amphotericin B indications/contra

Stem definitionDrug idCAS RN
antibiotics, polyene derivatives 197 1397-89-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • amphotericin B
  • abelcet
  • abelecet
  • amphocin
  • amphozone
  • apothecon
  • fungilin
  • Amphotericin B liposome
Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.
  • Molecular weight: 924.09
  • Formula: C47H73NO17
  • CLOGP: -3.65
  • LIPINSKI: 3
  • HAC: 18
  • HDO: 12
  • TPSA: 319.61
  • ALOGS: -4.05
  • ROTB: 3

Drug dosage:

DoseUnitRoute
40 mg O
0.40 g O
0.20 g V
35 mg P

Approvals:

DateAgencyCompanyOrphan
Nov. 12, 1964 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 ineffective 836.59 50.25 348 2166 115742 3267603
Hypokalaemia 754.92 50.25 194 2320 13611 3369734
Renal impairment 480.84 50.25 145 2369 18116 3365229
Acute kidney injury 449.06 50.25 177 2337 49506 3333839
Multiple organ dysfunction syndrome 321.62 50.25 101 2413 14309 3369036
Blood creatinine increased 314.88 50.25 110 2404 21708 3361637
Pyrexia 299.94 50.25 155 2359 80960 3302385
Renal failure 291.62 50.25 116 2398 32824 3350521
Aspergillus infection 289.59 50.25 61 2453 1726 3381619
Bronchopulmonary aspergillosis 216.34 50.25 49 2465 1950 3381395
Nephropathy toxic 210.18 50.25 52 2462 3037 3380308
Respiratory failure 199.13 50.25 80 2434 23061 3360284
Alanine aminotransferase increased 194.03 50.25 79 2435 23561 3359784
Immune reconstitution inflammatory syndrome 183.12 50.25 44 2470 2269 3381076
Aspartate aminotransferase increased 167.85 50.25 69 2445 21044 3362301
Sepsis 167.01 50.25 78 2436 32295 3351050
Septic shock 154.65 50.25 56 2458 12128 3371217
Drug resistance 152.52 50.25 44 2470 4619 3378726
Chills 151.68 50.25 65 2449 21957 3361388
Meningitis cryptococcal 149.45 50.25 28 2486 423 3382922
Pancytopenia 144.42 50.25 60 2454 18760 3364585
Mucormycosis 141.28 50.25 29 2485 716 3382629
Cholestasis 138.05 50.25 42 2472 5295 3378050
Off label use 137.31 50.25 81 2433 53896 3329449
Tachycardia 135.09 50.25 61 2453 23310 3360035
Thrombocytopenia 128.20 50.25 67 2447 35201 3348144
Condition aggravated 127.05 50.25 69 2445 39164 3344181
Blood bilirubin increased 124.75 50.25 46 2468 10463 3372882
Infusion related reaction 123.85 50.25 47 2467 11574 3371771
Fungal infection 121.80 50.25 39 2475 5810 3377535

Pharmacologic Action:

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SourceCodeDescription
ATC A01AB04 ALIMENTARY TRACT AND METABOLISM
STOMATOLOGICAL PREPARATIONS
STOMATOLOGICAL PREPARATIONS
Antiinfectives and antiseptics for local oral treatment
ATC A07AA07 ALIMENTARY TRACT AND METABOLISM
ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
INTESTINAL ANTIINFECTIVES
Antibiotics
ATC G01AA03 GENITO URINARY SYSTEM AND SEX HORMONES
GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
Antibiotics
ATC J02AA01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOTICS FOR SYSTEMIC USE
ANTIMYCOTICS FOR SYSTEMIC USE
Antibiotics
FDA EPC N0000175510 Lipid-based Polyene Antifungal
FDA EPC N0000175498 Polyene Antifungal
FDA Chemical/Ingredient N0000007672 Polyenes
MeSH PA D000563 Amebicides
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000935 Antifungal Agents
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
CHEBI has role CHEBI:35820 antiprotozoal drug

