Fluoxetine

Details

• Internal ID: 5b65d46c-6f75-4df1-ac07-4e6b096ab0ad
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Trifluoromethylbenzenes
• IUPAC Name: N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
• SMILES (Canonical): CNCCC(C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F
• SMILES (Isomeric): CNCCC(C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F
• InChI: InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3
• InChI Key: RTHCYVBBDHJXIQ-UHFFFAOYSA-N
• Popularity: 28,676 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈F₃NO
• Molecular Weight: 309.33 g/mol
• Exact Mass: 309.13404868 g/mol
• Topological Polar Surface Area (TPSA): 21.30 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.44
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 54910-89-3
• Prozac
• Pulvules
• Eufor
• Animex-On
• Fluoxetina
• Fluval
• Portal
• Fluoxetinum
• Fluoxetin
• Fluoxetina [Spanish]
• N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
• Fluoxetinum [INN-Latin]
• Fluoxetina [INN-Spanish]
• Fluoxetin ratiopharm
• Fluoxetine [USAN:INN:BAN]
• Fluoxetine-d5
• (+-)-N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine
• Fluoxetine (TN)
• UNII-01K63SUP8D
• N-Methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine
• fluoxetine (Prozac)
• NSC-283480
• (+-)-N-Methyl-3-phenyl-3-((alpha,alpha,alpha-trifluoro-p-tolyl)oxy)propylamine
• dl-3-(p-Trifluoromethylphenoxy)-N-methyl-3-phenylpropylamine
• 01K63SUP8D
• C17H18F3NO
• Methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amine
• DTXSID7023067
• CHEMBL41
• Fluoxetine (USAN/INN)
• Methyl-[3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]-amine
• NSC-758685
• Lilly-110140
• CHEBI:5118
• DTXCID903067
• 57226-07-0
• CHEBI:86990
• Benzenepropamine, N-methyl-gamma-(4-(trifluoromethyl)phenoxy)-, (+-)-
• Benzenepropanamine, N-methyl-gamma-(4-(trifluoromethyl)phenoxy)-, (+-)-
• NSC 283480
• NSC 758685
• (+/-)-Fluoxetine
• NCGC00015428-08
• N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine
• n-methyl-3-phenyl-3-(4-(trifluoromethyl)phenoxy)propan-1-amine
• Prozac (TN)
• (+) or (-)-N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine
• (+) or (-)-N-Methyl-3-phenyl-3-((alpha,alpha,alpha-trifluoro-p-tolyl)oxy)propylamine
• 3-(p-Trifluoromethylphenoxy)-N-methyl-3-phenylpropylamine
• Floxetine
• Reneuron
• (+/-)-N-Methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine
• (+/-)-N-Methyl-3-p-(p-trifluoromethylphenoxy)-3-phenylpropylamine
• (+/-)-N-Methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylamine]
• (+/-)-N-Methyl-gamma-[4-(trifluoromethyl)phenoxy]benzenepropanamine
• N-methyl-3-phenyl-3-{[4-(trifluoromethyl)phenyl]oxy}propan-1-amine
• (+/-)-N-Methyl-3-phenyl-3-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]propylamine
• FLUOXETINE (EMA EPAR VETERINARY)
• FLUOXETINE [EMA EPAR VETERINARY]
• CAS-54910-89-3
• N-Methyl-gamma-[4-(trifluoromethyl)phenoxy]benzenepropanamine
• (+-)-N-methyl-3-phenyl-3-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]propylamine
• Spectrum_001679
• FLUOXETINE [MI]
• SpecPlus_000723
• FLUOXETINE [INN]
• Prestwick0_000511
• Prestwick1_000511
• Prestwick2_000511
• Prestwick3_000511
• Spectrum2_001658
• Spectrum3_001648
• Spectrum4_000613
• Spectrum5_001518
• FLUOXETINE [USAN]
• FLUOXETINE [VANDF]
• Biomol-NT_000152
• D0TR5X
• Epitope ID:224550
• SCHEMBL8353
• LY-110140 free base
• FLUOXETINE [WHO-DD]
• Lopac0_000558
• BSPBio_000461
• BSPBio_003375
• GTPL203
• KBioGR_001166
• KBioSS_002159
• cid_62857
• DivK1c_006819
• Fluoxetine [USAN:BAN:INN]
• SPBio_001815
• SPBio_002382
• BPBio1_000354
• BPBio1_000509
• BDBM30130
• KBio1_001763
• KBio2_002159
• KBio2_004727
• KBio2_007295
• KBio3_002595
• N06AB03
• HMS2090H14
• AMY32526
• BCP28440
• HY-B0102
• Tox21_110144
• AB9783
• BBL012251
• MFCD00072041
• NS-140
• NSC283480
• STK734483
• AKOS003663021
• Tox21_110144_1
• AC-8478
