AMOXICILLIN

Search structure
Trade Names:
Synonyms:
Status: Approved (1974)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J01CA04
UNII: 804826J2HU

Structure
InChI Key LSQZJLSUYDQPKJ-NJBDSQKTSA-N
Smile CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O
InChI
InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H19N3O5S
Molecular Weight 365.41
AlogP 0.02
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 4.0
Polar Surface Area 132.96
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 25.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 0.87 - EXP
Henry's Law Constant 2.49E-21 atm-m3/mole EST
Atmospheric OH Rate Constant 1.39E-10 cm3/molecule-sec EST
Water Solubility 3430 mg/L EST
Vapor Pressure 4.69E-17 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Bacterial penicillin-binding protein inhibitor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - -16.8-15.6
Enzyme Oxidoreductase
- 9000000 - - -
Enzyme Protease Serine protease Serine protease unclassified
- 0.004-0.422 - - -
Enzyme Protease
- 0.004-0.422 - - -
Enzyme Transferase
- - - - 11.63
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -3.71--3.53
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC15 family of peptide transporters
- - - 179000-430000 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 75.16
Unclassified protein
- 0.029-0.22 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Pharyngitis 4 D010612 ClinicalTrials
Tonsillitis 4 D014069 ClinicalTrials
Urinary Tract Infections 4 D014552 ClinicalTrials
Otitis Media 4 D010033 ClinicalTrials
Tonsillitis 4 D014069 ClinicalTrials
Hernia 3 D006547 ClinicalTrials
Bronchitis, Chronic 3 D029481 ClinicalTrials
Communicable Diseases 3 D003141 ClinicalTrials
Periodontitis 3 D010518 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Otitis Media, Suppurative 3 D010035 ClinicalTrials
Helicobacter Infections 3 D016481 ClinicalTrials
Enterobacteriaceae Infections 3 D004756 ClinicalTrials
Hepatitis, Alcoholic 3 D006519 ClinicalTrials
Hemorrhage 3 D006470 ClinicalTrials
Dyspepsia 3 D004415 ClinicalTrials
Pyelonephritis 3 D011704 ClinicalTrials
Cholecystitis 3 D002764 ClinicalTrials
Fever 3 D005334 ClinicalTrials
Low Back Pain 3 D017116 ClinicalTrials
Endocarditis 3 D004696 ClinicalTrials
Neutropenia 3 D009503 ClinicalTrials
Gastritis 3 D005756 ClinicalTrials
Stomach Ulcer 3 D013276 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Influenza, Human 3 D007251 ClinicalTrials
Malaria, Falciparum 3 D016778 ClinicalTrials
Malnutrition 3 D044342 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Hypersensitivity 3 D006967 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Cystitis, Hemorrhagic 3 D000096722 ClinicalTrials
Liver Diseases, Alcoholic 3 D008108 ClinicalTrials
Bronchitis 3 D001991 ClinicalTrials
Clostridium Infections 3 D003015 ClinicalTrials
Asthma 2 D001249 ClinicalTrials
Tuberculosis 2 D014376 ClinicalTrials
Colitis, Ulcerative 2 D003093 ClinicalTrials
Head and Neck Neoplasms 2 D006258 ClinicalTrials
Chlamydia Infections 2 D002690 ClinicalTrials
Pseudomyxoma Peritonei 2 D011553 ClinicalTrials
Lymphoma, B-Cell, Marginal Zone 2 D018442 ClinicalTrials
Tuberculosis, Pulmonary 2 D014397 ClinicalTrials
Pneumonia, Bacterial 2 D018410 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Periapical Periodontitis 2 D010485 ClinicalTrials
Mastitis 2 D008413 ClinicalTrials
Vaginosis, Bacterial 2 D016585 ClinicalTrials
Buruli Ulcer 2 D054312 ClinicalTrials
Periodontal Diseases 2 D010510 ClinicalTrials
Bacteremia 2 D016470 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 1 D064129 ClinicalTrials
Brain Neoplasms 1 D001932 ClinicalTrials
Central Serous Chorioretinopathy 1 D056833 ClinicalTrials
Postoperative Complications 1 D011183 ClinicalTrials
Pregnancy 1 D011247 ClinicalTrials
Obesity 1 D009765 ClinicalTrials
Diarrhea 1 D003967 ClinicalTrials
Cholangitis, Sclerosing 1 D015209 ClinicalTrials
Inflammation 1 D007249 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Obesity, Morbid 1 D009767 ClinicalTrials
Tooth Diseases 1 D014076 ClinicalTrials
Osteomyelitis 1 D010019 ClinicalTrials
Astrocytoma 1 D001254 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture
Mixture
Mixture

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Skin and subcutaneous tissue disorders
17.51
Immune system disorders
13.15
General disorders and administration site conditions
9.43
Gastrointestinal disorders
9.26
Respiratory, thoracic and mediastinal disorders
6.15
Nervous system disorders
5.94
Vascular disorders
5.03
Injury, poisoning and procedural complications
4.54
Cardiac disorders
4.22
Psychiatric disorders
3.59
Investigations
3.03
Infections and infestations
2.76
Pregnancy, puerperium and perinatal conditions
2.4
Musculoskeletal and connective tissue disorders
2.18
Renal and urinary disorders
2.15

Cross References

Resources Reference
CAS NUMBER 26787-78-0
ChEBI 2676
ChEMBL CHEMBL1082
DrugBank DB01060
DrugCentral 192
EPA CompTox DTXSID3037044
FDA SRS 804826J2HU
Human Metabolome Database HMDB15193
Guide to Pharmacology 10895
KEGG C06827
PharmGKB PA448406
PubChem 33613
SureChEMBL SCHEMBL3427
ZINC ZINC000003830215
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