Reboxetine - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (1)Enzymes (2)Transporters (1)

Targets (1)Enzymes (2)Transporters (1)Biointeractions (5)

Identification

Name

Reboxetine

Accession Number

DB00234 (APRD00198)

Type

Small Molecule

Groups

Approved, Investigational

Description

Reboxetine is an antidepressant drug used in the treatment of clinical depression, panic disorder and ADD/ADHD. Its mesylate (i.e. methanesulfonate) salt is sold under tradenames including Edronax, Norebox, Prolift, Solvex, Davedax or Vestra. Reboxetine has two chiral centers, but it only exists as two enantiomers, (R,R)-(-)- and (S,S)-(+)-reboxetine.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Not Available

External IDs

Not Available

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Reboxetine mesilate	L94J81YNNY	98769-84-7	CGTZMJIMMUNLQD-STYNFMPRSA-N	Details

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Davedax	Not Available
Edronax	Not Available
Norebox	Not Available
Prolift	Not Available
Solvex	Not Available
Vestra	Not Available

Brand mixtures

Not Available

Categories

UNII

947S0YZ36I

CAS number

71620-89-8

Weight

Average: 313.397
Monoisotopic: 313.167793605

Chemical Formula

C₁₉H₂₃NO₃

InChI Key

CBQGYUDMJHNJBX-RTBURBONSA-N

InChI

InChI=1S/C19H23NO3/c1-2-21-16-10-6-7-11-17(16)23-19(15-8-4-3-5-9-15)18-14-20-12-13-22-18/h3-11,18-20H,2,12-14H2,1H3/t18-,19-/m1/s1

IUPAC Name

(2R)-2-[(R)-(2-ethoxyphenoxy)(phenyl)methyl]morpholine

SMILES

[H][C@@](OC1=CC=CC=C1OCC)(C1=CC=CC=C1)[C@@]1([H])CNCCO1

Pharmacology

Indication

For the treatment of clinical depression.

Structured Indications

Not Available

Pharmacodynamics

Reboxetine is a selective noradrenaline reuptake inhibitor (NaRI), the first drug of new antidepressant class. Reboxetine is an a-ariloxybenzyl derivative of morpholine. Reboxetine is primarily used to treat depression but has also been found useful in the treatment of narcolepsy and panic disorders.

Mechanism of action

Reboxetine is a selective inhibitor of noradrenaline reuptake. It inhibits noradrenaline reuptake in vitro to a similar extent to the tricyclic antidepressant desmethylimipramine. Reboxetine does not affect dopamine or serotonin reuptake and it has low in vivo and in vitro affinity for adrenergic, cholinergic, histaminergic, dopaminergic and serotonergic receptors.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Sodium-dependent noradrenaline transporter	Protein	yes	inhibitor	Human	P23975	details

Absorption

Reboxetine is rapidly and extensively absorbed following oral administration.

Volume of distribution

Not Available

Protein binding

98%

Metabolism

Reboxetine is metabolized by dealkylation, hydroxylation and oxidation followed by glucuronide or sulphate conjugation. It is metabolized by the cytochrome P450 CYP isoenzyme 3A4.