• CCG-204648
• CS-O-01527
• DB00472
• SDCCGSBI-0050541.P004
• NCGC00015428-06
• NCGC00015428-07
• NCGC00015428-10
• NCGC00015428-11
• NCGC00015428-12
• NCGC00015428-13
• NCGC00015428-15
• NCGC00015428-27
• NCGC00024879-03
• NCGC00024879-04
• AS-44989
• LS-31040
• SBI-0050541.P003
• AB00053774
• FT-0626489
• D00326
• EN300-199668
• AB00053774-13
• AB00053774-14
• AB00053774_15
• AB00053774_16
• L000931
• Q422244
• BRD-A31159102-001-01-9
• BRD-A31159102-003-05-6
• BRD-A31159102-003-16-3
• SR-01000002988-18
• LY-110140;LY 110140;LY110140
• N-methyl 3-(p-trifluoromethylphenoxy)-3-phenylpropylamine
• N-Methyl-3-phenyl-3-(p-trifluoromethylphenoxy)propylamine
• Bencenoopropanamina,-N-metil-gama-[4-(trifluorometil)fenoxi]-
• Benzenepropanamine, N-methyl-?-[4-(trifluoromethyl)phenoxy]-
• N-methyl-gamma-(4-(trifluoromethyl)-phenoxy)-benzenepropanamine
• benzenepropanamine, N-methyl-gamma-[4-(trifluoromethyl)phenoxy]-
• DL-N-METHYL-3-(P-TRIFLUOROMETHYLPHENOXY)-3-PHENYLPROPYLAMINE
• N-Methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine
• N-Methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine #
• rac-N-methyl-3-phenyl-3-(4-(trifluoromethyl)phenoxy)propan-1-amine
• Benzenepropanamine, N-methyl-gamma-[4-(trifluoromethyl)phenoxy]-, (+/-)-
• N-METHYL-.GAMMA.-(4-(TRIFLUOROMETHYL)PHENOXY)BENZENEPROPANAMINE
• N-methyl-3-[4-(trifluoromethyl)phenoxy]-3-(3-tritiophenyl)propan-1-amine
• N-methyl-3-phenyl-3-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]propylamine
• (.+/-.)-N-Methyl-3-phenyl-3-[(.alpha.,.alpha.,.alpha.-trifluoro-p-tolyl)oxy]propylamine
• (.+/-.)-N-Methyl-3-phenyl-3-[(.alpha.,la,.alpha.-trifluoro-p-tolyl)oxy]propylamine
• Benzenepropanamine, N-methyl-.gamma.-[4-(trifluoromethyl)phenoxy]-, (.+.)-
• Benzenepropanamine, N-methyl-.gamma.-[4-(trifluoromethyl)phenoxy]-, (.+/-.)-
• BENZENEPROPANAMINE, N-METHYL-G-(4-(TRIFLUOROMETHYL)PHENOXY)-, (+/-)-
• (+/-)-N-METHYL-3-PHENYL-3-((.ALPHA.,ALPHA.,.ALPHA.-TRIFLUORO-P-TOLYL)OXY)PROPYLAMINE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.9286	92.86%
Subcellular localzation	Mitochondria	0.5725	57.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9291	92.91%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.8750	87.50%
BSEP inhibitior	+	0.8441	84.41%
P-glycoprotein inhibitior	-	0.7443	74.43%
P-glycoprotein substrate	-	0.8446	84.46%
CYP3A4 substrate	+	0.6340	63.40%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	+	0.6779	67.79%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	+	0.7149	71.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6756	67.56%
Carcinogenicity (trinary)	Non-required	0.7114	71.14%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.6520	65.20%
Skin corrosion	-	0.7758	77.58%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9161	91.61%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.8750	87.50%
skin sensitisation	-	0.8401	84.01%
Respiratory toxicity	+	0.9667	96.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5092	50.92%
Acute Oral Toxicity (c)	III	0.7805	78.05%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.6307	63.07%
Thyroid receptor binding	+	0.6494	64.94%
Glucocorticoid receptor binding	-	0.7332	73.32%
Aromatase binding	-	0.5099	50.99%
PPAR gamma	+	0.7852	78.52%
Honey bee toxicity	-	0.8641	86.41%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.7400	74.00%
Fish aquatic toxicity	+	0.6474	64.74%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	130 nM	IC50	PMID: 20053484
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	6.31 nM; 6.31 nM	Ki; Ki	PMID: 11262089; via Super-PRED
CHEMBL1942	P18089	Alpha-2b adrenergic receptor	1528 nM	IC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	40 nM	IC50	PMID: 26355532
CHEMBL289	P10635	Cytochrome P450 2D6	700 nM	IC50	via CMAUP
