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    Chemistry

    Click the arrow to open the dropdown
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    Also known as: 95233-18-4, Mepron, Wellvone, Acuvel, Atavaquone, 566c80
    Molecular Formula
    C22H19ClO3
    Molecular Weight
    366.8  g/mol
    InChI Key
    BSJMWHQBCZFXBR-UHFFFAOYSA-N
    FDA UNII
    F1W7QUV0KI
    Atovaquone
    A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.
    Atovaquone is an Antimalarial and Antiprotozoal.
    1 2D Structure

    Atovaquone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
    2.1.2 InChI
    InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,24H,5-8H2
    2.1.3 InChI Key
    BSJMWHQBCZFXBR-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    F1W7QUV0KI
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(4-(4'-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone

    2. 2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone

    3. 566c

    4. 566c80

    5. 566c80 Hydroxynaphthoquinone

    6. Compound 566

    7. Hydroxynaphthoquinone 566c80

    8. Hydroxynaphthoquinone, 566c80

    9. Mepron

    10. Wellvone

    2.3.2 Depositor-Supplied Synonyms

    1. 95233-18-4

    2. Mepron

    3. Wellvone

    4. Acuvel

    5. Atavaquone

    6. 566c80

    7. 94015-53-9

    8. Cis-atovaquone

    9. 137732-39-9

    10. Mepron (antipneumocystic)

    11. 566c

    12. Bw 566c

    13. 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione

    14. Atovaquone (atavaquone)

    15. 2-(trans-4-(p-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone

    16. F1w7quv0ki

    17. 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone

    18. Nsc-759582

    19. 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone

    20. 2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthalenedione

    21. Y883p1z2lt

    22. Chebi:575568

    23. 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione

    24. Ncgc00016961-01

    25. Atovaquone 100 Microg/ml In Acetonitrile

    26. 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione

    27. Cas-95233-18-4

    28. 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione

    29. Dsstox_cid_2629

    30. Trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione

    31. 1,4-naphthalenedione, 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-, Trans-

    32. 2-((1r,4r)-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione

    33. Dsstox_rid_76664

    34. Dsstox_gsid_22629

    35. 2-(cis-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthalenedione

    36. 2-[trans-4-(p-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone

    37. Cis-2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone

    38. 1,4-naphthalenedione, 2-(cis-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-

    39. 1,4-naphthalenedione, 2-[cis-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-

