amoxicillin Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, 6-aminopenicillanic acid derivatives 192 26787-78-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • amoxicillin trihydrate
  • amoxicillin
  • amocilline
  • amoxcillin
  • amoxycillin
  • amoxicillin sodium
  • amoxicillin anhydrous
  • amoxicillin hydrate
A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.
  • Molecular weight: 365.40
  • Formula: C16H19N3O5S
  • CLOGP: -1.87
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 4
  • TPSA: 132.96
  • ALOGS: -2.58
  • ROTB: 4

Drug dosage:

DoseUnitRoute
1 g O
1 g P
1 g O
3 g P

Approvals:

DateAgencyCompanyOrphan
Dec. 9, 1974 FDA APOTHECON

FDA Adverse Event Reporting System

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 4612.16 35.23 1298 8153 34382 3342026
Pruritus 1459.53 35.23 590 8861 46243 3330165
Rash 1436.93 35.23 658 8793 70163 3306245
Drug reaction with eosinophilia and systemic symptoms 1326.92 35.23 357 9094 7538 3368870
Urticaria 1253.21 35.23 463 8988 28264 3348144
Erythema 862.88 35.23 354 9097 28456 3347952
Diarrhoea 862.78 35.23 534 8917 103814 3272594
Cholestasis 731.73 35.23 206 9245 5131 3371277
Rash maculo-papular 730.32 35.23 210 9241 5657 3370751
Acute kidney injury 695.66 35.23 360 9091 49323 3327085
Pyrexia 615.11 35.23 394 9057 80721 3295687
Angioedema 606.61 35.23 230 9221 14905 3361503
Toxic epidermal necrolysis 571.26 35.23 164 9287 4381 3372027
Vomiting 548.64 35.23 381 9070 89150 3287258
Anaphylactic reaction 536.03 35.23 202 9249 12852 3363556
Hypersensitivity 510.62 35.23 243 9208 27657 3348751
Dyspnoea 496.42 35.23 379 9072 102555 3273853
Drug-induced liver injury 461.99 35.23 143 9308 4970 3371438
Hepatocellular injury 461.55 35.23 138 9313 4257 3372151
Jaundice 457.23 35.23 168 9283 9939 3366469
Stevens-Johnson syndrome 454.25 35.23 151 9300 6621 3369787
Rash generalised 451.40 35.23 165 9286 9617 3366791
Hepatitis 424.32 35.23 157 9294 9468 3366940
Eosinophilia 418.03 35.23 131 9320 4742 3371666
Anaphylactic shock 392.94 35.23 130 9321 5609 3370799
Enterocolitis haemorrhagic 387.57 35.23 80 9371 481 3375927
Acute generalised exanthematous pustulosis 380.26 35.23 101 9350 1998 3374410
Hepatitis cholestatic 370.22 35.23 97 9354 1816 3374592
Rash erythematous 351.29 35.23 130 9321 7832 3368576
Clostridium difficile infection 341.90 35.23 102 9349 3116 3373292
Face oedema 337.20 35.23 113 9338 5071 3371337
Malaise 324.02 35.23 245 9206 64932 3311476
Clostridium difficile colitis 313.89 35.23 94 9357 2909 3373499
Nausea 311.23 35.23 322 9129 129323 3247085
Lip oedema 307.53 35.23 74 9377 962 3375446
Generalised erythema 302.98 35.23 85 9366 2076 3374332
Liver injury 298.02 35.23 94 9357 3470 3372938
Drug interaction 291.83 35.23 202 9249 46610 3329798
Pruritus generalised 274.23 35.23 100 9351 5769 3370639
Lip swelling 268.40 35.23 100 9351 6131 3370277
Hypotension 267.87 35.23 196 9255 49318 3327090
Toxic skin eruption 257.87 35.23 81 9370 2947 3373461
Swelling face 256.93 35.23 115 9336 11301 3365107
Jaundice cholestatic 249.29 35.23 65 9386 1191 3375217
Abdominal pain 245.48 35.23 181 9270 46044 3330364
