1-[4-(Benzothiazol-2-yl-methyl-amino)-piperidin-1-yl]-3-(3,4-difluoro-phenoxy)-propan-2-ol (Lubeluzole)

ID: ALA281724

Chembl Id: CHEMBL281724

Cas Number: 144665-07-6

PubChem CID: 65998

Max Phase: Phase

Molecular Formula: C22H25F2N3O2S

Molecular Weight: 433.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Prosynap | R-87926 | Lubeluzole|144665-07-6|Prosynap|R-87926|CHEMBL281724|V2SIB71583|(2S)-1-[4-[1,3-benzothiazol-2-yl(methyl)amino]piperidin-1-yl]-3-(3,4-difluorophenoxy)propan-2-ol|(S)-1-(4-(benzo[d]thiazol-2-yl(methyl)amino)piperidin-1-yl)-3-(3,4-difluorophenoxy)propan-2-ol|Lubeluzole [INN]|Lubeluzole [USAN:INN:BAN]|UNII-V2SIB71583|Prosynap (TN)|R 87926|LUBELUZOLE [MI]|Lubeluzole dihydrochloride|Lubeluzole (USAN/INN)|R 86926; R 87926|LUBELUZOLE [USAN]|LUBELUZOLE [MART.]|LUBELUZOLE [WHO-DD]|SCHShow More⌵

Canonical SMILES:  CN(c1nc2ccccc2s1)C1CCN(C[C@H](O)COc2ccc(F)c(F)c2)CC1

Standard InChI:  InChI=1S/C22H25F2N3O2S/c1-26(22-25-20-4-2-3-5-21(20)30-22)15-8-10-27(11-9-15)13-16(28)14-29-17-6-7-18(23)19(24)12-17/h2-7,12,15-16,28H,8-11,13-14H2,1H3/t16-/m0/s1

Standard InChI Key:  OZFSWVOEXHGDES-INIZCTEOSA-N

Alternative Forms

1. Parent:

   

   ALA281724

   LUBELUZOLE

2. Alternative Forms:

   

   ALA281724

   LUBELUZOLE CHLORIDE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 433.52

Molecular Weight (Monoisotopic): 433.1636

AlogP: 3.92

#Rotatable Bonds: 7

Polar Surface Area: 48.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.86

CX LogP: 4.23

CX LogD: 3.64

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.61

Np Likeness Score: -2.12

References

1. Anger T, Madge DJ, Mulla M, Riddall D..  (2001)  Medicinal chemistry of neuronal voltage-gated sodium channel blockers.,  44  (2): [PMID:11170622] [10.1021/jm000155h]

2. Maillard MC, Perlman ME, Amitay O, Baxter D, Berlove D, Connaughton S, Fischer JB, Guo JQ, Hu LY, McBurney RN, Nagy PI, Subbarao K, Yost EA, Zhang L, Durant GJ..  (1998)  Design, synthesis, and pharmacological evaluation of conformationally constrained analogues of N,N'-diaryl- and N-aryl-N-aralkylguanidines as potent inhibitors of neuronal Na+ channels.,  41  (16): [PMID:9685245] [10.1021/jm980124a]

3. Grauert M, Bechtel WD, Weiser T, Stransky W, Nar H, Carter AJ..  (2002)  Synthesis and structure-activity relationships of 6,7-benzomorphan derivatives as use-dependent sodium channel blockers for the treatment of stroke.,  45  (17): [PMID:12166948] [10.1021/jm020875j]

4. Berellini G, Springer C, Waters NJ, Lombardo F..  (2009)  In silico prediction of volume of distribution in human using linear and nonlinear models on a 669 compound data set.,  52  (14): [PMID:19603833] [10.1021/jm9004658]

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

6. Cavalluzzi MM, Viale M, Bruno C, Carocci A, Catalano A, Carrieri A, Franchini C, Lentini G..  (2013)  A convenient synthesis of lubeluzole and its enantiomer: evaluation as chemosensitizing agents on human ovarian adenocarcinoma and lung carcinoma cells.,  23  (17): [PMID:23886686] [10.1016/j.bmcl.2013.06.077]

7. Bruno C, Cavalluzzi MM, Rusciano MR, Lovece A, Carrieri A, Pracella R, Giannuzzi G, Polimeno L, Viale M, Illario M, Franchini C, Lentini G..  (2016)  The chemosensitizing agent lubeluzole binds calmodulin and inhibits Ca(2+)/calmodulin-dependent kinase II.,  116  [PMID:27043269] [10.1016/j.ejmech.2016.03.045]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names