amikacin indications/contra

Stem definitionDrug idCAS RN
antibiotics, kanamycin and bekanamycin derivatives (obtained from Streptomyces kanamyceticus) 157 37517-28-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • amikacin
  • amicacin
  • amikacillin
  • arikace
  • lukadin
  • amikacin sulfate
  • amikacin hydrate
A broad-spectrum antibiotic derived from KANAMYCIN. It is reno- and oto-toxic like the other aminoglycoside antibiotics.
  • Molecular weight: 585.61
  • Formula: C22H43N5O13
  • CLOGP: -4.12
  • LIPINSKI: 3
  • HAC: 18
  • HDO: 13
  • TPSA: 331.94
  • ALOGS: -1.07
  • ROTB: 10

Drug dosage:

DoseUnitRoute
1 g P

Approvals:

DateAgencyCompanyOrphan
Jan. 22, 1981 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
Acute kidney injury 185.48 55.81 73 960 49610 3335216
Drug ineffective 177.08 55.81 91 942 115999 3268827
Systemic candida 173.88 55.81 29 1004 564 3384262
Drug resistance 170.60 55.81 40 993 4623 3380203
Drug reaction with eosinophilia and systemic symptoms 168.89 55.81 44 989 7851 3376975
Ototoxicity 166.32 55.81 27 1006 441 3384385
Deafness 149.41 55.81 35 998 4019 3380807
Pyrexia 135.94 55.81 68 965 81047 3303779
Thrombocytopenia 117.83 55.81 48 985 35220 3349606
Renal failure 117.50 55.81 47 986 32893 3351933
Septic shock 115.45 55.81 36 997 12148 3372678
Acute generalised exanthematous pustulosis 98.02 55.81 22 1011 2077 3382749
Multiple organ dysfunction syndrome 97.51 55.81 33 1000 14377 3370449
Acute respiratory distress syndrome 93.55 55.81 26 1007 5868 3378958
Toxic epidermal necrolysis 90.60 55.81 24 1009 4521 3380305
Pathogen resistance 89.92 55.81 19 1014 1352 3383474
Multiple-drug resistance 88.34 55.81 15 1018 324 3384502
Pancytopenia 85.23 55.81 32 1001 18788 3366038
Toxic skin eruption 79.91 55.81 20 1013 3008 3381818
Nephropathy toxic 79.51 55.81 20 1013 3069 3381757
Rash maculo-papular 75.58 55.81 22 1011 5845 3378981
Deafness neurosensory 66.90 55.81 14 1019 948 3383878
Sepsis 65.38 55.81 31 1002 32342 3352484
Neutropenia 64.47 55.81 31 1002 33355 3351471
Paradoxical drug reaction 60.52 55.81 12 1021 620 3384206
Mycobacterium abscessus infection 60.01 55.81 9 1024 84 3384742
Anaemia 58.11 55.81 34 999 54299 3330527

Pharmacologic Action:

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SourceCodeDescription
ATC D06AX12 DERMATOLOGICALS
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
ANTIBIOTICS FOR TOPICAL USE
Other antibiotics for topical use
ATC J01GB06 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
AMINOGLYCOSIDE ANTIBACTERIALS
Other aminoglycosides
ATC S01AA21 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFECTIVES
Antibiotics
ATC J01RA06 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
COMBINATIONS OF ANTIBACTERIALS
Combinations of antibacterials
FDA EPC N0000175477 Aminoglycoside Antibacterial
FDA Chemical/Ingredient N0000007853 Aminoglycosides
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
Septicemia due to Escherichia coli indication 9323009
Bacterial septicemia indication 10001005
Infection due to Pseudomonas aeruginosa indication 11218009
Staphylococcal meningitis indication 12166008
Infection of skin AND/OR subcutaneous tissue indication 19824006
Staphylococcal pneumonia indication 22754005
Pneumonia due to Pseudomonas indication 41381004
Pneumonia due to Escherichia coli indication 51530003
Bacterial pneumonia indication 53084003 DOID:874
Osteomyelitis indication 60168000
Infection due to Escherichia coli indication 71057007
Bacterial infection due to Serratia indication 71120004
Rhinoscleroma indication 72409005 DOID:11336
Septicemia due to Serratia indication 82091000
Cholangitis indication 82403002 DOID:9446
Bacterial meningitis indication 95883001 DOID:9470
Infection of bone indication 111253001
Staphylococcal septicemia indication 111821004
Infectious disease of abdomen indication 128070006
Infection due to Enterobacteriaceae indication 128945009
Bacterial infection due to Klebsiella pneumoniae indication 186435004
Escherichia coli meningitis indication 192655005
Proteus pneumonia indication 195888009
Sepsis of the newborn indication 206376005
Neonatal pneumonia indication 233619008
Diverticulitis of gastrointestinal tract indication 271366000
Neonatal meningitis indication 276674008
Proteus septicemia indication 300986008
Escherichia coli urinary tract infection indication 301011002
Proteus meningitis indication 302877009
Bacterial urinary infection indication 312124009
Infectious disorder of joint indication 363162000 DOID:381
Meningitis due to Klebsiella mobilis indication 420585007
Nosocomial pneumonia indication 425464007
Bacterial meningitis due to Gram-negative bacteria indication 425887005
Pneumonia due to Gram negative bacteria indication 430395005
Sepsis due to Pseudomonas indication 448813005
Sepsis due to Gram negative bacteria indication 449082003
Urinary tract infection caused by Klebsiella indication 369001000119100
Skin and Skin Structure Serratia Infection indication
Pseudomonas Aeruginosa Biliary Tract Infection indication
Klebsiella Septicemia indication
Complicated Urinary Tract Infections indication
Complicated UTI with Pseudomonas Aeruginosa indication
Pseudomonas Aeruginosa Meningitis indication
Pseudomonas Aeruginosa Osteomyelitis indication
Skin and Skin Structure Proteus Infection indication
Serratia Meningitis indication
Skin and Skin Structure Staphylococcus Infection indication
Enterobacter Meningitis indication
Skin and Skin Structure Pseudomonas Aeruginosa Infection indication
Burn Wound Infections indication
Gram-Negative Aerobic Bacillary Pneumonia indication
Complicated Bacterial Peritonitis indication
Complicated Proteus UTI indication
Complicated Urinary Tract Infection due to Acinetobacter indication
Pseudomonas Aeruginosa Joint Infection indication
Serratia Osteomyelitis indication
Serratia Complicated UTI indication
Enterobacter Pneumonia indication
Hypocalcemia contraindication 5291005
Parkinsonism contraindication 32798002 DOID:13548
Dehydration contraindication 34095006
Tinnitus contraindication 60862001
Kidney disease contraindication 90708001 DOID:2527
Myasthenia gravis contraindication 91637004 DOID:437
Pregnancy, function contraindication 289908002
Vertigo contraindication 399153001
Infant Botulism contraindication
Amikacin Toxicity contraindication
Disorder of the 8th Cranial Nerve contraindication
Necrotizing enterocolitis in fetus OR newborn off-label use 2707005 DOID:8677
Pyrexia of unknown origin off-label use 7520000
Enteric campylobacteriosis off-label use 18081009
Acute tuberculosis off-label use 25629007
Pseudotuberculosis off-label use 36753006
Infection by Yersinia enterocolitica off-label use 80960004
Pulmonary tuberculosis off-label use 154283005 DOID:2957
Citrobacter Osteomyelitis off-label use
Citrobacter Pneumonia off-label use
Citrobacter Septicemia off-label use
Skin and Skin Structure Acinetobacter Infection off-label use
Synergy for Nosocomial Pneumonia due to Pseudomonas Aeruginosa off-label use
Synergy for Bacterial Meningitis off-label use
Synergy for Staphylococcal Endocarditis off-label use
Synergy for Neonatal Meningitis off-label use
Synergy for Staphylococcal Infections off-label use
Skin and Skin Structure Citrobacter Infection off-label use
Citrobacter Complicated UTI off-label use
Synergy for Group B Streptococcal Septicemia off-label use
Citrobacter Meningitis off-label use
Listeria Monocytogenes Septicemia off-label use
Synergy for P. Aeruginosa Infection in Cystic Fibrosis off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.04 acidic
pKa2 12.95 acidic
pKa3 13.39 acidic
pKa4 13.72 acidic
pKa5 9.4 Basic
pKa6 7.84 Basic
pKa7 7.41 Basic
pKa8 6.86 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Macrolide 2'-phosphotransferase II; Macrolide 2'-phosphotransferase II protein MphB; Macrolide 2-phosphotransferase, mph(B) Enzyme Km 4.20 WOMBAT-PK

External reference:

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IDSource
DB00479 DRUGBANK_ID
4019602 VUID
N0000147698 NUI
C0002499 UMLSCUI
D00865 KEGG_DRUG
641 RXNORM
387266001 SNOMEDCT_US
48836000 SNOMEDCT_US
d00087 MMSL
4019602 VANDF
N0000147698 NDFRT
N0000006770 NDFRT
004899 NDDF
84319SGC3C UNII
3492 INN_ID
CHEMBL177 ChEMBL_ID
CHEMBL1164318 ChEMBL_ID
37768 PUBCHEM_CID
39831-55-5 SECONDARY_CAS_RN
D000583 MESH_DESCRIPTOR_UI
CHEBI:2637 CHEBI
AKN PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Amikacin Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6166 INJECTION 250 mg INTRAMUSCULAR ANDA 14 sections
Amikacin Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6167 INJECTION 250 mg INTRAMUSCULAR ANDA 14 sections
Amikacin Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0703-9032 INJECTION, SOLUTION 500 mg INTRAVENOUS ANDA 13 sections
Amikacin Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0703-9040 INJECTION, SOLUTION 1 g INTRAVENOUS ANDA 13 sections
Amikacin Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 23155-290 INJECTION, SOLUTION 250 mg INTRAMUSCULAR ANDA 14 sections
amikacin sulfate HUMAN PRESCRIPTION DRUG LABEL 1 25021-173 INJECTION, SOLUTION 250 mg INTRAVENOUS ANDA 14 sections
Amikacin Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 63323-815 INJECTION, SOLUTION 250 mg INTRAVENOUS ANDA 14 sections