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Atovaquone

Atovaquone structure

CAS No:
95233-18-4
Formula:
C22H19ClO3
Chemical Name:
Atovaquone
Synonyms:
1,4-Naphthalenedione,2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-;1,4-Naphthalenedione,2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-,trans-;2-[trans-4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione;566C80;566C;Atovaquone;Mepron;Mepron (antipneumocystic);BW 556C-80;BW 566C;Acuvel;Wellvone;Meprone;Samtirel
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

Atovaquone is a medication used to treat or prevent for pneumocystis pneumonia, toxoplasmosis, malaria, and babesia.Target: AntiparasiticAtovaquone (atavaquone) is a chemical compound that belongs to the class of naphthalenes. Atovaquone is a hydroxy-1,4-naphthoquinone, an analog of ubiquinone, with antipneumocystic activity [1]. Atovaquone is an anti-protozoal mitochondrial electron transport inhibitor; Antimalarial; Antipneumocystic, and has also been used to treat toxoplasmosis. It ac

Atovaquone Basic Attributes

Molecular Weight：

36684

Exact Mass：

366.84

HScode：

2914700090

Characteristics

PSA：

54.4

XLogP3：

5.2

Appearance：

yellow

Density：

1.4±0.1 g/cm3

Melting Point：

216-219 °C

Boiling Point：

542.2°C at 760 mmHg

Flash Point：

281.7±30.1 °C

Refractive Index：

1.653

Water Solubility：

Practically insoluble in water;DMSO: >10mg/mL

Storage Conditions：

-20°C Freezer

Safety Information

Transport codes：

3077

wgk germany：

hazard class code：

50/53

safety instructions：

60-61

RTECS Number：

QJ5616500

Marks：

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H413

Atovaquone Use and Manufacturing

Methods of Manufacturing

Cis-2-[4-(4-chlorophenyl)cyclohexyl]-3 -hydroxy- 1, 4-naphthoquinone (1 g, 2.7 mmol) was stirred in 8 ml concentrated HTo 1a-(4-(4-chlorophenyl)cyclohexyl)naphtho[2, 3-b]oxirene-2, 7(laH, 7aH)-dione (13.5g, 1.6 mmol) taken in a reactor was added cone. HExample 5 Preparation of the Atovaquone by Epimerization of the Cis/Trans Atovaquone with Concentrated Sulfuric Acid at +5° C.8 g (21.8 mmoles) of CIS/TRANS atovaquone in a ratio of 58/42 are added portionwise in 15 minutes to 80 ml of sulfuric acid 96percent at +5° C. At the end of the addition it is left under agitation at 5° C. for 30 minutes and the temperature is then brought to 20-25° C. The reaction mixture is poured slowly onto 230 ml of water pre-cooled to 5° C. without exceeding the internal temperature of 25° C. 340 ml of methyl ethyl ketone are added and the mixture is heated to 70° C. The acid aqueous phase is separated and the organic phase is washed with a solution of 8 g of sodium chloride in 80 ml of water, maintaining the temperature at 60° C. The organic phase is concentrated to approximately 1/6 of the initial volume by distillation of the solvent at atmospheric pressure. It is gradually cooled to 0-5° C. and maintained cold for 1 hour. The solid is filtered and washed with 10 ml of water. The damp product is dried at 45° C. at reduced pressure for 6-8 hours, providing 6.5 g of atovaquone (yield 81percent) with HPLC purity >99percent (CIS isomer=0.45percent).

Uses

Hydroxynaphthoquinone derivative that inhibits mitochondrial electron transport. Antipneumocystic beta-adrenergic blocker

Material

Cyclohexane

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