Basmisanil | RG-1662 | RO5186582 | CAS#1159600-41-5 | GABAA receptor

MedKoo Cat#: 319638 | Name: Basmisanil (RG1662)

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Basmisanil, also known as RG1662, RO5186582, is a highly selective inverse agonist/negative allosteric modulator of α5 subunit-containing GABAA receptors which is under development by Roche for the treatment of cognitive impairment associated with Down syndrome. As of August 2015, it is in phase II clinical trials for this indication. Down syndrome (DS) is the most commonly identifiable genetic form of intellectual disability. Individuals with DS have considerable deficits in intellectual functioning (i.e., low intellectual quotient, delayed learning and/or impaired language development) and adaptive behavior.

Chemical Structure

Basmisanil (RG1662)

CAS#1159600-41-5

Theoretical Analysis

MedKoo Cat#: 319638

Name: Basmisanil (RG1662)

CAS#: 1159600-41-5

Chemical Formula: C21H20FN3O5S

Exact Mass: 445.1108

Molecular Weight: 445.47

Elemental Analysis: C, 56.62; H, 4.53; F, 4.26; N, 9.43; O, 17.96; S, 7.20

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 550.00	2 Weeks
100mg	USD 950.00	2 Weeks
200mg	USD 1,650.00	2 Weeks
500mg	USD 2,950.00	2 Weeks
1g	USD 4,250.00	2 Weeks

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Related CAS #

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Synonym

RG 1662; RG-1662; RG1662; RO5186582; RO-5186582; RO 5186582; Basmisanil.

IUPAC/Chemical Name

(1,1-dioxidothiomorpholino)(6-((3-(4-fluorophenyl)-5-methylisoxazol-4-yl)methoxy)pyridin-3-yl)methanone

InChi Key

VCGRFBXVSFAGGA-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H20FN3O5S/c1-14-18(20(24-30-14)15-2-5-17(22)6-3-15)13-29-19-7-4-16(12-23-19)21(26)25-8-10-31(27,28)11-9-25/h2-7,12H,8-11,13H2,1H3

SMILES Code

O=C(N1CCS(CC1)(=O)=O)C2=CC=C(OCC3=C(C)ON=C3C4=CC=C(F)C=C4)N=C2

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, not in water

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

View handling instruction

Biological target:

Basmisanil is a GABAAα5 negative allosteric modulator.

In vitro activity:

To assess the intrinsic efficacy of basmisanil, two electrode voltage-clamp experiments were performed in Xenopus oocytes. GABA was applied repetitively at a concentration evoking approximately 10% of the maximal response (8 µM for α1β2γ2, 6 µM for α2β3γ2, 10 µM for α3β3γ2 and 5 µM for α5β3γ2). The maximum possible negative allosteric modulation of the GABA responses was determined by using the non-selective NAM, methyl beta-carboline-3-carboxylate (β-CCM). Basmisanil showed a highly selective inhibition of GABAA-α5 (Fig. 2b). At the highest concentration tested (1 µM), basmisanil reduced the GABA-evoked current by up to 42 ± 1%. Reference: Sci Rep. 2021 Apr 8;11(1):7700. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8032764/

In vivo activity:

Basmisanil attenuated diazepam-induced spatial learning impairment in rats. In the water maze, rats were challenged to find a hidden platform position when placed in a large pool filled with opaque water. The platform was removed before the seventh trial. The vehicle group demonstrated spatial learning of the platform position, as indicated by the significant (F(3,27) = 9, p < 0.001) increase in percent time spent in the platform quadrant compared to left (p < 0.001), right (p < 0.001) and opposite (p < 0.001), quadrants (Fig. 4a). Diazepam significantly disrupted learning of the new platform position since subjects spent an equivalent amount of time in each quadrant during the probe trial (F(3,27) = 0.1, p = 0.9). Basmisanil at 10 mg/kg p.o. significantly (F(3,27) = 4, p = 0.01) attenuated the diazepam-induced deficit as revealed by an increase in percent time spent in the previous platform quadrant compared to left (p < 0.05), right (p < 0.05) and opposite (p < 0.05) quadrants (Fig. 4a). Reference: Sci Rep. 2021 Apr 8;11(1):7700. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8032764/

	Solvent	mg/mL	mM
Solubility
	DMSO	65.0	145.91
	DMF	30.0	67.34

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 445.47 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.

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. Hipp JF, Knoflach F, Comley R, Ballard TM, Honer M, Trube G, Gasser R, Prinssen E, Wallace TL, Rothfuss A, Knust H, Lennon-Chrimes S, Derks M, Bentley D, Squassante L, Nave S, Nöldeke J, Wandel C, Thomas AW, Hernandez MC. Basmisanil, a highly selective GABAA-α5 negative allosteric modulator: preclinical pharmacology and demonstration of functional target engagement in man. Sci Rep. 2021 Apr 8;11(1):7700. doi: 10.1038/s41598-021-87307-7. PMID: 33833333; PMCID: PMC8032764.

In vitro protocol:

In vivo protocol:

1: Liogier d'Ardhuy X, Edgin JO, Bouis C, de Sola S, Goeldner C, Kishnani P, Nöldeke J, Rice S, Sacco S, Squassante L, Spiridigliozzi G, Visootsak J, Heller J, Khwaja O. Assessment of Cognitive Scales to Examine Memory, Executive Function and Language in Individuals with Down Syndrome: Implications of a 6-month Observational Study. Front Behav Neurosci. 2015 Nov 18;9:300. doi: 10.3389/fnbeh.2015.00300. eCollection 2015. PubMed PMID: 26635554; PubMed Central PMCID: PMC4650711. 1: Costa AC, Scott-McKean JJ. Prospects for improving brain function in individuals with Down syndrome. CNS Drugs. 2013 Sep;27(9):679-702. doi: 10.1007/s40263-013-0089-3. Review. PubMed PMID: 23821040.