atovaquone indications/contra

Stem definitionDrug idCAS RN
258 95233-18-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • 566C80
  • atovaquone
  • mepron
A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.
  • Molecular weight: 366.84
  • Formula: C22H19ClO3
  • CLOGP: 6.35
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 1
  • TPSA: 54.37
  • ALOGS: -5.66
  • ROTB: 2

Drug dosage:

DoseUnitRoute
2.25 g O

Approvals:

DateAgencyCompanyOrphan
Nov. 25, 1992 FDA

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
Malaria 346.99 36.42 46 819 196 3384798
Pyrexia 238.69 36.42 95 770 81020 3303974
Diarrhoea 134.48 36.42 69 796 104279 3280715
Hallucination 122.97 36.42 37 828 13303 3371691
Nausea 117.69 36.42 68 797 129577 3255417
Exposure during pregnancy 111.28 36.42 41 824 27522 3357472
Vomiting 108.68 36.42 57 808 89474 3295520
Headache 90.45 36.42 51 814 91929 3293065
Malaise 83.11 36.42 43 822 65134 3319860
Abdominal pain 75.11 36.42 36 829 46189 3338805
Thrombocytopenia 71.37 36.42 32 833 35236 3349758
Plasmodium falciparum infection 69.67 36.42 9 856 29 3384965
Urticaria 67.61 36.42 29 836 28698 3356296
Transaminases increased 67.36 36.42 20 845 6804 3378190
Decreased appetite 66.40 36.42 32 833 41458 3343536
Fatigue 65.64 36.42 44 821 107196 3277798
Rash 63.30 36.42 37 828 70784 3314210
Asthenia 63.19 36.42 36 829 65629 3319365
Alanine aminotransferase increased 59.35 36.42 25 840 23615 3361379
Anxiety 58.68 36.42 29 836 39600 3345394
Gamma-glutamyltransferase increased 57.58 36.42 19 846 9109 3375885
Angioedema 55.34 36.42 21 844 15114 3369880
Drug ineffective 51.05 36.42 39 826 116051 3268943
Maternal exposure before pregnancy 50.64 36.42 11 854 1065 3383929
Psychotic disorder 50.38 36.42 17 848 8717 3376277
Pruritus 48.53 36.42 27 838 46806 3338188
Rash maculo-papular 48.46 36.42 15 850 5852 3379142
Jaundice 47.95 36.42 17 848 10090 3374904
Dizziness 45.69 36.42 31 834 76481 3308513
Aspartate aminotransferase increased 45.31 36.42 20 845 21093 3363901

Pharmacologic Action:

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SourceCodeDescription
ATC P01AX06 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
Other agents against amoebiasis and other protozoal diseases
FDA EPC N0000175485 Antiprotozoal
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000962 Antimalarials
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
MeSH PA D004791 Enzyme Inhibitors
CHEBI has role CHEBI:38068 antimalarial

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Falciparum malaria indication 62676009 DOID:14067
Pneumocystosis jiroveci pneumonia indication 415125002 DOID:11339
Pneumocystis Carinii Pneumonia Prevention indication
Chloroquine-Resistant Plasmodium Falciparum Malaria Prevention indication
Plasmodium Falciparum Malaria Prevention indication
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Hyperglycemia contraindication 80394007 DOID:4195
Anemia due to enzyme deficiency contraindication 111577008
Disease of liver contraindication 235856003 DOID:409
Chronic diarrhea contraindication 236071009
Vomiting contraindication 422400008
Malabsorption States contraindication
Babesiosis off-label use 21061004 DOID:9643
Vivax malaria off-label use 27052006 DOID:12978
Toxoplasmosis off-label use 187192000 DOID:9965
Toxoplasmosis associated with acquired immunodeficiency syndrome off-label use 421666009
Toxoplasmosis Prevention off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.18 acidic

