General Information of Drug (ID: DMNEXZF)

Drug Name
Cefamandole
Synonyms
Cefadole; Cefamandolum; Cefamandole (USAN/INN); (6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid; (6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7beta-[(2R)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Bacteremia 1A73 Approved [1]
Microorganisms infection 1A00-1A09 Approved [2]
Peritonitis N.A. Approved [1]
Pneumonia CA40 Approved [1]
Staphylococcal pneumonia N.A. Approved [1]
Staphylococcus aureus infection N.A. Approved [1]
Urinary tract infection GC08 Approved [1]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 462.5
Logarithm of the Partition Coefficient (xlogp) -0.9
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 10
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability
96% of drug becomes completely available to its intended biological destination(s) [4]
Clearance
The drug present in the plasma can be removed from the body at the rate of 3.6 mL/min/kg [5]
Elimination
96% 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 32 minutes [5]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 334.5 micromolar/kg/day [6]
Unbound Fraction
The unbound fraction of drug in plasma is 0.25% [5]
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 0.16 L/kg [5]
Water Solubility
The ability of drug to dissolve in water is measured as 333 mg/mL [3]
Chemical Identifiers
Formula
C18H18N6O5S2
IUPAC Name
(6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES
CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)[C@@H](C4=CC=CC=C4)O)SC2)C(=O)O
InChI
InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
InChIKey
OLVCFLKTBJRLHI-AXAPSJFSSA-N
Cross-matching ID
PubChem CID
456255
ChEBI ID
CHEBI:3480
CAS Number
34444-01-4
DrugBank ID
DB01326
TTD ID
D06YHL
VARIDT ID
DR00551
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 [7]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [8]
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 Cefamandole (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Cefamandole and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [9]
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Cefamandole and Plazomicin. Urinary tract infection [GC08] [10]

References

1 Cefamandole FDA Label
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 BDDCS applied to over 900 drugs
4 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 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
7 The impact of penicillinase on cefamandole treatment and prophylaxis of experimental endocarditis due to methicillin-resistant Staphylococcus aureus. J Infect Dis. 1998 Jan;177(1):146-54.
8 Intestinal transport of beta-lactam antibiotics: analysis of the affinity at the H+/peptide symporter (PEPT1), the uptake into Caco-2 cell monolayers and the transepithelial flux. Pharm Res. 1999 Jan;16(1):55-61.
9 Cerner Multum, Inc. "Australian Product Information.".
10 Engle JE, Drago J, Carlin B, Schoolwerth AC "Letter: Reversible acute renal failure after cephalothin." Ann Intern Med 83 (1975): 232-3. [PMID: 1147461]