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    Chemistry

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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
    26-Sep-2024
    KGS
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    Average Price (USD/KGS)

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    Total Quantity (KGS)

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

    API Imports and Exports

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    Virtual BoothQuotient Sciences- Molecule to Cure. Fast.

    Quotient Doses Volunteers in Malaria Venture’s Long-Acting Injectable Prevention Study

    Details:

    MMV371 is a prodrug of atovaquone (selective inhibitor of cytochrome bc1 complex), ben investigated for malaria in adults.


    Lead Product(s): Atovaquone

    Therapeutic Area: Infections and Infectious Diseases Brand Name: MMV371-Prodrug

    Study Phase: Phase IProduct Type: Small molecule

    Sponsor: Medicines for Malaria Venture

    Deal Size: Not Applicable Upfront Cash: Not Applicable

    Deal Type: Not Applicable October 28, 2024

    Quotient

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    Quotient Sciences

    United Kingdom
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    Lead Product(s) : Atovaquone

    Therapeutic Area : Infections and Infectious Diseases

    Highest Development Status : Phase I

    Partner/Sponsor/Collaborator : Medicines for Malaria Venture

    Deal Size : Not Applicable

    Deal Type : Not Applicable

    DEALS_DEV arrow-down

    Quotient Doses Volunteers in Malaria Venture’s Long-Acting Injectable Prevention Study

    Details : MMV371 is a prodrug of atovaquone (selective inhibitor of cytochrome bc1 complex), ben investigated for malaria in adults.

    Brand Name : MMV371-Prodrug

    Molecule Type : Small molecule

    Upfront Cash : Not Applicable

    October 28, 2024

    Quotient

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    TGen and HonorHealth trial atovaquone plus azithromycin for Covid-19

    Details:

    Atovaquone plus azithromycin combination was studied in other infectious disease and is expected to offer a well-tolerated option for patients infected with the novel coronavirus.


    Lead Product(s): Atovaquone,Azithromycin

    Therapeutic Area: Infections and Infectious Diseases Brand Name: Undisclosed

    Study Phase: Phase IIProduct Type: Small molecule

    Sponsor: Not Applicable

    Deal Size: Not Applicable Upfront Cash: Not Applicable

    Deal Type: Not Applicable May 06, 2020

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    Translational Genomics Research Institute

    Country
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    Medlab Asia & Asia Health
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    Translational Genomics Research Institute

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    Lead Product(s) : Atovaquone,Azithromycin

    Therapeutic Area : Infections and Infectious Diseases

    Highest Development Status : Phase II

    Partner/Sponsor/Collaborator : Not Applicable

    Deal Size : Not Applicable

    Deal Type : Not Applicable

    DEALS_DEV arrow-down

    TGen and HonorHealth trial atovaquone plus azithromycin for Covid-19

    Details : Atovaquone plus azithromycin combination was studied in other infectious disease and is expected to offer a well-tolerated option for patients infected with the novel coronavirus.

    Brand Name : Undisclosed

    Molecule Type : Small molecule

    Upfront Cash : Not Applicable

    May 06, 2020

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    INTERMEDIATES SUPPLIERS

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    01

    Beijing Lunarsun Pharmaceutical Co....

    China
    Medlab Asia & Asia Health
    Not Confirmed
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    Beijing Lunarsun Pharmaceutical Co....

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    2-Chloro-1,4-naphthoquinone

    CAS Number : 1010-60-2

    End Use API : Atovaquone

    About The Company : Beijing Lunarsun pharma is a professional manufacturer of API and intermediates. The factory is approved by US FDA. According to EU and US FDA's requirement, we...

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    Dalian Richon Chem

    China
    Medlab Asia & Asia Health
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    Not Confirmed
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    Trans-4-(4-Chlorophenyl)cyclohexanecarboxylic acid

    CAS Number : 49708-81-8

    End Use API : Atovaquone

    About The Company : Dalian Richon Chem. Co., Ltd is a high-tech enterprise professionally involved in research and development, manufacturing process and sales service of pharmaceu...

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    Suraj Labs

    India
    Medlab Asia & Asia Health
    Not Confirmed
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    Suraj Labs

    India
    Medlab Asia & Asia Health
    Not Confirmed
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    2-Chloro-1,4-Naphthaquinone

    CAS Number : 1010-60-2

    End Use API : Atovaquone

    About The Company : Suraj Laboratories Private Limited, established in 2021, is a pharmaceutical firm providing Contract Research and Manufacturing Services (CRAMS), Custom Synthes...

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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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    01

    Brand Name : Atovaquone

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    CPHI Middle east
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    Company :

    Atovaquone

    Drug Cost (USD) : 53,128,369

    Year : 2022

    Prescribers : 18247

    Prescriptions : 63361

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    Brand Name : Malarone

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    CPHI Middle east
    Not Confirmed

    Brand Name : Malarone

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    Company :

    Atovaquone/Proguanil HCl

    Drug Cost (USD) : 3,317

    Year : 2022

    Prescribers : 17

    Prescriptions : 19

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    Brand Name : Mepron

    Country
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    CPHI Middle east
    Not Confirmed

    Brand Name : Mepron

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    Not Confirmed
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    Company :

    Atovaquone

    Drug Cost (USD) : 316,549

    Year : 2022

    Prescribers : 44

    Prescriptions : 177

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    04

    Brand Name : Atovaquone

    Country
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    CPHI Middle east
    Not Confirmed

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    Company :

    Atovaquone

    Drug Cost (USD) : 48,269,825

    Year : 2021

    Prescribers : 17655

    Prescriptions : 62469

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    05

    Brand Name : Mepron

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    CPHI Middle east
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    Brand Name : Mepron

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    Company :

    Atovaquone

    Drug Cost (USD) : 435,587

    Year : 2021

    Prescribers : 63

    Prescriptions : 234

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    Brand Name : Mepron

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    Company :

    Atovaquone

    Drug Cost (USD) : 423,828

    Year : 2020

    Prescribers : 78

    Prescriptions : 255

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    Brand Name : Atovaquone

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    Company :

    Atovaquone

    Drug Cost (USD) : 48,037,443

    Year : 2020

    Prescribers : 15537

    Prescriptions : 58197

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    08

    Brand Name : Atovaquone

    Country
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    Company :

    Atovaquone

    Drug Cost (USD) : 42,987,141

    Year : 2019

    Prescribers : 14368

    Prescriptions : 49764

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    09

    Brand Name : Mepron

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    Company :

    Atovaquone

    Drug Cost (USD) : 449,752

    Year : 2019

    Prescribers : 93

    Prescriptions : 294

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    Brand Name : Atovaquone

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    Company :

    Atovaquone

    Drug Cost (USD) : 41,076,584

    Year : 2018

    Prescribers : 12171

    Prescriptions : 42589

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    Market Place

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    Patents & EXCLUSIVITIES

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    Health Canada Patents

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    01

    GlaxoSmithKline Inc.

    Atovaquone
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    GlaxoSmithKline Inc.

    United Kingdom
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    Patent Expiration Date : 2013-12-23

    Date Granted : 2001-10-16

    Atovaquone

    Brand Name : MEPRON

    Patent Number : 2152615

    Filing Date : 1993-12-23

    Strength per Unit : 750 mg / 5ml

    Dosage Form : Suspension

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2013-12-23

    Date Granted : 2001-10-16

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    GlaxoSmithKline Inc.

    Atovaquone
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    GlaxoSmithKline Inc.

    United Kingdom
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    Not Confirmed

    Patent Expiration Date : 2012-07-11

    Date Granted : 1995-07-11

    Atovaquone

    Brand Name : MEPRON

    Patent Number : 1336266

    Filing Date :

    Strength per Unit : 250 mg

    Dosage Form : Tablet

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2012-07-11

    Date Granted : 1995-07-11

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    REF. STANDARDS & IMPURITIES

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    USP

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    01

    USP

    U.S.A
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    USP

    U.S.A
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    Atovaquone (200 mg)

    CAS Number : 95233-18-4

    Quantity Per Vial :

    Price ($) : 230

    Catalog Number : 1044651

    Current Lot : R003Y0

    Previous Lot : G0H328 (31-OCT-2015)

    NDC Code :

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