Details of the Drug

General Information of Drug (ID: DM26PRD)

Drug Name
Reboxetine
Synonyms
71620-89-8; (2r)-2-[(R)-(2-Ethoxyphenoxy)(Phenyl)methyl]morpholine; Morpholine, 2-[(2-ethoxyphenoxy)phenylmethyl]-, (R*,R*)-; Morpholine, 2-[(R)-(2-ethoxyphenoxy)phenylmethyl]-, (2R)-rel-; Reboxetine [INN:BAN]; Morpholine, 2-((R)-(2-ethoxyphenoxy)phenylmethyl)-, (2R)-rel-; HSDB 7701; Edronax (TN); (R,R)-Reboxetine; AC1L2RJ0; SCHEMBL34533; CHEMBL383921; DTXSID1048257; MolPort-005-943-618; CHEBI:135342; ZINC3996032; BCP12060; AKOS015966368; DB00234; AN-34535; AK431803; AJ-47614
Indication
Disease Entry ICD 11 Status REF
Depression 6A70-6A7Z Approved [1]
Major depressive disorder 6A70.3 Approved [2]
Pain MG30-MG3Z Approved [3]
Diabetic neuropathy 8C0Z Investigative [4]
Therapeutic Class
Antidepressants
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 313.4
Logarithm of the Partition Coefficient (xlogp) 3
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [5]
Bioavailability
94% of drug becomes completely available to its intended biological destination(s) [6]
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.82 mL/min/kg [7]
Elimination
10% of drug is excreted from urine in the unchanged form [5]
Half-life
The concentration or amount of drug in body reduced by one-half in 12.5 hours [7]
Metabolism
The drug is metabolized via the dealkylation, hydroxylation and oxidation followedby glucuronide or sulphate conjugation []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.547 micromolar/kg/day [8]
Unbound Fraction
The unbound fraction of drug in plasma is 0.019% [7]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.65 L/kg [7]
Water Solubility
The ability of drug to dissolve in water is measured as 8 mg/mL [5]
Chemical Identifiers
Formula
C19H23NO3
IUPAC Name
(2R)-2-[(R)-(2-ethoxyphenoxy)-phenylmethyl]morpholine
Canonical SMILES
CCOC1=CC=CC=C1O[C@@H]([C@H]2CNCCO2)C3=CC=CC=C3
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
InChIKey
CBQGYUDMJHNJBX-RTBURBONSA-N
Cross-matching ID
PubChem CID
127151
ChEBI ID
CHEBI:135342
CAS Number
71620-89-8
DrugBank ID
DB00234
TTD ID
D0N8FQ
VARIDT ID
DR00650
INTEDE ID
DR1400
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Norepinephrine transporter (NET) TTAWNKZ SC6A2_HUMAN Inhibitor [9]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [10]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Angiotensinogen (AGT) OTBZLYR3 ANGT_HUMAN Gene/Protein Processing [11]
Renin (REN) OT52GZR2 RENI_HUMAN Gene/Protein Processing [11]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4808).
2 Comparative efficacy and acceptability of 21 antidepressant drugs for the acute treatment of adults with major depressive disorder: a systematic review and network meta-analysis. Lancet. 2018 Apr 7;391(10128):1357-1366.
3 Gastrointestinal side effects associated with antidepressant treatments in patients with major depressive disorder: A systematic review and meta-analysis. Prog Neuropsychopharmacol Biol Psychiatry. 2021 Jul 13;109:110266.
4 Catecholaminergic and opioidergic system mediated effects of reboxetine on diabetic neuropathic pain. Psychopharmacology (Berl). 2020 Apr;237(4):1131-1145.
5 BDDCS applied to over 900 drugs
6 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
7 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
8 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
9 Reboxetine: the first selective noradrenaline re-uptake inhibitor. Expert Opin Pharmacother. 2000 May;1(4):771-82.
10 Clinical pharmacokinetics of reboxetine, a selective norepinephrine reuptake inhibitor for the treatment of patients with depression. Clin Pharmacokinet. 2000 Dec;39(6):413-27.
11 Influences of norepinephrine transporter function on the distribution of sympathetic activity in humans. Hypertension. 2006 Jul;48(1):120-6. doi: 10.1161/01.HYP.0000225424.13138.5d. Epub 2006 May 22.