Abdominal pain upper 243.63 35.23 143 9308 24773 3351635
Alanine aminotransferase increased 229.33 35.23 135 9316 23505 3352903
Tubulointerstitial nephritis 228.42 35.23 81 9370 4305 3372103
Rash pruritic 227.76 35.23 99 9352 9065 3367343
International normalised ratio increased 226.89 35.23 114 9337 14501 3361907
Erythema multiforme 223.77 35.23 74 9377 3179 3373229
Acute hepatic failure 202.83 35.23 73 9378 4050 3372358
Chromaturia 202.39 35.23 75 9376 4523 3371885
Dermatitis exfoliative 191.07 35.23 63 9388 2680 3373728
Drug eruption 176.80 35.23 70 9381 5055 3371353
Skin exfoliation 174.50 35.23 79 9372 7958 3368450
Aspartate aminotransferase increased 167.32 35.23 106 9345 21007 3355401
Swollen tongue 163.72 35.23 72 9379 6771 3369637
Bronchospasm 163.47 35.23 63 9388 4231 3372177
Purpura 163.38 35.23 57 9394 2883 3373525
Rash macular 159.91 35.23 62 9389 4232 3372176
Blood alkaline phosphatase increased 154.03 35.23 79 9372 10474 3365934
Asthenia 152.91 35.23 161 9290 65504 3310904
Pneumonia 152.81 35.23 166 9285 69977 3306431
Kounis syndrome 150.54 35.23 36 9415 454 3375954
Tongue oedema 147.48 35.23 42 9409 1082 3375326
Thrombocytopenia 145.38 35.23 119 9332 35149 3341259
Renal failure 143.92 35.23 115 9336 32825 3343583
Transaminases increased 141.58 35.23 65 9386 6759 3369649
Gamma-glutamyltransferase increased 140.97 35.23 71 9380 9057 3367351
Treatment failure 138.04 35.23 63 9388 6461 3369947
Medication error 136.99 35.23 76 9375 11795 3364613
Eyelid oedema 136.63 35.23 52 9399 3373 3373035
Agranulocytosis 133.91 35.23 58 9393 5254 3371154
Liver function test abnormal 133.76 35.23 77 9374 12824 3363584
Blood bilirubin increased 131.54 35.23 71 9380 10438 3365970
Dermatitis allergic 128.17 35.23 45 9406 2318 3374090
Tachycardia 127.13 35.23 93 9358 23278 3353130
Pharyngeal oedema 126.37 35.23 53 9398 4434 3371974
Oedema peripheral 125.20 35.23 108 9343 34253 3342155
Decreased appetite 124.73 35.23 117 9334 41373 3335035
Drug ineffective 121.05 35.23 191 9260 115899 3260509
Blister 120.58 35.23 63 9388 8671 3367737
Meningitis aseptic 119.33 35.23 34 9417 877 3375531
Maternal exposure during pregnancy 119.16 35.23 66 9385 10205 3366203
Exposure during pregnancy 117.74 35.23 95 9356 27468 3348940
Swelling 115.53 35.23 81 9370 18963 3357445
Dehydration 113.02 35.23 101 9350 33548 3342860
Lymphadenopathy 111.74 35.23 58 9393 7874 3368534
Neutropenia 111.72 35.23 100 9351 33286 3343122
Cholestatic liver injury 110.82 35.23 27 9424 370 3376038
Dizziness 108.95 35.23 146 9305 76366 3300042
Mixed liver injury 107.56 35.23 26 9425 344 3376064
Rash morbilliform 107.11 35.23 30 9421 726 3375682
Pseudomembranous colitis 106.14 35.23 31 9420 875 3375533
Anaemia 105.15 35.23 121 9330 54212 3322196
Intentional overdose 104.75 35.23 70 9381 15155 3361253
Wheezing 104.46 35.23 56 9395 8115 3368293
Rash papular 104.35 35.23 43 9408 3439 3372969
Skin test positive 103.90 35.23 25 9426 324 3376084
Eczema 103.82 35.23 45 9406 4081 3372327
Hepatic failure 103.57 35.23 61 9390 10591 3365817
Tooth demineralisation 101.70 35.23 17 9434 21 3376387
Hepatitis acute 100.42 35.23 37 9414 2191 3374217
