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Drug

D0317 | Atovaquone

Molecular Formula C22H19ClO3
Molecular Weight 366.8
Structure
State solid
Clearance * 10.4 +/- 5.5 ml/min [HIV-infected patients receiving IV administration]
Volume of distribution * 0.60 ± 0.17 L/kg
Route of elimination The half-life of atovaquone is long due to presumed enterohepatic cycling and eventual fecal elimination. There was little or no excretion of atovaquone in the urine (less than 0.6%).
Protein binding Atovaquone is extensively bound to plasma proteins (99.9%) over the concentration range of 1 to 90 µg/mL.
Half life 2.2 to 3.2 days
Absorption The bioavailability of atovaquone is low and variable and is highly dependent on formulation and diet. Bioavailability of the suspension increases two-fold when administered with meals. When administered with food, bioavailability is approximately 47%. Without food, the bioavailability is 23%.

P

P01AX06 Atovaquone


[P01AX] Other agents against amoebiasis and other protozoal diseases


[P01A] AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES


[P01] ANTIPROTOZOALS


[P] Antiparasitic products, insecticides and repellents

Pictogram Signal Statements Precautionary Statement Codes
Warning

Aggregated GHS information provided by 47 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 40 of 47 companies. For more detailed information, please visit ECHA C&L website


Of the 5 notification(s) provided by 7 of 47 companies with hazard statement code(s):


H315 (28.57%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (28.57%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (28.57%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]


H410 (57.14%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]


H413 (14.29%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Warning

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.


H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


 P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • Acquired immunodeficiency syndrome

  • Autoimmune disorder

  • Bacterial infection

  • Death

  • Lymphoma

  • Mycotic aneurysm

  • Non-Hodgkin's lymphoma

  • Pneumocystis jirovecii pneumonia

  • Pneumothorax

  • Sepsis

  • Vomiting

  • Alanine aminotransferase increased (6e-04)

  • Blood alkaline phosphatase increased (8e-04)

  • Bronchospasm (2e-04)

  • Constipation (3e-04)

  • Leukopenia (4e-04)

  • Pruritus (5e-04)