    40. 2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione

    41. Drg-0084

    42. Bw 566c-80

    43. Mepron (tn)

    44. Bw-a 566c

    45. Hsdb 7083

    46. Sr-05000001438

    47. Bw-566c-80

    48. Atovacuona

    49. Crl-8131 & Atovaquone

    50. Unii-y883p1z2lt

    51. Atovaquona

    52. 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone

    53. Atovaquone & Interleukin 12

    54. 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-naphthalene-1,4-dione

    55. 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione

    56. Cis-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone

    57. Trans-2-(4-(4-chlorophenyl) Cyclohexyl)-3-hydroxynaphthalene-1,4-dione

    58. Ato & Il-12

    59. Atovaquone [usan:usp:inn:ban]

    60. Atovaquone-[d5]

    61. Atovaquone- Bio-x

    62. Bw 566c80

    63. Spectrum_001743

    64. Starbld0018905

    65. Atovaquone [mi]

    66. Specplus_000686

    67. Atovaquone [inn]

    68. Atovaquone [jan]

    69. Prestwick0_000534

    70. Prestwick1_000534

    71. Prestwick2_000534

    72. Prestwick3_000534

    73. Spectrum2_001665

    74. Spectrum3_000991

    75. Spectrum4_001117

    76. Spectrum5_001382

    77. Unii-f1w7quv0ki

    78. Atovaquone [hsdb]

    79. Atovaquone [usan]

    80. Atovaquone Ep Impurity B

    81. Atovaquone [vandf]

    82. Atovaquone [mart.]

    83. Atovaquone [usp-rs]

    84. Atovaquone [who-dd]

    85. Schembl21694

    86. Schembl21695

    87. Atovaquone (jan/usp/inn)

    88. Bspbio_000547

    89. Bspbio_002681

    90. Kbiogr_001594

    91. Kbioss_002223

    92. Atovaquone Related Compound A

    93. Mls002153863

    94. Bidd:gt0849

    95. Divk1c_006782

    96. Schembl637069

    97. Spectrum1504210

    98. Spbio_001849

    99. Spbio_002468

    100. Bpbio1_000603

    101. Chembl222334

    102. Chembl471792

    103. Chembl519462

    104. Gtpl9695

    105. Schembl1542719

    106. Schembl1649508

    107. Schembl9975142

    108. Schembl9975229

    109. Atovaquone [orange Book]

    110. Atovaquone, >=98% (hplc)

    111. Cis-atovaquone (racemic)

    112. Dtxsid7022629

    113. Atovaquone For System Suitability

    114. Chebi:95346

    115. Kbio1_001726

    116. Kbio2_002223

    117. Kbio2_004791

    118. Kbio2_007359

    119. Kbio3_001901

    120. Atovaquone [ep Monograph]

    121. Dtxsid20916694

    122. Atovaquone [usp Monograph]

    123. Bdbm192009

    124. Hms1569l09

    125. Hms1922f19

    126. Hms2089m14

    127. Hms2093c10

    128. Hms2096l09

    129. Hms2235n08

    130. Hms3369n09

    131. Hms3651n20

    132. Hms3713l09

    133. Pharmakon1600-01504210

    134. Amy15339

    135. Bcp09477

    136. Malarone Component Atovaquone

    137. Tox21_110714

    138. 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxy-naphthalene-1,2-dione

    139. Atovaquone Related Compound A [usp]

    140. Ccg-39090

    141. Fd7252

    142. Mfcd00889188

    143. Nsc759582

    144. S3079

    145. Stk636160

    146. Trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone

    147. Zinc12504271

    148. 1,4-naphthalenedione, 2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-

    149. 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-dihydronaphthalene-1,4-dione

    150. Akos005567953

    151. Akos015895691

    152. Akos015961933

    153. Tox21_110714_1

    154. Zinc100017856

    155. Zinc100345537

    156. Zinc116473771

    157. Zinc299873031

    158. Atovaquone Component Of Malarone

    159. Bw-556c-80

    160. Ccg-220534

    161. Db01117

    162. Nsc 759582

    163. Ncgc00016961-02

    164. Ncgc00016961-03

    165. Ncgc00016961-04

    166. Ncgc00016961-06

    167. Ncgc00016961-07

    168. Ncgc00016961-11

    169. Ncgc00095113-01

    170. Ncgc00095113-02

    171. Ac-30251

    172. As-12809

    173. Ba164228

    174. Hy-13832

    175. Smr001233220

    176. Sbi-0052893.p002

    177. Ab00513855

    178. Ft-0602868

    179. Sw219222-1

    180. Malarone Pediatric Component Atovaquone

    181. A13708

    182. Atovaquone Related Compound A [usp-rs]

    183. C06835

    184. D00236

    185. F18448

    186. Ab00053222-03

    187. Ab00053222_04

    188. Ab00053222_05

    189. Atovaquone Component Of Malarone Pediatric

    190. 233a184

    191. A853147

    192. Q418179

    193. Atovaquone Related Compound A [usp Impurity]

    194. Sr-05000001438-1

    195. Sr-05000001438-2

    196. Sr-05000001438-4

    197. Sr-05000001438-5

    198. Z1541632806

    199. 2-[4-(4-chlorophenyl)cyclohexy]-3-hydroxy-1,4-naphthoquinone

    200. 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-napthoquinone

    201. 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1.4-naphthoquinone

    202. 2-hydroxy-3-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthoquinone

    203. 3-[4-(p-chlorophenyl)cyclohexyl]-4-hydroxy-1,2-naphthoquinone

    204. 1,2-naphthalenedione, 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxy-