Leukopenia 99.94 35.23 69 9382 15754 3360654
Condition aggravated 99.82 35.23 101 9350 39132 3337276
Dysphagia 97.45 35.23 74 9377 19577 3356831
Faeces pale 97.26 35.23 25 9426 431 3375977
Haematuria 96.78 35.23 57 9394 9895 3366513
Hypersensitivity vasculitis 95.99 35.23 35 9416 2012 3374396
Loss of consciousness 95.51 35.23 85 9366 28062 3348346
Hepatotoxicity 94.20 35.23 46 9405 5485 3370923
Rash pustular 93.84 35.23 35 9416 2145 3374263
C-reactive protein increased 91.92 35.23 54 9397 9329 3367079
Pancytopenia 91.40 35.23 70 9381 18750 3357658
Premature baby 87.95 35.23 48 9403 7205 3369203
Hyperthermia 86.31 35.23 34 9417 2418 3373990
Weight decreased 85.53 35.23 94 9357 40017 3336391
Acute psychosis 85.39 35.23 26 9425 849 3375559
Petechiae 83.30 35.23 35 9416 2939 3373469
Dermatitis bullous 83.20 35.23 32 9419 2134 3374274
Skin lesion 83.09 35.23 42 9409 5391 3371017
Hepatic necrosis 82.39 35.23 30 9421 1717 3374691
Tongue discolouration 81.85 35.23 25 9426 825 3375583
Hyperhidrosis 81.47 35.23 72 9379 23538 3352870
Throat tightness 81.44 35.23 40 9411 4828 3371580
Inflammation 81.09 35.23 46 9405 7439 3368969
Hepatic enzyme increased 80.39 35.23 57 9394 13568 3362840
Paraesthesia oral 79.40 35.23 32 9419 2416 3373992
Septic shock 78.97 35.23 54 9397 12130 3364278
Mouth ulceration 78.68 35.23 38 9413 4422 3371986
Oedema 76.58 35.23 57 9394 14623 3361785
Overdose 76.56 35.23 82 9369 33896 3342512
Clostridial infection 75.92 35.23 27 9424 1443 3374965
Foetal exposure during pregnancy 75.84 35.23 58 9393 15493 3360915
Periorbital oedema 75.71 35.23 27 9424 1455 3374953
Multiple organ dysfunction syndrome 75.27 35.23 56 9395 14354 3362054
Suicide attempt 74.87 35.23 58 9393 15789 3360619
Clostridium test positive 74.70 35.23 21 9430 515 3375893
Pallor 74.47 35.23 40 9411 5815 3370593
Documented hypersensitivity to administered product 73.54 35.23 17 9434 183 3376225
Hepatomegaly 72.56 35.23 32 9419 3023 3373385
Confusional state 72.38 35.23 84 9367 37914 3338494
Conjunctivitis 71.75 35.23 31 9420 2787 3373621
Rhabdomyolysis 70.92 35.23 56 9395 15673 3360735
Cell death 70.40 35.23 20 9431 510 3375898
Abdominal distension 67.00 35.23 51 9400 13525 3362883
General physical health deterioration 65.52 35.23 60 9391 20529 3355879
Drug abuse 65.43 35.23 57 9394 18273 3358135
Tremor 65.29 35.23 69 9382 28075 3348333
Headache 65.28 35.23 128 9323 91852 3284556
Eye swelling 65.19 35.23 35 9416 5082 3371326
Haemolytic anaemia 64.76 35.23 30 9421 3179 3373229
Chills 63.97 35.23 61 9390 21961 3354447
Candida infection 62.80 35.23 31 9420 3781 3372627
Pain 62.60 35.23 109 9342 71448 3304960
Hypoglycaemia 62.45 35.23 50 9401 14268 3362140
Influenza B virus test positive 62.24 35.23 11 9440 23 3376385
Presyncope 61.70 35.23 34 9417 5197 3371211
Leukocytosis 60.90 35.23 35 9416 5798 3370610
Pharyngitis 60.80 35.23 27 9424 2593 3373815
Cardiac arrest 59.89 35.23 65 9386 27254 3349154
Serum sickness 59.88 35.23 20 9431 884 3375524
Crystalluria 59.79 35.23 12 9439 61 3376347
Fatigue 59.56 35.23 135 9316 107105 3269303
Laryngeal oedema 59.52 35.23 24 9427 1814 3374594
Rectal haemorrhage 57.16 35.23 40 9411 9318 3367090
