Atovaquone
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317258

CAS#: 95233-18-4

Description: Atovaquone is a synthetic hydroxynaphthoquinone with antiprotozoal activity that has antimicrobial activity and is being used in antimalarial protocols. Atovoquone blocks the mitochondrial electron transport at complex III of the respiratory chain of protozoa, thereby inhibiting pyrimidine synthesis, preventing DNA synthesis and leading to protozoal death. It is an analog of protozoan mitochondrial protein ubiquinone, and acts by inhibiting the cytochrome bc(1) complex via interactions with the Rieske iron-sulfur protein and cytochrome b in the ubiquinol oxidation pocket.


Chemical Structure

img
Atovaquone
CAS# 95233-18-4

Theoretical Analysis

MedKoo Cat#: 317258
Name: Atovaquone
CAS#: 95233-18-4
Chemical Formula: C22H19ClO3
Exact Mass: 366.10227
Molecular Weight: 366.84
Elemental Analysis: C, 72.03; H, 5.22; Cl, 9.66; O, 13.08

Size Price Shipping out time Quantity
200mg USD 90 Same Day
500mg USD 190 Same Day
1g USD 350 Same Day
2g USD 550 Same Day
5g USD 1150 Same Day
10g USD 2050 Same Day
Inquire bulk and customized quantity

Pricing updated 2021-03-01. Prices are subject to change without notice.

Atovaquone, purity > 98%, is in stock. The same day shipping after order received.

Synonym: 566C; 566C80; 566C80 hydroxynaphthoquinone; 566C80, hydroxynaphthoquinone; Atovaquone; atovaquone GlaxoSmithKline brand; compound 566; Glaxo Wellcome brand of atovaquone; GlaxoSmithKline brand of atovaquone; hydroxynaphthoquinone 566C80; hydroxynaphthoquinone, 566C80; Mepron; Wellvone

IUPAC/Chemical Name: trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione

InChi Key: KUCQYCKVKVOKAY-CTYIDZIISA-N

InChi Code: 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/h1-4,9-13,15,26H,5-8H2/t13-,15-

SMILES Code: O=C1C([C@H]2CC[C@H](C3=CC=C(Cl)C=C3)CC2)=C(O)C(C4=C1C=CC=C4)=O

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 366.84 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Nuralitha S, Siregar JE, Syafruddin D, Roelands J, Verhoef J, Hoepelman AI,
Marzuki S. Within-Host Selection of Drug Resistance in a Mouse Model of Repeated
Incomplete Malaria Treatment: Comparison between Atovaquone and Pyrimethamine.
Antimicrob Agents Chemother. 2015 Oct 26. pii: AAC.00538-15. [Epub ahead of
print] PubMed PMID: 26503662.

2: Teo BH, Lansdell P, Smith V, Blaze M, Nolder D, Beshir KB, Chiodini PL, Cao J,
Färnert A, Sutherland CJ. Delayed Onset of Symptoms and Atovaquone-Proguanil
Chemoprophylaxis Breakthrough by Plasmodium malariae in the Absence of Mutation
at Codon 268 of pmcytb. PLoS Negl Trop Dis. 2015 Oct 20;9(10):e0004068. doi:
10.1371/journal.pntd.0004068. eCollection 2015 Oct. PubMed PMID: 26485258; PubMed
Central PMCID: PMC4618945.

3: Dinter D, Gajski G, Domijan AM, Garaj-Vrhovac V. Cytogenetic and oxidative
status of human lymphocytes after exposure to clinically relevant concentrations
of antimalarial drugs atovaquone and proguanil hydrochloride in vitro. Fundam
Clin Pharmacol. 2015 Sep 10. doi: 10.1111/fcp.12153. [Epub ahead of print] PubMed
PMID: 26434663.

4: de Oliveira Silva E, Dos Santos Gonçalves N, Alves Dos Santos R, Jacometti
Cardoso Furtado NA. Microbial Metabolism of Atovaquone and Cytotoxicity of the
Produced Phase I Metabolite. Eur J Drug Metab Pharmacokinet. 2015 Aug 8. [Epub
ahead of print] PubMed PMID: 26253156.

5: de Lima LP, Seabra SH, Carneiro H, Barbosa HS. Effect of 3-bromopyruvate and
atovaquone on infection during in vitro interaction of Toxoplasma gondii and
LLC-MK2 cells. Antimicrob Agents Chemother. 2015 Sep;59(9):5239-49. doi:
10.1128/AAC.00337-15. Epub 2015 Jun 15. PubMed PMID: 26077255; PubMed Central
PMCID: PMC4538506.

6: Mendorf A, Klyuchnikov E, Langebrake C, Rohde H, Ayuk F, Regier M, Christopeit
M, Zabelina T, Bacher A, Stübig T, Wolschke C, Bacher U, Kröger N. Atovaquone for
Prophylaxis of Toxoplasmosis after Allogeneic Hematopoietic Stem Cell
Transplantation. Acta Haematol. 2015;134(3):146-54. doi: 10.1159/000380757. Epub
2015 May 5. PubMed PMID: 25968483.

7: Song Z, Clain J, Iorga BI, Yi Z, Fisher N, Meunier B. Saccharomyces
cerevisiae-based mutational analysis of the bc1 complex Qo site residue 279 to
study the trade-off between atovaquone resistance and function. Antimicrob Agents
Chemother. 2015 Jul;59(7):4053-8. doi: 10.1128/AAC.00710-15. Epub 2015 Apr 27.
PubMed PMID: 25918152; PubMed Central PMCID: PMC4468654.

