3-(4-Methoxy-phenoxymethyl)-1-methyl-4-phenyl-piperidine (femoxetine)

ID: ALA94739

Chembl Id: CHEMBL94739

Cas Number: 59859-58-4

PubChem CID: 3012003

Max Phase: Phase

Molecular Formula: C20H25NO2

Molecular Weight: 311.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Femoxetine | Femoxetine|59859-58-4|(+)-Femoxetine|Femoxetine [INN]|(3R,4S)-3-[(4-methoxyphenoxy)methyl]-1-methyl-4-phenylpiperidine|CHEMBL94739|8Y719ZLX8C|FG-4963|Femoxetina|Femoxetinum|(+)-trans-3-((p-Methoxyphenoxy)methyl)-1-methyl-4-phenylpiperidine|(3R,4S)-3-(4-Methoxy-phenoxymethyl)-1-methyl-4-phenyl-piperidine|Femoxetinum [INN-Latin]|Femoxetina [INN-Spanish]|UNII-8Y719ZLX8C|NNC-20-4963|FEMOXETINE [MI]|FEMOXETINE [MART.]|FEMOXETINE [WHO-DD]|SCHEMBL49869|fg4963|DTXSID70208576|CHEBI:135330|BDShow More⌵

Canonical SMILES:  COc1ccc(OC[C@H]2CN(C)CC[C@@H]2c2ccccc2)cc1

Standard InChI:  InChI=1S/C20H25NO2/c1-21-13-12-20(16-6-4-3-5-7-16)17(14-21)15-23-19-10-8-18(22-2)9-11-19/h3-11,17,20H,12-15H2,1-2H3/t17-,20-/m1/s1

Standard InChI Key:  OJSFTALXCYKKFQ-YLJYHZDGSA-N

Alternative Forms

1. Parent:

   

   ALA94739

   FEMOXETINE

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: 311.43

Molecular Weight (Monoisotopic): 311.1885

AlogP: 3.81

#Rotatable Bonds: 5

Polar Surface Area: 21.70

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.92

CX LogP: 3.61

CX LogD: 2.08

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -0.01

References

1. Robertson DW, Jones ND, Swartzendruber JK, Yang KS, Wong DT..  (1988)  Molecular structure of fluoxetine hydrochloride, a highly selective serotonin-uptake inhibitor.,  31  (1): [PMID:3257267] [10.1021/jm00396a030]

2. Maryanoff BE, Vaught JL, Shank RP, McComsey DF, Costanzo MJ, Nortey SO..  (1990)  Pyrroloisoquinoline antidepressants. 3. A focus on serotonin.,  33  (10): [PMID:2213832] [10.1021/jm00172a018]

3. Wei P, Kaatz GW, Kerns RJ..  (2004)  Structural differences between paroxetine and femoxetine responsible for differential inhibition of Staphylococcus aureus efflux pumps.,  14  (12): [PMID:15149651] [10.1016/j.bmcl.2004.04.018]

4. Brincat JP, Carosati E, Sabatini S, Manfroni G, Fravolini A, Raygada JL, Patel D, Kaatz GW, Cruciani G..  (2011)  Discovery of novel inhibitors of the NorA multidrug transporter of Staphylococcus aureus.,  54  (1): [PMID:21141825] [10.1021/jm1011963]

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

6. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

Source

Source(2):

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