Route of elimination

Not Available

Half life

12.5 hours

Clearance

Not Available

Toxicity

Reports of seizures (rare) have been reported

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
Acebutolol	The serum concentration of Acebutolol can be increased when it is combined with Reboxetine.	Approved
Acetaminophen	The serum concentration of Acetaminophen can be increased when it is combined with Reboxetine.	Approved
Acetylsalicylic acid	The serum concentration of Acetylsalicylic acid can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Afatinib	The serum concentration of Afatinib can be increased when it is combined with Reboxetine.	Approved
Aldosterone	The serum concentration of Aldosterone can be increased when it is combined with Reboxetine.	Experimental
Alitretinoin	The serum concentration of Alitretinoin can be increased when it is combined with Reboxetine.	Approved, Investigational
Ambrisentan	The serum concentration of Ambrisentan can be increased when it is combined with Reboxetine.	Approved, Investigational
Amiodarone	The metabolism of Reboxetine can be decreased when combined with Amiodarone.	Approved, Investigational
Amitriptyline	The serum concentration of Amitriptyline can be increased when it is combined with Reboxetine.	Approved
Apixaban	The serum concentration of Apixaban can be increased when it is combined with Reboxetine.	Approved
Aprepitant	The serum concentration of Reboxetine can be increased when it is combined with Aprepitant.	Approved, Investigational
Arsenic trioxide	The serum concentration of Arsenic trioxide can be increased when it is combined with Reboxetine.	Approved, Investigational
Atazanavir	The metabolism of Reboxetine can be decreased when combined with Atazanavir.	Approved, Investigational
Atenolol	The serum concentration of Atenolol can be increased when it is combined with Reboxetine.	Approved
Atomoxetine	The metabolism of Reboxetine can be decreased when combined with Atomoxetine.	Approved
Axitinib	The serum concentration of Axitinib can be increased when it is combined with Reboxetine.	Approved, Investigational
Betamethasone	The serum concentration of Betamethasone can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Bexarotene	The serum concentration of Reboxetine can be decreased when it is combined with Bexarotene.	Approved, Investigational
Boceprevir	The metabolism of Reboxetine can be decreased when combined with Boceprevir.	Approved, Investigational
Bortezomib	The metabolism of Reboxetine can be decreased when combined with Bortezomib.	Approved, Investigational
Bosentan	The serum concentration of Reboxetine can be decreased when it is combined with Bosentan.	Approved, Investigational
Bosutinib	The serum concentration of Bosutinib can be increased when it is combined with Reboxetine.	Approved
Brentuximab vedotin	The serum concentration of Brentuximab vedotin can be increased when it is combined with Reboxetine.	Approved
Bromocriptine	The serum concentration of Bromocriptine can be increased when it is combined with Reboxetine.	Approved, Investigational
Cabazitaxel	The serum concentration of Cabazitaxel can be increased when it is combined with Reboxetine.	Approved
Caffeine	The serum concentration of Caffeine can be increased when it is combined with Reboxetine.	Approved
Camptothecin	The serum concentration of Camptothecin can be increased when it is combined with Reboxetine.	Experimental
Canagliflozin	The serum concentration of Canagliflozin can be increased when it is combined with Reboxetine.	Approved
Carbamazepine	The metabolism of Reboxetine can be increased when combined with Carbamazepine.	Approved, Investigational
Carfilzomib	The serum concentration of Carfilzomib can be increased when it is combined with Reboxetine.	Approved
Ceritinib	The serum concentration of Reboxetine can be increased when it is combined with Ceritinib.	Approved
Cerivastatin	The serum concentration of Cerivastatin can be increased when it is combined with Reboxetine.	Withdrawn
Chlorpromazine	The serum concentration of Chlorpromazine can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Cimetidine	The serum concentration of Cimetidine can be increased when it is combined with Reboxetine.	Approved
Ciprofloxacin	The serum concentration of Ciprofloxacin can be increased when it is combined with Reboxetine.	Approved, Investigational
Cisplatin	The serum concentration of Cisplatin can be increased when it is combined with Reboxetine.	Approved
Citalopram	The serum concentration of Citalopram can be increased when it is combined with Reboxetine.	Approved
Clarithromycin	The metabolism of Reboxetine can be decreased when combined with Clarithromycin.	Approved
Clemastine	The metabolism of Reboxetine can be decreased when combined with Clemastine.	Approved
Clobazam	The serum concentration of Clobazam can be increased when it is combined with Reboxetine.	Approved, Illicit
Clomifene	The serum concentration of Clomifene can be increased when it is combined with Reboxetine.	Approved, Investigational
Clonidine	The serum concentration of Clonidine can be increased when it is combined with Reboxetine.	Approved
Clopidogrel	The serum concentration of Clopidogrel can be increased when it is combined with Reboxetine.	Approved, Nutraceutical
Clotrimazole	The metabolism of Reboxetine can be decreased when combined with Clotrimazole.	Approved, Vet Approved
Clozapine	The serum concentration of Clozapine can be increased when it is combined with Reboxetine.	Approved
Cobicistat	The metabolism of Reboxetine can be decreased when combined with Cobicistat.	Approved
Cobimetinib	The serum concentration of Cobimetinib can be increased when it is combined with Reboxetine.	Approved
