ACT-462206
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MedKoo CAT#: 531401

CAS#: 1361321-96-1

Description: ACT-462206 is an orally active, potent, brain-penetrant dual orexin 1/orexin 2 receptor antagonist. The orexin system consists of two G-protein-coupled receptors, the orexin 1 and orexin 2 receptors, widely expressed in diverse regions of the brain, and two peptide agonists, orexin A and orexin B, which are produced in a small assembly of neurons in the lateral hypothalamus. The orexin system plays an important role in the maintenance of wakefulness.

Chemical Structure

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ACT-462206
CAS# 1361321-96-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 531401
Name: ACT-462206
CAS#: 1361321-96-1
Chemical Formula: C20H24N2O4S
Exact Mass: 388.15
Molecular Weight: 388.482
Elemental Analysis: C, 61.84; H, 6.23; N, 7.21; O, 16.47; S, 8.25

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 weeks
25mg USD 850 2 weeks
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Synonym: ACT-462206

IUPAC/Chemical Name: (2S)-N-(3,5-dimethylphenyl)-1-(4-methoxyphenyl)sulfonylpyrrolidine-2-carboxamide

InChi Key: NHPQGZOBHSVTAQ-IBGZPJMESA-N

InChi Code: InChI=1S/C20H24N2O4S/c1-14-11-15(2)13-16(12-14)21-20(23)19-5-4-10-22(19)27(24,25)18-8-6-17(26-3)7-9-18/h6-9,11-13,19H,4-5,10H2,1-3H3,(H,21,23)/t19-/m0/s1

SMILES Code: O=C([C@H]1N(S(=O)(C2=CC=C(OC)C=C2)=O)CCC1)NC3=CC(C)=CC(C)=C3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Potent, dual orexin receptor antagonist.
In vitro activity: TBD
In vivo activity: In the present study, it was demonstrated that icv administration of DORA, ACT462206, a novel orexin receptor antagonist, significantly suppressed centrally administered ghrelin-induced feeding in rats. In addition, Fos immunohistochemistry revealed that centrally administered ghrelin induced Fos expression in the PVN, the Arc, and the LHA, which are areas related to feeding behavior. Fos expression was significantly inhibited by pretreatment with DORA; however, it remained significantly increased in those nuclei when compared to that after icv administration of ghrelin without DORA. It is worth noting that Fos expression of orexin-A-IR neurons induced by icv administration of ghrelin was significantly inhibited by pretreatment with DORA, but the Fos expression in orexin-A-IR neurons remained significantly increased. Reference: J Physiol Sci. 2018; 68(2): 129–136. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6394659/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 38.9 100.00
Ethanol 38.9 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 388.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. So M, Hashimoto H, Saito R, Yamamoto Y, Motojima Y, Ueno H, Sonoda S, Yoshimura M, Maruyama T, Kusuhara K, Ueta Y. Inhibition of ghrelin-induced feeding in rats by pretreatment with a novel dual orexin receptor antagonist. J Physiol Sci. 2018 Mar;68(2):129-136. doi: 10.1007/s12576-016-0517-5. Epub 2017 Jan 4. Erratum in: J Physiol Sci. 2019 Feb 14;: PMID: 28054308; PMCID: PMC6394659. 2. Boss C, Roch-Brisbare C, Steiner MA, Treiber A, Dietrich H, Jenck F, von Raumer M, Sifferlen T, Brotschi C, Heidmann B, Williams JT, Aissaoui H, Siegrist R, Gatfield J. Structure-activity relationship, biological, and pharmacological characterization of the proline sulfonamide ACT-462206: a potent, brain-penetrant dual orexin 1/orexin 2 receptor antagonist. ChemMedChem. 2014 Nov;9(11):2486-96. doi: 10.1002/cmdc.201402258. Epub 2014 Aug 21. PMID: 25147058.
In vitro protocol: TBD
In vivo protocol: 1. So M, Hashimoto H, Saito R, Yamamoto Y, Motojima Y, Ueno H, Sonoda S, Yoshimura M, Maruyama T, Kusuhara K, Ueta Y. Inhibition of ghrelin-induced feeding in rats by pretreatment with a novel dual orexin receptor antagonist. J Physiol Sci. 2018 Mar;68(2):129-136. doi: 10.1007/s12576-016-0517-5. Epub 2017 Jan 4. Erratum in: J Physiol Sci. 2019 Feb 14;: PMID: 28054308; PMCID: PMC6394659. 2. Boss C, Roch-Brisbare C, Steiner MA, Treiber A, Dietrich H, Jenck F, von Raumer M, Sifferlen T, Brotschi C, Heidmann B, Williams JT, Aissaoui H, Siegrist R, Gatfield J. Structure-activity relationship, biological, and pharmacological characterization of the proline sulfonamide ACT-462206: a potent, brain-penetrant dual orexin 1/orexin 2 receptor antagonist. ChemMedChem. 2014 Nov;9(11):2486-96. doi: 10.1002/cmdc.201402258. Epub 2014 Aug 21. PMID: 25147058.

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1: Hoch M, van Gorsel H, van Gerven J, Dingemanse J. Entry-into-humans study with ACT-462206, a novel dual orexin receptor antagonist, comparing its pharmacodynamics with almorexant. J Clin Pharmacol. 2014 Sep;54(9):979-86. doi: 10.1002/jcph.297. Epub 2014 Apr 21. PMID: 24691844.


2: Parekh RU, White A, Leffler KE, Biancardi VC, Eells JB, Abdel-Rahman AA, Sriramula S. Hypothalamic kinin B1 receptor mediates orexin system hyperactivity in neurogenic hypertension. Sci Rep. 2021 Oct 26;11(1):21050. doi: 10.1038/s41598-021-00522-0. PMID: 34702886; PMCID: PMC8548389.


3: Boss C, Roch-Brisbare C, Steiner MA, Treiber A, Dietrich H, Jenck F, von Raumer M, Sifferlen T, Brotschi C, Heidmann B, Williams JT, Aissaoui H, Siegrist R, Gatfield J. Structure-activity relationship, biological, and pharmacological characterization of the proline sulfonamide ACT-462206: a potent, brain- penetrant dual orexin 1/orexin 2 receptor antagonist. ChemMedChem. 2014 Nov;9(11):2486-96. doi: 10.1002/cmdc.201402258. Epub 2014 Aug 21. PMID: 25147058.


4: Boss C. 20 Years of Medicinal Chemistry - Always Look at the Bright Side (of Life). Chimia (Aarau). 2020 Aug 12;74(7):549-560. doi: 10.2533/chimia.2020.549. PMID: 32778207.