| Version |
1.0 |
| Creation Date |
2009-07-21 20:26:28 |
| Update Date |
2010-05-18 20:59:34 |
| Accession Number |
T3D2737 |
| Name |
Atomoxetine |
| Compound Type |
- Adrenergic Uptake Inhibitor
- Antidepressant
- Central Nervous System Agent
- Drug
|
| 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] |
| Synonyms |
- Tomoxetina [Spanish]
- Tomoxetine
- Tomoxetine [INN]
- Tomoxetinum [Latin]
|
| Chemical IUPAC Name |
methyl[3-(2-methylphenoxy)-3-phenylpropyl]amine |
| Chemical Formula |
C17H21NO |
| Chemical Structure |
 |
| CAS Registry Number |
82248-59-7 |
| InChI Identifier |
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 |
| InChI Key |
InChIKey=VHGCDTVCOLNTBX-UHFFFAOYSA-N |
| PubChem Compound ID |
54841  |
| KEGG ID |
Not Available |
| UniProt ID |
Not Available |
| OMIM ID |
Not Available |
| ChEBI ID |
Not Available |
| BioCyc ID |
Not Available |
| SuperToxic ID |
Not Available |
| CTD ID |
Not Available |
| Stitch ID |
Atomoxetine |
| DrugBank ID |
DB00289 |
| PDB ID |
Not Available |
| ACToR ID |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Atomoxetine |
| Monoisotopic Mass |
255.162314 |
| MOL File |
Show |
| PDB File |
Show |
| SDF File |
Show |
| SMILES |
CNCCC(OC1=CC=CC=C1C)C1=CC=CC=C1 |
| Appearance |
Not Available |
| Melting Point |
Not Available |
| Solubility |
27.8 mg/mL |
| Predicted LogP |
3.8088 |
| Route of Exposure |
Oral |
| Mechanism of Action |
The precise mechanism by which atomoxetine produces its therapeutic effects in Attention-Deficit/Hyperactivity Disorder (ADHD) is unknown, but is thought to be related to selective inhibition of the pre-synaptic norepinephrine transporter, as determined in ex vivo uptake and neurotransmitter depletion studies. |
| Metabolism |
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). |
| Toxicity Values |
Not Available |
| Lethal Dose |
Not Available |
| Carcinogenicity (IARC Classification) |
Not Available |
| Uses/Sources |
Not Available |
| Minimum Risk Level |
Not Available |
| Health Effects |
Not Available |
| Symptoms |
The most commonly reported symptoms accompanying acute and chronic overdoses are somnolence, agitation, hyperactivity, abnormal behavior, and gastrointestinal symptoms. |
| Treatment |
An airway should be established. Monitoring of cardiac and vital signs is recommended, along with appropriate symptomatic and supportive measures. Gastric lavage may be indicated if performed soon after ingestion. Activated charcoal may be useful in limiting absorption. Because atomoxetine is highly protein-bound, dialysis is not likely to be useful in the treatment of overdose. (V650) |
| General References |
- T470 - 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 ]
- T469 - 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 ]
- T467 - 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 ]
- T466 - 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 ]
- T468 - 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 ]
- T465 - Drugs.com
|
| Targets |
- Sodium-dependent noradrenaline transporter