Colchicine	The serum concentration of Colchicine can be increased when it is combined with Reboxetine.	Approved
Conivaptan	The serum concentration of Reboxetine can be increased when it is combined with Conivaptan.	Approved, Investigational
Conjugated estrogens	The serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Reboxetine.	Approved
Crizotinib	The metabolism of Reboxetine can be decreased when combined with Crizotinib.	Approved
Cyclosporine	The metabolism of Reboxetine can be decreased when combined with Cyclosporine.	Approved, Investigational, Vet Approved
Dabigatran etexilate	The serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Reboxetine.	Approved
Dabrafenib	The serum concentration of Reboxetine can be decreased when it is combined with Dabrafenib.	Approved
Dactinomycin	The serum concentration of Dactinomycin can be increased when it is combined with Reboxetine.	Approved
Dapagliflozin	The serum concentration of Dapagliflozin can be increased when it is combined with Reboxetine.	Approved
Darunavir	The metabolism of Reboxetine can be decreased when combined with Darunavir.	Approved
Dasatinib	The serum concentration of Reboxetine can be increased when it is combined with Dasatinib.	Approved, Investigational
Daunorubicin	The serum concentration of Daunorubicin can be increased when it is combined with Reboxetine.	Approved
Debrisoquin	The serum concentration of Debrisoquin can be increased when it is combined with Reboxetine.	Approved
Deferasirox	The serum concentration of Reboxetine can be decreased when it is combined with Deferasirox.	Approved, Investigational
Delavirdine	The metabolism of Reboxetine can be decreased when combined with Delavirdine.	Approved
Dexamethasone	The serum concentration of Reboxetine can be decreased when it is combined with Dexamethasone.	Approved, Investigational, Vet Approved
Diazepam	The serum concentration of Diazepam can be increased when it is combined with Reboxetine.	Approved, Illicit, Vet Approved
Diethylstilbestrol	The serum concentration of Diethylstilbestrol can be increased when it is combined with Reboxetine.	Approved
Digitoxin	The serum concentration of Digitoxin can be increased when it is combined with Reboxetine.	Approved
Digoxin	The serum concentration of Digoxin can be increased when it is combined with Reboxetine.	Approved
Dihydroergotamine	The metabolism of Reboxetine can be decreased when combined with Dihydroergotamine.	Approved
Dihydrotestosterone	The serum concentration of Dihydrotestosterone can be increased when it is combined with Reboxetine.	Illicit
Diltiazem	The metabolism of Reboxetine can be decreased when combined with Diltiazem.	Approved
Dipyridamole	The serum concentration of Dipyridamole can be increased when it is combined with Reboxetine.	Approved
Docetaxel	The serum concentration of Docetaxel can be increased when it is combined with Reboxetine.	Approved, Investigational
Domperidone	The serum concentration of Domperidone can be increased when it is combined with Reboxetine.	Approved, Investigational, Vet Approved
Doxorubicin	The serum concentration of Doxorubicin can be increased when it is combined with Reboxetine.	Approved, Investigational
Doxycycline	The metabolism of Reboxetine can be decreased when combined with Doxycycline.	Approved, Investigational, Vet Approved
Dronedarone	The metabolism of Reboxetine can be decreased when combined with Dronedarone.	Approved
Edoxaban	The serum concentration of Edoxaban can be increased when it is combined with Reboxetine.	Approved
Efavirenz	The serum concentration of Reboxetine can be decreased when it is combined with Efavirenz.	Approved, Investigational
Eletriptan	The serum concentration of Eletriptan can be increased when it is combined with Reboxetine.	Approved, Investigational
Enzalutamide	The serum concentration of Reboxetine can be decreased when it is combined with Enzalutamide.	Approved
Epinastine	The serum concentration of Epinastine can be increased when it is combined with Reboxetine.	Approved, Investigational
Erlotinib	The serum concentration of Erlotinib can be increased when it is combined with Reboxetine.	Approved, Investigational
Erythromycin	The metabolism of Reboxetine can be decreased when combined with Erythromycin.	Approved, Vet Approved
Eslicarbazepine acetate	The serum concentration of Reboxetine can be decreased when it is combined with Eslicarbazepine acetate.	Approved
Estradiol	The serum concentration of Estradiol can be increased when it is combined with Reboxetine.	Approved, Investigational, Vet Approved
Estriol	The serum concentration of Estriol can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Estrone	The serum concentration of Estrone can be increased when it is combined with Reboxetine.	Approved
Ethinyl Estradiol	The serum concentration of Ethinyl Estradiol can be increased when it is combined with Reboxetine.	Approved
Etoposide	The serum concentration of Etoposide can be increased when it is combined with Reboxetine.	Approved
Etravirine	The serum concentration of Reboxetine can be decreased when it is combined with Etravirine.	Approved
Everolimus	The serum concentration of Everolimus can be increased when it is combined with Reboxetine.	Approved
Ezetimibe	The serum concentration of Ezetimibe can be increased when it is combined with Reboxetine.	Approved
Fesoterodine	The serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Reboxetine.	Approved
Fexofenadine	The serum concentration of Fexofenadine can be increased when it is combined with Reboxetine.	Approved
Fidaxomicin	The serum concentration of Fidaxomicin can be increased when it is combined with Reboxetine.	Approved
