N-[3-[4-[4-[(Cyclohexylmethylsulfonyl)amino]butyl]piperazin-1-yl]phenyl]acetamide
N-[3-[4-[4-[(Cyclohexylmethylsulfonyl)amino]butyl]piperazin-1-yl]phenyl]acetamide Basic information
- Product Name:
- N-[3-[4-[4-[(Cyclohexylmethylsulfonyl)amino]butyl]piperazin-1-yl]phenyl]acetamide
- Synonyms:
-
- N-[3-[4-[4-[(Cyclohexylmethylsulfonyl)amino]butyl]piperazin-1-yl]phenyl]acetamide
- Naluzotan
- Unii-lq54E5B4ew
- PRX 00023
- TAK-448
- Acetamide, N-[3-[4-[4-[[(cyclohexylmethyl)sulfonyl]amino]butyl]-1-piperazinyl]phenyl]-
- CAS:
- 740873-06-7
- MF:
- C23H38N4O3S
- MW:
- 450.64
- Mol File:
- 740873-06-7.mol
N-[3-[4-[4-[(Cyclohexylmethylsulfonyl)amino]butyl]piperazin-1-yl]phenyl]acetamide Chemical Properties
- Density
- 1.169
- storage temp.
- Store at -20°C
- solubility
- Soluble in DMSO
- form
- Solid
- pka
- 11.49±0.40(Predicted)
- color
- White to light yellow
N-[3-[4-[4-[(Cyclohexylmethylsulfonyl)amino]butyl]piperazin-1-yl]phenyl]acetamide Usage And Synthesis
Uses
Naluzotan is a novel, potent, and selective amidosulfonamide 5-HT1A agonist with IC50 and Ki of appr 20 nM and 5.1 nM, used for the treatment of anxiety and depression; Also a weak hERG K+ channel blocker, with IC50 of 3800 nM.
in vivo
In rats Naluzotan shows 11% oral bioavailability with a serum t1/2 of 2?3.5 h when administrated po, attaining a Cmax level of 24 ± 13 ng/mL (3 mg/kg, po). Naluzotan shows significant brain penetration, achieving a brain:serum concentration ratio of approximately 0.5 in the rat at 1 h following either intravenous or oral administration and reaching brain concentration approximately equivalent to that of buspirone. In dogs the pharmacokinetic profile of naluzotan shows 16% oral bioavailability, a serum t1/2 of 1.1 h po, and a Cmax level of 174 ± 141 ng/mL (3 mg/kg, po)[1]. PRX-00023 (0.01-0.05 mg/kg, i.p.) significantly reduces USV rates, but done of these doses produce sedation in rats[2].
IC 50
5-HT1A Receptor: 20 nM (IC50); 5-HT1A Receptor: 5.1 nM (Ki); hERG K+ channel: 3800 nM (IC50)
References
[1] Becker OM, et al. An integrated in silico 3D model-driven discovery of a novel, potent, and selective amidosulfonamide 5-HT1A agonist (PRX-00023) for the treatment of anxiety and depression. J Med Chem. 2006 Jun 1;49(11):3116-35. DOI:10.1021/jm0508641
[2] Brunelli SA, et al. PRX-00023, a selective serotonin 1A receptor agonist, reduces ultrasonic vocalizations in infant rats bred for high infantile anxiety. Pharmacol Biochem Behav. 2009 Nov;94(1):8-15. DOI:10.1016/j.pbb.2009.06.014
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