Reboxetine

Reboxetine
	(R,R)-(–)-reboxetine (top),; (S,S)-(+)-reboxetine (bottom)
Clinical data
Trade names	Edronax, others
Pregnancy; category	AU: B1; ;
Routes of; administration	By mouth
Drug class	Norepinephrine reuptake inhibitor
ATC code	N06AX18 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); UK: POM (Prescription only); US: Not approved;
Pharmacokinetic data
Bioavailability	≥94%
Protein binding	97–98%
Metabolism	Liver (CYP3A4-mediated)
Elimination half-life	12–12.5 hours
Excretion	Urine (78%; 9–10% unchanged)
Identifiers
	IUPAC name rel-(2R)-2-[(R)-(2-Ethoxyphenoxy)(phenyl)methyl]morpholine;
CAS Number	71620-89-8 ; Mesylate: 98769-84-7 ;
PubChem CID	127151;
DrugBank	DB00234 ;
ChemSpider	112870 ;
UNII	947S0YZ36I; Mesylate: L94J81YNNY ;
KEGG	D08472 ;
ChEMBL	ChEMBL383921 ;
Chemical and physical data
Formula	C19H23NO3
Molar mass	313.397 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemate
	SMILES CCOC1=C(C=CC=C1)O[C@@H]([C@@H]2OCCNC2)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 ; Key:CBQGYUDMJHNJBX-RTBURBONSA-N ;
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Reboxetine, sold under the brand name Edronax among others, is a selective norepinephrine reuptake inhibitor (sNRI) medication marketed as an antidepressant by Pfizer for use in the treatment of major depressive disorder, although it has also been used off-label for panic disorder and attention deficit hyperactivity disorder (ADHD).^[4] It is approved for use in many countries worldwide, but has not been approved for use in the United States.^[5]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b ^c ^d ^e "PRODUCT INFORMATION EDRONAX® Reboxetine mesilate" (PDF). TGA eBusiness Services. Pfizer Australia Pty Ltd. 17 October 2012. Retrieved 10 November 2013.
^ ^a ^b ^c ^d Holm KJ, Spencer CM (July 1999). "Reboxetine". CNS Drugs. 12 (1): 65–83. doi:10.2165/00023210-199912010-00006. S2CID 72813017.
^ Reboxetine Mesilate. The Royal Pharmaceutical Society of Great Britain. 8 November 2011. Retrieved 10 November 2013. {{cite book}}: |work= ignored (help)
^ Eyding D, Lelgemann M, Grouven U, Härter M, Kromp M, Kaiser T, Kerekes MF, Gerken M, Wieseler B (October 2010). "Reboxetine for acute treatment of major depression: systematic review and meta-analysis of published and unpublished placebo and selective serotonin reuptake inhibitor controlled trials". BMJ. 341: c4737. doi:10.1136/bmj.c4737. PMC 2954275. PMID 20940209.

Clinical data
(R,R)-(–)-reboxetine (top), (S,S)-(+)-reboxetine (bottom)
Trade names	Edronax, others
Pregnancy category	AU: B1
Routes of administration	By mouth
Drug class	Norepinephrine reuptake inhibitor
ATC code	N06AX18 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) BR: Class C1 (Other controlled substances)^[1] UK: POM (Prescription only) US: Not approved
Pharmacokinetic data
Bioavailability	≥94%^[2]^[3]
Protein binding	97–98%^[2]^[3]
Metabolism	Liver (CYP3A4-mediated)^[2]
Elimination half-life	12–12.5 hours^[2]^[3]
Excretion	Urine (78%; 9–10% unchanged)^[2]^[3]
Identifiers
IUPAC name rel-(2R)-2-[(R)-(2-Ethoxyphenoxy)(phenyl)methyl]morpholine
CAS Number	71620-89-8^N Mesylate: 98769-84-7^N
PubChem CID	127151
DrugBank	DB00234^Y
ChemSpider	112870^Y
UNII	947S0YZ36I Mesylate: L94J81YNNY^Y
KEGG	D08472^Y
ChEMBL	ChEMBL383921^N
Chemical and physical data
Formula	C₁₉H₂₃NO₃
Molar mass	313.397 g·mol⁻¹
3D model (JSmol)	Interactive image
Chirality	Racemate
SMILES CCOC1=C(C=CC=C1)O[C@@H]([C@@H]2OCCNC2)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^Y Key:CBQGYUDMJHNJBX-RTBURBONSA-N^Y
^NY (what is this?) (verify)