amoxicillin indications/contra

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

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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

Pharmacologic Action:

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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)

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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 Pneumonia indication
Genitourinary Tract Infection due to Proteus indication
Enterococcus Genitourinary Tract Infection indication
Moraxella Catarrhalis Acute Otitis Media indication
Haemophilus Influenzae Acute Otitis Media indication
Haemophilus Influenzae Pharyngitis indication
Duodenal Ulcer due to H. Pylori indication
Haemophilus Influenzae Chronic Bronchitis indication
Streptococcus Pneumoniae Chronic Bronchitis indication
Pneumococcal Acute Otitis Media indication
Haemophilus Parainfluenzae Pneumonia indication
Tonsillitis due to Haemophilus Influenzae indication
Genitourinary Tract Infections indication
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
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 Neonatal Group B Streptococcal Infection off-label use
Diabetic Foot Infection off-label use
Prevention of Bacterial Endocarditis off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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

Orange Book patent data (new drug applications)

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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:

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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:

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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:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
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