|
|
Target 1
[top]
|
| Target 1 ID |
1152 |
| Target 1 Name |
Sodium-dependent noradrenaline transporter |
| Target 1 Mechanism of Action |
The precise mechanism by which atomoxetine produces its therapeutic effects in Attention-Deficit/Hyperactivity Disorder (ADHD) is unknown, but is thought to be related to selective inhibition of the pre-synaptic norepinephrine transporter, as determined in ex vivo uptake and neurotransmitter depletion studies. |
| Target 1 Description |
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals |
| Target 1 Synonyms |
- Norepinephrine transporter; NET; Solute carrier family 6 member 2
|
| Target 1 Gene Name |
SLC6A2 |
| Target 1 Protein Sequence |
>Sodium-dependent noradrenaline transporter
MLLARMNPQVQPENNGADTGPEQPLRARKTAELLVVKERNGVQCLLAPRDGDAQPRETWG
KKIDFLLSVVGFAVDLANVWRFPYLCYKNGGGAFLIPYTLFLIIAGMPLFYMELALGQYN
REGAATVWKICPFFKGVGYAVILIALYVGFYYNVIIAWSLYYLFSSFTLNLPWTDCGHTW
NSPNCTDPKLLNGSVLGNHTKYSKYKFTPAAEFYERGVLHLHESSGIHDIGLPQWQLLLC
LMVVVIVLYFSLWKGVKTSGKVVWITATLPYFVLFVLLVHGVTLPGASNGINAYLHIDFY
RLKEATVWIDAATQIFFSLGAGFGVLIAFASYNKFDNNCYRDALLTSSINCITSFVSGFA
IFSILGYMAHEHKVNIEDVATEGAGLVFILYPEAISTLSGSTFWAVVFFVMLLALGLDSS
MGGMEAVITGLADDFQVLKRHRKLFTFGVTFSTFLLALFCITKGGIYVLTLLDTFAAGTS
ILFAVLMEAIGVSWFYGVDRFSNDIQQMMGFRPGLYWRLCWKFVSPAFLLFVVVVSIINF
KPLTYDDYIFPPWANWVGWGIALSSMVLVPIYVIYKFLSTQGSLWERLAYGITPENEHHL
VAQRDIRQFQLQHWLAI
|
| Target 1 Number of Residues |
617 |
| Target 1 Molecular Weight |
69331.4 |
| Target 1 Theoretical pI |
7.53 |
| Target 1 GO Classification |
|
Function
|
transporter activity
neurotransmitter transporter activity
neurotransmitter:sodium symporter activity |
|
Process
|
physiological process
cellular physiological process
transport
neurotransmitter transport |
|
Component
|
cell
membrane
intrinsic to membrane
integral to membrane
integral to plasma membrane |
|
| Target 1 General Function |
Involved in norephinephrine:sodium symporter activity |
| Target 1 Pathways |
Not Available |
| Target 1 Reactions |
Not Available |
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
- 65-85
- 93-112
- 136-156
- 235-253
- 262-279
- 315-332
- 344-365
- 398-417
- 444-462
- 478-498
- 519-538
- 557-575
|
| Target 1 Essentiality |
Non Essential |
| Target 1 Domain Function |
PF00209:SNF |
| Target 1 GenBank ID Protein |
Not Available |
| Target 1 UniProtKB ID |
P23975 |
| Target 1 Cellular Location |
Membrane |
| Target 1 Gene Sequence |
>1854 bp
ATGCTTCTGGCGCGGATGAACCCGCAGGTGCAGCCCGAGAACAACGGGGCGGACACGGGT
CCAGAGCAGCCCCTTCGGGCGCGCAAAACTGCGGAGCTGCTGGTGGTGAAGGAGCGCAAC
GGCGTCCAGTGCCTGCTGGCGCCCCGCGACGGCGACGCGCAGCCCCGGGAGACCTGGGGC
AAGAAGATCGACTTCCTGCTGTCCGTAGTCGGCTTCGCAGTGGACCTGGCCAACGTGTGG
CGCTTCCCCTACCTCTGCTACAAGAACGGCGGCGGTGCCTTCTTGATCCCGTACACACTG
TTCCTTATCATCGCGGGGATGCCCCTGTTCTACATGGAGCTGGCTCTGGGACAGTACAAC
CGGGAGGGGGCTGCCACCGTTTGGAAAATCTGCCCATTCTTCAAAGGCGTTGGCTATGCT
GTCATCCTGATCGCCCTGTACGTTGGCTTCTACTACAACGTCATCATCGCCTGGTCACTC
TACTACCTCTTCTCCTCCTTCACCCTCAACCTGCCCTGGACCGACTGTGGCCACACCTGG
AACAGCCCCAACTGTACCGACCCCAAGCTCCTCAATGGCTCCGTGCTTGGCAACCACACC
