Amoxicillin
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1974
- First approval year
- 1974
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Amoxicillin
- Molecular weight
- 365.41
- Structure (SMILES)
- CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O
- amix 125
- Amix 125
- amix 250
- Amix 250
- amix 500
- Amix 500
- amopen
- Amopen
- amoram
- Amoram
- amoxi inject
- amoxi tabs
- Amoxi-inject
- Amoxi-tabs
- amoxicillin
- Amoxicillin
- amoxicillin component of augmentin
- Amoxicillin component of augmentin
- Amoxicillin component of clavulox trihydrate
- amoxicillin component of clavulox trihydrate
- amoxicillin component of prevpac
- Amoxicillin component of prevpac
- amoxicillin component of talicia
- Amoxicillin component of talicia
- amoxicillin pediatric
And 51 more, listed on the interactive page.
- amoxi gobens
- amoxicilina
- Amoxicilina
- amoxicillin
- Amoxicillin
- Amoxicillin (anhydrous)
- Amoxicillin (as trihydrate)
- amoxicillin [INN]
- AMOXICILLIN [MART.]
- AMOXICILLIN [MI]
- Amoxicillin [WHO-DD]
- amoxicillin anhydrous
- Amoxicillin anhydrous
- AMOXICILLIN ANHYDROUS [HSDB]
- amoxicillin anhydrous hsdb
- amoxicillin as trihydrate
- amoxicillin hydrate
- Amoxicillin hydrate
- amoxicillin inn
- amoxicillin mart
- amoxicillin mi
- amoxicillin trihydrate
- Amoxicillin trihydrate
- amoxicillin who dd
- amoxicilline
And 34 more, listed on the interactive page.
- ATC classification codes
- J01CA04
Sources for recorded values
- CAS registry numbers
- 26787-78-0
- ChEMBL ID
- CHEMBL1082
- InChIKey
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N
- FDA ingredient codes (UNII)
- 9EM05410Q9
- 33613
- 40467057
- 723
- 133008
- 1297882
- Applicant
- GLAXOSMITHKLINE
- Approval date
- 18 Jan 1974
- Application number
- NDA050459
- Patents
- 3
- Designations
- 0
- Earliest recorded loss of exclusivity
- 7 May 2027
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- No
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Pharmacology name
- amoxicillin
- Type
- Synthetic organic
- Drug name stem
- -cillin
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P02918
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P02919
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P08506
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P0AD65
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P0AD68
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P0AEB2
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
- Protein identifier
- P24228
Open Targets mechanisms
- Mechanism
- Bacterial penicillin-binding protein inhibitor
- Action type
- Inhibitor
- Target
- Bacterial penicillin-binding protein
DrugCentral mechanisms
- Action type
- Inhibitor
- Gene symbol
- mrcA|mrcB|dacC|mrdA|ftsI|dacA|dacB
- Protein identifier
- P02918|P02919|P08506|P0AD65|P0AD68|P0AEB2|P24228
- Organism
- Escherichia coli (strain K12)
- Condition
- Soft Tissue Infections
- Highest recorded phase
- 4
- Subject identifier
- D018461
- Condition
- Gonorrhea
- Highest recorded phase
- 4
- Condition identifier
- DOID:7551
- Subject identifier
- D006069
- Condition
- Lymphoma, B-Cell, Marginal Zone
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000191
- Subject identifier
- D018442
- Condition
- Gastritis
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000217
- Subject identifier
- D005756
- Condition
- Glioblastoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000519
- Subject identifier
- D005909
- Condition
- Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000544
- Subject identifier
- D007239
- Condition
- Lymphoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000574
- Subject identifier
- D008223
- Condition
- Periodontitis
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000649
- Subject identifier
- D010518
- Condition
- Colitis, Ulcerative
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000729
- Subject identifier
- D003093
- Condition
- Bacterial Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000771
- Subject identifier
- D001424
- Condition
- Obesity
- Highest recorded phase
- 1
- Condition identifier
- EFO:0001073
- Subject identifier
- D009765
- Condition
- Obesity, Morbid
- Highest recorded phase
- 1
- Condition identifier
- EFO:0001074
- Subject identifier
- D009767
- Condition
- Astrocytoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0002499
- Subject identifier
- D001254
- Condition
- Pregnancy
- Highest recorded phase
- 1
- Condition identifier
- EFO:0002950
- Subject identifier
- D011247
- Condition
- Bacteremia
- Highest recorded phase
- 2
- Condition identifier
- EFO:0003033
- Subject identifier
- D016470
- Condition
- Osteomyelitis
- Highest recorded phase
- 0.5
- Condition identifier
- EFO:0003102
- Subject identifier
- D010019
- Condition
- Urinary Tract Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003103
- Subject identifier
- D014552
- Condition
- Pneumonia
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003106
- Subject identifier
- D011014
- Condition
- Brain Neoplasms
- Highest recorded phase
- 1
- Condition identifier
- EFO:0003833
- Subject identifier
- D001932
- Condition
- Pain
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003843
- Subject identifier
- D010146
- Condition
- Vaginosis, Bacterial
- Highest recorded phase
- 2
- Condition identifier
- EFO:0003932
- Subject identifier
- D016585
- Condition
- Cholangitis, Sclerosing
- Highest recorded phase
- 0.5
- Condition identifier
- EFO:0004268
- Subject identifier
- D015209
- Condition
- Duodenal Ulcer
- Highest recorded phase
- 4
- Condition identifier
- EFO:0004607
- Subject identifier
- D004381
- Condition
- Otitis Media
- Highest recorded phase
- 4
- Condition identifier
- EFO:0004992
- Subject identifier
- D010033
- Condition
- Postoperative Complications
- Highest recorded phase
- 1
- Condition identifier
- EFO:0005323
- Subject identifier
- D011183
And 49 more, listed on the interactive page.
