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

Affected Organisms

Humans and other mammals

ATC Code

N06AX18: Reboxetine

N06AX: Other antidepressants

N06A: ANTIDEPRESSANTS

N06: PSYCHOANALEPTICS

N: NERVOUS SYSTEM

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)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEMBL383921
CAS Number: 71620-89-8
UNII: 947S0YZ36I
DrugBank ID: DB00234
TTD ID: D0N8FQ
VARIDT ID: DR00650
INTEDE ID: DR1400

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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
Renin (REN)	OT52GZR2	RENI_HUMAN	Gene/Protein Processing	[11]

Molecular Interaction Atlas (MIA)

MIA Detail

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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.