Centanafadine

Centanafadine (INN) (former developmental code name EB-1020) is a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI) that began its development with Euthymics Bioscience after they acquired DOV Pharmaceutical. It was developed as a treatment for attention-deficit hyperactivity disorder (ADHD) and inhibits the reuptake of norepinephrine, dopamine, and serotonin with an IC₅₀ ratio of 1:6:14, respectively.^[1][2][3][4] In 2011, Euthymics Bioscience spun off its development of centanafadine to a new company called Neurovance.^[5][6] In March 2017, Otsuka Pharmaceutical acquired Neurovance and the rights to centanafadine.^[7] As of January 2018, Otsuka's pipeline indicates it is in Phase II and III clinical trials for a number of different applications to medical conditions.^[8][9][10]

Centanafadine

Legal status
Legal status	US: Investigational New Drug
Identifiers
IUPAC name (1R,5S)-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane
CAS Number	924012-43-1
PubChem CID	16095349
ChemSpider	17253639
UNII	D2A6T4UH9C
KEGG	D10697 Y
CompTox Dashboard (EPA)	DTXSID201045788
Chemical and physical data
Formula	C15H15N
Molar mass	209.292 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=C(C=CC2=CC=CC=C12)[C@@]34C[C@@H]3CNC4
InChI InChI=1S/C15H15N/c1-2-4-12-7-13(6-5-11(12)3-1)15-8-14(15)9-16-10-15/h1-7,14,16H,8-10H2/t14-,15+/m1/s1 Key:HKHCSWPSUSWGLI-CABCVRRESA-N

Centanafadine ^[1]

Site	IC50 (nM)	Action	Ref
SERTTooltip Serotonin transporter	83 nM	Blocker	[1]
NETTooltip Norepinephrine transporter	6 nM	Blocker	[1]
DATTooltip Dopamine transporter	38 nM	Blocker	[1]

See also

• Amitifadine
• Bicifadine
• Dasotraline
• DOV-216,303
• Tesofensine

References

1. "Neurovance's EB-1020 SR for Adult ADHD Shows Stimulant-Like Efficacy and Good Tolerability in Phase 2a Trial" (PDF). Neurovance. Retrieved 14 January 2018.
2. "3-Neurotransmitters, 1-Molecule: Optimized Ratios". Neurovance.
3. "EB-1020, a Non-Stimulant Norepinephrine and Dopamine - Preferring Reuptake Inhibitor for the Treatment of Adult ADHD" (PDF). Neurovance. Archived from the original (PDF) on 2015-11-17. Retrieved 2015-11-14.
4. Bymaster FP, Golembiowska K, Kowalska M, Choi YK, Tarazi FI (June 2012). "Pharmacological characterization of the norepinephrine and dopamine reuptake inhibitor EB-1020: implications for treatment of attention-deficit hyperactivity disorder". Synapse. 66 (6): 522–32. doi:10.1002/syn.21538. PMID 22298359. S2CID 38850652.
5. "Euthymics". Ethismos Research Inc. Retrieved 14 January 2018.
6. "EUTHYMICS BIOSCIENCE, INC. PRESENTS DATA THAT SUPPORT ADVANCING EB-1020 INTO CLINICAL TRIALS FOR ADULT ADHD" (PDF). Neurovance. December 7, 2011. Retrieved 14 January 2018.
7. "Otsuka Pharmaceutical to Acquire Neurovance, Inc". Otsuka. Retrieved 14 January 2018.
8. "Otsuka U.S. Research & Development Programs". Otsuka U.S. Otsuka. Retrieved 14 January 2018.^{[permanent dead link‍]}
9. Otsuka Pharmaceutical Development & Commercialization, Inc. (2021-09-17). "A Phase 3, Randomized, Double-blind, Multicenter, Placebo-controlled, Parallel-group Trial Evaluating the Efficacy, Safety, and Tolerability of Centanafadine Sustained-release Tablets in Adults With Attention-deficit/Hyperactivity Disorder". {{cite journal}}: Cite journal requires |journal= (help)
10. Gunduz-Bruce H (2018-09-26). "SAGE-217 in major depressive disorder: a multicenter, randomized, double-blind, Phase 2 placebo-controlled trial". doi:10.26226/morressier.5b68175eb56e9b005965c44b. S2CID 266120058. Retrieved 2023-06-26.

External links

• Centanafadine - AdisInsight