| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H12N2S |
| Molecular Weight | 204.291 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CN2C[C@@H](N=C2S1)C3=CC=CC=C3
InChI
InChIKey=HLFSDGLLUJUHTE-SNVBAGLBSA-N
InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1
| Molecular Formula | C11H12N2S |
| Molecular Weight | 204.291 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Levamisole (the trade name Ergamisol), an anthelminthic drug with immunological properties. It also has antitumor activity when administered with 5-fluorouracil in patients with Duke's C colorectal carcinoma; however, this use was discontinued. The mechanism of the antitumor effect is unknown but has been postulated to be related to levamisole's immunomodulatory properties. Levamisole can stimulate antibody formation to various antigens, enhance T-cell responses by stimulating T-cell activation and proliferation, potentiate monocyte and macrophage functions including phagocytosis, chemotaxis and increases motility, adherence, and chemotaxis. Levamisole inhibits alkaline phosphatase and possesses cholinergic activity. The mechanism of action of levamisole as an antiparasitic agent, for example, to treat ascariasis, relates to its agonistic activity to L-subtype nicotinic acetylcholine receptors in nematode muscles. In addition, levamisole was studied for preventing relapses of the steroid-sensitive idiopathic nephrotic syndrome (SSINS). It was shown, that alone or in combination with steroids, the drug can prolong the time to relapse and prevented recurrence during one year of treatment. However, these studies also were also discontinued.
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Sample Use Guides
The combination of ERGAMISOL (levamisole hydrochloride) and 5-fluorouracil is administered according to the following dosage schedule:
Initial Therapy: Week 1 (3rd to 4th week post surgery): 5-fluorouracil 450 mg/m² i.v. push days 1 –5 and ERGAMISOL 50 mg orally t.i.d days 1 –3; Week 3 only ERGAMISOL 50 mg orally t.i.d days 1 –3. Therapy should commence 3 –4 weeks post surgery.
5-Fluorouracil (450 mg/m²) is administered by rapid i.v. injection for the first 5 days of Week 1.
ERGAMISOL 50 mg tablet is administered orally three times a day for the first 3 days of Week 1, and again on the first 3 days of Week 3.
Route of Administration:
Oral
It was examined the immunological effects of levamisole in vitro. Experiments utilized peripheral blood mononuclear cells from normal donors incubated in the presence of increasing concentrations of levamisole (0.1 to 100 micrograms/ml). Levamisole had no consistent effect on induction of 2',5'-oligoadenylate synthetase activity or indoleamine-2,3-dioxygenase activity, or production of tumor necrosis factor. Levamisole had no effect on monocyte cytotoxicity or expression of HLA-DR, HLA-DQ, HLA-DP, and the Fc receptor. Similarly, levamisole had no significant effect on NK or LAK cytotoxicity or the immunological activation of T-lymphocytes, assessed by expression of CD3, CD4, CD8, CD16, CD25, and CD56. No significant enhancement in the expression of three tumor-associated antigens (880364, NRCO-4, and ING-1) and the intercellular adhesion molecule-1 (ICAM-1) antigen on four human cancer cell lines was observed following in vitro exposure to levamisole. In conclusion, was revealed, that levamisole was not a potent modulator of the immune parameters.
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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RACEMATE -> ENANTIOMER |
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