U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C17H18F3NO.C2H2O4
Molecular Weight 399.361
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUOXETINE OXALATE

SMILES

OC(=O)C(O)=O.CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C2=CC=CC=C2

InChI

InChIKey=CKOSCBUBUNGPOY-UHFFFAOYSA-N
InChI=1S/C17H18F3NO.C2H2O4/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20;3-1(4)2(5)6/h2-10,16,21H,11-12H2,1H3;(H,3,4)(H,5,6)

HIDE SMILES / InChI

Molecular Formula C2H2O4
Molecular Weight 90.0349
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H18F3NO
Molecular Weight 309.3261
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

LY94939 was discovered as a result of efforts to develop agents that inhibit the uptake of 5-HT from the synaptic cleft. A selected analogue of LY94939, the compound LY82816 (3-p-trifluoromethyl-phenoxyN-methyl-3-phenylpropylamine oxalate or (fluoxetine oxalate), which was a secondary amine (later named as fluoxetine oxalate), and its primary amine or N-demethylated compound (later named as norfluoxetine), were the most potent inhibitors of [3 H]-5-HT uptake in nerve endings, with Ki values of 0.07 uM. The first salt form of fluoxetine tested in serotonin reuptake assays in the early 1970s was the oxalate salt (LY82816); however, the marketed version is the hydrochloride salt (fluoxetine hydrochloride (LY110140), or Prozac.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
17.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
Case history: the discovery of fluoxetine hydrochloride (Prozac).
2005 Sep
Patents

Sample Use Guides

In Vitro Use Guide
LY82816 (fluoxetine oxalate) was the most potent and selective 5-HT uptake inhibitor (NE IC50 = 2.7 uM, 5-HT IC50 = 17 nM, >150-fold selective) selective)
Substance Class Chemical
Created
by admin
on Tue Oct 22 19:18:38 UTC 2019
Edited
by admin
on Tue Oct 22 19:18:38 UTC 2019
Record UNII
640AZ74IZB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUOXETINE OXALATE
MI  
Common Name English
N-METHYL-3-(P-TRIFLUOROMETHYLPHENOXY)-3-PHENYLPROPYLAMINE OXALATE
Common Name English
FLUOXETINE OXALATE [MI]
Common Name English
BENZENEPROPANAMINE, N-METHYL-.GAMMA.-(4-(TRIFLUOROMETHYL)PHENOXY)-, ETHANEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
MERCK INDEX
M5487
Created by admin on Tue Oct 22 19:18:38 UTC 2019 , Edited by admin on Tue Oct 22 19:18:38 UTC 2019
PRIMARY Merck Index
PUBCHEM
13013909
Created by admin on Tue Oct 22 19:18:38 UTC 2019 , Edited by admin on Tue Oct 22 19:18:38 UTC 2019
PRIMARY
CAS
114414-02-7
Created by admin on Tue Oct 22 19:18:38 UTC 2019 , Edited by admin on Tue Oct 22 19:18:38 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE