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82248-59-7 molecular structure
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methyl[(3R)-3-(2-methylphenoxy)-3-phenylpropyl]amine

ChemBase ID: 174
Molecular Formular: C17H21NO
Molecular Mass: 255.35474
Monoisotopic Mass: 255.1623143
SMILES and InChIs

SMILES:
O([C@H](CCNC)c1ccccc1)c1c(cccc1)C
Canonical SMILES:
CNCC[C@H](c1ccccc1)Oc1ccccc1C
InChI:
InChI=1S/C17H21NO/c1-14-8-6-7-11-16(14)19-17(12-13-18-2)15-9-4-3-5-10-15/h3-11,17-18H,12-13H2,1-2H3/t17-/m1/s1
InChIKey:
VHGCDTVCOLNTBX-QGZVFWFLSA-N

Cite this record

CBID:174 http://www.chembase.cn/molecule-174.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
methyl[(3R)-3-(2-methylphenoxy)-3-phenylpropyl]amine
IUPAC Traditional name
atomoxetine
Brand Name
Strattera
Synonyms
Tomoxetina [Spanish]
Tomoxetine
Tomoxetine [INN]
Tomoxetinum [Latin]
Atomoxetine
CAS Number
82248-59-7
PubChem SID
46506160
160963637
PubChem CID
54841

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 54841 external link
DrugBank DB00289 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 0.6029279  LogD (pH = 7.4) 1.4627138 
Log P 3.8087924  Molar Refractivity 79.435 cm3
Polarizability 31.315735 Å3 Polar Surface Area 21.26 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 3.95  LOG S -4.82 
Solubility (Water) 3.90e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
27.8 mg/mL expand Show data source
Hydrophobicity(logP)
3.9 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00289 external link
Item Information
Drug Groups approved
Description Atomoxetine is the first non-stimulant drug approved for the treatment of attention-deficit hyperactivity disorder (ADHD). It is sold in the form of the hydrochloride salt of atomoxetine. This chemical is manufactured and marketed under the brand name Strattera; by Eli Lilly and Company and as a generic Attentin by Torrent Pharmaceuticals. There is currently no generic available within the United States due to patent restrictions. [Wikipedia]
Indication For the treatment of Attention-Deficit/Hyperactivity Disorder (ADHD) alone or in combination with behavioral treatment, as an adjunct to psychological, educational, social, and other remedial measures.
Pharmacology Atomoxetine is the first non-stimulant drug approved for the treatment of attention-deficit hyperactivity disorder (ADHD). Atomoxetine is classified as a norepinephrine reuptake inhibitor, and is approved for use in children, adolescents, and adults. However, its efficacy has not been studied in children under six years old. Its advantage over stimulants for the treatment of ADHD is that it has less abuse potential than stimulants, is not scheduled as a controlled substance and has proven in clinical trials to offer 24 hour coverage of symptoms associated with ADHD in adults and children.
Toxicity The most commonly reported symptoms accompanying acute and chronic overdoses are somnolence, agitation, hyperactivity, abnormal behavior, and gastrointestinal symptoms.
Affected Organisms
Humans and other mammals
Biotransformation Atomoxetine is primarily metabolized by the CYP2D6 pathway to 4-hydroxyatomoxetine. 4-Hydroxyatomoxetine is equipotent to atomoxetine as an inhibitor of the norepinephrine transporter but circulates in plasma at much lower concentrations (1% of atomoxetine concentration in EMs and 0.1% of atomoxetine concentration in PMs).
Absorption Atomoxetine is rapidly absorbed after oral administration, with absolute bioavailability of about 63% in EMs and 94% in PMs. Drugs that elevate gastric pH (magnesium hydroxide/aluminum hydroxide, omeprazole) have no effect on atomoxetine bioavailability. Absorption is minimally affected by food.
Half Life 5 hours
Protein Binding At therapeutic concentrations, 98% of atomoxetine in plasma is bound to protein, primarily albumin.
Distribution * 0.85 L/kg
Clearance * 0.35 L/hr/kg [after oral administration in adult extensive metabolizers]
* 0.03 L/hr/kg [administration of atomoxetine to poor metabolizers]
References
Spencer TJ, Faraone SV, Michelson D, Adler LA, Reimherr FW, Glatt SJ, Biederman J: Atomoxetine and adult attention-deficit/hyperactivity disorder: the effects of comorbidity. J Clin Psychiatry. 2006 Mar;67(3):415-20. [Pubmed]
Pilhatsch MK, Burghardt R, Wandinger KP, Bauer M, Adli M: Augmentation with atomoxetine in treatment-resistant depression with psychotic features. A case report. Pharmacopsychiatry. 2006 Mar;39(2):79-80. [Pubmed]
Carpenter LL, Milosavljevic N, Schecter JM, Tyrka AR, Price LH: Augmentation with open-label atomoxetine for partial or nonresponse to antidepressants. J Clin Psychiatry. 2005 Oct;66(10):1234-8. [Pubmed]
Kratochvil CJ, Newcorn JH, Arnold LE, Duesenberg D, Emslie GJ, Quintana H, Sarkis EH, Wagner KD, Gao H, Michelson D, Biederman J: Atomoxetine alone or combined with fluoxetine for treating ADHD with comorbid depressive or anxiety symptoms. J Am Acad Child Adolesc Psychiatry. 2005 Sep;44(9):915-24. [Pubmed]
McElroy SL, Guerdjikova A, Kotwal R, Welge JA, Nelson EB, Lake KA, Keck PE Jr, Hudson JI: Atomoxetine in the treatment of binge-eating disorder: a randomized placebo-controlled trial. J Clin Psychiatry. 2007 Mar;68(3):390-8. [Pubmed]
Purper-Ouakil D, Fourneret P, Wohl M, Reneric JP: [Atomoxetine: a new treatment for Attention Deficit/Hyperactivity Disorder (ADHD) in children and adolescents] Encephale. 2005 May-Jun;31(3):337-48. [Pubmed]
Simpson D, Plosker GL: Atomoxetine: a review of its use in adults with attention deficit hyperactivity disorder. Drugs. 2004;64(2):205-22. [Pubmed]
Montoya A, Hervas A, Cardo E, Artigas J, Mardomingo MJ, Alda JA, Gastaminza X, Garcia-Polavieja MJ, Gilaberte I, Escobar R: Evaluation of atomoxetine for first-line treatment of newly diagnosed, treatment-naive children and adolescents with attention deficit/hyperactivity disorder. Curr Med Res Opin. 2009 Nov;25(11):2745-54. [Pubmed]
Gaillez C, Sorbara F, Perrin E: [Atomoxetine (Strattera), an alternative in the treatment of attention-deficit/hyperactivity disorder (ADHD) in children] Encephale. 2007 Sep;33(4 Pt 1):621-8. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Spencer TJ, Faraone SV, Michelson D, Adler LA, Reimherr FW, Glatt SJ, Biederman J: Atomoxetine and adult attention-deficit/hyperactivity disorder: the effects of comorbidity. J Clin Psychiatry. 2006 Mar;67(3):415-20. Pubmed
  • • Pilhatsch MK, Burghardt R, Wandinger KP, Bauer M, Adli M: Augmentation with atomoxetine in treatment-resistant depression with psychotic features. A case report. Pharmacopsychiatry. 2006 Mar;39(2):79-80. Pubmed
  • • Carpenter LL, Milosavljevic N, Schecter JM, Tyrka AR, Price LH: Augmentation with open-label atomoxetine for partial or nonresponse to antidepressants. J Clin Psychiatry. 2005 Oct;66(10):1234-8. Pubmed
  • • Kratochvil CJ, Newcorn JH, Arnold LE, Duesenberg D, Emslie GJ, Quintana H, Sarkis EH, Wagner KD, Gao H, Michelson D, Biederman J: Atomoxetine alone or combined with fluoxetine for treating ADHD with comorbid depressive or anxiety symptoms. J Am Acad Child Adolesc Psychiatry. 2005 Sep;44(9):915-24. Pubmed
  • • McElroy SL, Guerdjikova A, Kotwal R, Welge JA, Nelson EB, Lake KA, Keck PE Jr, Hudson JI: Atomoxetine in the treatment of binge-eating disorder: a randomized placebo-controlled trial. J Clin Psychiatry. 2007 Mar;68(3):390-8. Pubmed
  • • Purper-Ouakil D, Fourneret P, Wohl M, Reneric JP: [Atomoxetine: a new treatment for Attention Deficit/Hyperactivity Disorder (ADHD) in children and adolescents] Encephale. 2005 May-Jun;31(3):337-48. Pubmed
  • • Simpson D, Plosker GL: Atomoxetine: a review of its use in adults with attention deficit hyperactivity disorder. Drugs. 2004;64(2):205-22. Pubmed
  • • Montoya A, Hervas A, Cardo E, Artigas J, Mardomingo MJ, Alda JA, Gastaminza X, Garcia-Polavieja MJ, Gilaberte I, Escobar R: Evaluation of atomoxetine for first-line treatment of newly diagnosed, treatment-naive children and adolescents with attention deficit/hyperactivity disorder. Curr Med Res Opin. 2009 Nov;25(11):2745-54. Pubmed
  • • Gaillez C, Sorbara F, Perrin E: [Atomoxetine (Strattera), an alternative in the treatment of attention-deficit/hyperactivity disorder (ADHD) in children] Encephale. 2007 Sep;33(4 Pt 1):621-8. Pubmed
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PATENTS

PATENTS

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