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116539-59-4

116539-59-4 Structure

116539-59-4 Structure
IdentificationBack Directory
[Name]

Duloxetine
[CAS]

116539-59-4
[Synonyms]

DULOXETIN
DULOXETINE
DULOXETINE-D3
(S)-DULOXETINE
DULOXETINE HCI
Duloxetine Hcl(S)
Duloxetine & Intermediates
methyl-[(3S)-3-(1-naphthyloxy)-3-(2-thienyl)propyl]amine
N-Methyl-gama-(1-naphthalenyloxy)-2-thiophenepropanamine
Methyl[(3S)-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl]aMine
(3S)-N-methyl-3-naphthalen-1-yloxy-3-thiophen-2-yl-propan-1-amine
(3R)-N-methyl-3-(naphthalen-1-yloxy)-3-thiophen-2-ylpropan-1-amine
(S)-N-Methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-aMine
[EINECS(EC#)]

601-438-0
[Molecular Formula]

C18H19NOS
[MDL Number]

MFCD06801358
[MOL File]

116539-59-4.mol
[Molecular Weight]

297.41
Chemical PropertiesBack Directory
[Boiling point ]

466.2±40.0 °C(Predicted)
[density ]

1.158±0.06 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

Soluble in DMSO
[pka]

10.02±0.10(Predicted)
[BCS Class]

2
[InChI]

InChI=1/C18H19NOS.ClH/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16;/h2-10,13,17,19H,11-12H2,1H3;1H/t17-;/s3
[InChIKey]

BFFSMCNJSOPUAY-VOPAOICTNA-N
[SMILES]

C1(=CC=CS1)[C@H](CCNC)OC1=CC=CC2=CC=CC=C12.Cl |&1:5,r|
[EPA Substance Registry System]

2-Thiophenepropanamine, N-methyl-?-(1-naphthalenyloxy)-, (?S)- (116539-59-4)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

1-Fluoronaphthalene
Safety DataBack Directory
[Hazardous Substances Data]

116539-59-4(Hazardous Substances Data)
Hazard InformationBack Directory
[Uses]

Antidepressant.
[Definition]

ChEBI: (S)-duloxetine is a duloxetine. It is an enantiomer of a (R)-duloxetine.
[Brand name]

Cymbalta (Lilly).
[General Description]

Duloxetine (Cymbalta) is a newer antidepressant. It islargely like venlafaxine, which is an SNERI (selective norepinephrinereuptake inhibitor).
[Pharmacokinetics]

Duloxetine appears to be fairly well absorbed after oral doses, with peak plasma levels in 6 to 10 hours and linear pharmacokinetics. The drug is extensively metabolized in the liver to active metabolites, with 72% of an oral dose primarily excreted in the urine as conjugated metabolites and up to 15% appearing in the feces.
N-demethylation to an active metabolite (CYP2D6) and hydroxylation of the naphthyl ring (CYP1A2) at either the 4-, 5-, or 6-positions are the main metabolic pathways for duloxetine. Its metabolites are primarily excreted into the urine as glucuronide, sulfate, and O-methylated conjugation products. The major metabolites found in plasma also were found in the urine. Preclinical data for 4-hydroxyduloxetine suggests it has a similar pharmacological profile to duloxetine, with selective inhibition of SERT but less activity at the NET.
[Clinical Use]

Duloxetine has been approved for the treatment of depression and diabetic peripheral neuropathic pain. It is another analogue in the line of fluoxetine-based products from Lilly, in which the phenyl and phenoxy groups of fluoxetine have been respectively replaced with the benzene isostere, thiophene, and a naphthyloxy group (previously described under fluoxetine). Duloxetine exhibits dual inhibition with high affinity for the SERTs and NETs, with a five times preferential inhibition of the SERT. Duloxetine appears to be a more potent in vitro blocker of SERTs and NETs than venlafaxine. In humans, duloxetine has a low affinity for the other neuroreceptors, suggesting low incidence of unwanted adverse effects.
[Synthesis]

Reaction of 2-acetylthiophene with paraformaldehyde and dimethylamine in ethanol gives 3-(dimethylamino)-1-(2-thienyl)- 1-propanone, which is enantioselectively reduced with a 2:1 complex of (2R,3S)-4-(dimethylamino)- 3-methyl-1,2-diphenyl-2-butanol and LiAlH4 in toluene to yield (S)-3-(dimethylamino)- 1-(2-thienyl)-1-propanol. The condensation of (S)-3-(dimethylamino)-1-(2- thienyl)-1-propanol with 1-fluoronaphthalene catalyzed by NaH in DMSO affords the corresponding naphthyl ether (S)-N,N-dimethyl-3- (naphthalen-1-yloxy)-3-(thiophen-2-yl)propan- 1-amine, which is finally monodemethylated with 2,2,2-trichloroethyl chloroformate and zinc in toluene and treated with oxalic acid .
Synthesis_116539-59-4
[Drug interactions]

Potentially hazardous interactions with other drugs
Antibacterials: metabolism inhibited by ciprofloxacin - avoid.
Anticoagulants: possibly increased risk of bleeding with dabigatran.
Other CNS medication: enhanced effect.
Antidepressants: avoid with MAOIs, moclobemide, St John’s wort, tryptophan, venlaflaxine, amitriptyline, clomipramine and SSRIs due to increased risk of serotonin syndrome; increased risk of side effects with tricyclic antidepressants; fluvoxamine decreases the clearance of duloxetine by 77% - avoid; possible increased risk of convulsions with vortioxetine.
Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol.
Dapoxetine: avoid concomitant use.
Methylthioninium: risk of CNS toxicity - avoid if possible.
[Metabolism]

Duloxetine is extensively metabolised and the metabolites are excreted principally in urine. Both cytochromes P450-2D6 and 1A2 catalyse the formation of the two major metabolites, glucuronide conjugate of 4-hydroxy duloxetine and sulphate conjugate of 5-hydroxy, 6-methoxy duloxetine. Based upon in vitro studies, the circulating metabolites of duloxetine are considered pharmacologically inactive
Spectrum DetailBack Directory
[Spectrum Detail]

Duloxetine(116539-59-4)1HNMR
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