Fluconazole	The metabolism of Reboxetine can be decreased when combined with Fluconazole.	Approved
Fluticasone furoate	The serum concentration of Fluticasone furoate can be increased when it is combined with Reboxetine.	Approved
Fluvoxamine	The metabolism of Reboxetine can be decreased when combined with Fluvoxamine.	Approved, Investigational
Fosamprenavir	The metabolism of Reboxetine can be decreased when combined with Fosamprenavir.	Approved
Fosaprepitant	The serum concentration of Reboxetine can be increased when it is combined with Fosaprepitant.	Approved
Fosphenytoin	The metabolism of Reboxetine can be increased when combined with Fosphenytoin.	Approved
Fusidic Acid	The serum concentration of Reboxetine can be increased when it is combined with Fusidic Acid.	Approved
Gefitinib	The serum concentration of Gefitinib can be increased when it is combined with Reboxetine.	Approved, Investigational
Gemcitabine	The serum concentration of Gemcitabine can be increased when it is combined with Reboxetine.	Approved
Grazoprevir	The serum concentration of Grazoprevir can be increased when it is combined with Reboxetine.	Approved
Grepafloxacin	The serum concentration of Grepafloxacin can be increased when it is combined with Reboxetine.	Withdrawn
Haloperidol	The serum concentration of Haloperidol can be increased when it is combined with Reboxetine.	Approved
Hydrocortisone	The serum concentration of Hydrocortisone can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Ibuprofen	The serum concentration of Ibuprofen can be increased when it is combined with Reboxetine.	Approved
Idelalisib	The serum concentration of Reboxetine can be increased when it is combined with Idelalisib.	Approved
Imatinib	The metabolism of Reboxetine can be decreased when combined with Imatinib.	Approved
Imipramine	The serum concentration of Imipramine can be increased when it is combined with Reboxetine.	Approved
Indacaterol	The serum concentration of Indacaterol can be increased when it is combined with Reboxetine.	Approved
Indinavir	The metabolism of Reboxetine can be decreased when combined with Indinavir.	Approved
Indomethacin	The serum concentration of Indomethacin can be increased when it is combined with Reboxetine.	Approved, Investigational
Irinotecan	The serum concentration of Irinotecan can be increased when it is combined with Reboxetine.	Approved, Investigational
Isavuconazonium	The metabolism of Reboxetine can be decreased when combined with Isavuconazonium.	Approved, Investigational
Isradipine	The metabolism of Reboxetine can be decreased when combined with Isradipine.	Approved
Itraconazole	The metabolism of Reboxetine can be decreased when combined with Itraconazole.	Approved, Investigational
Ivacaftor	The serum concentration of Reboxetine can be increased when it is combined with Ivacaftor.	Approved
Ivermectin	The serum concentration of Ivermectin can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Ketazolam	The serum concentration of Ketazolam can be increased when it is combined with Reboxetine.	Approved
Ketoconazole	The metabolism of Reboxetine can be decreased when combined with Ketoconazole.	Approved, Investigational
Lamivudine	The serum concentration of Lamivudine can be increased when it is combined with Reboxetine.	Approved, Investigational
Lamotrigine	The serum concentration of Lamotrigine can be increased when it is combined with Reboxetine.	Approved, Investigational
Lansoprazole	The serum concentration of Lansoprazole can be increased when it is combined with Reboxetine.	Approved, Investigational
Ledipasvir	The serum concentration of Ledipasvir can be increased when it is combined with Reboxetine.	Approved
Lenalidomide	The serum concentration of Lenalidomide can be increased when it is combined with Reboxetine.	Approved
Lenvatinib	The serum concentration of Lenvatinib can be increased when it is combined with Reboxetine.	Approved
Levetiracetam	The serum concentration of Levetiracetam can be increased when it is combined with Reboxetine.	Approved, Investigational
Levofloxacin	The serum concentration of Levofloxacin can be increased when it is combined with Reboxetine.	Approved, Investigational
Levomilnacipran	The serum concentration of Levomilnacipran can be increased when it is combined with Reboxetine.	Approved
Linagliptin	The serum concentration of Linagliptin can be increased when it is combined with Reboxetine.	Approved
Loperamide	The serum concentration of Loperamide can be increased when it is combined with Reboxetine.	Approved
Lopinavir	The metabolism of Reboxetine can be decreased when combined with Lopinavir.	Approved
Losartan	The serum concentration of Losartan can be increased when it is combined with Reboxetine.	Approved
Lovastatin	The metabolism of Reboxetine can be decreased when combined with Lovastatin.	Approved, Investigational
Luliconazole	The serum concentration of Reboxetine can be increased when it is combined with Luliconazole.	Approved
Lumacaftor	The metabolism of Reboxetine can be increased when combined with Lumacaftor.	Approved
Mannitol	The serum concentration of Mannitol can be increased when it is combined with Reboxetine.	Approved, Investigational
Methotrexate	The serum concentration of Methotrexate can be increased when it is combined with Reboxetine.	Approved
Methylprednisolone	The serum concentration of Methylprednisolone can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Metoprolol	The serum concentration of Metoprolol can be increased when it is combined with Reboxetine.	Approved, Investigational
Midazolam	The serum concentration of Midazolam can be increased when it is combined with Reboxetine.	Approved, Illicit
