Details of the Drug

General Information of Drug (ID: DMMKHBJ)

Drug Name

Cefotaxime

Synonyms

Cefotaxim; Cefotaxima; Cefotaximum; Cephotaxim; Cephotaxime; Claforan; Klaforan; Cefotaxim Hikma; Cefotaxime acid; CE3; RU 24662; Cefotaxim Hikma (TN); Cefotaxima [INN-Spanish]; Cefotaxime (INN); Cefotaxime [INN:BAN]; Cefotaximum [INN-Latin]; Claforan (TN); Ru-24756; Claforan (*Sodium salt*)

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]

Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

455.5

Topological Polar Surface Area (xlogp)

-1.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Clearance: The drug present in the plasma can be removed from the body at the rate of 2.7 mL/min/kg [3]
Elimination: 30% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.2 hours [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 376.37631 micromolar/kg/day [4]
Unbound Fraction: The unbound fraction of drug in plasma is 0.6% [3]
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 0.19 L/kg [3]

Chemical Identifiers

Formula: C16H17N5O7S2
IUPAC Name: (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\\OC)/C3=CSC(=N3)N)SC1)C(=O)O
InChI: InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1
InChIKey: GPRBEKHLDVQUJE-QSWIMTSFSA-N

Cross-matching ID

PubChem CID: 5742673
ChEBI ID: CHEBI:204928
CAS Number: 63527-52-6
DrugBank ID: DB00493
TTD ID: D0D1HA
VARIDT ID: DR00427

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial DD-carboxypeptidase (Bact vanYB)	TTLP6GN	VANY_ENTFA	Inhibitor	[5], [6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Cefotaxime

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Kanamycin	DM2DMPO	Moderate	Increased risk of nephrotoxicity by the combination of Cefotaxime and Kanamycin.	Bacterial infection [1A00-1C4Z]	[14]
Streptomycin	DME1LQN	Moderate	Increased risk of nephrotoxicity by the combination of Cefotaxime and Streptomycin.	Bacterial infection [1A00-1C4Z]	[14]
Gentamicin	DMKINJO	Moderate	Increased risk of nephrotoxicity by the combination of Cefotaxime and Gentamicin.	Bacterial infection [1A00-1C4Z]	[14]
Netilmicin	DMRD1QK	Moderate	Increased risk of nephrotoxicity by the combination of Cefotaxime and Netilmicin.	Bacterial infection [1A00-1C4Z]	[14]
Tobramycin	DMUI0CH	Moderate	Increased risk of nephrotoxicity by the combination of Cefotaxime and Tobramycin.	Bacterial infection [1A00-1C4Z]	[14]
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Coadministration of a Drug Treating the Disease Different from Cefotaxime (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Framycetin	DMF8DNE	Moderate	Increased risk of nephrotoxicity by the combination of Cefotaxime and Framycetin.	Alcoholic liver disease [DB94]	[14]
Mycophenolic acid	DMU65NK	Moderate	Altered absorption of Cefotaxime due to GI flora changes caused by Mycophenolic acid.	Crohn disease [DD70]	[15]
Ethacrynic acid	DM60QMR	Moderate	Increased risk of nephrotoxicity by the combination of Cefotaxime and Ethacrynic acid.	Essential hypertension [BA00]	[16]
Furosemide	DMMQ8ZG	Moderate	Increased risk of nephrotoxicity by the combination of Cefotaxime and Furosemide.	Heart failure [BD10-BD1Z]	[16]
Bumetanide	DMRV7H0	Moderate	Increased risk of nephrotoxicity by the combination of Cefotaxime and Bumetanide.	Heart failure [BD10-BD1Z]	[16]
Givosiran	DM5PFIJ	Moderate	Increased risk of nephrotoxicity by the combination of Cefotaxime and Givosiran.	Inborn porphyrin/heme metabolism error [5C58]	[17]
Probenecid	DMMFWOJ	Moderate	Decreased elimination of Cefotaxime caused by Probenecid mediated competitive inhibition of renal tubular secretion.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[18]
Porfimer Sodium	DM7ZWNY	Moderate	Increased risk of photosensitivity reactions by the combination of Cefotaxime and Porfimer Sodium.	Lung cancer [2C25]	[19]
Mycophenolate mofetil	DMPQAGE	Moderate	Altered absorption of Cefotaxime due to GI flora changes caused by Mycophenolate mofetil.	Transplant rejection [NE84]	[15]
Plazomicin	DMKMBES	Moderate	Increased risk of nephrotoxicity by the combination of Cefotaxime and Plazomicin.	Urinary tract infection [GC08]	[14]
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⏷ Show the Full List of 10 DDI Information of This Drug

References

1	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 064200.
2	BDDCS applied to over 900 drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	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
5	Extended-spectrum cephalosporinases: structure, detection and epidemiology. Future Microbiol. 2007 Jun;2:297-307.
6	Binding of cephalothin and cefotaxime to D-ala-D-ala-peptidase reveals a functional basis of a natural mutation in a low-affinity penicillin-binding protein and in extended-spectrum beta-lactamases. Biochemistry. 1995 Jul 25;34(29):9532-40.
7	Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92.
8	A 1.2-A snapshot of the final step of bacterial cell wall biosynthesis. Proc Natl Acad Sci U S A. 2001 Feb 13;98(4):1427-31.
9	How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
10	Synthesis and evaluation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors. J Med Chem. 2009 Oct 8;52(19):6097-106.
11	DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Nucleic Acids Res. 2011 Jan;39(Database issue):D1035-41.
12	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
13	The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
14	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
15	Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
16	Chrysos G, Gargalianos P, Lelekis M, Stefanou J, Kosmidis J "Pharmacokinetic interactions of ceftazidime and frusemide." J Chemother 7 Suppl (1995): 107-10. [PMID: 8904125]
17	Cerner Multum, Inc. "Australian Product Information.".
18	Brown G, Zemcov SJ, Clarke AM "Effect of probenecid on cefazolin serum concentrations." J Antimicrob Chemother 31 (1993): 1009-11. [PMID: 8360120]
19	Blakely KM, Drucker AM, Rosen CF "Drug-induced photosensitivity-an update: Culprit drugs, prevention and management." Drug Saf 42 (2019): 827-47. [PMID: 30888626]