  • Abdominal pain

  • Amylase increased

  • Anaemia

  • Anxiety

  • Aspartate aminotransferase increased

  • Asthenia

  • Blood creatinine increased

  • Body temperature increased

  • Cough

  • Decreased appetite

  • Dermatitis

  • Diarrhoea

  • Dizziness

  • Dysgeusia

  • Dyspepsia

  • Dyspnoea

  • Gastrointestinal pain

  • Headache

  • Hyperglycaemia

  • Hyperkalaemia

  • Hypersensitivity

  • Hypoglycaemia

  • Hyponatraemia

  • Hypotension

  • Infection

  • Insomnia

  • Nausea

  • Neutropenia

  • Pain

  • Rash

  • Rhinitis

  • Sinusitis

  • Vomiting

    • 1,4-Naphthalenedione, 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy- 1,4-Naphthalenedione, 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-, trans- 1,4-Naphthalenedione, 2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-
    1,4-Naphthalenedione, 2-[cis-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy- 1,4-Naphthalenedione, 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy 1,4-naphthalenedione,2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-
    137732-39-9 2-((1r,4r)-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione 2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-nap
    2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone 2-(TRANS-4-(4-CHLOROPHENYL)CYCLOHEXYL)-3-HYDROXY-1,4-NAPHTHALENEDIONE 2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione
    2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone 2-Hydroxy-3-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthoquinone 2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxynaphthoquinone, trans-
    2-[4-(4-chlorophenyl)cyclohexy]-3-hydroxy-1,4-naphthoquinone 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-dihydronaphthalene-1,4-dione 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
    2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-napthoquinone 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1.4-naphthoquinone 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-naphthalene-1,4-dione
    2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione 2-[trans-4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
    2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione 2-[trans-4-(p-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone 233A184
    3-[4-(4-Chlorophenyl)cyclohexyl]-4-hydroxy-1,2-naphthalenedione 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxy-naphthalene-1,2-dione 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
    3-[4-(p-chlorophenyl)cyclohexyl]-4-hydroxy-1,2-naphthoquinone 566C 566C80
    78668-EP2307343A1 94015-53-9 95233-18-4
    A13708 AB00053222-03 AB00053222_04
    AB00053222_05 AB0012456 AB00513855
    AB0107187 AB0211463 AC-30251
    AK544285 AKOS005567953 AKOS015895691
    AKOS015961933 AS-12809 ATO & IL-12
    ATOVAQUONE Acuvel Atavaquone
    Atovakvon Atovaquone & Interleukin 12 Atovaquone (Atavaquone)
    Atovaquone (JAN/USP/INN) Atovaquone EP Impurity B Atovaquone [USAN:BAN:INN]
    Atovaquone [USAN:USP:INN:BAN] Atovaquone, >=98% (HPLC) BCP09477
    BDBM192009 BIDD:GT0849 BPBio1_000603
    BSPBio_000547 BSPBio_002681 BW 566C
    BW 566C-80 BW 566C80 BW-556C-80
    BW-566C-80 BW-A 566C C06835
    C22H19ClO3 CAS-95233-18-4 CCG-220534
    CCG-39090 CHEBI:575568 CHEBI:95346
    CHEMBL222334 CHEMBL519462 CRL-8131 & Atovaquone
    CS-2702 CTK5H7581 Cis-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
    D00236 DB01117 DRG-0084
    DSSTox_CID_2629 DSSTox_GSID_22629 DSSTox_RID_76664
    DTXSID20916694 DTXSID7022629 DivK1c_006782
    FD7252 FT-0081084 FT-0602868
    GTPL9695 HMS1569L09 HMS1922F19
    HMS2089M14 HMS2093C10 HMS2096L09
    HMS2235N08 HMS3369N09 HMS3651N20
    HMS3713L09 HSDB 7083 HY-13832
    J90007 KBio1_001726 KBio2_002223
    KBio2_004791 KBio2_007359 KBio3_001901
    KBioGR_001594 KBioSS_002223 KS-00000FO3
    KUCQYCKVKVOKAY-CTYIDZIISA-N KUCQYCKVKVOKAY-OTVXOJSOSA-N KUCQYCKVKVOKAY-UHFFFAOYSA-N
    LS-178256 MCULE-7318126574 MLS002153863
    Mepron Mepron (TN) Mepron (antipneumocystic)
    NAP016 NCGC00016961-01 NCGC00016961-02
    NCGC00016961-03 NCGC00016961-04 NCGC00016961-06
    NCGC00016961-07 NCGC00095113-01 NCGC00095113-02
    NSC-759582 NSC759582 Pharmakon1600-01504210
    Prestwick0_000534 Prestwick1_000534 Prestwick2_000534
    Prestwick3_000534 Q418179 SBI-0052893.P002
    SC-15688 SC-21393 SCHEMBL1542719
    SCHEMBL1649508 SCHEMBL21694 SCHEMBL21695
    SCHEMBL637069 SCHEMBL9975142 SCHEMBL9975229
    SMR001233220 SPBio_001849 SPBio_002468
    SPECTRUM1504210 SR-05000001438 SR-05000001438-1
    SR-05000001438-2 SR-05000001438-4 SR-05000001438-5
    STK636160 SW219222-1 SpecPlus_000686
    Spectrum2_001665 Spectrum3_000991 Spectrum4_001117
    Spectrum5_001382 Spectrum_001743 TX-010638
    Tox21_110714 Tox21_110714_1 UNII-Y883P1Z2LT
    Wellvone Y883P1Z2LT Z1541632806
    ZINC100017856 ZINC100345537 ZINC116473771
    ZINC12504271 ZINC299873031 atovaquone-atavaquone
    cis -2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione cis-Atovaquone s3079
    trans-2-(4-(4-chlorophenyl) cyclohexyl)-3-hydroxynaphthalene-1,4-dione trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone

    DrugBank Name Atovaquone
    DrugBank DB01117
    CAS Number 137732-39-9, 94015-53-9, 95233-18-4, 996-42-9
    PubChem Compound 74989
    KEGG Compound ID C06835
    KEGG Drug D00236
    PubChem.Substance 46507298
    ChEBI 575568
    PharmGKB PA448502
    ChemSpider 10482034
    BindingDB 16301.0
    TTD DAP000156
    Wikipedia Atovaquone
    HET AOQ
    DPD 8317