8: Plucinski MM, Huber CS, Akinyi S, Dalton W, Eschete M, Grady K, Silva-Flannery
L, Mathison BA, Udhayakumar V, Arguin PM, Barnwell JW. Novel Mutation in
Cytochrome B of Plasmodium falciparum in One of Two Atovaquone-Proguanil
Treatment Failures in Travelers Returning From Same Site in Nigeria. Open Forum
Infect Dis. 2014 Aug 5;1(2):ofu059. doi: 10.1093/ofid/ofu059. eCollection 2014
Sep. PubMed PMID: 25734129; PubMed Central PMCID: PMC4281801.

9: Ingasia LA, Akala HM, Imbuga MO, Opot BH, Eyase FL, Johnson JD, Bulimo WD,
Kamau E. Molecular characterization of the cytochrome b gene and in vitro
atovaquone susceptibility of Plasmodium falciparum isolates from Kenya.
Antimicrob Agents Chemother. 2015 Mar;59(3):1818-21. doi: 10.1128/AAC.03956-14.
Epub 2015 Jan 12. PubMed PMID: 25583715; PubMed Central PMCID: PMC4325819.

10: Boggild AK, Lau R, Reynaud D, Kain KC, Gerson M. Failure of
atovaquone-proguanil malaria chemoprophylaxis in a traveler to Ghana. Travel Med
Infect Dis. 2015 Jan-Feb;13(1):89-93. doi: 10.1016/j.tmaid.2014.12.010. Epub 2014
Dec 31. PubMed PMID: 25582377.

11: Sönmez N, Büyükbaba Boral O, Kaşali K, Tekeli F. [Effects of atovaquone and
astragalus combination on the treatment and IL-2, IL-12, IFN-γ levels on mouse
models of acute toxoplasmosis]. Mikrobiyol Bul. 2014 Oct;48(4):639-51. Turkish.
PubMed PMID: 25492659.

12: Grynberg S, Lachish T, Kopel E, Meltzer E, Schwartz E.
Artemether-lumefantrine compared to atovaquone-proguanil as a treatment for
uncomplicated Plasmodium falciparum malaria in travelers. Am J Trop Med Hyg. 2015
Jan;92(1):13-7. doi: 10.4269/ajtmh.14-0249. Epub 2014 Nov 4. PubMed PMID:
25371188; PubMed Central PMCID: PMC4347368.

13: Akhoon BA, Singh KP, Varshney M, Gupta SK, Shukla Y, Gupta SK. Understanding
the mechanism of atovaquone drug resistance in Plasmodium falciparum cytochrome b
mutation Y268S using computational methods. PLoS One. 2014 Oct 15;9(10):e110041.
doi: 10.1371/journal.pone.0110041. eCollection 2014. PubMed PMID: 25334024;
PubMed Central PMCID: PMC4198183.

14: Guler JL, White J 3rd, Phillips MA, Rathod PK. Atovaquone tolerance in
Plasmodium falciparum parasites selected for high-level resistance to a
dihydroorotate dehydrogenase inhibitor. Antimicrob Agents Chemother. 2015
Jan;59(1):686-9. doi: 10.1128/AAC.02347-14. Epub 2014 Oct 20. PubMed PMID:
25331708; PubMed Central PMCID: PMC4291421.

15: Oz HS. Toxoplasmosis complications and novel therapeutic synergism
combination of diclazuril plus atovaquone. Front Microbiol. 2014 Sep 15;5:484.
doi: 10.3389/fmicb.2014.00484. eCollection 2014. PubMed PMID: 25309522; PubMed
Central PMCID: PMC4164033.

16: Siregar JE, Kurisu G, Kobayashi T, Matsuzaki M, Sakamoto K, Mi-ichi F,
Watanabe Y, Hirai M, Matsuoka H, Syafruddin D, Marzuki S, Kita K. Direct evidence
for the atovaquone action on the Plasmodium cytochrome bc1 complex. Parasitol
Int. 2015 Jun;64(3):295-300. doi: 10.1016/j.parint.2014.09.011. Epub 2014 Sep 28.
PubMed PMID: 25264100.

17: Maude RJ, Nguon C, Dondorp AM, White LJ, White NJ. The diminishing returns of
atovaquone-proguanil for elimination of Plasmodium falciparum malaria: modelling
mass drug administration and treatment. Malar J. 2014 Sep 24;13:380. doi:
10.1186/1475-2875-13-380. PubMed PMID: 25249272; PubMed Central PMCID:
PMC4192368.

18: Rijpma SR, van den Heuvel JJ, van der Velden M, Sauerwein RW, Russel FG,
Koenderink JB. Atovaquone and quinine anti-malarials inhibit ATP binding cassette
transporter activity. Malar J. 2014 Sep 13;13:359. doi: 10.1186/1475-2875-13-359.
PubMed PMID: 25218605; PubMed Central PMCID: PMC4172838.

19: Oz HS. Novel Synergistic Protective Efficacy of Atovaquone and Diclazuril on
Fetal-Maternal Toxoplasmosis. Int J Clin Med. 2014 Aug;5(15):921-932. PubMed
PMID: 25210646; PubMed Central PMCID: PMC4157831.

20: Tahar R, Almelli T, Debue C, Foumane Ngane V, Djaman Allico J, Whegang Youdom
S, Basco LK. Randomized trial of artesunate-amodiaquine, atovaquone-proguanil,
and artesunate-atovaquone-proguanil for the treatment of uncomplicated falciparum
malaria in children. J Infect Dis. 2014 Dec 15;210(12):1962-71. doi:
10.1093/infdis/jiu341. Epub 2014 Jun 18. PubMed PMID: 24943722.