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SML2117

Sigma-Aldrich

TCS-1102

≥98% (HPLC)

Synonym(s):

BBAC, (2S)-N-[1,1′-Biphenyl]-2-yl-1-[2-[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl]-2-pyrrolidinecarboxamide, DORA-1, N-(1,1′-Biphenyl-2-yl)-1-{[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl}-L-prolinamide, TCS 1102, TCS1102, (2S)-N-[1,1′-Biphenyl]-2-yl-1-[2-[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl]-2-pyrrolidinecarboxamide

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About This Item

Empirical Formula (Hill Notation):
C27H26N4O2S
CAS Number:
916141-36-1
Molecular Weight:
470.59
MDL number:
MFCD18086894
UNSPSC Code:
12352200

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CN1C2=CC=CC=C2N=C1SCC(N3CCC[C@H]3C(NC4=CC=CC=C4C5=CC=CC=C5)=O)=O

InChI

1S/C27H26N4O2S/c1-30-23-15-8-7-14-22(23)29-27(30)34-18-25(32)31-17-9-16-24(31)26(33)28-21-13-6-5-12-20(21)19-10-3-2-4-11-19/h2-8,10-15,24H,9,16-18H2,1H3,(H,28,33)/t24-/m0/s1

InChI key

YSBGRVXJEMSEQY-DEOSSOPVSA-N

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Biochem/physiol Actions

TCS-1102 (DORA-1) is a high-affinity (Ki = 3 nM against [3H]-TCS-1102 for binding hOX1R and Ki = 0.2 nM against [3H]-pyrrolylphenyl analog for binding hOX2R) dual orexin receptor antagonist (DORA) that potently inhibits calcium mobilization in hOX1R & hOX2R CHO transfectants (IC50 = 17 & 4 nM, respectively). TCS-1102 promotes sleep (50-100 mg/kg p.o.), decreases fear/anxiety (10-20 mg/kg i.p.), and inhibits ADL-orexin B peptide-induced locomotion (by 56%/74%/100% with 15/50/100 mg/kg i.p. 30 min before ADL-XB ICV injection) with good pharmacokinetic properties, brain penetration (Brain/plasma conc. = 2.37 μM/3.50 μM 3 hrs post 100 mg/kg i.p.), and oral availability (Cmax/AUC(0–24h) = 1.21 μM/6.8 μM h and 3.01 μM/12.5 μM h, respectively post 50 and 100 mg/kg p.o. dosage) in rats in vivo.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Jyrki P Kukkonen
Cellular signalling, 28(2), 51-60 (2015-11-20)
There are two subtypes of orexin receptors, OX1 and OX2. Signalling pathways have been mapped in much higher detail for OX1 receptors than OX2 receptors. Almost all the detailed studies have been performed in Chinese hamster ovary cells, and we
Guan-Ling Lu et al.
Neuropharmacology, 107, 168-180 (2016-03-12)
The orexin system consists of two peptides, orexin A and B and two receptors, OX1R and OX2R. It is implicated in learning and memory regulation while controversy remains on its role in modulating hippocampal synaptic plasticity in vivo and in vitro. Here
Yuhei Nishimura et al.
Frontiers in pharmacology, 6, 257-257 (2015-11-19)
Sleep-wake states are impaired in various neurological disorders. Impairment of sleep-wake states can be an early condition that exacerbates these disorders. Therefore, treating sleep-wake dysfunction may prevent or slow the development of these diseases. Although many gene products are likely
Jeffrey M Bergman et al.
Bioorganic & medicinal chemistry letters, 18(4), 1425-1430 (2008-01-22)
A series of OX(2)R/OX(1)R dual orexin antagonists was prepared based on a proline bis-amide identified as a screening lead. Through a combination of classical and library synthesis, potency enhancing replacements for both amide portions were discovered. N-methylation of the benzimidazole
Xiaoyu Chen et al.
Brain structure & function, 219(6), 2103-2118 (2013-08-21)
Orexins (hypocretins) are peptides that have been shown to regulate behavioral arousal and wakefulness. Recent evidence indicates that orexin neurons are activated by stress and that orexins play a role in anxiety. The present paper describes a series of experiments
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