Vascular purpura 57.08 35.23 16 9435 388 3376020
Liver disorder 56.24 35.23 41 9410 10182 3366226
Faeces discoloured 55.79 35.23 29 9422 3943 3372465
Seizure 55.69 35.23 76 9375 40324 3336084
Norovirus test positive 55.65 35.23 11 9440 51 3376357
Pseudomonas infection 55.11 35.23 23 9428 1898 3374510
Klebsiella infection 55.06 35.23 20 9431 1136 3375272
Caesarean section 54.99 35.23 30 9421 4496 3371912
Cheilitis 54.81 35.23 20 9431 1151 3375257
Hyperkalaemia 54.78 35.23 42 9409 11252 3365156
White blood cell count increased 54.46 35.23 44 9407 12716 3363692
Sopor 54.36 35.23 28 9423 3736 3372672
Abdominal discomfort 54.25 35.23 52 9399 18832 3357576
Skin reaction 54.19 35.23 25 9426 2623 3373785
Haematochezia 54.01 35.23 35 9416 7186 3369222
Abnormal faeces 53.90 35.23 18 9433 795 3375613
Sinusitis 53.60 35.23 49 9402 16719 3359689
Hypokalaemia 53.48 35.23 45 9406 13760 3362648
Cough 53.46 35.23 74 9377 39784 3336624
Drug dispensing error 53.37 35.23 28 9423 3880 3372528
Coagulopathy 53.11 35.23 30 9421 4809 3371599
Cardio-respiratory arrest 53.06 35.23 47 9404 15393 3361015
Coma 52.97 35.23 43 9408 12509 3363899
Chest pain 52.87 35.23 74 9377 40201 3336207
Linear IgA disease 52.19 35.23 15 9436 399 3376009
Oropharyngeal pain 51.81 35.23 42 9409 12192 3364216
Dermatitis 51.81 35.23 26 9425 3284 3373124
Hepatosplenomegaly 51.27 35.23 18 9433 926 3375482
Hallucination 50.68 35.23 43 9408 13297 3363111
Acute respiratory distress syndrome 50.15 35.23 31 9420 5863 3370545
Burning sensation 49.64 35.23 36 9415 8868 3367540
Diarrhoea haemorrhagic 49.44 35.23 21 9430 1810 3374598
Tonsillitis 49.06 35.23 18 9433 1052 3375356
Respiratory failure 48.86 35.23 54 9397 23087 3353321
Tachycardia foetal 48.05 35.23 11 9440 113 3376295
Hyponatraemia 47.97 35.23 48 9403 18311 3358097
Epistaxis 47.70 35.23 43 9408 14408 3362000
Atrial fibrillation 47.36 35.23 54 9397 23887 3352521
Flushing 46.59 35.23 42 9409 14071 3362337
Somnolence 46.53 35.23 62 9389 32142 3344266
Sepsis 46.27 35.23 62 9389 32311 3344097
Henoch-Schonlein purpura 46.25 35.23 15 9436 604 3375804
Chest discomfort 44.80 35.23 45 9406 17240 3359168
Hepatic steatosis 44.74 35.23 27 9424 4893 3371515
Foetal distress syndrome 44.60 35.23 15 9436 677 3375731
Paraesthesia 44.42 35.23 56 9395 27492 3348916
Type I hypersensitivity 44.37 35.23 14 9437 515 3375893
Product quality issue 44.15 35.23 55 9396 26680 3349728
Aggression 43.86 35.23 37 9414 11348 3365060
Histiocytosis haematophagic 43.74 35.23 20 9431 2056 3374352
Lymphopenia 43.30 35.23 24 9427 3709 3372699
Asthma 43.10 35.23 38 9413 12364 3364044
Fungal infection 42.88 35.23 28 9423 5821 3370587
Brain oedema 42.87 35.23 24 9427 3780 3372628
Respiratory distress 42.45 35.23 32 9419 8356 3368052
Lower respiratory tract infection 41.88 35.23 29 9422 6640 3369768
Tachypnoea 41.62 35.23 23 9428 3533 3372875
Arthralgia 41.06 35.23 83 9368 60778 3315630
Renal impairment 40.96 35.23 44 9407 18217 3358191
Moraxella test positive 40.89 35.23 7 9444 11 3376397
Shock 40.85 35.23 29 9422 6908 3369500
Proteinuria 40.67 35.23 25 9426 4681 3371727
Contusion 40.60 35.23 40 9411 14970 3361438