    205. 1,4-naphthalenedione, 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-

    206. 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthoquinone, Trans-

    207. 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxy-1,2-naphthalenedione

    208. Cis -2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione

    2.4 Create Date
    2005-03-28
    3 Chemical and Physical Properties
    Molecular Weight 366.8 g/mol
    Molecular Formula C22H19ClO3
    XLogP35.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count2
    Exact Mass366.1022722 g/mol
    Monoisotopic Mass366.1022722 g/mol
    Topological Polar Surface Area54.4 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity595
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameAtovaquone
    PubMed HealthAtovaquone (By mouth)
    Drug ClassesAntiprotozoal
    Drug LabelAtovaquone is an antiprotozoal agent. The chemical name of atovaquone is trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione. Atovaquone is a yellow crystalline solid that is practically insoluble in water. It has a molecular weight...
    Active IngredientAtovaquone
    Dosage FormSuspension
    RouteOral
    Strength750mg/5ml
    Market StatusPrescription
    CompanyAmneal Pharms

    2 of 4  
    Drug NameMepron
    PubMed HealthAtovaquone (By mouth)
    Drug ClassesAntiprotozoal
    Drug LabelMEPRON (atovaquone) is an antiprotozoal agent. The chemical name of atovaquone is trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione. Atovaquone is a yellow crystalline solid that is practically insoluble in water. It has a molecul...
    Active IngredientAtovaquone
    Dosage FormSuspension
    RouteOral
    Strength750mg/5ml
    Market StatusPrescription
    CompanyGlaxosmithkline

    3 of 4  
    Drug NameAtovaquone
    PubMed HealthAtovaquone (By mouth)
    Drug ClassesAntiprotozoal
    Drug LabelAtovaquone is an antiprotozoal agent. The chemical name of atovaquone is trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione. Atovaquone is a yellow crystalline solid that is practically insoluble in water. It has a molecular weight...
    Active IngredientAtovaquone
    Dosage FormSuspension
    RouteOral
    Strength750mg/5ml
    Market StatusPrescription
    CompanyAmneal Pharms

    4 of 4  
    Drug NameMepron
    PubMed HealthAtovaquone (By mouth)
    Drug ClassesAntiprotozoal
    Drug LabelMEPRON (atovaquone) is an antiprotozoal agent. The chemical name of atovaquone is trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione. Atovaquone is a yellow crystalline solid that is practically insoluble in water. It has a molecul...
    Active IngredientAtovaquone
    Dosage FormSuspension
    RouteOral
    Strength750mg/5ml
    Market StatusPrescription
    CompanyGlaxosmithkline

    4.2 Therapeutic Uses

    Antipneumocystic

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 149

    A tablet containing a fixed dose of 250 mg of atovaquone and 100 mg of proguanil hydrochloride, taken orally, has been highly effective and safe in a 3-day regimen for treating mild to moderate attacks of chloroquine- and multidrug-resistant falciparum malaria.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1076

    Atovaquone is indicated in the treatment of mild to moderate Pneumocystis carinii pneumonia (A-a gradient < or = 45 mmHg and pO2 > or = 60 mmHg on room air) in patients who are intolerant of sulfamethoxazole and trimethoprim combination. /Included in US product labeling/

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 502

    Atovaquone is indicated in the prevention of Pneumocystis carinii pneumonia in patients who are intolerant of sulfamethoxazole and trimethoprim combination. /Included in US product labeling/

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 502

    For more Therapeutic Uses (Complete) data for ATOVAQUONE (18 total), please visit the HSDB record page.

