Levamisole hydrochloride

An imidazothiazole anthelmintic used primarily in veterinary medicine to treat gastrointestinal and pulmonary nematode infections. Levamisole activates nicotinic acetylcholine receptors in nematode muscle, causing sustained depolarization, spastic paralysis, and expulsion of the parasites. It also exhibits immunomodulatory properties and was formerly used in human medicine for selected parasitic infections and as an adjunct in cancer therapy. Human use has been substantially restricted because of serious adverse effects, including agranulocytosis and vasculitis

CAS Number: 16595-80-5

Molecular Mass: 240.75 g/mol

Formula: C₁₁H₁₃ClN₂S

Smiles: Cl.c1ccc([C@H]2CN3CCSC3=N2)cc1

Synonymes:

Levamisole hydrochloride, 16595-80-5, Levamisole HCl, Ergamisol, Ascaridil, Tramisol, Decaris, Levasole, Solaskil, NSC-177023, Spartakon l, L-narpenol, R 12,564, L-Tetramisole hydrochloride, R 12564, DTXSID7047518, Tetramisole hydrochloride, (s)-, Levamisoli hydrochloridum, DL9055K809, Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (S)-, DTXCID5027518, R 12654, R-12564, NSC177023, Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (6S)-, Ergamisole, Immunol, Trimisol, LevaMed, Tramisol Gel, Ripercol L, PROHIBIT, Cloridrato de Levamizol, RefChem:5942, Hydrochloride, Levamisole, LevaMed Soluble Pig Wormer, Levasole Soluble Pig Wormer, Levasole Cattle Wormer Bolus, LevaMed Soluble Drench Powder, Prohibit Soluble Drench Powder, Ripercol L Soluble Drench Powder, ICI-59623, RP-20605, Ripercol L Bolus, Tramisol Cattle Wormer Bolus, Ripercol L, Tramisol Soluble Drench Powder for Sheep, Ripercol L Wormer Oblets, Tramisol Sheep Wormer Oblets, Levasole Sheep Wormer Bolus, Tramisole Sheep Wormer Oblets Tablets, (S)-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole Monohydrochloride, 240-654-6, Levamisole Soluble Drench Powder, Levasole, Levasole Soluble Drench Powder, Tramisol Soluble Drench Powder, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride, Tramisole, Levamisol hydrochloride, Niratic hydrochloride, Stimamizol hydrochloride, Niratic-puron hydrochloride, R-12,564, (-)-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole monohydrochloride, MFCD00012675, Dekaris, Levacide, Levadin, Nemicide, Meglum, Nilverm forte, Worm-chek, (6S)-6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole hydrochloride, Ripercol-L, Citarin L, Levomysol hydrochloride, Levamisole (hydrochloride), (6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole, hydrochloride, KW 2LE-T, SMR001230807, KW-2-LE-T, Levamisole hydrochloride [USAN], Levamisole Hydrochloride (1.0 mg/mL in Methanol), SR-01000075969, EINECS 240-654-6, 74191-78-9, (-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole Hydrochloride, UNII-DL9055K809, LEV hydrochloride, Ergamisol (TN), NCGC00094446-03, Prestwick_294, Levamisole hydrochloride [USAN:USP], Levamisole HCl(Ergamisol), Levamisole hydrochloride RS, 16595-80-5 (HCL), L-(-)-2,3,5,6-Tetrahydro-6-phenyl-imidazo(2,1-b)thiazole hydrochloride, Ergamisol (TN) (Janssen), CAS-16595-80-5, Levamisole hydrochloride CRS, CHEMBL1770, SCHEMBL19226, BMK1-H6, Imidazo[2, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, MLS002153440, MLS002222198, MLS002695941, orb134393, SPECTRUM1503245, CHEBI:6433, Levamisole hydrochloride (USP), MSK5587A, orb3139781, GLXC-07877, HMS1568F05, HMS1922M11, MSK5587A-100M, Levamisole Hydrochloride (Ergamisol), MSK5587A-1000M, Tox21_111282, Tox21_500690, CCG-40301, EBC-06511, HY-13666R, LEVAMISOLE HYDROCHLORIDE [MI], s1939, Levamisole HCl - Bio-X trade mark, LEVAMISOLE HYDROCHLORIDE [JAN], AKOS015951350, Levamisole (hydrochloride) (Standard), Tox21_111282_1, FL29670, KW-2299, LP00690, Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (-)-, Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, L-(-)-, LEVAMISOLE HYDROCHLORIDE [MART.], LEVAMISOLE HYDROCHLORIDE [USP-RS], LEVAMISOLE HYDROCHLORIDE [WHO-DD], LEVAMISOLE HYDROCHLORIDE [WHO-IP], NCGC00094046-01, NCGC00261375-01, NCGC00263461-01, AC-23973, AS-13370, BL166245, HY-13666, EU-0100690, L0231, LEVAMISOLE HYDROCHLORIDE [GREEN BOOK], NS00076395, (-)-Tetramisole hydrochloride, >=99% (GC), LEVAMISOLE HYDROCHLORIDE [ORANGE BOOK], C07906, D00750, D78137, EN300-122366, L 9756, Levamisole Hydrochloride (1 mg/mL in Methanol), LEVAMISOLE HYDROCHLORIDE [EP MONOGRAPH], LEVAMISOLE HYDROCHLORIDE [USP MONOGRAPH], LEVAMISOLI HYDROCHLORIDUM [WHO-IP LATIN], F094384, Levamisole hydrochloride for system suitability CRS, SR-01000075969-1, SR-01000075969-6, Levamisol hydrochloride 100 microg/mL in Acetonitrile, Q27107205, Levamisole hydrochloride Solution in Methanol, 100ug/mL, Z1550648764, Levamisol hydrochloride, VETRANAL(TM), analytical standard, Levamisole hydrochloride Solution in Methanol, 1000ug/mL, Levamisole Hydrochloride 1.0 mg/ml in Methanol (as free base), Imidazo[2, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (-)-, Imidazo[2, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (S)-, (-)-2,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole monohydrochloride, (6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole, hydrochloride, (S)-(-)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazolehydrochloride, Imidazo[2, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, L-(-)-, L(-)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole hydrochloride, Levamisole Hydrochloride Working Standard (Secondary Reference Standard), Levamisole hydrochloride, European Pharmacopoeia (EP) Reference Standard, (6S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole--hydrogen chloride (1/1), Levamisole Hydrochloride, Pharmaceutical Secondary Standard, Certified Reference Material, Levamisole hydrochloride, United States Pharmacopeia (USP) Reference Standard, Levamisole hydrochloride for system suitability, European Pharmacopoeia (EP) Reference Standard

