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Compound Detail

CHEMBL174

AMPICILLIN
💊 Approved Drug
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💊 Approved Drug
CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL174
Name AMPICILLIN
Phase Approved
Structure Type MOL
InChI Key AVKUERGKIZMTKX-NJBDSQKTSA-N
Therapeutic ✓ Yes

Known Names

Alpha-aminobenzylpenicillin Amcill Amfipen Aminobenzylpenicillin Aminobenzylpenicillin trihydrate Ampicilina Ampicillin Ampicillin (anhydrous) Ampicillin anhydrous Ampicillin hydrate Ampicillin trihydrate Ampicillin, anhydrous +18 more
15
Targets
46
Activities
4
Assay Types
12
PK Parameters
20
Publications
30
Known Names
12
Indications
1
Mechanisms

Molecular Properties

349.4
MW (Da)
0.32
ALogP
5
HBA
3
HBD
112.7
PSA (Ų)
0.67
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1965
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem -cillin
USAN Year 1962

Extended Properties

Molecular Formula C16H19N3O4S
MW 349.41
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness 0.74

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial penicillin-binding protein inhibitor INHIBITOR Bacterial penicillin-binding protein ✓ ✓

Indications

Bacterial Infections Eye Infections Gonorrhea Infections Meningitis Kidney Calculi Premature Birth Sepsis Chorioamnionitis Cleft Palate Dystonic Disorders Osteomyelitis

ATC Classification

J01CA01
ampicillin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
J01CA51
ampicillin, combinations
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AA19
ampicillin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

EC50 20 meas. best 7.23
IC50 18 meas. best 7.7
Ki 7 meas. best 2.89
Kd 1 meas. best 4.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Staphylococcus aureus
CHEMBL352
 IC50 7.7 6.835 20.0 4
Staphylococcus aureus
CHEMBL352
 EC50 7.23 6.2225 59.0 4
Escherichia coli
CHEMBL354
 IC50 6.84 5.71 146.0 3
Bacillus subtilis
CHEMBL359
 EC50 6.82 5.785 150.0 2
Bacillus subtilis
CHEMBL359
 IC50 6.52 6.1425 300.0 4
Pseudomonas aeruginosa
CHEMBL348
 IC50 6.36 6.36 436.0 1
Enterococcus faecium
CHEMBL357
 IC50 6.22 6.22 600.0 1
Enterococcus faecium
CHEMBL357
 EC50 6.2 5.68 630.0 2
Erythrocyte
CHEMBL4296518
 IC50 6.05 6.05 900.0 1
Streptococcus pneumoniae
CHEMBL347
 IC50 5.97 5.97 1080.0 1
Micrococcus luteus
CHEMBL614421
 IC50 5.96 5.96 1100.0 1
Acinetobacter baumannii
CHEMBL614425
 EC50 5.6 5.6 2500.0 1
Staphylococcus epidermidis
CHEMBL353
 IC50 5.07 5.07 8500.0 1
Pseudoalteromonas ulvae
CHEMBL4296595
 EC50 5.03 5.03 9300.0 3
Pseudoalteromonas lipolytica
CHEMBL4296594
 EC50 4.75 4.75 17900.0 3
Pseudomonas aeruginosa
CHEMBL348
 EC50 4.57 4.57 27000.0 1
Angiopoietin-1 receptor
CHEMBL4128
 Kd 4.09 4.09 82000.0 1
Klebsiella pneumoniae subsp. pneumoniae
CHEMBL613207
 EC50 4.05 4.05 89000.0 1
Solute carrier family 15 member 2
CHEMBL1743125
 Ki 2.89 2.89 1288249.6 2