Pierre Robin syndrome 40.48 35.23 9 9442 80 3376328
Haemoglobin decreased 40.24 35.23 56 9395 30238 3346170
Hepatic function abnormal 40.22 35.23 35 9416 11192 3365216
Gastroenteritis 40.13 35.23 24 9427 4277 3372131
Oliguria 39.98 35.23 19 9432 2131 3374277
Jarisch-Herxheimer reaction 39.84 35.23 11 9440 252 3376156
Dysgeusia 39.69 35.23 35 9416 11389 3365019
Circulatory collapse 39.63 35.23 27 9424 6022 3370386
Biliary sepsis 39.36 35.23 10 9441 164 3376244
Feeding disorder 39.33 35.23 17 9434 1529 3374879
Therapeutic product cross-reactivity 39.19 35.23 11 9440 268 3376140
Aphthous ulcer 39.01 35.23 17 9434 1560 3374848
Metabolic acidosis 39.00 35.23 31 9420 8747 3367661
Cholelithiasis 38.98 35.23 30 9421 8078 3368330
Anxiety 38.08 35.23 63 9388 39566 3336842
Blood creatinine increased 37.82 35.23 46 9405 21772 3354636
Feeling hot 37.69 35.23 29 9422 7807 3368601
Palpitations 37.66 35.23 43 9408 19040 3357368
Inhibitory drug interaction 37.61 35.23 12 9439 458 3375950
Abnormal behaviour 37.42 35.23 32 9419 9996 3366412
Bronchitis 37.28 35.23 38 9413 14807 3361601
Disorientation 37.28 35.23 32 9419 10047 3366361
Melaena 37.24 35.23 28 9423 7284 3369124
Balance disorder 37.14 35.23 35 9416 12404 3364004
Prothrombin time shortened 36.62 35.23 12 9439 499 3375909
Mucosal discolouration 36.62 35.23 9 9442 128 3376280
Syncope 36.48 35.23 49 9402 25584 3350824
Peripheral swelling 36.41 35.23 39 9412 16093 3360315
Myalgia 36.35 35.23 55 9396 32020 3344388
Conjunctival hyperaemia 36.07 35.23 14 9437 956 3375452

Pharmacologic Action:

SourceCodeDescription
ATC J01CA04 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Penicillins with extended spectrum
ATC A02BD01 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Combinations for eradication of Helicobacter pylori
ATC A02BD03 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Combinations for eradication of Helicobacter pylori
ATC A02BD04 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Combinations for eradication of Helicobacter pylori
ATC A02BD05 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Combinations for eradication of Helicobacter pylori
ATC A02BD06 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Combinations for eradication of Helicobacter pylori
ATC A02BD07 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Combinations for eradication of Helicobacter pylori
ATC A02BD10 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Combinations for eradication of Helicobacter pylori
ATC A02BD11 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Combinations for eradication of Helicobacter pylori
ATC J01CR02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Combinations of penicillins, incl. beta-lactamase inhibitors
FDA EPC N0000175497 Penicillin-class Antibacterial
FDA Chemical/Ingredient N0000011281 Penicillins
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:36047 antibacterial drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute otitis media indication 3110003
Staphylococcal tonsillitis indication 11461005
Infection of skin AND/OR subcutaneous tissue indication 19824006
Pneumonia due to Streptococcus indication 34020007