CHEMBL238	Q01959	Dopamine transporter	19500 nM; 19500 nM; 9120.11 nM; 18400 nM; 6000 nM; 18400 nM; 6000 nM; 4400 nM; 4400 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 19256502; PMID: 19014888; PMID: 23602445; PMID: 24974340; PMID: 18667309; PMID: 25221656; PMID: 18550369; PMID: 16750363; PMID: 16750359
CHEMBL240	Q12809	HERG	10 nM; 457.09 nM; 3100 nM; 10 nM; 1513.56 nM; 1513.56 nM; 1513.56 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50	via Super-PRED; PMID: 21185626; PMID: 20637635; PMID: 23919353; PMID: 18448342; PMID: 12873512; PMID: 15911273
CHEMBL264	Q9Y5N1	Histamine H3 receptor	7300 nM; 7300 nM; 7300 nM; 7300 nM	Ki; Ki; Ki; Ki	PMID: 17616397; PMID: 17307358; PMID: 17127059; PMID: 17107798
CHEMBL5514	P42858	Huntingtin	35481.3 nM	Potency	via CMAUP
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	3203 nM	IC50	via CMAUP
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	3595 nM	IC50	via CMAUP
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	1358 nM	IC50	via CMAUP
CHEMBL222	P23975	Norepinephrine transporter	440 nM; 5200 nM; 5200 nM; 1020 nM; 1303 nM; 2000 nM; 2000 nM; 4410 nM; 563 nM; 1020 nM; 6309.57 nM; 563 nM	Ki; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	via Super-PRED; PMID: 16750363; PMID: 16750359; PMID: 19256502; via CMAUP; PMID: 18550369; PMID: 18667309; PMID: 24974340; PMID: 19329313; PMID: 19014888; PMID: 23602445; PMID: 18771916
CHEMBL1293235	P02545	Prelamin-A/C	1412.5 nM	Potency	via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	26121.6 nM; 18492.7 nM; 23280.9 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	710 nM; 194 nM	IC50; IC50	via Super-PRED; via CMAUP
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	160 nM; 119 nM	IC50; IC50	via Super-PRED; via CMAUP
CHEMBL3371	P50406	Serotonin 6 (5-HT6) receptor	1661 nM	IC50	via CMAUP
CHEMBL228	P31645	Serotonin transporter	9.4 nM; 7.3 nM; 9.4 nM; 10 nM; 9.4 nM; 7.2 nM; 9.4 nM; 9.4 nM; 2.5 nM; 10 nM; 16 nM; 9.4 nM; 9.4 nM; 5.012 nM; 16 nM; 7 nM; 3.1 nM; 8.6 nM; 9.4 nM; 5.2 nM; 9.4 nM; 5.012 nM; 0.72 nM; 0.51 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; Ki; IC50	PMID: 20462211; PMID: 19256502; PMID: 18557608; PMID: 19329313; PMID: 19632110; PMID: 24012181; PMID: 19713106; PMID: 19722525; PMID: 20034793; PMID: 18771916; PMID: 16750359; PMID: 20131864; PMID: 20378347; PMID: 21739935; PMID: 16750363; PMID: 19014888; PMID: 20724153; PMID: 23403082; PMID: 21916421; PMID: 21093273; PMID: 18951020; PMID: 21310612; via Super-PRED; via CMAUP
CHEMBL287	Q99720	Sigma opioid receptor	851.14 nM; 499 nM	IC50; IC50	PMID: 7990111; via CMAUP
CHEMBL1940	Q13936	Voltage-gated L-type calcium channel alpha-1C subunit	5400 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.07%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.33%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	92.38%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.41%	99.17%
CHEMBL2337	P48067	Glycine transporter 1	89.89%	95.45%
CHEMBL2039	P27338	Monoamine oxidase B	89.86%	92.51%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.07%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.04%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.72%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.35%	86.33%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.59%	94.23%
CHEMBL3401	O75469	Pregnane X receptor	83.98%	94.73%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.94%	94.08%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.52%	82.69%
CHEMBL1907	P15144	Aminopeptidase N	83.20%	93.31%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.54%	96.00%
CHEMBL4422	O14842	Free fatty acid receptor 1	81.00%	93.33%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.61%	100.00%
CHEMBL2535	P11166	Glucose transporter	80.58%	98.75%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.38%	94.80%

Plants that contains it

• Hordeum vulgare
• Salvia miltiorrhiza

Cross-Links

• PubChem: 3386
• NPASS: NPC328267
• ChEMBL: CHEMBL41
• LOTUS: LTS0036822
• wikiData: Q422244