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Atovaquone

CAS# 95233-18-4

Atovaquone

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Chemical structure

Atovaquone

3D structure

Chemical Properties of Atovaquone

Cas No. 95233-18-4 SDF Download SDF
PubChem ID 74989 Appearance Powder
Formula C22H19ClO3 M.Wt 366.84
Type of Compound N/A Storage Desiccate at -20°C
Solubility >17.03mg/mL in DMSO
Chemical Name 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
SMILES C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
Standard InChIKey BSJMWHQBCZFXBR-UHFFFAOYSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Atovaquone

DescriptionBroad spectrum antiparasitic and antipneumocystic compound. Inhibits bc1 complex (complex III) of mitochondrial electron transport chain (EC50 = 0.26 μM), causing cell death in Plasmodium yoelii infected erythrocytes. Also inhibits DHODH.

Atovaquone Dilution Calculator

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Atovaquone Molarity Calculator

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Preparing Stock Solutions of Atovaquone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.726 mL 13.6299 mL 27.2598 mL 54.5197 mL 68.1496 mL
5 mM 0.5452 mL 2.726 mL 5.452 mL 10.9039 mL 13.6299 mL
10 mM 0.2726 mL 1.363 mL 2.726 mL 5.452 mL 6.815 mL
50 mM 0.0545 mL 0.2726 mL 0.5452 mL 1.0904 mL 1.363 mL
100 mM 0.0273 mL 0.1363 mL 0.2726 mL 0.5452 mL 0.6815 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Atovaquone

Atovaquone is a medication used to treat or prevent for pneumocystis pneumonia, toxoplasmosis, malaria, and babesia.

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References on Atovaquone

Within-Host Selection of Drug Resistance in a Mouse Model Reveals Dose-Dependent Selection of Atovaquone Resistance Mutations.[Pubmed:28193656]

Antimicrob Agents Chemother. 2017 Apr 24;61(5). pii: AAC.01867-16.

The evolutionary selection of malaria parasites within an individual host plays a critical role in the emergence of drug resistance. We have compared the selection of Atovaquone resistance mutants in mouse models reflecting two different causes of failure of malaria treatment, an inadequate subtherapeutic dose and an incomplete therapeutic dose. The two models are based on cycles of insufficient treatment of Plasmodium berghei-infected mice: repeated inadequate treatment associated with a subtherapeutic dose (RIaT) (0.1 mg kg(-1) of body weight) and repeated incomplete treatment with a therapeutic dose (RIcT) (14.4 mg kg(-1) of body weight). The number of treatment cycles for the development of a stable resistance phenotype during RIaT was 2.00 +/- 0.00 cycles (n = 9), which is not statistically different from that during RIcT (2.57 +/- 0.85 cycles; combined n = 14; P = 0.0591). All mutations underlying Atovaquone resistance selected by RIaT (M133I, T142N, and L144S) were found to be in the Qo1 (quinone binding 1) domain of the mitochondrial cytochrome b gene, in contrast to those selected by RIcT (Y268N/C, L271V, K272R, and V284F) in the Qo2 domain or its neighboring sixth transmembrane region. Exposure of mixed populations of resistant parasites from RIaT to the higher therapeutic dose of RIcT revealed further insights into the dynamics of within-host selection of resistance to antimalarial drugs. These results suggest that both inadequate subtherapeutic doses and incomplete therapeutic doses in malaria treatment pose similar threats to the emergence of drug resistance. RIcT and RIaT could be developed as useful tools to predict the potential emergence of resistance to newly introduced and less-understood antimalarials.

Effectiveness of twice a week prophylaxis with atovaquone-proguanil (Malarone(R)) in long-term travellers to West Africa.[Pubmed:27625401]

J Travel Med. 2016 Sep 13;23(6). pii: taw064.