Streptococcal tonsillitis indication 41582007
Lower respiratory tract infection indication 50417007
Bacterial pneumonia indication 53084003 DOID:874
Klebsiella cystitis indication 60867007
Pneumonia due to Klebsiella pneumoniae indication 64479007
Urinary tract infectious disease indication 68566005
Haemophilus influenzae pneumonia indication 70036007
Infection due to Escherichia coli indication 71057007
Rhinoscleroma indication 72409005 DOID:11336
Acute bacterial sinusitis indication 75498004
Staphylococcal pharyngitis indication 82228008
Pneumococcal pneumonia indication 233607000
Escherichia coli urinary tract infection indication 301011002
Streptococcus pyogenes infection indication 302809008
Bacterial urinary infection indication 312124009
Infective otitis media indication 312218008
Pharyngitis indication 405737000 DOID:2275
Infection due to Staphylococcus aureus indication 406602003
Acute exacerbation of chronic bronchitis indication 425748003
Pneumonia due to Staphylococcus aureus indication 441658007
Helicobacter pylori-associated gastritis indication 708164002
Skin and Skin Structure Streptococcus Infection indication
E. Coli Genitourinary Tract Infection indication
Moraxella Catarrhalis Acute Otitis Media indication
Duodenal Ulcer due to H. Pylori indication
Haemophilus Influenzae Chronic Bronchitis indication
Moraxella Catarrhalis Pneumonia indication
Tonsillitis due to Haemophilus Influenzae indication
Genitourinary Tract Infections indication
Haemophilus Influenzae Pharyngitis indication
Genitourinary Tract Infection due to Proteus indication
Haemophilus Influenzae Acute Otitis Media indication
Pneumococcal Acute Otitis Media indication
Haemophilus Parainfluenzae Pneumonia indication
Streptococcus Pneumoniae Chronic Bronchitis indication
Enterococcus Genitourinary Tract Infection indication
Typhoid fever off-label use 4834000 DOID:13258
Pyrexia of unknown origin off-label use 7520000
Lyme disease off-label use 23502006 DOID:11729
Chronic purulent otitis media off-label use 38394007 DOID:11506
Cholangitis off-label use 82403002 DOID:9446
Human bite - wound off-label use 262555007
Chancroid off-label use 266143009 DOID:13778
Diverticulitis of gastrointestinal tract off-label use 271366000
Dog bite - wound off-label use 283734005
Cat bite - wound off-label use 283782004
Prevention of Bacterial Endocarditis off-label use
Diabetic Foot Infection off-label use
Prevention of Neonatal Group B Streptococcal Infection off-label use
Ventricular tachycardia contraindication 25569003
Obstruction of bile duct contraindication 30144000 DOID:13580
Torsades de pointes contraindication 31722008
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Osteoporosis contraindication 64859006 DOID:11476
Kidney disease contraindication 90708001 DOID:2527
Myasthenia gravis contraindication 91637004 DOID:437
Cholestatic hepatitis contraindication 95556007
Prolonged QT interval contraindication 111975006
Fracture of bone contraindication 125605004
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Disease of liver contraindication 235856003 DOID:409
Infectious mononucleosis contraindication 271558008 DOID:8568