Pharmacokinetic Data

Parameter Value Units Species
CL 2.8 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 2.8 mL.min-1.kg-1 Homo sapiens
CL 2.8 mL.min-1.kg-1 Homo sapiens
Cmax 9158.3 nM Homo sapiens
Fu 0.85 - Homo sapiens
Fu 0.85 - Homo sapiens
MRT 1.3 hr Homo sapiens
T1/2 0.08333 hr -
T1/2 1.4 hr Homo sapiens
T1/2 0.25 hr -
Vd 0.3 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Staphylococcus aureus IC50 = 20.0 nM 7.7 Antibacterial activity against Staphylococcus aureus measured by broth microdilu... 33895275
Staphylococcus aureus EC50 = 59.0 nM 7.23 Antibacterial activity against multidrug resistant Staphylococcus aureus subsp. ... 27184767
Staphylococcus aureus IC50 = 60.0 nM 7.22 Antibacterial activity against Staphylococcus aureus CGMCC 1.24465 after 24 hrs 21158423
Staphylococcus aureus IC50 = 100.0 nM 7.0 Antibacterial activity against Staphylococcus aureus NCIM 2010 after 12 hrs by s... 29738954
Escherichia coli IC50 = 146.0 nM 6.84 Antibacterial activity against Escherichia coli NCIM 2688 after 8 hrs by serial ... 29738954
Staphylococcus aureus EC50 = 150.0 nM 6.82 Antibacterial activity against Staphylococcus aureus NCIM 2010 assessed as reduc... 35696863
Bacillus subtilis EC50 = 150.0 nM 6.82 Antibacterial activity against Bacillus subtilis NCIM 2079 assessed as reduction... 35696863
Staphylococcus aureus EC50 = 190.0 nM 6.72 Antibacterial activity against Staphylococcus aureus ATCC 25923 after 6 to 8 hrs... 30392371
Bacillus subtilis IC50 = 300.0 nM 6.52 Antibacterial activity against Bacillus subtilis measured by broth microdilution... 33895275
Pseudomonas aeruginosa IC50 = 436.0 nM 6.36 Antibacterial activity against Pseudomonas aeruginosa NCIM 2036 after 8 hrs by s... 29738954
Enterococcus faecium IC50 = 600.0 nM 6.22 Antibacterial activity against Enterococcus faecium assessed as bacterial growth... 35271771
Enterococcus faecium EC50 = 630.0 nM 6.2 Antibacterial activity against multidrug resistant Enterococcus faecium NCTC 717... 27184767
Erythrocyte IC50 = 900.0 nM 6.05 Hemolytic activity against human RBC incubated for 1 hr by microplate reader ana... 39116273
Bacillus subtilis IC50 = 900.0 nM 6.05 Antibacterial activity against Bacillus subtilis ATCC 6633 assessed as reduction... 32119543
Bacillus subtilis IC50 = 1000.0 nM 6.0 Antibacterial activity against Bacillus subtilis NCIM 2079 after 12 hrs by seria... 29738954
Bacillus subtilis IC50 = 1000.0 nM 6.0 Antibacterial activity against Bacillus subtilis assessed as reduction in bacter... 38771638
Streptococcus pneumoniae IC50 = 1080.0 nM 5.97 Antibacterial activity against Streptococcus pneumoniae CGMCC 1.1692 after 24 hr... 21158423
Micrococcus luteus IC50 = 1100.0 nM 5.96 Antibacterial activity against Micrococcus luteus assessed as reduction in bacte... 38771638
Escherichia coli IC50 = 1500.0 nM 5.82 Antibacterial activity against Escherichia coli assessed as reduction in bacteri... 38771638
Acinetobacter baumannii EC50 = 2500.0 nM 5.6 Antibacterial activity against multidrug resistant Acinetobacter baumannii 2208 ... 27184767

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 320
18955526 10.1128/aac.00441-08 NON-PROTEIN TARGET 168
19581457 10.1128/aac.00908-08 NON-PROTEIN TARGET 108
19029333 10.1128/aac.00485-08 Acinetobacter pittii 92
17420206 10.1128/aac.00052-07 Escherichia coli 86
20713660 10.1128/aac.00009-10 Pseudomonas aeruginosa 71
20421396 10.1128/aac.00197-10 Escherichia coli 69
17470649 10.1128/aac.00354-07 Haemophilus influenzae 51
17043131 10.1128/aac.00600-06 Salmonella typhimurium 44
18443129 10.1128/aac.00214-08 Haemophilus influenzae 41
19884366 10.1128/aac.00966-09 Haemophilus influenzae 36
20498317 10.1128/aac.01336-09 Escherichia coli 35
18458127 10.1128/aac.00298-08 Mycobacterium tuberculosis variant bovis BCG 34
20679504 10.1128/aac.00356-10 NON-PROTEIN TARGET 33
19651910 10.1128/aac.00192-09 Haemophilus influenzae 32
17646161 10.1074/jbc.m704286200 Unchecked 26
17698631 10.1128/aac.00422-07 Haemophilus influenzae 26
19506058 10.1128/aac.01655-08 Campylobacter jejuni 25
18541727 10.1128/aac.00461-08 Streptococcus sp. 'group B' 25
21078949 10.1128/aac.00098-10 Unchecked 24

Data from ChEMBL 36 via Core Engine