Actarit Chemical Properties

Melting point:

173-175°C

Boiling point:

449.1±28.0 °C(Predicted)

Density 

1.288±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO, Ethanol, Methanol

form 

Solid

pka

4.34±0.10(Predicted)

color 

White to Off-White

Merck 

14,133

CAS DataBase Reference

18699-02-0(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

RTECS 

CY1542000

HS Code 

29163990

Toxicity

LD50 in male, female mice, male, female rats (mg/kg): 1.06, 1.30, 1.95, 2.03 i.p.; 5.68, 5.48, 5.48, 6.12 s.c.; 15.3, 14.7, 14.8, 15.4 orally (Toshida)

Actarit Usage And Synthesis

Description

Actarit is an orally administered disease-modifying antirheumatic drug launched in Japan. Although its structure resembles that of non-steroidal anti-inflammatory drugs, it has no effect on experimental acute inflammation and has no analgesic or antipyretic effects. Its preventative and therapeutic effects on adjuvant arthritis are mediated via modulation of production and serum level of interleukin-2 which enhances production of suppressor T-cells to the immune system, thereby, preventing development of articular lesions.

Chemical Properties

Crystalline Solid

Originator

Nippon Shlnyaku;Mltaublshl Kasel (Japan)

Uses

Antiarthritic

Uses

Chronic rheumatoid arthritis

Definition

ChEBI: Actarit is an anilide and a member of acetamides.

brand name

Orcl; Mover

Synthesis

General procedure: 1.02 mmol of p-aminophenylacetic acid (Wako Pure Pharmaceutical Industries, Ltd.) was dissolved in 50 mL of a solvent mixture of dichloromethane-methanol-water (1:3:1, v/v). Under ice bath cooling conditions, 2.12 mmol of acetic anhydride was slowly added. The reaction mixture was gradually brought to room temperature with stirring and continued to stir overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give 196.4 mg of 2-(4-acetylaminophenyl)acetic acid in 99% yield. The structure of the product was confirmed by 1H-NMR (500 MHz, CD3OD): δ 2.11 (3H, s, Ac), 3.55 (2H, s, Ph-CH2-), 7.21-7.49 (4H, m, aromatic H).

Purification Methods

Crystallise the acid from MeOH/Me2CO, aqueous EtOH or H2O. The amide has m 231o (from 50% aqueous EtOH). [Gabriel Chem Ber 15 841 1882, Cerecedo et al. J Biol Chem 42 238 1924, Tramontano et al. J Am Chem Soc 110 2282 1988, Beilstein 14 II 281.]

References

[1] Patent: EP3363463, 2018, A2. Location in patent: Paragraph 0148
[2] Asian Journal of Chemistry, 2012, vol. 24, # 4, p. 1538 - 1540
[3] Journal of the American Chemical Society, 1988, vol. 110, # 7, p. 2282 - 2286
[4] Journal of the American Chemical Society, 2009, vol. 131, p. 456 - 457
[5] Patent: WO2015/145371, 2015, A1. Location in patent: Page/Page column 40

Actarit(18699-02-0)Related Product Information

• Acetaminophen
• 4-Hydroxyphenylacetic acid
• 4-Methoxyphenylacetic acid
• 2-Hydroxyphenylacetic acid
• ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID
• dexindoprofen
• 7-Diethylamino-3-(4'-maleimidylphenyl)-4- methylcoumarin
• Phenylacetic acid
• Indobufen
• 4-Aminophenylacetic acid
• PKSI 527
• 7-Diethylamino-3-[4-(iodoacetamido)phenyl]-4-methylcoumarin
• (4-[(3-METHYL-FURAN-2-CARBONYL)-AMINO]-PHENYL)-ACETIC ACID
• Actarit-d4
• Desacetyl Actarit-d4
• Actarit
• ASISCHEM D13241
• N-(3-METHYL-4-(2-OXO-2H-CHROMEN-3-YL)PHENYL)-2-(O-TOLYLOXY)ACETAMIDE