Mifepristone	The serum concentration of Reboxetine can be increased when it is combined with Mifepristone.	Approved, Investigational
Mirabegron	The serum concentration of Mirabegron can be increased when it is combined with Reboxetine.	Approved
Mitotane	The serum concentration of Reboxetine can be decreased when it is combined with Mitotane.	Approved
Mitoxantrone	The serum concentration of Mitoxantrone can be increased when it is combined with Reboxetine.	Approved, Investigational
Modafinil	The serum concentration of Reboxetine can be decreased when it is combined with Modafinil.	Approved, Investigational
Morphine	The serum concentration of Morphine can be increased when it is combined with Reboxetine.	Approved, Investigational
Mycophenolate mofetil	The serum concentration of Mycophenolate mofetil can be increased when it is combined with Reboxetine.	Approved, Investigational
Nadolol	The serum concentration of Nadolol can be increased when it is combined with Reboxetine.	Approved
Nafcillin	The serum concentration of Reboxetine can be decreased when it is combined with Nafcillin.	Approved
Naloxegol	The serum concentration of Naloxegol can be increased when it is combined with Reboxetine.	Approved
Naloxone	The serum concentration of Naloxone can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Nefazodone	The metabolism of Reboxetine can be decreased when combined with Nefazodone.	Approved, Withdrawn
Nelfinavir	The metabolism of Reboxetine can be decreased when combined with Nelfinavir.	Approved
Netupitant	The serum concentration of Reboxetine can be increased when it is combined with Netupitant.	Approved
Nevirapine	The metabolism of Reboxetine can be increased when combined with Nevirapine.	Approved
Nicardipine	The serum concentration of Nicardipine can be increased when it is combined with Reboxetine.	Approved
Nifedipine	The serum concentration of Nifedipine can be increased when it is combined with Reboxetine.	Approved
Nilotinib	The metabolism of Reboxetine can be decreased when combined with Nilotinib.	Approved, Investigational
Nintedanib	The serum concentration of Nintedanib can be increased when it is combined with Reboxetine.	Approved
Nizatidine	The serum concentration of Nizatidine can be increased when it is combined with Reboxetine.	Approved
Olanzapine	The serum concentration of Olanzapine can be increased when it is combined with Reboxetine.	Approved, Investigational
Olaparib	The metabolism of Reboxetine can be decreased when combined with Olaparib.	Approved
Ombitasvir	The serum concentration of Ombitasvir can be increased when it is combined with Reboxetine.	Approved
Osimertinib	The serum concentration of Reboxetine can be increased when it is combined with Osimertinib.	Approved
Paclitaxel	The serum concentration of Paclitaxel can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Palbociclib	The serum concentration of Reboxetine can be increased when it is combined with Palbociclib.	Approved
Panobinostat	The serum concentration of Panobinostat can be increased when it is combined with Reboxetine.	Approved, Investigational
Pazopanib	The serum concentration of Pazopanib can be increased when it is combined with Reboxetine.	Approved
Pentobarbital	The metabolism of Reboxetine can be increased when combined with Pentobarbital.	Approved, Vet Approved
Phenobarbital	The metabolism of Reboxetine can be increased when combined with Phenobarbital.	Approved
Phenytoin	The metabolism of Reboxetine can be increased when combined with Phenytoin.	Approved, Vet Approved
Pitavastatin	The serum concentration of Pitavastatin can be increased when it is combined with Reboxetine.	Approved
Pomalidomide	The serum concentration of Pomalidomide can be increased when it is combined with Reboxetine.	Approved
Ponatinib	The serum concentration of Ponatinib can be increased when it is combined with Reboxetine.	Approved
Posaconazole	The metabolism of Reboxetine can be decreased when combined with Posaconazole.	Approved, Investigational, Vet Approved
Pravastatin	The serum concentration of Pravastatin can be increased when it is combined with Reboxetine.	Approved
Prazosin	The serum concentration of Prazosin can be increased when it is combined with Reboxetine.	Approved
Prednisolone	The serum concentration of Prednisolone can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Prednisone	The serum concentration of Prednisone can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Primidone	The metabolism of Reboxetine can be increased when combined with Primidone.	Approved, Vet Approved
Progesterone	The serum concentration of Progesterone can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Propranolol	The serum concentration of Propranolol can be increased when it is combined with Reboxetine.	Approved, Investigational
Prucalopride	The serum concentration of Prucalopride can be increased when it is combined with Reboxetine.	Approved
Quetiapine	The serum concentration of Quetiapine can be increased when it is combined with Reboxetine.	Approved
Quinidine	The serum concentration of Quinidine can be increased when it is combined with Reboxetine.	Approved
Quinine	The serum concentration of Quinine can be increased when it is combined with Reboxetine.	Approved
Ranitidine	The serum concentration of Ranitidine can be increased when it is combined with Reboxetine.	Approved
Ranolazine	The serum concentration of Ranolazine can be increased when it is combined with Reboxetine.	Approved, Investigational
Reserpine	The serum concentration of Reserpine can be increased when it is combined with Reboxetine.	Approved
Rifabutin	The metabolism of Reboxetine can be increased when combined with Rifabutin.	Approved
Rifampicin	The metabolism of Reboxetine can be increased when combined with Rifampicin.	Approved
