FEMOXETINE

ID: ALA94739

Max Phase: Phase

Molecular Formula: C20H25NO2

Molecular Weight: 311.43

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Representations

Synonyms (1): Femoxetine
Synonyms from Alternative Forms(1):

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

Associated Targets(non-human)

Staphylococcus aureus 210822 Activities

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus 284745 Activities

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Dopamine transporter 139 Activities

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Norepinephrine transporter 42 Activities

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Serotonin transporter 150 Activities

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus 775804 Activities

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Quinolone resistance protein norA 2171 Activities

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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

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: 0
#RO5 Violations: 0	HBA (Lipinski): 3	HBD (Lipinski): 0	#RO5 Violations (Lipinski): 0
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]