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Compound Detail

CHEMBL1730

CEFOTAXIME
💊 Approved Drug
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💊 Approved Drug
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(C)=O)CS[C@H]12)c1csc(N)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1730
Name CEFOTAXIME
Phase Approved
Structure Type MOL
InChI Key GPRBEKHLDVQUJE-QSWIMTSFSA-N
Therapeutic ✓ Yes

Known Names

Cefotaxim hikma Cefotaxima Cefotaxime
10
Targets
17
Activities
3
Assay Types
23
PK Parameters
20
Publications
3
Known Names
5
Indications

Molecular Properties

455.5
MW (Da)
-0.62
ALogP
11
HBA
3
HBD
173.5
PSA (Ų)
0.21
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1981
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem cef-
USAN Year 1979

Extended Properties

Molecular Formula C16H17N5O7S2
MW 455.47
Aromatic Rings 1
Heavy Atoms 30
NP-Likeness 0.13

Indications

Bacterial Infections Peritonitis Sepsis Appendicitis Osteomyelitis

ATC Classification

J01DD01
cefotaxime
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

Ki 11 meas. best 8.3
IC50 5 meas. best 7.52
Kd 1 meas. best 4.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 8.3 7.41 5.0 2
Pseudomonas aeruginosa
CHEMBL348
 IC50 7.52 7.52 30.0 1
Staphylococcus aureus
CHEMBL352
 IC50 7.52 7.52 30.0 1
Escherichia coli
CHEMBL354
 IC50 7.0 7.0 100.0 1
Organic anion transporter 3
CHEMBL1641348
 Ki 6.54 6.54 290.0 1
Beta-lactamase ADC-33
CHEMBL1667700
 Ki 6.3 6.3 500.0 1
ADC-11
CHEMBL1667701
 Ki 5.6 5.6 2500.0 1
Solute carrier family 22 member 6
CHEMBL1641347
 Ki 5.5 5.5 3130.0 1
Solute carrier family 22 member 11
CHEMBL2073677
 Ki 5.21 5.21 6150.0 1
Albumin
CHEMBL3253
 Kd 4.92 4.92 12000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 46700.0 ng.hr.mL-1 Canis lupus familiaris
CL 2.7 mL.min-1.kg-1 Homo sapiens
CL 0.36 L/hr Homo sapiens
CL 0.26 L/hr Homo sapiens
CL 0.3 L/hr Homo sapiens
CL 0.22 L/hr Homo sapiens
CL 0.4 L/hr Homo sapiens
CL 1.46 L/hr Homo sapiens
CL 1.37 L/hr Homo sapiens
CL 0.18 L/hr Homo sapiens
CL 1.38 L/hr Homo sapiens
CL 2.7 mL.min-1.kg-1 Homo sapiens
Fu 0.6 - Homo sapiens
Fu 0.59 - Rattus norvegicus
MRT 1.2 hr Homo sapiens
T1/2 0.25 hr Rattus norvegicus
T1/2 0.5 hr Callithrix
T1/2 1.6 hr Homo sapiens
T1/2 0.8 hr Homo sapiens
T1/2 1.2 hr Homo sapiens
Vd 1.82 l Homo sapiens
Vd 11.0 l Homo sapiens
Vd 0.912 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 5.0 nM 8.3 Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-2 using cephalothin as ... 19470510
Staphylococcus aureus IC50 = 30.0 nM 7.52 Antimicrobial activity against methicillin-resistant Staphylococcus aureus ATCC ... 31287681
Pseudomonas aeruginosa IC50 = 30.0 nM 7.52 Antimicrobial activity against Pseudomonas aeruginosa ATCC 27853 assessed as inh... 31287681
Escherichia coli IC50 = 100.0 nM 7.0 Antimicrobial activity against Escherichia coli ATCC 35218 assessed as inhibitio... 31287681
Organic anion transporter 3 Ki = 290.0 nM 6.54 TP_TRANSPORTER: inhibition of Estrone sulfate uptake in OAT3-expressing S2 cells 11909604
Unchecked Ki = 300.0 nM 6.52 Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-30 using cephalothin as... 19470510
Beta-lactamase ADC-33 Ki = 500.0 nM 6.3 Activity of Acinetobacter baumannii ADC-33 beta-lactamase 20547808
ADC-11 Ki = 2500.0 nM 5.6 Activity of Acinetobacter baumannii ADC-11 beta-lactamase 20547808
Solute carrier family 22 member 6 Ki = 3130.0 nM 5.5 TP_TRANSPORTER: inhibition of PAH uptake in OAT1-expressing S2 cells 11909604
Solute carrier family 22 member 11 Ki = 6150.0 nM 5.21 TP_TRANSPORTER: inhibition of Estrone sulfate uptake in OAT4-expressing S2 cells 11909604
Albumin Kd = 12000.0 nM 4.92 Binding affinity to first site on human serum albumin by SPR 19164148

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 320
19805565 10.1128/aac.01099-09 Klebsiella pneumoniae 40
18663030 10.1128/aac.00877-08 Escherichia coli 40
18347108 10.1128/aac.01440-07 Klebsiella pneumoniae 40
17470649 10.1128/aac.00354-07 Haemophilus influenzae 38
20194704 10.1128/aac.00019-10 Unchecked 36
19884366 10.1128/aac.00966-09 Haemophilus influenzae 35
20713660 10.1128/aac.00009-10 Pseudomonas aeruginosa 35
18212109 10.1128/aac.01060-07 Escherichia coli 33
20194693 10.1128/aac.00816-09 Pseudomonas aeruginosa 32
19001116 10.1128/aac.00746-08 Klebsiella pneumoniae 30
18809939 10.1128/aac.00830-08 Enterobacter cloacae 28
18443114 10.1128/aac.01658-07 Escherichia coli 26
20660683 10.1128/aac.01301-09 Klebsiella pneumoniae 26
18541727 10.1128/aac.00461-08 Streptococcus sp. 'group B' 25
18981261 10.1128/aac.00642-08 Escherichia coli 24
18809939 10.1128/aac.00830-08 Klebsiella pneumoniae 24
18725443 10.1128/aac.00712-08 Streptococcus pneumoniae 24
17724156 10.1128/aac.01512-06 Acinetobacter baumannii 24
19506058 10.1128/aac.01655-08 Campylobacter jejuni 24

Data from ChEMBL 36 via Core Engine