Rifapentine	The metabolism of Reboxetine can be increased when combined with Rifapentine.	Approved
Rifaximin	The serum concentration of Rifaximin can be increased when it is combined with Reboxetine.	Approved, Investigational
Risperidone	The serum concentration of Risperidone can be increased when it is combined with Reboxetine.	Approved, Investigational
Ritonavir	The metabolism of Reboxetine can be decreased when combined with Ritonavir.	Approved, Investigational
Rivaroxaban	The serum concentration of Rivaroxaban can be increased when it is combined with Reboxetine.	Approved
Romidepsin	The serum concentration of Romidepsin can be increased when it is combined with Reboxetine.	Approved, Investigational
Salicylic acid	The serum concentration of Salicylic acid can be increased when it is combined with Reboxetine.	Approved, Vet Approved
Saquinavir	The metabolism of Reboxetine can be decreased when combined with Saquinavir.	Approved, Investigational
Selexipag	The serum concentration of Selexipag can be increased when it is combined with Reboxetine.	Approved
Sildenafil	The metabolism of Reboxetine can be decreased when combined with Sildenafil.	Approved, Investigational
Silodosin	The serum concentration of Silodosin can be increased when it is combined with Reboxetine.	Approved
Siltuximab	The serum concentration of Reboxetine can be decreased when it is combined with Siltuximab.	Approved
Simeprevir	The serum concentration of Reboxetine can be increased when it is combined with Simeprevir.	Approved
Sitagliptin	The serum concentration of Sitagliptin can be increased when it is combined with Reboxetine.	Approved, Investigational
Sofosbuvir	The serum concentration of Sofosbuvir can be increased when it is combined with Reboxetine.	Approved
Sorafenib	The serum concentration of Sorafenib can be increased when it is combined with Reboxetine.	Approved, Investigational
Sparfloxacin	The serum concentration of Sparfloxacin can be increased when it is combined with Reboxetine.	Approved
Sphingosine	The serum concentration of Sphingosine can be increased when it is combined with Reboxetine.	Experimental
St. John's Wort	The serum concentration of Reboxetine can be decreased when it is combined with St. John's Wort.	Nutraceutical
Stiripentol	The serum concentration of Reboxetine can be increased when it is combined with Stiripentol.	Approved
Sulfisoxazole	The metabolism of Reboxetine can be decreased when combined with Sulfisoxazole.	Approved, Vet Approved
Tacrolimus	The serum concentration of Tacrolimus can be increased when it is combined with Reboxetine.	Approved, Investigational
Tamoxifen	The serum concentration of Tamoxifen can be increased when it is combined with Reboxetine.	Approved
Taurocholic Acid	The serum concentration of Taurocholic Acid can be increased when it is combined with Reboxetine.	Experimental
Technetium Tc-99m sestamibi	The serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Reboxetine.	Approved
Telaprevir	The metabolism of Reboxetine can be decreased when combined with Telaprevir.	Withdrawn
Telithromycin	The metabolism of Reboxetine can be decreased when combined with Telithromycin.	Approved
Temsirolimus	The serum concentration of Temsirolimus can be increased when it is combined with Reboxetine.	Approved
Thioridazine	The serum concentration of Thioridazine can be increased when it is combined with Reboxetine.	Withdrawn
Ticagrelor	The serum concentration of Ticagrelor can be increased when it is combined with Reboxetine.	Approved
Ticlopidine	The metabolism of Reboxetine can be decreased when combined with Ticlopidine.	Approved
Timolol	The serum concentration of Timolol can be increased when it is combined with Reboxetine.	Approved
Tocilizumab	The serum concentration of Reboxetine can be decreased when it is combined with Tocilizumab.	Approved
Tolvaptan	The serum concentration of Tolvaptan can be increased when it is combined with Reboxetine.	Approved
Topotecan	The serum concentration of Topotecan can be increased when it is combined with Reboxetine.	Approved, Investigational
Toremifene	The serum concentration of Toremifene can be increased when it is combined with Reboxetine.	Approved, Investigational
Trastuzumab emtansine	The serum concentration of Trastuzumab emtansine can be increased when it is combined with Reboxetine.	Approved
Ulipristal	The serum concentration of Ulipristal can be increased when it is combined with Reboxetine.	Approved
Umeclidinium	The serum concentration of Umeclidinium can be increased when it is combined with Reboxetine.	Approved
Vecuronium	The serum concentration of Vecuronium can be increased when it is combined with Reboxetine.	Approved
Venetoclax	The serum concentration of Venetoclax can be increased when it is combined with Reboxetine.	Approved
Venlafaxine	The metabolism of Reboxetine can be decreased when combined with Venlafaxine.	Approved
Verapamil	The metabolism of Reboxetine can be decreased when combined with Verapamil.	Approved
Vinblastine	The serum concentration of Vinblastine can be increased when it is combined with Reboxetine.	Approved
Vincristine	The serum concentration of Vincristine can be increased when it is combined with Reboxetine.	Approved, Investigational
Vismodegib	The serum concentration of Vismodegib can be increased when it is combined with Reboxetine.	Approved
Voriconazole	The metabolism of Reboxetine can be decreased when combined with Voriconazole.	Approved, Investigational
Zidovudine	The serum concentration of Zidovudine can be increased when it is combined with Reboxetine.	Approved
Ziprasidone	The metabolism of Reboxetine can be decreased when combined with Ziprasidone.	Approved