Pseudomembranous enterocolitis contraindication 397683000 DOID:0060185
Porphyria contraindication 418470004 DOID:13268

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.79 acidic
pKa2 9.72 acidic
pKa3 7.63 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
1GM AUGMENTIN XR DR REDDYS LABS INC N050785 Sept. 25, 2002 RX TABLET, EXTENDED RELEASE ORAL 6878386 April 4, 2020 MGT SPECIFIC BACTERIAL INFECTIONS. TREATMENT PTS W/ COMMUNITY ACQUIRED PNEUMONIA OR BACTERIAL SINUSITIS DUE TO CONFIRMED, OR SUSPECTED B-LACTAMASE PRODUCING PATHOGENS & S. PNEUMONIAE WITH REDUCED SUSCEPTIBILITY TO PENICILLIN (MIC=2MC/ML)
1GM AUGMENTIN XR DR REDDYS LABS INC N050785 Sept. 25, 2002 RX TABLET, EXTENDED RELEASE ORAL 7217430 April 4, 2020 MGT SPECIFIC BACTERIAL INFECTIONS. TREATMENT PTS W/ COMMUNITY ACQUIRED PNEUMONIA OR BACTERIAL SINUSITIS DUE TO CONFIRMED, OR SUSPECTED B-LACTAMASE PRODUCING PATHOGENS & S. PNEUMONIAE WITH REDUCED SUSCEPTIBILITY TO PENICILLIN (MIC=2MC/ML)
1GM AUGMENTIN XR DR REDDYS LABS INC N050785 Sept. 25, 2002 RX TABLET, EXTENDED RELEASE ORAL 7250176 April 4, 2020 MGT SPECIFIC BACTERIAL INFECTIONS. TREATMENT PTS W/ COMMUNITY ACQUIRED PNEUMONIA OR BACTERIAL SINUSITIS DUE TO CONFIRMED, OR SUSPECTED B-LACTAMASE PRODUCING PATHOGENS & S. PNEUMONIAE WITH REDUCED SUSCEPTIBILITY TO PENICILLIN (MIC=2MC/ML)
775MG MOXATAG VERNALIS R AND D LTD N050813 Jan. 23, 2008 RX TABLET, EXTENDED RELEASE ORAL 6544555 Oct. 13, 2020 METHOD OF TREATING TONSILLITIS AND/OR PHARYNGITIS SECONDARY TO STREPTOCOCCUS PYOGENES IN A ONCE-A-DAY AMOXICILLIN PRODUCT
775MG MOXATAG VERNALIS R AND D LTD N050813 Jan. 23, 2008 RX TABLET, EXTENDED RELEASE ORAL 6669948 Oct. 13, 2020 METHOD OF TREATING TONSILLITIS AND/OR PHARYNGITIS SECONDARY TO STREPTOCOCCUS PYOGENES IN A ONCE-A-DAY AMOXICILLIN PRODUCT
775MG MOXATAG VERNALIS R AND D LTD N050813 Jan. 23, 2008 RX TABLET, EXTENDED RELEASE ORAL 6723341 Oct. 13, 2020 METHOD OF TREATING TONSILLITIS AND/OR PHARYNGITIS SECONDARY TO STREPTOCOCCUS PYOGENES IN A ONCE-A-DAY AMOXICILLIN PRODUCT
775MG MOXATAG VERNALIS R AND D LTD N050813 Jan. 23, 2008 RX TABLET, EXTENDED RELEASE ORAL 8778924 Dec. 8, 2026 METHOD OF TREATING TONSILLITIS AND/OR PHARYNGITIS SECONDARY TO STREPTOCOCCUS PYOGENES IN A ONCE-A-DAY AMOXICILLIN PRODUCT
775MG MOXATAG VERNALIS R AND D LTD N050813 Jan. 23, 2008 RX TABLET, EXTENDED RELEASE ORAL 8299052 May 7, 2027 USE OF ONCE-A-DAY AMOXICILLIN PRODUCT TO TREAT TONSILLITIS AND/OR PHARYNGITIS SECONDARY TO STREPTOCOCCUS PYOGENES

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 2A GPCR IC50 6.22 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR IC50 5.80 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR IC50 5.96 WOMBAT-PK
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK

External reference:

IDSource
4017605 VUID
N0000145985 NUI
C0002645 UMLSCUI
D00229 KEGG_DRUG
544Y3D6MYH UNII
34642-77-8 SECONDARY_CAS_RN
DB01060 DRUGBANK_ID
4017605 VANDF
3600 MMSL
723 RXNORM
27658006 SNOMEDCT_US
372687004 SNOMEDCT_US
11786 MMSL
d00088 MMSL
N0000145985 NDFRT
N0000005840 NDFRT
003675 NDDF
3230 INN_ID
CHEMBL1082 ChEMBL_ID
33613 PUBCHEM_CID
CHEMBL2105950 ChEMBL_ID