AAGTACTCCAAGTACAAGTTCACGCCGGCAGCCGAGTTTTATGAGCGTGGTGTCCTGCAC
CTTCACGAGAGCAGCGGGATTCATGACATCGGCCTGCCCCAGTGGCAGCTCTTGCTCTGT
CTGATGGTCGTCGTCATCGTCTTGTATTTTAGCCTCTGGAAAGGGGTGAAGACATCAGGA
AAGGTGGTGTGGATCACAGCCACGCTGCCTTACTTCGTGCTGTTCGTGCTCCTGGTCCAT
GGCGTCACGCTGCCCGGAGCCTCCAATGGCATCAATGCCTACCTGCACATCGACTTCTAC
CGCTTGAAAGAGGCCACGGTATGGATTGATGCCGCAACTCAGATATTTTTTTCCTTGGGG
GCTGGATTTGGAGTATTGATTGCATTTGCCAGTTACAACAAATTTGACAACAACTGTTAC
AGGGATGCCCTGCTGACCAGCAGCATCAACTGTATCACCAGCTTCGTCTCTGGGTTCGCC
ATCTTCTCCATCCTTGGTTACATGGCCCATGAACACAAGGTCAACATTGAGGATGTGGCC
ACAGAAGGAGCTGGCCTAGTGTTCATCCTGTATCCAGAGGCCATTTCTACCCTGTCTGGA
TCTACATTCTGGGCTGTTGTGTTTTTCGTCATGCTCCTGGCGCTGGGCCTTGACAGCTCA
ATGGGAGGCATGGAGGCTGTCATCACGGGCCTGGCAGATGACTTCCAGGTCCTGAAGCGA
CACCGGAAACTCTTCACATTTGGCGTCACCTTCAGCACTTTCCTTCTCGCCCTGTTCTGC
ATAACCAAGGGTGGAATTTACGTCTTGACCCTCCTGGACACCTTTGCTGCGGGCACCTCC
ATCCTTTTTGCTGTCCTCATGGAAGCCATCGGAGTTTCCTGGTTTTATGGAGTGGACAGG
TTCAGCAACGACATCCAGCAGATGATGGGGTTCAGGCCGGGTCTATACTGGAGACTGTGC
TGGAAGTTCGTCAGTCCTGCCTTCCTCCTGTTCGTGGTTGTGGTCAGCATCATCAACTTC
AAGCCACTCACCTACGACGACTACATCTTCCCGCCCTGGGCCAACTGGGTGGGGTGGGGC
ATCGCCCTGTCCTCCATGGTCCTGGTGCCCATCTACGTCATCTATAAGTTCCTCAGCACG
CAGGGCTCTCTTTGGGAGAGACTGGCCTATGGCATCACGCCAGAGAACGAGCACCACCTG
GTGGCTCAGAGGGACATCAGACAGTTCCAGTTGCAACACTGGCTGGCCATCTGA
|
| Target 1 GenBank Gene ID |
Not Available |
| Target 1 GeneCard ID |
SLC6A2 |
| Target 1 GenAtlas ID |
SLC6A2 |
| Target 1 HGNC ID |
HGNC:11048 |
| Target 1 Chromosome Location |
Chromosome:16 |
| Target 1 Locus |
16q12.2 |
| Target 1 SNPs |
SNPJam Report |
| Target 1 Toxin References |
- T474 - Wernicke JF, Faries D, Girod D, Brown J, Gao H, Kelsey D, Quintana H, Lipetz R, Michelson D, Heiligenstein J: Cardiovascular effects of atomoxetine in children, adolescents, and adults. Drug Saf. 2003;26(10):729-40. [PubMed ]
- T473 - Michelson D, Adler L, Spencer T, Reimherr FW, West SA, Allen AJ, Kelsey D, Wernicke J, Dietrich A, Milton D: Atomoxetine in adults with ADHD: two randomized, placebo-controlled studies. Biol Psychiatry. 2003 Jan 15;53(2):112-20. [PubMed ]
- T472 - Spencer T, Heiligenstein JH, Biederman J, Faries DE, Kratochvil CJ, Conners CK, Potter WZ: Results from 2 proof-of-concept, placebo-controlled studies of atomoxetine in children with attention-deficit/hyperactivity disorder. J Clin Psychiatry. 2002 Dec;63(12):1140-7. [PubMed ]
- T475 - Wernicke JF, Adler L, Spencer T, West SA, Allen AJ, Heiligenstein J, Milton D, Ruff D, Brown WJ, Kelsey D, Michelson D: Changes in symptoms and adverse events after discontinuation of atomoxetine in children and adults with attention deficit/hyperactivity disorder: a prospective, placebo-controlled assessment. J Clin Psychopharmacol. 2004 Feb;24(1):30-5. [PubMed ]
- T471 - Biederman J, Heiligenstein JH, Faries DE, Galil N, Dittmann R, Emslie GJ, Kratochvil CJ, Laws HF, Schuh KJ: Efficacy of atomoxetine versus placebo in school-age girls with attention-deficit/hyperactivity disorder. Pediatrics. 2002 Dec;110(6):e75. [PubMed ]
|
| Target 1 General References |
2008212; 7488042; 11343649; 10684912 |