Food Interactions

Not Available

References

Synthesis Reference

Not Available

General References

Fleishaker JC: Clinical pharmacokinetics of reboxetine, a selective norepinephrine reuptake inhibitor for the treatment of patients with depression. Clin Pharmacokinet. 2000 Dec;39(6):413-27. [PubMed:11192474 ]
Edwards DM, Pellizzoni C, Breuel HP, Berardi A, Castelli MG, Frigerio E, Poggesi I, Rocchetti M, Dubini A, Strolin Benedetti M: Pharmacokinetics of reboxetine in healthy volunteers. Single oral doses, linearity and plasma protein binding. Biopharm Drug Dispos. 1995 Aug;16(6):443-60. [PubMed:7579027 ]
Wienkers LC, Allievi C, Hauer MJ, Wynalda MA: Cytochrome P-450-mediated metabolism of the individual enantiomers of the antidepressant agent reboxetine in human liver microsomes. Drug Metab Dispos. 1999 Nov;27(11):1334-40. [PubMed:10534319 ]
Kasper S, el Giamal N, Hilger E: Reboxetine: the first selective noradrenaline re-uptake inhibitor. Expert Opin Pharmacother. 2000 May;1(4):771-82. [PubMed:11249515 ]

External Links

Resource	Link
ChemSpider	112870
ChEBI	135342
ChEMBL	CHEMBL383921
Therapeutic Targets Database	DAP000720
PharmGKB	PA144614921
HET	41X
Wikipedia	Reboxetine

