Drug Details

General Information of the Drug (ID: DR1288)
Name
Cefotaxime
Synonyms
cefotaxime; Cephotaxime; 63527-52-6; Cefotaxime acid; E-cefotaxime; UNII-N2GI8B1GK7; Cefotaximum; Cefotaxima; CHEBI:204928; N2GI8B1GK7; 60846-21-1; (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; Omnatax; Taxim; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-(((2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, (6R,7R)-; Cefotaxime [INN:BAN]; Cefotaximum [INN-Latin]; Cefotaxima [INN-Spanish]; Cefotaxima acid; 4kot; (6R,7R)-3-(acetoxymethyl)-7-((E)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-(acetoxymethyl)-7-[[(2Z)-2-(2-aminothiazol-4-yl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6r,7r)-3-(Acetyloxymethyl)-7-[[(2z)-2-(2-Amino-1,3-Thiazol-4-Yl)-2-Methoxyimino-Ethanoyl]amino]-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]oct-2-Ene-2-Carboxylic Acid; (6R,7R)-3-Acetoxymethyl-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R,Z)-3-(acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)-; Cefotaxime (INN); EINECS 264-299-1; Cefotaxim Hikma (TN); RU 24662; Prestwick2_000139; Prestwick3_000139; Claforan (*Sodium salt*); CHEMBL1730; Lopac0_000278; BSPBio_000218; BPBio1_000240; SCHEMBL3731931; DTXSID6022761; HY-A0088A; HMS2090M11; (6R,7R)-3-(acetoxymethyl)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; ZINC3830437; AC-217; BDBM50482777; MFCD00864971; s4720; AKOS015951267; DB00493; SDCCGSBI-0050266.P002; (6R,7R)-3-(Acetoxymethyl)-7-(()-2-(2-amino-4-thiazolyl)-2-methoxyiminoglyoxylamino)-8-oco-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure; 3-(Acetyloxymethyl)-7-(((2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; AS-12690; clo[4.2.0]oct-2-ene-2-carboxylic acid; CS-0013515; C06885; D07647; J90010; 527C526; BRD-K78364995-236-03-5; Q27262497; Di- poundg-chlorotetrakis[2,4-dimethyl-6-(2-quinolinyl-KN)phenyl-KC]di-iridium; (6R)-3-(Acetoxymethyl)-7alpha-[[(2-amino-4-thiazolyl)[(E)-methoxyimino]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid; (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-ethanoyl]amino]-8-oxo-5-thia-1-azabicy; (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-ethanoyl]amino]-8-oxo-5-thia-1-azabicy clo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-[(acetyloxy)methyl]-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-[(acetyloxy)methyl]-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 1056874-43-1; 3-(Acetoxymethyl)-7beta-[(2-amino-4-thiazolyl)(methoxyimino)acetylamino]cepham-3-ene-4-carboxylic acid; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, (6R-(6alpha,7beta(Z)))-
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Molecular Type
Small molecule
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption
The drug is rapidly absorbed following intramuscular injection
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Clearance
The drug present in the plasma can be removed from the body at the rate of 2.7 mL/min/kg
Elimination
30% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 1 hours
Half-life
The concentration or amount of drug in body reduced by one-half in 1.2 hours
Metabolism
The drug is metabolized via the kidneys
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 376.37631 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.6%
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
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Formula
C16H17N5O7S2
PubChem CID
5742673
Canonical SMILES
CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(=NOC)C3=CSC(=N3)N)SC1)C(=O)O
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
CAS Number
CAS 63527-52-6
ChEBI ID
CHEBI:204928
TTD Drug ID
D0D1HA
DrugBank ID
DB00493
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          1,4-naphthoquinone      Setaria palmifolia     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Micrococcus luteus Microorganism model Micrococcus luteus
Bacillus cereus Microorganism model Bacillus cereus
Methicillin-sensitive Staphylococcus aureus Microorganism model Staphylococcus aureus
Methicillin-Resistant Staphylococcus aureus Microorganism model Staphylococcus aureus
Escherichia coli Microorganism model Escherichia coli
Klebsiella pneumoniae Microorganism model Klebsiella pneumoniae
Pseudomonas aeruginosa Microorganism model Pseudomonas aeruginosa
Salmonella choleraesuis Microorganism model Salmonella choleraesuis
                    Experimental
                    Result(s)		 1,4-naphthoquinone combined with ascorbate have significant antitumor effects against MCF-7 cells in vitro and Ehrlich-ascites carcinoma in mice.
          Amentoflavone      Gingko biloba     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Enterococcus faecium ATCC 19434 Microorganism model Enterococcus faecium
Staphylococcus aureus ATCC 25923 Microorganism model Staphylococcus aureus
Streptococcus mutans ATCC 3065 Microorganism model Streptococcus mutans
Escherichia coli ATCC 43895 Microorganism model Escherichia coli
Escherichia coli ATCC 25922 Microorganism model Escherichia coli
Pseudomonas aeruginosa ATCC 27853 Microorganism model Pseudomonas aeruginosa
                    Experimental
                    Result(s)		 Amentoflavone had a considerable antibacterial effect and synergistic interaction with antibiotics against various bacterial strains. The formation of hydroxyl radical would be a cause of the synergistic effect and that this oxidative stress originated from a transient NADH depletion. .
          Tea Polyphenols      Theaceae     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Klebsiella pneumoniae Microorganism model Klebsiella pneumoniae
                    Experimental
                    Result(s)		 Tea polyphenols used in combination with commonly used antibiotics showed synergistic bactericidal effect against multidrug-resistant Klebsiella pneumoniae.
Target and Pathway
Target(s) Bacterial DD-carboxypeptidase (Bact vanYB)  Molecule Info  [5]
References
Reference 1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 064200.
Reference 2 Synergistic Antibacterial Activity Between 1,4-Naphthoquinone and Beta-Lactam Antibiotics Against Methicillin-Resistant Staphylococcus aureus. Microb Drug Resist. 2021 Feb;27(2):234-240.
Reference 3 Antibacterial effect of amentoflavone and its synergistic effect with antibiotics. J Microbiol Biotechnol. 2013;23(7):953-8.
Reference 4 In-vitro antibacterial effect of tea polyphenols combined with common antibiotics on multidrug-resistant Klebsiella pneumoniae. Minerva Med. 2020 Dec;111(6):536-543.
Reference 5 Extended-spectrum cephalosporinases: structure, detection and epidemiology. Future Microbiol. 2007 Jun;2:297-307.
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