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Trachoma indication 2576002 DOID:11265
Invasive pulmonary aspergillosis indication 3214003
Actinomycotic infection indication 11817007 DOID:8478
Histoplasmosis indication 12962009 DOID:1731
Gonorrhea indication 15628003 DOID:7551
Infection of skin AND/OR subcutaneous tissue indication 19824006
Gingivostomatitis indication 20607006
Candidiasis of the esophagus indication 20639004 DOID:13146
Acute gonococcal cervicitis indication 20943002 DOID:10615
Pulmonary cryptococcosis indication 20953001
Fungal meningitis indication 24321005 DOID:11608
Granuloma inguinale indication 28867007 DOID:9113
Acute gonococcal urethritis indication 29864006
Bronchitis indication 32398004 DOID:6132
Sinusitis indication 36971009
Cryptococcosis indication 42386007 DOID:12053
Gonorrhea of rectum indication 42746002
Candidal meningitis indication 45021001
Candidiasis of skin indication 49883006
Coccidioidomycosis indication 60826002 DOID:13450
Candidal endocarditis indication 63553008
Fungal infection of lung indication 63741006
Aspergillosis indication 65553006 DOID:13564
Urinary tract infectious disease indication 68566005
Blastomycosis indication 69996000 DOID:12663
Disseminated candidiasis indication 70572005
Yaws indication 70647001 DOID:10371
Gonorrhea of pharynx indication 74372003
Rickettsialpox indication 75096007 DOID:11103
Ornithosis indication 75116005 DOID:11262
Brucellosis indication 75702008 DOID:11077
Syphilis indication 76272004
Mucormycosis indication 76627001
Candidiasis indication 78048006 DOID:14262
Candidiasis of mouth indication 79740000 DOID:14262
Leishmaniasis indication 80612004 DOID:9065
Mycotic endocarditis indication 86348002
Acne vulgaris indication 88616000
Disseminated sporotrichosis indication 91051003
Diaper rash indication 91487003
Infectious disease of abdomen indication 128070006
Rocky Mountain spotted fever indication 186772009
Q fever indication 186788009 DOID:11100
Visceral leishmaniasis indication 186803007 DOID:9146
Lymphogranuloma venereum indication 186946009 DOID:13819
Candidal septicemia indication 187022007
Pneumonia indication 233604007 DOID:552
Inclusion conjunctivitis indication 266109000 DOID:13800
Infective otitis media indication 312218008
Pharyngitis indication 405737000 DOID:2275
Anthrax indication 409498004 DOID:7427
Relapsing fever indication 420079008 DOID:13034
Chlamydia trachomatis infection of genital structure indication 428015005
Candidemia indication 432261003
Septicemia due to fungus indication 446903007
Candida Peritonitis indication
Cryptococcal Meningitis in HIV indication
Female Urethral Syndrome indication
Rhinocerebral Phycomycosis indication
Rectal Chlamydia Trachomatis Infection indication
Opportunistic Fungal Infection indication
Cryptococcal Septicemia indication
Sexually Transmitted Epididymo-Orchitis indication
Typhus Infections indication
Inflammatory Disease of Female Pelvic Organs indication
Refractory Aspergillosis indication
Fungal Urinary Tract Infection indication
Hypokalemia contraindication 43339004
Kidney disease contraindication 90708001 DOID:2527
Hypomagnesemia contraindication 190855004
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Pseudomembranous enterocolitis contraindication 397683000 DOID:0060185
Breastfeeding (mother) contraindication 413712001
Cryptococcal meningitis off-label use 14232007
Tularemia off-label use 19265001
Pneumonia due to Mycoplasma pneumoniae off-label use 46970008
Tropical sprue off-label use 47384003 DOID:10607
Meningoencephalitis due to Naegleria off-label use 52281009
Plague off-label use 58750007 DOID:10773
Paracoccidioidomycosis off-label use 59925007 DOID:12662
Malaria off-label use 61462000 DOID:12365
Cholangitis off-label use 82403002 DOID:9446
Chlamydial infection off-label use 105629000
Ocular rosacea off-label use 200933006
Selective decontamination of the digestive tract off-label use 235453002
Infection due to Penicillium marneffei off-label use 372936000
Rosacea off-label use 398909004 DOID:8881
Ventilator-acquired pneumonia off-label use 429271009
Helicobacter pylori-associated gastritis off-label use 708164002
Oropharyngeal Candidiasis off-label use
Candidal Urinary Tract Infection off-label use
Chloroquine Resistant Plasmodium Falciparum Malaria off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.46 acidic
pKa2 10.11 acidic
pKa3 12.11 acidic
pKa4 12.74 acidic
pKa5 13.7 acidic
pKa6 8.62 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
Ergosterol Metabolite SEQUESTERING AGENT UNKNOWN DRUG LABEL

External reference:

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IDSource
4017616 VUID
N0000145996 NUI
C0002679 UMLSCUI
D00203 KEGG_DRUG
CHEMBL267345 ChEMBL_ID
7XU7A7DROE UNII
869 INN_ID
DB00681 DRUGBANK_ID
4017616 VANDF
3777 MMSL
732 RXNORM
77703004 SNOMEDCT_US
4190 MMSL
d00077 MMSL
N0000145996 NDFRT
N0000005870 NDFRT
002887 NDDF
714520003 SNOMEDCT_US
5280965 PUBCHEM_CID
C068538 MESH_SUPPLEMENTAL_RECORD_UI
D000666 MESH_DESCRIPTOR_UI
CHEBI:2682 CHEBI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
AmBisome HUMAN PRESCRIPTION DRUG LABEL 1 0469-3051 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS NDA 13 sections
Amphotericin B HUMAN PRESCRIPTION DRUG LABEL 1 39822-1055 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 12 sections
ABELCET HUMAN PRESCRIPTION DRUG LABEL 3 57665-101 INJECTION 5 mg INTRAVENOUS NDA 11 sections