Bioactivity: Anthelmintic agent; agonist of nematode nicotinic acetylcholine receptors; immunomodulatory agent

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	283.15	-	4.851	[113]
1-Butanol	288.15	-	6.239	[113]
1-Butanol	293.15	-	8.206	[113]
1-Butanol	298.15	-	10.68	[113]
1-Butanol	303.15	-	14.2	[113]
1-Butanol	308.15	-	18.26	[113]
1-Butanol	313.15	-	23.11	[113]
1-Butanol	318.15	-	28.88	[113]
1-Butanol	323.15	-	35.94	[113]
1-Hexanol	283.15	-	1.415	[113]
1-Hexanol	288.15	-	1.911	[113]
1-Hexanol	293.15	-	2.637	[113]
1-Hexanol	298.15	-	3.818	[113]
1-Hexanol	303.15	-	4.34	[113]
1-Hexanol	308.15	-	5.403	[113]
1-Hexanol	313.15	-	6.662	[113]
1-Hexanol	318.15	-	8.282	[113]
1-Hexanol	323.15	-	9.888	[113]
1-Pentanol	283.15	-	1.678	[113]
1-Pentanol	288.15	-	2.517	[113]
1-Pentanol	293.15	-	3.577	[113]
1-Pentanol	298.15	-	4.632	[113]
1-Pentanol	303.15	-	6.485	[113]
1-Pentanol	308.15	-	8.295	[113]
1-Pentanol	313.15	-	10.34	[113]
1-Pentanol	318.15	-	13.24	[113]
1-Pentanol	323.15	-	16.25	[113]
1-Propanol	283.15	-	13.46	[113]
1-Propanol	288.15	-	16.01	[113]
1-Propanol	293.15	-	20.43	[113]
1-Propanol	298.15	-	24.24	[113]
1-Propanol	303.15	-	29.06	[113]
1-Propanol	308.15	-	35.07	[113]
1-Propanol	313.15	-	41.52	[113]
1-Propanol	318.15	-	47.53	[113]
1-Propanol	323.15	-	53.65	[113]
2-Butanol	283.15	-	1.556	[113]
2-Butanol	288.15	-	1.901	[113]
2-Butanol	293.15	-	2.274	[113]
2-Butanol	298.15	-	2.738	[113]
2-Butanol	303.15	-	3.203	[113]
2-Butanol	308.15	-	3.832	[113]
2-Butanol	313.15	-	4.538	[113]
2-Butanol	318.15	-	5.436	[113]
2-Butanol	323.15	-	6.393	[113]
Dimethyl sulfoxide	293.15	-	40.07	[113]
Dimethyl sulfoxide	298.15	-	44.01	[113]
Dimethyl sulfoxide	303.15	-	47.81	[113]
Dimethyl sulfoxide	308.15	-	53.24	[113]
Dimethyl sulfoxide	313.15	-	58.68	[113]
Dimethyl sulfoxide	318.15	-	65.14	[113]
Dimethyl sulfoxide	323.15	-	73.58	[113]
Dimethyl sulfoxide	328.15	-	79.62	[113]
Dimethyl sulfoxide	333.15	-	88.81	[113]
Ethanol	283.15	-	31.61	[113]
Ethanol	288.15	-	36.86	[113]
Ethanol	293.15	-	42.18	[113]
Ethanol	298.15	-	49.56	[113]
Ethanol	303.15	-	63.28	[113]
Ethanol	308.15	-	73.36	[113]
Ethanol	313.15	-	82.6	[113]
Ethanol	318.15	-	100.3	[113]
Ethanol	323.15	-	118.6	[113]
Isoamyl Alcohol	283.15	-	2.412	[113]
Isoamyl Alcohol	288.15	-	2.983	[113]
Isoamyl Alcohol	293.15	-	4.026	[113]
Isoamyl Alcohol	298.15	-	5.164	[113]
Isoamyl Alcohol	303.15	-	6.307	[113]
Isoamyl Alcohol	308.15	-	8.778	[113]
Isoamyl Alcohol	313.15	-	11.81	[113]
Isoamyl Alcohol	318.15	-	14.69	[113]
Isoamyl Alcohol	323.15	-	18.89	[113]
Isobutanol	283.15	-	2.288	[113]
Isobutanol	288.15	-	3.425	[113]
Isobutanol	293.15	-	4.739	[113]
Isobutanol	298.15	-	6.412	[113]
Isobutanol	303.15	-	8.645	[113]
Isobutanol	308.15	-	11.54	[113]
Isobutanol	313.15	-	14.83	[113]
Isobutanol	318.15	-	19.12	[113]
Isobutanol	323.15	-	23.91	[113]
Isopropanol	283.15	-	2.728	[113]
Isopropanol	288.15	-	3.298	[113]
Isopropanol	293.15	-	4.352	[113]
Isopropanol	298.15	-	5.62	[113]
Isopropanol	303.15	-	7.013	[113]
Isopropanol	308.15	-	8.543	[113]
Isopropanol	313.15	-	9.857	[113]
Isopropanol	318.15	-	12.32	[113]
Isopropanol	323.15	-	14.52	[113]
Methanol	283.15	-	184.8	[113]
Methanol	288.15	-	221.3	[113]
Methanol	293.15	-	266.5	[113]
Methanol	298.15	-	319.4	[113]
Methanol	303.15	-	371.6	[113]
Methanol	308.15	-	436.4	[113]
Methanol	313.15	-	515.2	[113]
Methanol	318.15	-	608.8	[113]
Methanol	323.15	-	698.8	[113]
Water	283.15	-	950.8	[113]
Water	285.65	-	1033.0	[113]
Water	288.15	-	1112.0	[113]
Water	290.65	-	1200.4	[113]
Water	293.15	-	1286.1	[113]
Water	295.65	-	1388.0	[113]
Water	298.15	-	1488.7	[113]
Water	300.65	-	1583.8	[113]
Water	303.15	-	1690.0	[113]
Water	305.65	-	1807.8	[113]
Water	308.15	-	1930.8	[113]

Molecule 3D descriptors

Descriptor	Value
PMI1	290.1864
PMI2	1591.6180
PMI3	1663.8693
NPR1	0.1744
NPR2	0.9566
RadiusOfGyration	2.7136
InertialShapeFactor	0.0033
Eccentricity	0.9847
Asphericity	0.5705
SpherocityIndex	0.1921
PBF	0.6022