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136434-34-9 molecular structure
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methyl[(3S)-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl]amine

ChemBase ID: 359
Molecular Formular: C18H19NOS
Molecular Mass: 297.41456
Monoisotopic Mass: 297.11873523
SMILES and InChIs

SMILES:
s1c([C@@H](Oc2c3c(ccc2)cccc3)CCNC)ccc1
Canonical SMILES:
CNCC[C@@H](c1cccs1)Oc1cccc2c1cccc2
InChI:
InChI=1S/C18H19NOS/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/t17-/m0/s1
InChIKey:
ZEUITGRIYCTCEM-KRWDZBQOSA-N

Cite this record

CBID:359 http://www.chembase.cn/molecule-359.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
methyl[(3S)-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl]amine
IUPAC Traditional name
duloxetine
Brand Name
Cymbalta
Yentreve
Synonyms
(+-)-duloxetine
Duloxetine HCl
Duloxetine Hydrochloride
Duloxetine
CAS Number
136434-34-9
116539-59-4
PubChem SID
46507937
160963822
PubChem CID
60835
CHEBI ID
36795
ATC CODE
N06AX21
CHEMBL
1175
Chemspider ID
54822
DrugBank ID
DB00476
IUPHAR ligand ID
202
KEGG ID
D07880
Unique Ingredient Identifier
O5TNM5N07U
Wikipedia Title
Duloxetine
Medline Plus
a604030

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.0008107  LogD (pH = 7.4) 1.9402544 
Log P 4.197729  Molar Refractivity 87.7339 cm3
Polarizability 35.708214 Å3 Polar Surface Area 21.26 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 4.72  LOG S -5.0 
Solubility (Water) 2.96e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
0.00296 mg/mL [Predicted by ALOGPS] expand Show data source
Hydrophobicity(logP)
4 expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
~ 50% (32% to 80%) expand Show data source
Excretion
70% in urine, 20% in feces expand Show data source
Half Life
12.1 hours expand Show data source
Metabolism
Liver, two P450 isozymes, CYP2D6 and CYP1A2 expand Show data source
Protein Bound
~ 95% expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
C (US) expand Show data source
US Licence
duloxetine expand Show data source
EU Licence
Ariclaim expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00476 external link
Item Information
Drug Groups approved
Description Duloxetine (brand names Cymbalta, Yentreve, and in parts of Europe, Xeristar or Ariclaim) is a drug which primarily targets major depressive disorder (MDD), generalized anxiety disorder (GAD), pain related to diabetic peripheral neuropathy and in some countries stress urinary incontinence (SUI). It is manufactured and marketed by Eli Lilly and Company.

Duloxetine has not yet been FDA approved for stress urinary incontinence or for fibromyalgia.

Duloxetine is a selective SNRI (selective serotonin-norepinephrine reuptake inhibitor). Duloxetine is a systemic drug therapy which affects the body as a whole. Known also under the code name LY248686, it is a potent dual reuptake inhibitor of serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE), possessing comparable affinities in binding to NE- and 5-HT transporter sites. It is a less potent inhibitor of dopamine reuptake.
Indication For the acute and maintenance treatment of major depressive disorder (MDD), as well as acute management of generalized anxiety disorder. Also used for the management of neuropathic pain associated with diabetic peripheral neuropathy, and fibromyalgia. Has been used in the management of moderate to severe stress urinary incontinence (SUI) in women.
Pharmacology Duloxetine is in a class of medications called selective serotonin and norepinephrine reuptake inhibitors (SSNRIs) and primarily targets major depressive disorders (MDD) and stress urinary incontinence (SUI). Duloxetine is also used to treat pain and tingling caused by diabetic neuropathy (damage to nerves that can develop in people who have diabetes). Known also as LY248686, it is a potent dual inhibitor of serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE) reuptake, possessing comparable affinities in binding to NE and 5-HT transport sites. Interestingly, its behavior contrasts to most other dual-reuptake inhibitors. Furthermore, duloxentine lacks affinity for monoamine receptors within the central nervous system.
Toxicity Oral, rat LD50: 491 mg/kg for males and 279 mg/kg for females. Symptoms of overdose include tremors, convulsions, reduced activity, slow pupillary response, intermittent tremors, and rigidity.
Affected Organisms
Humans and other mammals
Biotransformation The major biotransformation pathways for duloxetine involve oxidation of the naphthyl ring followed by conjugation and further oxidation. Both CYP2D6 and CYP1A2 catalyze the oxidation of the naphthyl ring in vitro. Metabolites found in plasma include 4-hydroxy duloxetine glucuronide and 5-hydroxy, 6-methoxy duloxetine sulfate. The major circulating metabolites have not been shown to contribute significantly to the pharmacologic activity of duloxetine.
Absorption Orally administered duloxetine hydrochloride is well absorbed.
Half Life 12 hours (range 8-17 hours)
Protein Binding Protein binding is greater than 90%.
Elimination Many additional metabolites have been identified in urine, some representing only minor pathways of elimination. Most (about 70%) of the duloxetine dose appears in the urine as metabolites of duloxetine; about 20% is excreted in the feces.
Distribution * 1640 L
References
Turcotte JE, Debonnel G, de Montigny C, Hebert C, Blier P: Assessment of the serotonin and norepinephrine reuptake blocking properties of duloxetine in healthy subjects. Neuropsychopharmacology. 2001 May;24(5):511-21. [Pubmed]
Anttila S, Leinonen E: Duloxetine Eli Lilly. Curr Opin Investig Drugs. 2002 Aug;3(8):1217-21. [Pubmed]
Karpa KD, Cavanaugh JE, Lakoski JM: Duloxetine pharmacology: profile of a dual monoamine modulator. CNS Drug Rev. 2002 Winter;8(4):361-76. [Pubmed]
van Groeningen CJ, Peters GJ, Pinedo HM: Lack of effectiveness of combined 5-fluorouracil and leucovorin in patients with 5-fluorouracil-resistant advanced colorectal cancer. Eur J Cancer Clin Oncol. 1989 Jan;25(1):45-9. [Pubmed]
Jost W, Marsalek P: Duloxetine: mechanism of action at the lower urinary tract and Onuf's nucleus. Clin Auton Res. 2004 Aug;14(4):220-7. [Pubmed]
Carter NJ, McCormack PL: Duloxetine: a review of its use in the treatment of generalized anxiety disorder. CNS Drugs. 2009;23(6):523-41. doi: 10.2165/00023210-200923060-00006. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Anttila S, Leinonen E: Duloxetine Eli Lilly. Curr Opin Investig Drugs. 2002 Aug;3(8):1217-21. Pubmed
  • • Turcotte JE, Debonnel G, de Montigny C, Hebert C, Blier P: Assessment of the serotonin and norepinephrine reuptake blocking properties of duloxetine in healthy subjects. Neuropsychopharmacology. 2001 May;24(5):511-21. Pubmed
  • • Karpa KD, Cavanaugh JE, Lakoski JM: Duloxetine pharmacology: profile of a dual monoamine modulator. CNS Drug Rev. 2002 Winter;8(4):361-76. Pubmed
  • • van Groeningen CJ, Peters GJ, Pinedo HM: Lack of effectiveness of combined 5-fluorouracil and leucovorin in patients with 5-fluorouracil-resistant advanced colorectal cancer. Eur J Cancer Clin Oncol. 1989 Jan;25(1):45-9. Pubmed
  • • Jost W, Marsalek P: Duloxetine: mechanism of action at the lower urinary tract and Onuf's nucleus. Clin Auton Res. 2004 Aug;14(4):220-7. Pubmed
  • • Carter NJ, McCormack PL: Duloxetine: a review of its use in the treatment of generalized anxiety disorder. CNS Drugs. 2009;23(6):523-41. doi: 10.2165/00023210-200923060-00006. Pubmed
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