BACKGROUND: Current guidelines recommend daily dosing of Atovaquone-proguanil (AP), beginning a day before travel to endemic areas and continuing for 7 days after departure. Adherence of long-term travellers to daily malaria chemoprophylaxis tends to be poor, even when residing in highly endemic malaria regions. Evidence from a volunteer challenging study suggests that non-daily, longer intervals dosing of AP provides effective protection against Plasmodium falciparum This study examines the effectiveness of twice weekly AP prophylaxis in long-term travellers to highly endemic P. falciparum areas in West Africa. METHODS: An observational surveillance study aimed to detect prophylactic failures associated with twice weekly AP, during the years 2013-2014, among long-term expatriates in two sites in West Africa. The expatriates were divided according to the malaria prophylaxis regimen taken: AP twice weekly; mefloquine once weekly and a group refusing to take prophylaxis. Malaria events were recorded for each group. The incidence-density of malaria was calculated by dividing malaria events per number of person-months at risk. RESULTS: Among 122 expatriates to West Africa the malaria rates were: 11.7/1000 person-months in the group with no-prophylaxis (n = 63); 2.06/1000 person-months in the 40 expatriates taking mefloquine (P = 0.006) and no cases of malaria (0/391 person-months, P = 0.01) in the twice weekly AP group (n = 33). CONCLUSIONS: No prophylaxis failures were detected among the group of expatriates taking AP prophylaxis twice weekly compared with 11.7/1000 person-months among the no-prophylaxis group. Twice weekly AP prophylaxis may be an acceptable approach for long-term travellers who are unwilling to adhere to malaria chemoprophylaxis guidelines.

Efficacy, safety and tolerance of imidocarb dipropionate versus atovaquone or buparvaquone plus azithromycin used to treat sick dogs naturally infected with the Babesia microti-like piroplasm.[Pubmed:28292316]

Parasit Vectors. 2017 Mar 13;10(1):145.

BACKGROUND: Piroplasmosis caused by the Babesia microti-like piroplasm (Bml) is increasingly being detected in dogs in Europe. Sick dogs show acute disease with severe anaemia associated with thrombocytopenia with a poor response to current available drugs. This study assesses the safety and tolerance of three treatments and compares their efficacy over a full year of follow up in dogs naturally infected with Bml. METHODS: Fifty-nine dogs naturally infected with Bml were randomly assigned to a treatment group: imidocarb dipropionate (5 mg/kg SC, 2 doses 14 d apart) (IMI); Atovaquone (13.3 mg/kg PO q 8 h, 10 d)/azithromycin (10 mg/kg PO q 24 h, 10 d) (ATO); or buparvaquone (5 mg/kg IM, 2 d apart)/azithromycin (same dosage) (BUP). Before and after treatment (days 15, 45, 90 and 360), all dogs underwent a physical exam, blood tests and parasite detection (blood cytology and PCR). Clinical efficacy was assessed by grading 24 clinical and 8 clinicopathological signs from low to high severity. RESULTS: Before treatment, most dogs had severe regenerative anaemia (88.13%) and thrombocytopenia (71.4%). On treatment Day 45, clinical signs were mostly reduced in all dogs, and by Day 90, practically all dogs under the ATO or BUP regimen were clinically healthy (76.4 and 88%, respectively). Highest percentage reductions in laboratory abnormalities (82.04%) were detected in animals treated with ATO. Over the year, clinical relapse of Bml was observed in 8 dogs (8/17) treated with IMI. However, on Day 360, these animals had recovered clinically, though clinicopathological abnormalities were still present in some of them. Parasitaemia was PCR-confirmed on Days 90 and 360 in 47.05 and 50% of dogs treated with ATO, 68 and 60.08% with BUP, and 94.1 and 73.3% with IMI, respectively. Even after 360 days, 13.3% of the dogs treated with IMI returned a positive blood cytology result. CONCLUSIONS: IMI showed the worse clinical and parasitological, efficacy such that its use to treat Bml infection in dogs is not recommended. The treatments ATO and BUP showed better efficacy, though they were still incapable to completely eliminate PCR-proven infection at the recommended dose. All three treatments showed good tolerance and safety with scarce adverse events observed.

Description

Atovaquone (Atavaquone) is a potent, selective and orally active inhibitor of the parasite’s mitochondrial cytochrome bc1 complex. Atovaquone is against human and P. falciparum cytochrome bc1 activity with IC50 values of 460 nM and 2.0 nM, respectively. Atovaquone is an antimalarial agent and has the potential for the investigation of neumocystis pneumonia, toxoplasmosis, malaria, and babesia.

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