D000658 MESH_DESCRIPTOR_UI
CHEBI:2676 CHEBI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2263 TABLET, FILM COATED 500 mg ORAL ANDA 18 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2264 TABLET, FILM COATED 875 mg ORAL ANDA 18 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2267 TABLET, CHEWABLE 125 mg ORAL ANDA 18 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2268 TABLET, CHEWABLE 250 mg ORAL ANDA 18 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0093-2270 TABLET, CHEWABLE 200 mg ORAL ANDA 17 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0093-2272 TABLET, CHEWABLE 400 mg ORAL ANDA 17 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0093-2274 TABLET, FILM COATED 500 mg ORAL ANDA 17 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0093-2275 TABLET, FILM COATED 875 mg ORAL ANDA 17 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0093-2277 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 17 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0093-2279 POWDER, FOR SUSPENSION 400 mg ORAL ANDA 17 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0093-3107 CAPSULE 250 mg ORAL ANDA 18 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0093-3109 CAPSULE 500 mg ORAL ANDA 18 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0093-4150 POWDER, FOR SUSPENSION 125 mg ORAL ANDA 18 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0093-4155 POWDER, FOR SUSPENSION 250 mg ORAL ANDA 18 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0093-4160 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 18 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0093-4161 POWDER, FOR SUSPENSION 400 mg ORAL ANDA 18 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0093-8675 POWDER, FOR SUSPENSION 600 mg ORAL ANDA 17 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0143-9249 TABLET 875 mg ORAL ANDA 17 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0143-9853 SUSPENSION 600 mg ORAL ANDA 15 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9886 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 16 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9887 POWDER, FOR SUSPENSION 400 mg ORAL ANDA 16 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9888 POWDER, FOR SUSPENSION 125 mg ORAL ANDA 16 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9889 POWDER, FOR SUSPENSION 250 mg ORAL ANDA 16 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9938 CAPSULE 250 mg ORAL ANDA 14 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9939 CAPSULE 500 mg ORAL ANDA 14 sections
Amoxicillin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9951 TABLET, COATED 875 mg ORAL ANDA 18 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0143-9981 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 16 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0143-9982 POWDER, FOR SUSPENSION 400 mg ORAL ANDA 16 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0378-0830 TABLET, FILM COATED 500 mg ORAL ANDA 18 sections
Amoxicillin and Clavulanate Potassium HUMAN PRESCRIPTION DRUG LABEL 2 0378-0831 TABLET, FILM COATED 875 mg ORAL ANDA 18 sections