| Identification | Back Directory | [Name]
N-[3-[4-[4-[(Cyclohexylmethylsulfonyl)amino]butyl]piperazin-1-yl]phenyl]acetamide | [CAS]
740873-06-7 | [Synonyms]
TAK-448
Naluzotan
PRX 00023
Unii-lq54E5B4ew
N-[3-[4-[4-[(Cyclohexylmethylsulfonyl)amino]butyl]piperazin-1-yl]phenyl]acetamide
Acetamide, N-[3-[4-[4-[[(cyclohexylmethyl)sulfonyl]amino]butyl]-1-piperazinyl]phenyl]- | [Molecular Formula]
C23H38N4O3S | [MDL Number]
MFCD09833676 | [MOL File]
740873-06-7.mol | [Molecular Weight]
450.64 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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