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Atovaquone - ≥98%, high purity , CAS No.95233-18-4

6 Citations
Item Number
A151027
Grouped product items
SKUSizeAvailabilityPrice Qty
A151027-250mg
250mg
In stock
$133.90
A151027-1g
1g
In stock
$411.90
A151027-5g
5g
In stock
$1,851.90
A151027-25g
25g
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$569.90
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Broad-spectrum antiparasitic agent. Ubiquinone analog.

View related series
Plasmodium falciparum cytochrome b

Basic Description

SynonymsATOVAQUONE [MI] | 2-(TRANS-4-(4-CHLOROPHENYL)CYCLOHEXYL)-3-HYDROXY-1,4-NAPHTHALENEDIONE | Atovaquona | cis-Atovaquone | ATOVAQUONE [USAN] | CIS-ATOVAQUONE (RACEMIC) | Hexyl salicylic acid | KUCQYCKVKVOKAY-CTYIDZIISA-N | SpecPlus_000686 | trans-2-(4-(4-chl
Specifications & PurityMoligand™, ≥98%
Biochemical and Physiological MechanismsAtovaquone is an anti-protozoal mitochondrial electron transport inhibitor; Antimalarial; Antipneumocystic, and has also been used to treat toxoplasmosis. It is an analog of protozoan mitochondrial protein ubiquinone, and acts by inhibiting the cytochrome
Storage TempStore at -20°C
Shipped InIce chest + Ice pads
GradeMoligand™
NoteWherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
Product Description

Atovaquone is a medication used to treat or prevent for pneumocystis pneumonia, toxoplasmosis, malaria, and babesia.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Atovaquone belongs to the class of naphthoquinones with a broad-spectrum activity against parasitic infections including malaria, toxoplasmosis and Pneumocystis pneumonia. It is a potent antiprotozoal compound which aids in collapsing the mitochondrial membrane potential in a malaria parasite.

Names and Identifiers

Pubchem Sid488185008
Pubchem Sid Urlhttps://pubchem.ncbi.nlm.nih.gov/substance/488185008
IUPAC Name 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
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
InChi Key BSJMWHQBCZFXBR-UHFFFAOYSA-N
Canonical SMILES C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
Isomeric SMILES C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
WGK Germany 3
RTECS QJ5616500
PubChem CID 74989
Molecular Weight 366.84

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Find and download the COA for your product by matching the lot number on the packaging.

12 results found

Lot NumberCertificate TypeDateItem
G2410063Certificate of AnalysisNov 25, 2023 A151027
I2406030Certificate of AnalysisNov 25, 2023 A151027
L2308319Certificate of AnalysisNov 25, 2023 A151027
L2308320Certificate of AnalysisNov 25, 2023 A151027
L2308321Certificate of AnalysisNov 25, 2023 A151027
L2308322Certificate of AnalysisNov 25, 2023 A151027
C2306844Certificate of AnalysisAug 16, 2022 A151027
C2306852Certificate of AnalysisAug 16, 2022 A151027
G2305173Certificate of AnalysisAug 16, 2022 A151027
I2207208Certificate of AnalysisAug 16, 2022 A151027
I2207209Certificate of AnalysisAug 16, 2022 A151027
I2207245Certificate of AnalysisAug 16, 2022 A151027

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Chemical and Physical Properties

SolubilityInsoluble in water; Very soluble in Tetrahydrofuran; Slightly soluble in Acetone; Insoluble in Methanol
Sensitivityheat sensitive
Melt Point(°C)223 °C

Safety and Hazards(GHS)

Pictogram(s) GHS09,   GHS07
Signal Warning
Hazard Statements

H315:Causes skin irritation

H319:Causes serious eye irritation

H335:May cause respiratory irritation

H413:May cause long lasting harmful effects to aquatic life

H400:Very toxic to aquatic life

H410:Very toxic to aquatic life with long lasting effects

Precautionary Statements

P261:Avoid breathing dust/fume/gas/mist/vapors/spray.

P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing.

P273:Avoid release to the environment.

P280:Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352:IF ON SKIN: wash with plenty of water.

P321:Specific treatment (see ... on this label).

P405:Store locked up.

P501:Dispose of contents/container to ...

P264:Wash hands [and …] thoroughly after handling.

P271:Use only outdoors or in a well-ventilated area.

P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P403+P233:Store in a well-ventilated place. Keep container tightly closed.

P362+P364:Take off contaminated clothing and wash it before reuse.

P391:Collect spillage.

