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

CAS: 95233-18-4 Cat. No.: A151027 Fórmula: C₂₂H₁₉ClO₃ Peso molecular: 366.84 Número EC: 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) | Ácido hexil salicílico | KUCQYCKVKVOKAY-CTYIDZIISA-N | SpecPlus_000686 | trans-2-(4-(4-c

Storage

Conservar a -20°C

Shipped In

Hielera + almohadillas de hielo

Descripción general

La atovacuona es un medicamento utilizado para tratar o prevenir la neumonía por Pneumocystis, la toxoplasmosis, la malaria y la babesia. Los estándares secundarios farmacéuticos para su aplicación en el control de calidad proporcionan a los laboratorios farmacéuticos y a los fabricantes una alternativa cómoda y rentable a la preparación de estándares de trabajo internos. La atovacuona pertenece a la clase de las naftoquinonas con una actividad de amplio espectro contra las infecciones parasitarias, incluyendo la malaria, la toxoplasmosis y la neumonía por Pneumocystis. Es un potente compuesto antiprotozoario que ayuda a colapsar el potencial de la membrana mitocondrial en el parásito de la malaria.

Specifications

Sinónimos

ATOVAQUONE [MI] | 2-(TRANS-4-(4-CHLOROPHENYL)CYCLOHEXYL)-3-HYDROXY-1,4-NAPHTHALENEDIONE | Atovaquona | cis-Atovaquone | ATOVAQUONE [USAN] | CIS-ATOVAQUONE (RACEMIC) | Ácido hexil salicílico | KUCQYCKVKVOKAY-CTYIDZIISA-N | SpecPlus_000686 | trans-2-(4-(4-c

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

La atovacuona es un antiprotozoario inhibidor del transporte mitocondrial de electrones; antipalúdico; antineumocístico, y también se ha utilizado para tratar la toxoplasmosis. Es un análogo de la proteína mitocondrial protozoaria ubiquinona, y actúa inhi

Condiciones de almacenamiento de almacenamiento

Conservar a -20°C

Enviado en

Hielera + almohadillas de hielo

Grado

Moligand™

Nota

Siempre que sea posible, prepare y utilice las soluciones el mismo día. Sin embargo, si necesita preparar soluciones madre con antelación, le recomendamos que almacene la solución como alícuotas en viales herméticamente cerrados a -20°C. Por lo general, podrán utilizarse durante un mes. Antes de su uso, y antes de abrir el vial, le recomendamos que deje que el producto se equilibre a temperatura ambiente durante al menos 1 hora. ¿Necesita más consejos sobre solubilidad, uso y manipulación? Visite nuestra página de preguntas frecuentes (FAQ) para obtener más información.

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488185008
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488185008
• Sonrisas canónicas: 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
• Isómeros SMILES: C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
• WGK Alemania: 3
• RTECS: QJ5616500
• Peso molecular: 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
    • Clase Naphthalenes
      • Subclass Naphthoquinones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: 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
• Descripción: 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

Propiedades químicas y físicas

• Solubilidad: Insoluble in water; Very soluble in Tetrahydrofuran; Slightly soluble in Acetone; Insoluble in Methanol
• Sensibilidad: heat sensitive
• Punto de fusión (°C): 223 °C
• Peso molecular: 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

Referencias

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,      [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,      [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,      [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]

7. Enqin Zheng, Wenhao Gao, Qingyu Lu, Xiaoliang Deng, Shiting Xu, Zhihong Liu, Lingjun Zeng, Linlin Liu, Qian Zhang, Hongtao Song.  (2025)  Self-assembled metal-coordinated nanoparticles for synergistic energy metabolism inhibition and low-temperature photothermal therapy.  INTERNATIONAL JOURNAL OF PHARMACEUTICS,      [PMID:40089042] [10.1016/j.ijpharm.2025.125467]

8. Xiaoliang Deng, Xianquan Feng, Xiaohui Tang, Zhihui Zheng, Da Zheng, Enqin Zheng, Lingjun Zeng, Shiying Xu, Boxin Chen, Qian Zhang, Zhihong Liu, Hongtao Song.  (2025)  Self-Delivery Nanotherapeutics for Tumor Low-Temperature Photothermal Immunotherapy through Cascade Heat Shock Protein and Inflammation Inhibition.  ACS Applied Materials & Interfaces,      [PMID:40735962] [10.1021/acsami.5c10905]

9. Yilin Wang, Wenting Cheng, Yang Chen, Hailong Tian, Canhua Huang, Ka Li.  (2025)  Endoplasmic reticulum-mitochondria dual-targeting nanoplatform suppresses cancer stemness and enhances colorectal cancer immunotherapy.  JOURNAL OF CONTROLLED RELEASE,      [PMID:40945535] [10.1016/j.jconrel.2025.114230]

10. Shiying Xu, Lina Wu, Boxin Chen, Xiaoliang Deng, Zhihui Zheng, Fei Wu, Lingjun Zeng, Changqing Zheng, Xiaomu Hu, Aiwen Huang, Xin Zhou, Xianquan Feng, Zhihong Liu.  (2025)  A self-delivery albumin nanomedicine amplified photodynamic therapy against esophageal cancer through COX-2/PGE2 interruption and regulation of mitochondrial respiratory.  International Journal of Pharmaceutics-X,      [PMID:41089759] [10.1016/j.ijpx.2025.100407]