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
Dihydroorotate dehydrogenase (quinone), mitochondrial Enzyme IC50 5.03 WOMBAT-PK
Cytochrome b Enzyme INHIBITOR CHEMBL CHEMBL
Ubiquinol-cytochrome-c reductase complex core protein I, mitochondrial Enzyme WOMBAT-PK
Dihydroorotate dehydrogenase (quinone), mitochondrial Enzyme IC50 6.15 CHEMBL
Dihydroorotate dehydrogenase Unclassified Ki 4.57 CHEMBL

External reference:

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IDSource
4020594 VUID
N0000148284 NUI
C0165603 UMLSCUI
D00236 KEGG_DRUG
DB01117 DRUGBANK_ID
4020594 VANDF
60212 RXNORM
N0000005848 NDFRT
N0000148284 NDFRT
004112 NDDF
d01120 MMSL
4227 MMSL
108718008 SNOMEDCT_US
386899002 SNOMEDCT_US
213467 MMSL
CHEMBL1450 ChEMBL_ID
74989 PUBCHEM_CID
D053626 MESH_DESCRIPTOR_UI
Y883P1Z2LT UNII
6914 INN_ID
CHEBI:575568 CHEBI
AOQ PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
MEPRON HUMAN PRESCRIPTION DRUG LABEL 1 0173-0547 SUSPENSION 750 mg ORAL NDA 16 sections
MEPRON HUMAN PRESCRIPTION DRUG LABEL 1 0173-0665 SUSPENSION 750 mg ORAL NDA 16 sections
MALARONE HUMAN PRESCRIPTION DRUG LABEL 2 0173-0675 TABLET, FILM COATED 250 mg ORAL NDA 16 sections
MALARONE HUMAN PRESCRIPTION DRUG LABEL 2 0173-0676 TABLET, FILM COATED 62.50 mg ORAL NDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-4160 TABLET, FILM COATED 62.50 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-4162 TABLET, FILM COATED 250 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 10544-909 TABLET, FILM COATED 250 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 33261-900 TABLET, FILM COATED 250 mg ORAL ANDA 14 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 42254-150 TABLET 250 mg ORAL ANDA 12 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 43063-393 TABLET, FILM COATED 250 mg ORAL ANDA 16 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 43063-522 TABLET, FILM COATED 250 mg ORAL NDA authorized generic 12 sections
MALARONE HUMAN PRESCRIPTION DRUG LABEL 2 50090-0687 TABLET, FILM COATED 250 mg ORAL NDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 50090-1302 TABLET, FILM COATED 250 mg ORAL ANDA 16 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 50090-2980 TABLET, FILM COATED 250 mg ORAL NDA authorized generic 16 sections
MEPRON HUMAN PRESCRIPTION DRUG LABEL 1 53873-000 SUSPENSION 750 mg ORAL Approved Drug Product Manufactured Under Contract 1 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 54868-6393 TABLET, FILM COATED 250 mg ORAL ANDA 14 sections
MALARONE HUMAN PRESCRIPTION DRUG LABEL 2 55289-747 TABLET, FILM COATED 250 mg ORAL NDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 60760-498 TABLET, FILM COATED 250 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 63187-879 TABLET, FILM COATED 250 mg ORAL ANDA 16 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 63629-5531 TABLET, FILM COATED 250 mg ORAL NDA authorized generic 16 sections
ATOVAQUONE HUMAN PRESCRIPTION DRUG LABEL 1 65162-693 SUSPENSION 750 mg ORAL ANDA 16 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 66993-060 TABLET, FILM COATED 250 mg ORAL NDA authorized generic 16 sections
Atovaquone HUMAN PRESCRIPTION DRUG LABEL 1 66993-062 SUSPENSION 750 mg ORAL NDA authorized generic 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 68001-245 TABLET, FILM COATED 250 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 68258-1104 TABLET, FILM COATED 250 mg ORAL ANDA 14 sections
Atovaquone and Proguanil Hydrochloride Pediatric HUMAN PRESCRIPTION DRUG LABEL 2 68462-402 TABLET, FILM COATED 62.50 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 68462-404 TABLET, FILM COATED 250 mg ORAL ANDA 16 sections