P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes.

P337+P317:If eye irritation persists: Get medical help.

P332+P317:If skin irritation occurs: Get medical help.

P319:Get medical help if you feel unwell.

WGK Germany 3
RTECS QJ5616500
Merck Index 866

Related Documents

 SDS

 Specification Sheet

Citations of This Product

How to Cite Aladdin Scientific Products?
1. Liu Bin, Zheng Xin, Li Jiajun, Yao Peng, Guo Peng, Liu Wei, Zhao Gaoping.  (2023)  Atovaquone inhibits colorectal cancer metastasis by regulating PDGFRβ/NF-κB signaling pathway.  BMC CANCER,  23  (1): (1-13).  [PMID:37932661] [10.1186/s12885-023-11585-9]
2. Yifan Zhao, Min Zhang, Bai Lv, Guanghe Xue, Huimei Jiang, Gang Chen, Yi Ma, Yong Sun, Jie Cao.  (2023)  “Closed-Loop” O2-Economizer Induced In Situ Therapeutic Vaccine against Hypoxic Tumors.  ACS Nano,    (15):   [PMID:37877944] [10.1021/acsnano.3c05034]
3. Wenzhe Yang, Xue Pan, Peng Zhang, Xue Yang, Huashi Guan, Huan Dou, Qian Lu.  (2023)  Defeating Melanoma Through a Nano-Enabled Revision of Hypoxic and Immunosuppressive Tumor Microenvironment.  International Journal of Nanomedicine,      [PMID:37435153] [10.2147/IJN.S414882]
4. Wenhao Gao, Jialiang Zhang, Weifeng Wang, Zhihong Liu, Mulan Chen, Xiaomu Hu, Lingjun Zeng, Changqing Zheng, Hongtao Song, Qian Zhang.  (2022)  Drug self-delivery nanorods enhance photodynamic therapy of triple-negative breast cancer by inhibiting oxidative phosphorylation.  INTERNATIONAL JOURNAL OF PHARMACEUTICS,  621  (121775).  [PMID:35489603] [10.1016/j.ijpharm.2022.121775]
5. Dan Wang, Bin Xue, Tymish Y. Ohulchanskyy, Yubin Liu, Artem Yakovliev, Roman Ziniuk, Mengze Xu, Jun Song, Junle Qu, Zhen Yuan.  (2020)  Inhibiting tumor oxygen metabolism and simultaneously generating oxygen by intelligent upconversion nanotherapeutics for enhanced photodynamic therapy.  BIOMATERIALS,  251  (120088).  [PMID:32388167] [10.1016/j.biomaterials.2020.120088]
6. Donglin Xia, Peipei Xu, Xingyu Luo, Jianfeng Zhu, Haiying Gu, Da Huo, Yong Hu.  (2019)  Overcoming Hypoxia by Multistage Nanoparticle Delivery System to Inhibit Mitochondrial Respiration for Photodynamic Therapy.  ADVANCED FUNCTIONAL MATERIALS,  29  (13): (1807294).  [PMID:] [10.1002/adfm.201807294]

