Basic information
- CAS
82248-59-7- Standard SMILES
CNCC[C@@H](Oc1ccccc1C)c1ccccc1.Cl- InChIKey
LUCXVPAZUDVVBT-UNTBIKODSA-N- Molecular formula
- C17H22ClNO
- Average molar mass
- 291.8 g/mol
- Monoisotopic mass
- 291.138992
Overview
Atomoxetine hydrochloride is the hydrochloride salt of atomoxetine. It has a role as an antidepressant and an adrenergic uptake inhibitor. It contains an atomoxetine.
Names & identifiers
- Preferred name
- Atomoxetine Hydrochloride
- IUPAC
- (3R)-N-methyl-3-(2-methylphenoxy)-3-phenylpropan-1-amine;hydrochloride
- English name
- Atomoxetine hydrochloride
- Molecular formula
- C17H22ClNO
- Molecular weight
- 291.82
Names & synonyms
Atomoxetine hydrochloride82248-59-7Atomoxetine HCLTOMOXETINE HYDROCHLORIDE(R)-Tomoxetine hydrochloride(R)-(-)-Tomoxetine hydrochlorideDTXSID2044266LY-139603Atomoxetine (as hydrochloride)57WVB6I2W0(-)-N-Methyl-3-phenyl-3-(o-tolyloxy)propylamine hydrochlorideNSC-759104
Show more names
ATOMOXETINEStratteraATOMOXITINEAtomoxetine HCILY 139603LY 139603 HClAtazanavir HClAtomoxitine HCL
DTXCID0024266CHEBI:331697N-methyl-gamma-(2-methylphenoxy)benzenepropanamine hydrochloride(-)-N-methyl-3-phenyl-3-(o-tolyloxy)-propylamine hydrochlorideHCl, AtomoxetineRefChem:56722Hydrochloride, AtomoxetineATOMXETINE HYROCHLORIDE
Database identifiers
- CAS
82248-59-7- PubChem CID
- 54840
- DTXSID
DTXSID2044266
Properties
Computed structural properties
- Topological polar surface area
- 21.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 6
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 237
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section162.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 167 · 167-169°C
- alpha
- 25 · D25 -38.01°; 36525 -177.26° (c = 1 in methanol); D23 -41.37° (c = 1.02 in methanol); D25 -40.3° (c = 0.94 in ethanol)
- Flash point
- 9 ℃ · 9℃
- storage temp.
- 2 · 2-8°C
- solubility
- soluble in Methanol
- form
- solid
- pka
- 10.13 · 10.13(at 25℃)
- color
- White to Almost white
- optical activity
- -37.1 ° · -37.10°(C=0.01g/mL, MEOH, 589nm)
- Water Solubility
- 50 mM · Soluble to 50 mM in water with gentle warming
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (70%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P318, P319, P320, P321, P330, P337+P317, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 10 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (70%)
Toxicology
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. (L1712)
Exposure Routes
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.
Toxicity Summary
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 through in-vitro studies. Atomoxetine appears to have minimal affinity for other noradrenergic receptors or for other neurotransmitter transporters or receptors.
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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). Half Life: 5 hours
FDA Pharmacological Classification
ATOMOXETINE HYDROCHLORIDE
Norepinephrine Uptake Inhibitors [MoA]; Norepinephrine Reuptake Inhibitor [EPC]
MeSH Pharmacological Classification
Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
Uses & manufacturing
UsesFor 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.
Applications
DescriptionAtomoxetine is the first non-stimulant marketed for the treatment of attention deficit hyperactivity disorder (ADHD). It is the R-stereoisomer of the racemate tomoxetine and is a selective and potent norepinephrine uptake inhibitor (Ki=0.7–1.9 nM) that is devoid of binding to monoamine receptor. It also has little effect on dopamine and serotonin reuptake or acetylcholine, H1 histamine, alpha1 or alpha1-adrenergic or dopamine receptors. It is prepared from racemic 1-phenylbut-3-en-1-ol via a selective enzymatic acylation leaving the desired S-stereoisomer as the alcohol. This alcohol is converted via a Mitsunobu reaction with ortho-cresol to the corresponding ether with isomeric R-configuration. Ozonolysis and reduction steps provided the terminal alcohol that is mesylated and displaced with methylamine. Its selectivity for norepinephrine relative to dopamine inhibition was demonstrated in vivo preclinically. In a two-lever (two condition) discriminative stimulus effect study in squirrel monkeys, tomoxetine and other norepinephrine uptake inhibitors substituted for cocaine under low-dose training conditions, whereas dopamine uptake inhibitors substituted for cocaine in both low and high-dose conditions. In clinical ADHD studies in adolescents, it was significantly different from placebo in 1.2 and 1.8 mpk/day dosing. In the clinical study in adults using the CAARS scale a 95 mg/day dose provided greater than 30% improvement in total scores. Atomoxetine is about 63% orally bioavailable, is highly protein bound (98%, primarily to albumin) and has a half-life of about 5.2 h. It is metabolized by CYP2D6 resulting in differential clearance for poor metabolizers (halflife of 19 h with a 10 times higher AUC) relative to extensive metabolizers. The total daily dose for children, adolescents and adults is a maximum of 100 mg/day. Common side effects in children and adults include nausea, decreased appetite, and dizziness. Adults may also have insomnia.
Related reactions
10 records
Compound notes
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