levamisole-HCl;6-Phenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazole hydrochloride

ID: ALA554891

Cas Number: 4641-34-3

PubChem CID: 68628

Product Number: T424377, Order Now?

Max Phase: Unknown

Molecular Formula: C11H13ClN2S

Molecular Weight: 204.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Levamisole dl-form hydrochloride | Tetramisole hydrochloride | Tetramisole hydrochloride, dl- | MCN-JR-8299-11 | NSC-170985 | R 8299 | Tetramisole hydrochloride|5086-74-8|Anthelvet|Tetramisole HCl|Citarin|Concurat|Tetramisole (hydrochloride)|Ascarotrat|Nilverom|Ripercol|Nilverm|Pig Wormer|Solaskil hydrochloride|McN-JR-8299-11|McN JR 8299|R 8299|6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole hydrochloride|Tetramisole hydrochloride [USAN]|6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hShow More⌵

Canonical SMILES:  Cl.c1ccc(C2CN3CCSC3=N2)cc1

Standard InChI:  InChI=1S/C11H12N2S.ClH/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10;/h1-5,10H,6-8H2;1H

Standard InChI Key:  LAZPBGZRMVRFKY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    0.7167    1.6208    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1458    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833    0.5833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1458   -1.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5083    0.5833    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5083   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167    0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  2  1  0
  5  3  1  0
  6  4  1  0
  7  2  1  0
  8  5  1  0
  9  4  1  0
 10  7  1  0
 11  8  2  0
 12  8  1  0
 13 11  1  0
 14 12  2  0
 15 13  2  0
  9 10  1  0
  5  6  1  0
 14 15  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 204.30

Molecular Weight (Monoisotopic): 204.0721

AlogP: 2.15

#Rotatable Bonds: 1

Polar Surface Area: 15.60

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.98

CX LogP: 2.36

CX LogD: 2.22

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.70

Np Likeness Score: -0.47

References

1. Weikert RJ, Bingham S, Emanuel MA, Fraser-Smith EB, Loughhead DG, Nelson PH, Poulton AL..  (1991)  Synthesis and anthelmintic activity of 3'-benzoylurea derivatives of 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole.,  34  (5): [PMID:2033588] [10.1021/jm00109a015]

2. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

3. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

11. Li C, Lee MH, Sartorelli AC..  (1979)  Synthesis and biological evaluation of tetramisole analogues as inhibitors of alkaline phosphatase of the 6-thiopurine-resistant tumor sarcoma 180/TG.,  22  (9): [PMID:490546] [10.1021/jm00195a003]

12. Kinnamon KE, Steck EA, Hanson WL, Chapman WL..  (1977)  In search of anti-Trypanosoma cruzi drugs: new leads from a mouse model.,  20  (6): [PMID:69024] [10.1021/jm00216a001]

13. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• SARS-CoV-2 Screening Data 2020-21