Levamisole
Title: Levamisole
CAS Registry Number: 14769-73-4
CAS Name: (6S)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole
Additional Names: (-)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
Trademarks: Levovermax (Virbac); Totalon (Mallinckrodt)
Molecular Formula: C11H12N2S
Molecular Weight: 204.29
Percent Composition: C 64.67%, H 5.92%, N 13.71%, S 15.70%
Literature References: Biological response modifier with anthelmintic activity. Prepn of racemate: A. H. M. Raeymaekers et al., US 3274209 (1966 to Janssen); eidem, J. Med. Chem. 9, 545 (1966). Pharmacology: D. Thienpoint et al., Nature 209, 1084 (1966). Prepn and abs config of isomers: A. H. M. Raeymaekers et al., Tetrahedron Lett. 1967, 1467. See also: M. W. Bullock et al., J. Med. Chem. 11, 169 (1968); US 3565907 (1971 to Am. Cyanamid); Dewar et al., US 3579530 (1971 to ICI). Stereospecific inhibition of succinic dehydrogenase: H. Van den Bossche, P. A. J. Janssen, Biochem. Pharmacol. 18, 35 (1969). Exptl effect on IL-1 production: E. S. Kimball, Ann. N.Y. Acad. Sci. 685, 259 (1993). Review of pharmacology: H. Schneiden, Int. J. Immunopharmacol. 3, 9 (1981); of clinical use in parasitic infections: M. J. Miller, Drugs 20, 122-130 (1980). Determn in animal tissues by ELISA: J. J. Silverlight, R. Jackman: Analyst 119, 2705 (1994); by LC-MS: A. Cannavan et al., ibid. 120, 331 (1995). Clinical trial with fluorouracil in colon cancer: C. G. Moertel et al., Ann. Intern. Med. 122, 321 (1995). Review of immunopharmacology and clinical trials in cancer treatment: H. C. Stevenson et al., J. Clin. Oncol. 9, 2052-2066 (1991); M. De Brabander et al., Anticancer Res. 12, 177-188 (1992); W. K. Amery, J. P. Bruynseels, Int. J. Immunopharmacol. 14, 481-486 (1992).
Properties: mp 60-61.5°. [a]D25 -85.1° (c = 10 in chloroform).
Melting point: mp 60-61.5°
Optical Rotation: [a]D25 -85.1° (c = 10 in chloroform)
 
Derivative Type: Hydrochloride
CAS Registry Number: 16595-80-5
Manufacturers' Codes: R-12564
Trademarks: Ascaridil (Cilag); Decaris (Janssen); Ergamisol (Janssen); Levacide (Norbrook); Levadin (Univet); Levasole (Mallinckrodt); Meglum (Bago); Nemicide (Coopers); Nilverm (Mallinckrodt); Ripercol (Am. Cyanamid); Solaskil (RPR); Spartakon (Janssen); Tramisol (Am. Cyanamid)
Molecular Formula: C11H12N2S.HCl
Molecular Weight: 240.75
Percent Composition: C 54.88%, H 5.44%, N 11.64%, S 13.32%, Cl 14.73%
Properties: mp 227-229°. [a]D20 -124 ± 2° (c = 0.9, water). Sol in water. Stable in aq acid media.
Melting point: mp 227-229°
Optical Rotation: [a]D20 -124 ± 2° (c = 0.9, water)
 
Derivative Type: DL-Form
CAS Registry Number: 5036-02-2
Additional Names: Tetramisole; tetramizole
Properties: Crystals, mp 87-89°.
Melting point: mp 87-89°
 
Derivative Type: DL-Form hydrochloride
CAS Registry Number: 5086-74-8
Manufacturers' Codes: Bayer 9051; McN-JR-8299; R-8299
Properties: Crystals, mp 264-265°. Sol in water (21 g/100 ml at 20°), methanol, propylene glycol; sparingly sol in ethanol. Slightly sol in chloroform, hexane, acetone. LD50 in mice, rats (mg/kg): 22, 24 i.v.; 84, 130 s.c.; 210, 480 orally (Thienpoint).
Melting point: mp 264-265°
Toxicity data: LD50 in mice, rats (mg/kg): 22, 24 i.v.; 84, 130 s.c.; 210, 480 orally (Thienpoint)
 
Derivative Type: D-(+)-Form
Additional Names: Dexamisole
Properties: mp 60-61.5°. [a]D25 +85.1° (c = 10 in chloroform).
Melting point: mp 60-61.5°
Optical Rotation: [a]D25 +85.1° (c = 10 in chloroform)
 
Derivative Type: D-(+)-Form hydrochloride
Manufacturers' Codes: R-12563
Properties: mp 227-227.5°. [a]D20 +125° (c = 0.7 in water).
Melting point: mp 227-227.5°
Optical Rotation: [a]D20 +125° (c = 0.7 in water)
 
Therap-Cat: Anthelmintic (nematodes); immunomodulator.
Therap-Cat-Vet: Anthelmintic (Nematodes).
Keywords: Anthelmintic (Nematodes); Immunomodulator.

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