Atovaquone - Moligand™, ≥98% , CAS No.95233-18-4

CAS: 95233-18-4 Cat. No.: A151027 Formula: C₂₂H₁₉ClO₃ Molecular Weight: 366.84 EC Number: 630-425-2

GRADE & PURITY Moligand™, ≥98%

Synonyms

ATOVAQUONE [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

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

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.

Specifications

Synonyms

ATOVAQUONE [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 & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

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

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Note

Wherever 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.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488185008
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488185008
• Canonical Smiles: C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
• IUPAC Name: 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
• InChIKey: BSJMWHQBCZFXBR-UHFFFAOYSA-N
• 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
• Isomeric SMILES: C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
• WGK Germany: 3
• RTECS: QJ5616500
• Molecular Weight: 366.84
• Reaxy-Rn: 21564253
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=21564253&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes
      • Subclass Naphthoquinones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Naphthoquinones
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthoquinones
• Alternative Parents: Naphthols and derivatives Quinones Aryl ketones Chlorobenzenes Aryl chlorides Vinylogous acids Enols Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthoquinone - 1-naphthol - Quinone - Aryl ketone - Chlorobenzene - Halobenzene - Aryl chloride - Monocyclic benzene moiety - Aryl halide - Vinylogous acid - Ketone - Cyclic ketone - Enol - Hydrocarbon derivative - Organooxygen compound - Organochloride - Organohalogen compound - Organic oxide - Organic oxygen compound - Carbonyl group - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Insoluble in water; Very soluble in Tetrahydrofuran; Slightly soluble in Acetone; Insoluble in Methanol
• Sensitivity: heat sensitive
• Melt Point(°C): 223 °C
• Molecular Weight: 366.800 g/mol
• XLogP3: 5.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 366.102 Da
• Monoisotopic Mass: 366.102 Da
• Topological Polar Surface Area: 54.400 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 595.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1