- Condition identifier
- DOID_7551
- Condition identifier
- EFO_0000217
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000544
- Condition identifier
- EFO_0000544
- Highest recorded phase
- 4
- Condition identifier
- EFO_0000574
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000649
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000729
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000771
- Condition identifier
- EFO_0001073
- Condition identifier
- EFO_0001074
- Highest recorded phase
- 1
- Condition identifier
- EFO_0002950
- Highest recorded phase
- 1
- Condition identifier
- EFO_0003033
- Highest recorded phase
- 2
- Condition identifier
- EFO_0003102
- Condition identifier
- EFO_0003103
- Condition identifier
- EFO_0003106
- Condition identifier
- EFO_0003917
- Condition identifier
- EFO_0003932
- Highest recorded phase
- 2
- Condition identifier
- EFO_0004268
- Condition identifier
- EFO_0004607
- Condition identifier
- EFO_0004992
- Condition identifier
- EFO_0005323
- Condition identifier
- EFO_0005741
- Highest recorded phase
- 3
- Condition identifier
- EFO_0006505
- Highest recorded phase
- 3
- Condition identifier
- EFO_0006859
- Condition identifier
- EFO_0007149
And 124 more, listed on the interactive page.
- Event
- acute generalised exanthematous pustulosis
- Reports
- 353
- Reporting signal score
- 673.062
- Event
- acute kidney injury
- Reports
- 831
- Reporting signal score
- 420.913
- Event
- anaphylactic reaction
- Reports
- 664
- Reporting signal score
- 636.858
- Event
- anaphylactic shock
- Reports
- 574
- Reporting signal score
- 937.028
- Event
- angioedema
- Reports
- 635
- Reporting signal score
- 603.941
- Event
- cholestasis
- Reports
- 442
- Reporting signal score
- 613.052
- Event
- crystalluria
- Reports
- 85
- Reporting signal score
- 278.335
- Event
- drug hypersensitivity
- Reports
- 2,930
- Reporting signal score
- 3,396.86
- Event
- drug reaction with eosinophilia and systemic symptoms
- Reports
- 760
- Reporting signal score
- 1,240.26
- Event
- drug-induced liver injury
- Reports
- 335
- Reporting signal score
- 323.954
- Event
- eosinophilia
- Reports
- 373
- Reporting signal score
- 513.688
- Event
- erythema
- Reports
- 913
- Reporting signal score
- 591.164
- Event
- face oedema
- Reports
- 302
- Reporting signal score
- 348.408
- Event
- hepatitis cholestatic
- Reports
- 187
- Reporting signal score
- 315.912
- Event
- hepatocellular injury
- Reports
- 444
- Reporting signal score
- 590.298
- Event
- lip oedema
- Reports
- 211
- Reporting signal score
- 446.318
- Event
- pruritus
- Reports
- 1,464
- Reporting signal score
- 938.407
- Event
- rash
- Reports
- 1,517
- Reporting signal score
- 480.256
- Event
- rash maculo-papular
- Reports
- 806
- Reporting signal score
- 1,468.78
- Event
- therapeutic product cross-reactivity
- Reports
- 173
- Reporting signal score
- 504.467
- Event
- toxic skin eruption
- Reports
- 307
- Reporting signal score
- 495.755
- Event
- type i hypersensitivity
- Reports
- 139
- Reporting signal score
- 281.782
- Event
- type iv hypersensitivity reaction
- Reports
- 147
- Reporting signal score
- 313.727
- Event
- urticaria
- Reports
- 1,335
- Reporting signal score
- 1,165.06
- NCT00002682
- NCT00003151
- NCT00042718
- NCT00649831
- NCT00051753
- NCT00539149
- NCT00066066
- NCT01098448
- NCT02969928
- NCT03132714
- NCT03733379
- NCT00095368
- NCT00100126
- NCT00393744
- NCT00643149
- NCT00107081
- NCT00130013
- NCT00396526
- NCT00407394
- NCT00717561
- NCT00818610
- NCT00887276
- NCT00933049
- NCT01166932
- NCT01200706
And 147 more, listed on the interactive page.
- Dose
- 500mg or 875mg
- Route
- Oral
- How often
- Every 12 hours
Conditions of use
- Take with food
- Hydrogen bond acceptors
- 6
- Hydrogen bond donors
- 4
- Polar surface area
- 132.96
- Calculated partition coefficient (ALogP)
- 0.02
- Calculated partition coefficient (XLogP)
- -2
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Molecular formula
- C16H19N3O5S
- Monoisotopic mass
- 365.10454189
- Natural product
- Yes
- Recorded assays
- 5,197
- Active assays
- 95
- Confirmatory
- Other
- Screening
- Anti-Bacterial Agents
Distribution coefficient (LogD)
- Median
- -1.65
- Mean
- -1.62667
- Minimum
- -1.98
- Maximum
- -1.22
- Unit
- unitless
- Assays
- 6
- Standard deviation
- 0.24744
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- LogD
Solubility
- Median
- 3,900
- Mean
- 3,900
- Minimum
- 3,900
- Maximum
- 3,900
- Unit
- ug/mL
- Assays
- 1
- Standard deviation
- 0
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- Solubility
Oral bioavailability
- Median
- 45
- Mean
- 45
- Minimum
- 45
- Maximum
- 45
- Unit
- %
- Assays
- 1
- Standard deviation
- 0
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- F
Related records
Trials (585)
- "Is Antibiotic Therapy Necessary for Patients Undergoing Extraction of Teeth With Abscess?"
- 10 vs 14 Days Triple Therapy : H.Pylori Infection Eradication
- 14-day PCAB-based High-dose Dual Therapy and14-day PCAB-based Triple Therapy vs 14-day PPI-based Reverse Hybrid Therapy
- 14-day Quadruple Hybrid vs. Concomitant Therapies for Helicobacter Pylori Eradication
- 2-day Prophylactic Antibiotic is Effective in Transoral Endoscopic Thyroidectomy
- 3 Days Amoxicillin Versus Placebo for Fast Breathing Childhood Pneumonia in Malawi
- 3 Days Versus 5 Days Amoxicillin for Chest-indrawing Childhood Pneumonia in Malawi
- 3 vs. 5 Days of Amoxicillin for Childhood Pneumonia: An RCT
- 5 Day Concomitant Versus 10 Day Sequential Therapy for Eradication of H. Pylori Infection
- 600 mg Amoxicillin/42.9 mg Clavulanate Postassium /5 mL Suspension Under Fasting Conditions
- 600 mg Amoxicillin/42.9 mg Clavulanate Postassium /5 mL Suspension Under Fed Conditions
- 7 Days vs. 14 Days of Vonoprazan-based Triple Therapy for H. Pylori Eradication
- A "Screen and Treat" Helicobacter Pylori Eradication Trial in Adolescents in Three Regions of Chile
- A Clinical Study of Connective Tissue Graft and Enamel Matrix Derivative in the Treatment of Intrabony Periodontal Defects
- A Comparative, Single-Center, Pediatric Taste Test Study of Omnicef Versus Amoxicillin Antibiotic Suspension Medications
- A Comparison of High-dose Dual Therapy and Half-dose Clarithromycin-containing Bismuth Quadruple Therapy for H.P Eradication in Elderly Patients
- A Comparison of the Safety and Efficacy of Cefdinir Oral Suspension Versus Amoxicillin/Clavulanate in Pediatric Subjects With Acute Otitis Media
- A Controlled Human Pneumococcal Infection Model (PIM) Study
- A Multicenter, Randomized, Double-Blind, Double-Dummy Study Of Azithromycin SR Versus Amoxicillin For The Treatment Of Strep Throat In Children
- A Multicentre, Randomised, Open-Label Study To Compare The Efficacy And Safety Of Azithromycin For 5 Days With Those Of Amoxicillin-Clavulanic Acid In Patients With Chronic Bronchitis
Approved for (11)
- Bacterial infectious disease
- Duodenal ulcer
- Gonorrhea
- Infectious otitis media
- Otitis media
- Pharyngitis
- Pneumonia
- Respiratory tract infectious disorder
- Sinusitis
- Tonsillitis
- Urinary tract infection
In development for (51)
- Alcoholic hepatitis Phase 3
- Alcoholic liver disease Phase 3
- Allergic disease Phase 3
- Anaplastic astrocytoma Phase 1
- Asthma Phase 2
- Bacterial infectious disease with sepsis Phase 2
- Bacterial pneumonia Phase 2
- Bacterial vaginosis Phase 2
- Brain neoplasm Phase 1
- Bronchitis Phase 3
- Buruli ulcer disease Phase 2
- Central serous chorioretinopathy Phase 1
- Chlamydia trachomatis infectious disease Phase 2
- Cholecystitis Phase 3
- Chronic bronchitis Phase 3
- Clostridium infectious disease Phase 3
- COVID-19 Phase 3
- Cystitis Phase 3
- Diarrheal disease Early phase 1
- Dyspepsia Phase 3
Other linked conditions (5)
- Anal fistula
- Appendicitis
- Cleft palate
- Gastric mucosa-associated lymphoid tissue lymphoma
- Tic disorder