    4.3 Drug Warning

    Patients should be advised regarding pulmonary manifestations of possibly concurrent bacterial, viral, fungal, or mycobacterial infections associated with HIV infection and/or progression of the underlying Pneumocystis carinii pneumonia and to contact a clinician if pulmonary symptomatology develops or worsens during atovaquone therapy. Clinical deterioration during atovaquone therapy could represent secondary infection with a nonsusceptible pathogen and/or progression of the underlying P. carinii pneumonia. All patients for whom atovaquone therapy is being considered should be evaluated carefully for other possible causes of pulmonary disease and treated with additional agents as appropriate.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 846

    Fever was reported in up to 40% of patients receiving atovaquone in controlled clinical trials and occasionally has required discontinuance of the drug. Oral candidiasis was reported in 10%, cough in 25%, sweating in 10%, sinusitis in 7%, and rhinitis in 24% of patients receiving atovaquone in controlled clinical trials. Infection of dyspnea has occurred in 22 or 15% of patients receiving atovaquone. Hypotension, vortex keratopathy, transient sinus arrhythmia, increased serum creatine kinase (CK, creatine phosphokinase, CPK) concentrations, and transient conjunctivitis also have been reported rarely.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 846

    Hyperglycemia (exceeding 1.8 times the upper limit of normal) occurred in 9% of patients receiving atovaquone in controlled clinical trials. Hypoglycemia has occurred rarely.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 846

    Increased BUN and serum creatinine concentrations have been reported rarely in patients receiving atovaquone and occasionally have required discontinuance of the drug. Hyponatremia (less than 0.96 times the lower limit of normal range) was reported in up to 10% of patients receiving atovaquone in controlled clinical trials. Acute renal impairment has occurred in patients receiving atovaquone.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 846

    For more Drug Warnings (Complete) data for ATOVAQUONE (13 total), please visit the HSDB record page.

    4.4 Drug Indication

    For the treatment or prevention of Pneumocystis carinii pneumonia in patients who are intolerant to trimethoprim-sulfamethoxazole (TMP-SMX). Also indicated for the acute oral treatment of mild to moderate PCP in patients who are intolerant to TMP-SMX.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Atovaquone is a highly lipophilic drug that closely resembles the structure [ubiquinone]. Its inhibitory effect being comparable to ubiquinone, atovaquone can act by selectively affecting mitochondrial electron transport and parallel processes such as ATP and pyrimidine biosynthesis in atovaquone-responsive parasites. Cytochrome bc1 complex (complex III) seems to serve as a highly discriminating molecular target for atovaquone in Plasmodia. There is no significant risk for myelosuppression associated with atovaquone, making this drug a beneficial therapeutic agent for recipients of bone marrow transplantation.

    5.2 MeSH Pharmacological Classification

    Anti-Infective Agents

    Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    Antimalarials

    Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    ATOVAQUONE
    5.3.2 FDA UNII
    Y883P1Z2LT
    5.3.3 Pharmacological Classes
    Antiprotozoal [EPC]; Antimalarial [EPC]
    5.4 ATC Code

    P01AX06

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    P - Antiparasitic products, insecticides and repellents

    P01 - Antiprotozoals

    P01A - Agents against amoebiasis and other protozoal diseases

    P01AX - Other agents against amoebiasis and other protozoal diseases

    P01AX06 - Atovaquone

    5.5 Absorption, Distribution and Excretion

    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%.

    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%).

    Volume of Distribution

    0.60 0.17 L/kg

    Clearance

    10.4 +/- 5.5 ml/min [HIV-infected patients receiving IV administration]

    Drug absorption after a single oral dose is slow, erratic and variable; increased by 2- to 3-fold by fatty food; and dose-limited above 750 mg. More than 99% of the drug is bound to plasma protein, so its concentration in cerebrospinal fluid is less than 1% of that in plasma.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1076

    The bioavailability of atovaquone is low and variable, and decreases significantly with single doses greater than 750 mg. A standard breakfast containing 23 g of fat has been shown to enhance absorption significantly. Oral suspension: The oral suspension provides a two-fold increase in bioavailability in fasting or fed conditions compared to the tablets. Bioavailability of the suspension increases two-fold when administered with meals; when administered with food, bioavailability is approximately 47%. Tablets: Bioavailability increases three-fold when administered with meals; bioavailability of the tablets when administered with food is approximately 23%.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 502

    Fecal; > 94% of atovaquone was recovered in the feces over 21 days; < 0.6% was excreted in the urine.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 503

    Bioavailability is increased with meals. Time to peak blood level is 1 to 8 hours, with a second peak in 24 to 96 hours.

    Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 268

    For more Absorption, Distribution and Excretion (Complete) data for ATOVAQUONE (8 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Some evidence suggests limited metabolism (although no metabolites have been identified).

    Atovaquone is not significantly metabolized by human beings. It is excreted in bile and more than 94% of the drug is recovered unchanged in feces; only traces appear in the urine.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1076

    Atovaquone is an antiprotozoal compound with good in vitro stability against metabolic inactivation. Previous human studies which did not involve radiolabelling had not accounted for a substantial proportion of the dose. The possible metabolism of atovaquone in men was examined in a radiolabelling study involving four healthy male volunteers. Radioactivity was eliminated almost exclusively via the feces. All radioactivity in plasma, urine, and feces was accounted for by atovaquone, with no evidence of metabolites. Radiolabelled atovaquone was administered to a patient with an indwelling biliary tube after surgery. Biliary radioactivity was approximately 10- to 40-fold higher than that in plasma and was accounted for by atovaquone. Atovaquone is not significantly metabolized in humans but is excreted into bile against a high concentration gradient.

    PMID:9174191 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC163907 Rolan PE et al; Antimicrob Agents Chemother 41(6): 1319-1321 (1997)

    5.7 Biological Half-Life

    2.2 to 3.2 days

    Atovaquone has a half-life averaging 1.5 to 3 days

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1076

    2.2 to 3.2 days in adult patients with acquired immunodeficiency syndrome (AIDS), adult healthy volunteers, and immunocompromised children (ages 5 months to 13 years).

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 502

    5.8 Mechanism of Action

    The mechanism of action against Pneumocystis carinii has not been fully elucidated. In Plasmodium species, the site of action appears to be the cytochrome bc1 complex (Complex III). Several metabolic enzymes are linked to the mitochondrial electron transport chain via ubiquinone. Inhibition of electron transport by atovaquone will result in indirect inhibition of these enzymes. The ultimate metabolic effects of such blockade may include inhibition of nucleic acid and ATP synthesis. Atovaquone also has been shown to have good in vitro activity against Toxoplasma gondii.

    Hydroxynaphthoquinone derivative that inhibits /parasitic/ mitochondrial electron transport.

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 149

    Atovaquone has possible cidal activity against susceptible organisms. The action against Pneumocystis carinii is not fully understood. Atovaquone is structurally similar to ubiquinone, which inhibits the mitochondrial electron-transport chain at the site of the cytochrome bc1 complex (complex III) in Plasmodium species. This may ultimately inhibit the synthesis of nucleic acid and ATP. Atovaquone also has been shown to have good in vitro activity against Toxoplasma gondii.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 502

    At present, approaches to studying mitochondrial functions in malarial parasites are quite limited because of the technical difficulties in isolating functional mitochondria in sufficient quantity and purity. We have developed a flow cytometric assay as an alternate means to study mitochondrial functions in intact erythrocytes infected with Plasmodium yoelii, a rodent malaria parasite. By using a very low concentration (2 nM) of a lipophilic cationic fluorescent probe, 3,3'dihexyloxacarbocyanine iodide, we were able to measure mitochondrial membrane potential(DeltaPsim) in live intact parasitized erythrocytes through flow cytometry. The accumulation of the probe into parasite mitochondria was dependent on the presence of a membrane potential since inclusion of carbonyl cyanide m-chlorophenylhydrazone, a protonophore, dissipated the membrane potential and abolished the probe accumulation. We tested the effect of standard mitochondrial inhibitors such as myxothiazole, antimycin, cyanide and rotenone. All of them except rotenone collapsed the DeltaPsim and inhibited respiration. The assay was validated by comparing the EC50 of these compounds for inhibiting DeltaPsim and respiration. This assay was used to investigate the effect of various antimalarial drugs such as chloroquine, tetracycline and a broad spectrum antiparasitic drug atovaquone. We observed that only atovaquone collapsed DeltaPsim and inhibited parasite respiration within minutes after drug treatment. Furthermore, atovaquone had no effect on mammalian DeltaPsim. This suggests that atovaquone, shown to inhibit mitochondrial electron transport, also depolarizes malarial mitochondria with consequent cellular damage and death.

