Transporting This Drug MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [2]
OAT1 Transporter Info Organic anion transporter 1 Substrate [3]
OAT3 Transporter Info Organic anion transporter 3 Substrate [3]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [4]
PEPT1 Transporter Info Peptide transporter 1 Substrate [5]
Drug-Transporter Activity Data
Drug-Transporter Activity Data MRP4 Transporter Info Km =81 microM Human embryonic kidney cells (HEK293)-MRP4 [2]
References
1 Cefazolin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Oral availability of cefadroxil depends on ABCC3 and ABCC4. Drug Metab Dispos. 2012 Mar;40(3):515-21.
3 Expression levels of renal organic anion transporters (OATs) and their correlation with anionic drug excretion in patients with renal diseases. Pharm Res. 2004 Jan;21(1):61-7.
4 Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81.
5 Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1. J Med Chem. 2005 Jun 30;48(13):4410-9.

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