PHR1591

Atovaquone

Pharmaceutical Secondary Standard; Certified Reference Material

• Synonym(s): Atovaquone, Mepron, trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
• Empirical Formula (Hill Notation): C₂₂H₁₉ClO₃
• CAS Number: 95233-18-4
• Molecular Weight: 366.84
• UNSPSC Code: 41116107
• NACRES: NA.24

Properties

• grade: certified reference material; pharmaceutical secondary standard
• Quality Level: 300
• Agency: traceable to Ph. Eur. Y0001572; traceable to USP 1044651
• API family: atovaquone
• CofA: current certificate can be downloaded
• packaging: pkg of 500 mg
• technique(s): HPLC: suitable; gas chromatography (GC): suitable
• application(s): pharmaceutical (small molecule)
• format: neat
• storage temp.: 2-8°C
• SMILES string: OC1=C([C@H]2CC[C@@H](CC2)c3ccc(Cl)cc3)C(=O)c4ccccc4C1=O
• 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-
• InChI key: KUCQYCKVKVOKAY-CTYIDZIISA-N

Description

General description

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.

Application

Atovaquone may be used as a pharmaceutical secondary reference standard for the determination of the analyte in plasma samples by liquid-liquid extraction followed by reversed-phase high-performance liquid chromatography with ultraviolet detection.

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Biochem/physiol Actions

Atovaquone 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 bc(1) complex via interactions with the Rieske iron-sulfur protein and cytochrome b in the ubiquinol oxidation pocket.

Analysis Note

These secondary standards offer multi-traceability to the USP, EP and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAA4707 in the slot below. This is an example certificate only and may not be the lot that you receive.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable