Atomoxetine

Title: Atomoxetine
CAS Registry Number: 83015-26-3
CAS Name: (gR)-N-Methyl-g-(2-methylphenoxy)benzenepropanamine
Additional Names: (-)-N-methyl-3-(o-tolyloxy)-3-phenylpropylamine; tomoxetine
Molecular Formula: C17H21NO
Molecular Weight: 255.35
Percent Composition: C 79.96%, H 8.29%, N 5.49%, O 6.27%
Literature References: Norepinephrine reuptake inhibitor. Prepn (stereochem unspec): B. B. Molloy, K. K. Schmiegel, DE 2500110; eidem, US 4314081 (1975, 1982 both to Lilly). Prepn of (R)-form: B. J. Foster, E. R. Lavagnino, EP 52492 (1982 to Lilly); Y. Gao, K. B. Sharpless, J. Org. Chem. 53, 4081 (1988). Clinical pharmacokinetics: N. A. Farid et al., J. Clin. Pharmacol. 25, 296 (1985). Binding study: D. R. Gehlert et al., J. Neurochem. 64, 2792 (1995). Biotransformation by human liver microsomes: B. J. Ring et al., Drug Metab. Dispos. 30, 319 (2002). Evaluation of abuse potential: S. H. Heil et al., Drug Alcohol Depend. 67, 149 (2002). Clinical trial in pediatric ADHD: C. J. Kratochvil et al., J. Am. Acad. Child Adolesc. Psychiatry 41, 776 (2002); and comorbid tic disorders: A. J. Allen et al., Neurology 65, 1941 (2005). Review of clinical pharmacokinetics: J.-M. Sauer et al., Clin. Pharmacokinet. 44, 571-590 (2005).
Derivative Type: Hydrochloride
CAS Registry Number: 82248-59-7
Manufacturers' Codes: LY 139603
Trademarks: Strattera (Lilly)
Molecular Formula: C17H21NO.HCl
Molecular Weight: 291.82
Percent Composition: C 69.97%, H 7.60%, N 4.80%, O 5.48%, Cl 12.15%
Properties: Crystals, mp 166-168° (Foster, Lavagnino). [a]D25 -38.01°; [a]36525 -177.26° (c = 1 in methanol). Also reported as white solid from acetonitrile, mp 162-164° (Gao, Sharpless). [a]D23 -41.37° (c = 1.02 in methanol); [a]D25 -40.3° (c = 0.94 in ethanol). Soly in water: 27.8 mg/ml. pKa 10.13.
Melting point: mp 166-168°; mp 162-164° (Gao, Sharpless)
pKa: pKa 10.13
Optical Rotation: [a]D25 -38.01°; [a]36525 -177.26° (c = 1 in methanol); [a]D23 -41.37° (c = 1.02 in methanol); [a]D25 -40.3° (c = 0.94 in ethanol)
Therap-Cat: In treatment of attention deficit hyperactivity disorder (ADHD).
Atosiban Atovaquone Atractyloside Atracurium Besylate Atranorin

Atomoxetine
Atomoxetine structure.svg
Atomoxetine3Dan.gif
Systematic (IUPAC) name
(3R)-N-methyl-3-(2-methylphenoxy)-3-phenylpropan-1-amine; (R)-N-methyl-3-phenyl-3-(o-tolyloxy)propan-1-amine
Clinical data
Trade names Strattera
AHFS/Drugs.com monograph
MedlinePlus a603013
Pregnancy cat. B3 (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 63 to 94%[1][2][3]
Protein binding 98%[1][2][3]
Metabolism Hepatic, via CYP2D6[1][2][3]
Half-life 5.2 hours[1][2][3]
Excretion Renal (80%) and faecal (17%)[1][2][3]
Identifiers
CAS number 83015-26-3 N
ATC code N06BA09
PubChem CID 54841
DrugBank DB00289
ChemSpider 49516 YesY
UNII ASW034S0B8 YesY
KEGG D07473 YesY
ChEBI CHEBI:127342 YesY
ChEMBL CHEMBL641 YesY
Chemical data
Formula C17H21NO 
Mol. mass 255.36 g/mol
291.81 g/mol (hydrochloride)
 N (what is this?)  (verify)

Atomoxetine (brand name: Strattera) is a drug approved for the treatment of attention-deficit hyperactivity disorder (ADHD).[4] It is a selective norepinephrine reuptake inhibitor (NRI),[4] not to be confused with serotonin norepinephrine reuptake inhibitors (SNRIs) or selective serotonin reuptake inhibitors (SSRIs), both of which are currently the most prescribed form of antidepressants.[5]