ID: ALA2018453

Max Phase: Preclinical

Molecular Formula: C11H17NO2

Molecular Weight: 195.26

Molecule Type: Small molecule

Representations

Synonyms (1): Rac-M-Hydroxymexiletine
Synonyms from Alternative Forms(1):

Canonical SMILES:  Cc1ccc(O)c(C)c1OCC(C)N

Standard InChI:  InChI=1S/C11H17NO2/c1-7-4-5-10(13)9(3)11(7)14-6-8(2)12/h4-5,8,13H,6,12H2,1-3H3

Standard InChI Key:  LBHCZYGJQAXJSW-UHFFFAOYSA-N

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

Properties

Molecular Weight: 195.26

Molecular Weight (Monoisotopic): 195.1259

AlogP: 1.74

#Rotatable Bonds: 3

Polar Surface Area: 55.48

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.38

CX Basic pKa: 9.45

CX LogP: 1.87

CX LogD: 0.09

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.77

Np Likeness Score: 0.28

References

1. Catalano A, Desaphy JF, Lentini G, Carocci A, Di Mola A, Bruno C, Carbonara R, De Palma A, Budriesi R, Ghelardini C, Perrone MG, Colabufo NA, Conte Camerino D, Franchini C..  (2012)  Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.,  55  (3): [PMID:22191686] [10.1021/jm201197z]

2. Catalano A, Budriesi R, Bruno C, Di Mola A, Defrenza I, Cavalluzzi MM, Micucci M, Carocci A, Franchini C, Lentini G..  (2013)  Searching for new antiarrhythmic agents: evaluation of meta-hydroxymexiletine enantiomers.,  65  [PMID:23777871] [10.1016/j.ejmech.2013.05.008]

Source

Source(1):

• Scientific Literature