ATC Codes

N06AX18 — Reboxetine

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Basic Science	Amphetamine-Related Disorders / Moods Disorders / Substance-Related Disorders	1
1	Unknown Status	Treatment	Schizophrenic Disorders	1
3	Completed	Supportive Care	Bone Mineral Density Quantitative Trait Locus 7	1
3	Recruiting	Treatment	Anxiety Disorder / Dementias / Depressive State / Psychosomatic Disorders / Schizophrenic Disorders	1
4	Unknown Status	Treatment	Abdominal Pain (AP) / Major Depressive Disorder (MDD) / Pain	1
4	Unknown Status	Treatment	Cerebral Stroke	1
4	Unknown Status	Treatment	Depressive State	1
4	Unknown Status	Treatment	Schizophrenic Disorders	1
Not Available	Completed	Basic Science	Cognitive Performance in Major Depression	1
Not Available	Completed	Treatment	Major Depressive Disorder (MDD)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	170-171 °C (Mesylate salt)	Not Available
water solubility	8 mg/mL (Mesylate salt)	Not Available
logP	3.1	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0223 mg/mL	ALOGPS
logP	3.06	ALOGPS
logP	3.28	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	7.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	39.72 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	89.48 m³·mol^-1	ChemAxon
Polarizability	34.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9968
Blood Brain Barrier	+	0.9381
Caco-2 permeable	+	0.575
P-glycoprotein substrate	Substrate	0.7914
P-glycoprotein inhibitor I	Inhibitor	0.8825
P-glycoprotein inhibitor II	Non-inhibitor	0.5968
Renal organic cation transporter	Non-inhibitor	0.5581
CYP450 2C9 substrate	Non-substrate	0.8237
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.5402
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.8063
CYP450 2D6 inhibitor	Non-inhibitor	0.5687
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Inhibitor	0.6318
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.5218
Ames test	Non AMES toxic	0.9141
Carcinogenicity	Non-carcinogens	0.9083
Biodegradation	Not ready biodegradable	0.9372
Rat acute toxicity	2.0972 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.7754
hERG inhibition (predictor II)	Inhibitor	0.717

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

Taxonomy

Description

This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Phenoxy compounds / Aralkylamines / Alkyl aryl ethers / Morpholines / Oxacyclic compounds / Dialkylamines / Dialkyl ethers / Azacyclic compounds / Hydrocarbon derivatives

Substituents

Phenoxy compound / Phenol ether / Alkyl aryl ether / Aralkylamine / Monocyclic benzene moiety / Morpholine / Oxazinane / Dialkyl ether / Secondary aliphatic amine / Ether

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Targets

Details

1. Sodium-dependent noradrenaline transporter

Kind: Protein
Organism: Human
Pharmacological action: yes
Actions: inhibitor

General Function:: Norepinephrine:sodium symporter activity
Specific Function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular Weight:: 69331.42 Da

References

Rauhut AS, Mullins SN, Dwoskin LP, Bardo MT: Reboxetine: attenuation of intravenous nicotine self-administration in rats. J Pharmacol Exp Ther. 2002 Nov;303(2):664-72. [PubMed:12388649 ]
Wilson AA, Johnson DP, Mozley D, Hussey D, Ginovart N, Nobrega J, Garcia A, Meyer J, Houle S: Synthesis and in vivo evaluation of novel radiotracers for the in vivo imaging of the norepinephrine transporter. Nucl Med Biol. 2003 Feb;30(2):85-92. [PubMed:12623106 ]
Lin KS, Ding YS, Kim SW, Kil KE: Synthesis, enantiomeric resolution, F-18 labeling and biodistribution of reboxetine analogs: promising radioligands for imaging the norepinephrine transporter with positron emission tomography. Nucl Med Biol. 2005 May;32(4):415-22. [PubMed:15878511 ]
Spivak B, Strous RD, Shaked G, Shabash E, Kotler M, Weizman A: Reboxetine versus fluvoxamine in the treatment of motor vehicle accident-related posttraumatic stress disorder: a double-blind, fixed-dosage, controlled trial. J Clin Psychopharmacol. 2006 Apr;26(2):152-6. [PubMed:16633143 ]
Mitchell HA, Ahern TH, Liles LC, Javors MA, Weinshenker D: The effects of norepinephrine transporter inactivation on locomotor activity in mice. Biol Psychiatry. 2006 Nov 15;60(10):1046-52. Epub 2006 Aug 7. [PubMed:16893531 ]
Kasper S, el Giamal N, Hilger E: Reboxetine: the first selective noradrenaline re-uptake inhibitor. Expert Opin Pharmacother. 2000 May;1(4):771-82. [PubMed:11249515 ]

Enzymes

Details

1. Cytochrome P450 3A4

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: substrate

General Function:: Vitamin d3 25-hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular Weight:: 57342.67 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Details

2. Cytochrome P450 2D6

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitorinducer

General Function:: Steroid hydroxylase activity
Specific Function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular Weight:: 55768.94 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Details

1. Multidrug resistance protein 1

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

General Function:: Xenobiotic-transporting atpase activity
Specific Function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular Weight:: 141477.255 Da

References

Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE: Inhibition of P-glycoprotein by newer antidepressants. J Pharmacol Exp Ther. 2003 Apr;305(1):197-204. [PubMed:12649369 ]

Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:46

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Structure for DB00234 (Reboxetine)

Targets

References

Enzymes

References

References

Transporters

References