    PMID:9020100 Srivastava IK et al; J Biol Chem 272(7): 3961-3966 (1997)

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    07-Jan-2021
    28-Dec-2024
    KGS
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - SUSPENSION;ORAL - 750MG/5ML

    USFDA APPLICATION NUMBER - 20500

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    DOSAGE - TABLET;ORAL - 250MG;100MG

    USFDA APPLICATION NUMBER - 21078

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    DOSAGE - TABLET;ORAL - 62.5MG;25MG

    USFDA APPLICATION NUMBER - 21078

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    ABOUT THIS PAGE

    Atovaquone Manufacturers

    A Atovaquone manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Atovaquone, including repackagers and relabelers. The FDA regulates Atovaquone manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Atovaquone API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Atovaquone manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Atovaquone Suppliers

    A Atovaquone supplier is an individual or a company that provides Atovaquone active pharmaceutical ingredient (API) or Atovaquone finished formulations upon request. The Atovaquone suppliers may include Atovaquone API manufacturers, exporters, distributors and traders.

    click here to find a list of Atovaquone suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Atovaquone USDMF

    A Atovaquone DMF (Drug Master File) is a document detailing the whole manufacturing process of Atovaquone active pharmaceutical ingredient (API) in detail. Different forms of Atovaquone DMFs exist exist since differing nations have different regulations, such as Atovaquone USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Atovaquone DMF submitted to regulatory agencies in the US is known as a USDMF. Atovaquone USDMF includes data on Atovaquone's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Atovaquone USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of Atovaquone suppliers with USDMF on PharmaCompass.

    Atovaquone CEP

    A Atovaquone CEP of the European Pharmacopoeia monograph is often referred to as a Atovaquone Certificate of Suitability (COS). The purpose of a Atovaquone CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Atovaquone EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Atovaquone to their clients by showing that a Atovaquone CEP has been issued for it. The manufacturer submits a Atovaquone CEP (COS) as part of the market authorization procedure, and it takes on the role of a Atovaquone CEP holder for the record. Additionally, the data presented in the Atovaquone CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Atovaquone DMF.

    A Atovaquone CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Atovaquone CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

    click here to find a list of Atovaquone suppliers with CEP (COS) on PharmaCompass.

    Atovaquone WC

    A Atovaquone written confirmation (Atovaquone WC) is an official document issued by a regulatory agency to a Atovaquone manufacturer, verifying that the manufacturing facility of a Atovaquone active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Atovaquone APIs or Atovaquone finished pharmaceutical products to another nation, regulatory agencies frequently require a Atovaquone WC (written confirmation) as part of the regulatory process.

    click here to find a list of Atovaquone suppliers with Written Confirmation (WC) on PharmaCompass.

    Atovaquone NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Atovaquone as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Atovaquone API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Atovaquone as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Atovaquone and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Atovaquone NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Atovaquone suppliers with NDC on PharmaCompass.

    Atovaquone GMP

    Atovaquone Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Atovaquone GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Atovaquone GMP manufacturer or Atovaquone GMP API supplier for your needs.

    Atovaquone CoA

    A Atovaquone CoA (Certificate of Analysis) is a formal document that attests to Atovaquone's compliance with Atovaquone specifications and serves as a tool for batch-level quality control.

    Atovaquone CoA mostly includes findings from lab analyses of a specific batch. For each Atovaquone CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Atovaquone may be tested according to a variety of international standards, such as European Pharmacopoeia (Atovaquone EP), Atovaquone JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Atovaquone USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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