AVN-492
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MedKoo CAT#: 555161

CAS#: 1220646-23-0

Description: AVN-492 is a potent and selective 5-HT6R Antagonist. The affinity of AVN-492 to bind to 5-HT6R (Ki = 91 pM) was more than three orders of magnitude higher than that to bind to the only other target, 5-HT2BR, (Ki = 170 nM). AVN-492 demonstrates good in vitro and in vivo ADME profile with high oral bioavailability and good brain permeability in rodents.

Chemical Structure

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AVN-492
CAS# 1220646-23-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 555161
Name: AVN-492
CAS#: 1220646-23-0
Chemical Formula: C17H21N5O2S
Exact Mass: 359.14
Molecular Weight: 359.448
Elemental Analysis: C, 56.81; H, 5.89; N, 19.48; O, 8.90; S, 8.92

Price and Availability

Size Price Availability Quantity
50mg USD 250 2 Weeks
100mg USD 450 2 Weeks
200mg USD 650 2 Weeks
500mg USD 1450 2 Weeks
1g USD 2450 2 Weeks
2g USD 3850 2 weeks
5g USD 5850 2 Weeks
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Synonym: AVN-492; AVN 492; AVN492.

IUPAC/Chemical Name: N2,N6,N6,5,7-pentamethyl-3-(phenylsulfonyl)pyrazolo[1,5-a]pyrimidine-2,6-diamine

InChi Key: SNPPEHMSSOEYDH-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H21N5O2S/c1-11-14(21(4)5)12(2)22-17(19-11)15(16(18-3)20-22)25(23,24)13-9-7-6-8-10-13/h6-10H,1-5H3,(H,18,20)

SMILES Code: CNC1=NN2C(N=C(C)C(N(C)C)=C2C)=C1S(C3=CC=CC=C3)(=O)=O

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: In behavioral tests, AVN-492 shows anxiolytic effect in elevated plus-maze model, prevents an apomorphine-induced disruption of startle pre-pulse inhibition (the PPI model) and reverses a scopolamine- and MK-801-induced memory deficit in passive avoidance model. No anti-obesity effect of AVN-492 was found in a murine model. The data presented here strongly indicate that due to its high oral bioavailability, extremely high selectivity, and potency to block the 5-HT6 receptor, AVN-492 is a very promising tool for evaluating the role the 5-HT6 receptor might play in cognitive and neurodegenerative impairments. AVN-492 is an excellent drug candidate to be tested for treatment of such diseases, and is currently being tested in Phase I trials.

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: AVN-492 is a very specific and highly-selective antagonist with picomolar affinity to 5-HT6R (Ki=91 pM).
In vitro activity: The affinity of AVN-492 to bind to 5-HT6R (Ki = 91 pM) was more than three orders of magnitude higher than that to bind to the only other target, 5-HT2BR, (Ki = 170 nM). Thus, the compound displayed great 5-HT6R selectivity against all other serotonin receptor subtypes, and is extremely specific against any other receptors such as adrenergic, GABAergic, dopaminergic, histaminergic, etc. Reference: J Alzheimers Dis. 2017;58(4):1043-1063. https://pubmed.ncbi.nlm.nih.gov/28550249/
In vivo activity: In behavioral tests, AVN-492 shows anxiolytic effect in elevated plus-maze model, prevents an apomorphine-induced disruption of startle pre-pulse inhibition (the PPI model) and reverses a scopolamine- and MK-801-induced memory deficit in passive avoidance model. No anti-obesity effect of AVN-492 was found in a murine model. Reference: J Alzheimers Dis. 2017;58(4):1043-1063. https://pubmed.ncbi.nlm.nih.gov/28550249/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 62.5 173.88
DMF 25.0 69.55
DMF:PBS (pH 7.2) (1:20) 0.0 0.11
Ethanol 1.0 2.78

Preparing Stock Solutions

The following data is based on the product molecular weight 359.45 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. Ivachtchenko AV, Okun I, Aladinskiy V, Ivanenkov Y, Koryakova A, Karapetyan R, Mitkin O, Salimov R, Ivashchenko A. AVN-492, A Novel Highly Selective 5-HT6R Antagonist: Preclinical Evaluation. J Alzheimers Dis. 2017;58(4):1043-1063. doi: 10.3233/JAD-161262. PMID: 28550249.
In vitro protocol: 1. Ivachtchenko AV, Okun I, Aladinskiy V, Ivanenkov Y, Koryakova A, Karapetyan R, Mitkin O, Salimov R, Ivashchenko A. AVN-492, A Novel Highly Selective 5-HT6R Antagonist: Preclinical Evaluation. J Alzheimers Dis. 2017;58(4):1043-1063. doi: 10.3233/JAD-161262. PMID: 28550249.
In vivo protocol: 1. Ivachtchenko AV, Okun I, Aladinskiy V, Ivanenkov Y, Koryakova A, Karapetyan R, Mitkin O, Salimov R, Ivashchenko A. AVN-492, A Novel Highly Selective 5-HT6R Antagonist: Preclinical Evaluation. J Alzheimers Dis. 2017;58(4):1043-1063. doi: 10.3233/JAD-161262. PMID: 28550249.

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1: Ivachtchenko AV, Okun I, Aladinskiy V, Ivanenkov Y, Koryakova A, Karapetyan R,
Mitkin O, Salimov R, Ivashchenko A. AVN-492, A Novel Highly Selective 5-HT6R
Antagonist: Preclinical Evaluation. J Alzheimers Dis. 2017;58(4):1043-1063. doi:
10.3233/JAD-161262. PubMed PMID: 28550249.