Details of the Drug

General Information of Drug (ID: DMPDYFR)

Drug Name
Cefazolin
Synonyms
CEZ; Cefamezin; Cefamezine; Cefazolina; Cefazoline; Cefazolinum; Cephamezine; Cephazolidin; Cephazolin; Cephazoline; Elzogram; Cephazolin Sodium; Ancef (TN); Cefacidal (TN); Cefamezin (TN); Cefazolin (USP); Cefazolin [USAN:INN]; Cefazolin(usp); Cefazolina [INN-Spanish]; Cefazoline [INN-French]; Cefazolinum [INN-Latin]; Cefrina (TN); Elzogram (TN); Faxilen (TN); Gramaxin (TN); Kefazol (TN); Kefol (TN); Kefzol (TN); Kefzolan (TN); Kezolin (TN); Novaporin (TN); Zolicef (TN); (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
Indication
Disease Entry ICD 11 Status REF
Bacteremia 1A73 Approved [1]
Bacterial infection 1A00-1C4Z Approved [2]
Cholangitis N.A. Approved [1]
Staphylococcal pneumonia N.A. Approved [1]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 454.5
Logarithm of the Partition Coefficient (xlogp) -0.4
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 12
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.89 mL/min/kg [4]
Elimination
80% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.8 hours [4]
Metabolism
The drug is not metabolised []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 146.75116 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.18% [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.12 L/kg [4]
Water Solubility
The ability of drug to dissolve in water is measured as 33 mg/mL [3]
Chemical Identifiers
Formula
C14H14N8O4S3
IUPAC Name
(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
Canonical SMILES
CC1=NN=C(S1)SCC2=C(N3[C@@H]([C@@H](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
Cross-matching ID
PubChem CID
33255
ChEBI ID
CHEBI:474053
CAS Number
25953-19-9
DrugBank ID
DB01327
TTD ID
D09KDN
VARIDT ID
DR00577
INTEDE ID
DR2503
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Binder [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [7]
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [8]
Organic anion transporter 1 (SLC22A6) DTQ23VB S22A6_HUMAN Substrate [9]
Organic anion transporting polypeptide 1B1 (SLCO1B1) DT3D8F0 SO1B1_HUMAN Substrate [10]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [9]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Thiopurine methyltransferase (TPMT) DEFQ8VO TPMT_HUMAN Substrate [11]
Beta-lactamase (blaB) DEP0IWS A0A378EHS6_KLEPR Substrate [12]
Beta-lactamase (blaB) DE7IH52 AMPC_CITFR Substrate [13], [14]
Beta-lactamase (blaB) DENJ2SQ BLAB_BACFG Substrate [15], [16]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Cefazolin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Cefazolin and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [17]
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Cefazolin and Plazomicin. Urinary tract infection [GC08] [18]

References

1 Cefazolin FDA Label
2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 065244.
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Bacteriological characteristics of Staphylococcus aureus isolates from humans and bulk milk. J Dairy Sci. 2008 Feb;91(2):564-9.
7 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.
8 Oral availability of cefadroxil depends on ABCC3 and ABCC4. Drug Metab Dispos. 2012 Mar;40(3):515-21.
9 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.
10 Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81.
11 Cefazolin administration and 2-methyl-1,3,4-thiadiazole-5-thiol in human tissue: possible relationship to hypoprothrombinemia. Drug Metab Dispos. 2002 Oct;30(10):1123-8.
12 Analysis of the drug-resistant characteristics of Klebsiella pneumoniae isolated from the respiratory tract and CTX-M ESBL genes. Genet Mol Res. 2015 Oct 5;14(4):12043-8.
13 Citrobacter freundii bacteremia: Risk factors of mortality and prevalence of resistance genes. J Microbiol Immunol Infect. 2018 Aug;51(4):565-572.
14 Identification and functional characterization of arylamine N-acetyltransferases in eubacteria: evidence for highly selective acetylation of 5-aminosalicylic acid. J Bacteriol. 2001 Jun;183(11):3417-27.
15 Prevalence of antimicrobial resistance genes in Bacteroides spp. and Prevotella spp. Dutch clinical isolates. Clin Microbiol Infect. 2019 Sep;25(9):1156.e9-1156.e13.
16 Antibacterial activity of cefoperazone against anaerobic bacteria (author's transl). Jpn J Antibiot. 1980 Nov;33(11):1171-82.
17 Cerner Multum, Inc. "Australian Product Information.".
18 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".