References

1. Krause PJ, Lepore T, Sikand VK, Gadbaw Jr J, Burke G, Telford 3rd SR, Brassard P, Pearl D, Azlanzadeh J, Christianson D et al..  (2000)  Atovaquone and azithromycin for the treatment of babesiosis..  N Engl J Med,  343  (20): (1454-8).  [PMID:11078770] [10.1021/op500134e]
2. Boggild AK, Parise ME, Lewis LS, Kain KC.  (2007)  Atovaquone-proguanil: report from the CDC expert meeting on malaria chemoprophylaxis (II)..  Am J Trop Med Hyg,  76  (2): (208-23).  [PMID:17297027] [10.1021/op500134e]
3. Painter HJ, Morrisey JM, Mather MW, Vaidya AB.  (2007)  Specific role of mitochondrial electron transport in blood-stage Plasmodium falciparum..  Nature,  446  (7131): (88-91).  [PMID:17330044] [10.1021/op500134e]
4. Fisher N, Abd Majid R, Antoine T, Al-Helal M, Warman AJ, Johnson DJ, Lawrenson AS, Ranson H, O'Neill PM, Ward SA et al..  (2012)  Cytochrome b mutation Y268S conferring atovaquone resistance phenotype in malaria parasite results in reduced parasite bc1 catalytic turnover and protein expression..  J Biol Chem,  287  (13): (9731-41).  [PMID:22282497] [10.1021/op500134e]
5. Canfield CJ, Pudney M, Gutteridge WE.  (1995)  Interactions of atovaquone with other antimalarial drugs against Plasmodium falciparum in vitro..  Exp Parasitol,  80  (3): (373-81).  [PMID:7729473] [10.1021/op500134e]
6. Vaidya AB, Lashgari MS, Pologe LG, Morrisey J.  (1993)  Structural features of Plasmodium cytochrome b that may underlie susceptibility to 8-aminoquinolines and hydroxynaphthoquinones..  Mol Biochem Parasitol,  58  (1): (33-42).  [PMID:8459834] [10.1021/op500134e]
7. Hughes W, Leoung G, Kramer F, Bozzette SA, Safrin S, Frame P, Clumeck N, Masur H, Lancaster D, Chan C et al..  (1993)  Comparison of atovaquone (566C80) with trimethoprim-sulfamethoxazole to treat Pneumocystis carinii pneumonia in patients with AIDS..  N Engl J Med,  328  (21): (1521-7).  [PMID:8479489] [10.1021/op500134e]
8. Looareesuwan S, Viravan C, Webster HK, Kyle DE, Hutchinson DB, Canfield CJ.  (1996)  Clinical studies of atovaquone, alone or in combination with other antimalarial drugs, for treatment of acute uncomplicated malaria in Thailand..  Am J Trop Med Hyg,  54  (1): (62-6).  [PMID:8651372] [10.1021/op500134e]
9. Srivastava IK, Rottenberg H, Vaidya AB.  (1997)  Atovaquone, a broad spectrum antiparasitic drug, collapses mitochondrial membrane potential in a malarial parasite..  J Biol Chem,  272  (7): (3961-6).  [PMID:9020100] [10.1021/op500134e]
10. Liu Bin, Zheng Xin, Li Jiajun, Yao Peng, Guo Peng, Liu Wei, Zhao Gaoping.  (2023)  Atovaquone inhibits colorectal cancer metastasis by regulating PDGFRβ/NF-κB signaling pathway.  BMC CANCER,  23  (1): (1-13).  [PMID:37932661] [10.1186/s12885-023-11585-9]
11. Yifan Zhao, Min Zhang, Bai Lv, Guanghe Xue, Huimei Jiang, Gang Chen, Yi Ma, Yong Sun, Jie Cao.  (2023)  “Closed-Loop” O2-Economizer Induced In Situ Therapeutic Vaccine against Hypoxic Tumors.  ACS Nano,    (15):   [PMID:37877944] [10.1021/acsnano.3c05034]
12. Wenzhe Yang, Xue Pan, Peng Zhang, Xue Yang, Huashi Guan, Huan Dou, Qian Lu.  (2023)  Defeating Melanoma Through a Nano-Enabled Revision of Hypoxic and Immunosuppressive Tumor Microenvironment.  International Journal of Nanomedicine,      [PMID:37435153] [10.2147/IJN.S414882]
13. Wenhao Gao, Jialiang Zhang, Weifeng Wang, Zhihong Liu, Mulan Chen, Xiaomu Hu, Lingjun Zeng, Changqing Zheng, Hongtao Song, Qian Zhang.  (2022)  Drug self-delivery nanorods enhance photodynamic therapy of triple-negative breast cancer by inhibiting oxidative phosphorylation.  INTERNATIONAL JOURNAL OF PHARMACEUTICS,  621  (121775).  [PMID:35489603] [10.1016/j.ijpharm.2022.121775]
14. Dan Wang, Bin Xue, Tymish Y. Ohulchanskyy, Yubin Liu, Artem Yakovliev, Roman Ziniuk, Mengze Xu, Jun Song, Junle Qu, Zhen Yuan.  (2020)  Inhibiting tumor oxygen metabolism and simultaneously generating oxygen by intelligent upconversion nanotherapeutics for enhanced photodynamic therapy.  BIOMATERIALS,  251  (120088).  [PMID:32388167] [10.1016/j.biomaterials.2020.120088]
15. Donglin Xia, Peipei Xu, Xingyu Luo, Jianfeng Zhu, Haiying Gu, Da Huo, Yong Hu.  (2019)  Overcoming Hypoxia by Multistage Nanoparticle Delivery System to Inhibit Mitochondrial Respiration for Photodynamic Therapy.  ADVANCED FUNCTIONAL MATERIALS,  29  (13): (1807294).  [PMID:] [10.1002/adfm.201807294]

Solution Calculators

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