AMG-3969
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MedKoo CAT#: 530955

CAS#: 1361224-53-4

Description: AMG-3969 is a GK-GKRP disruptor. AMG-3969 normalized blood glucose levels in several rodent models of diabetes. AMG-3969 potently reversed the inhibitory effect of GKRP on GK activity and promoted GK translocation both in vitro (isolated hepatocytes) and in vivo (liver). AMG-3969 blood glucose lowering was restricted to diabetic and not normoglycaemic animals.


Chemical Structure

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AMG-3969
CAS# 1361224-53-4

Theoretical Analysis

MedKoo Cat#: 530955
Name: AMG-3969
CAS#: 1361224-53-4
Chemical Formula: C21H20F6N4O3S
Exact Mass: 522.116
Molecular Weight: 522.4664
Elemental Analysis: C, 48.28; H, 3.86; F, 21.82; N, 10.72; O, 9.19; S, 6.14

Price and Availability

Size Price Availability Quantity
5.0mg USD 250.0 2 Weeks
10.0mg USD 450.0 2 Weeks
25.0mg USD 750.0 2 Weeks
50.0mg USD 1250.0 2 Weeks
100.0mg USD 1950.0 2 Weeks
200.0mg USD 2950.0 2 Weeks
500.0mg USD 3950.0 2 Weeks
1.0g USD 5650.0 2 Weeks
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Synonym: AMG-3969; AMG 3969; AMG3969.

IUPAC/Chemical Name: 2-(4-((2S)-4-((6-amino-3-pyridinyl)sulphonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

InChi Key: SIFKNECWLVONIH-INIZCTEOSA-N

InChi Code: InChI=1S/C21H20F6N4O3S/c1-2-3-16-13-30(35(33,34)17-8-9-18(28)29-12-17)10-11-31(16)15-6-4-14(5-7-15)19(32,20(22,23)24)21(25,26)27/h4-9,12,16,32H,10-11,13H2,1H3,(H2,28,29)/t16-/m0/s1

SMILES Code: OC(C(F)(F)F)(C1=CC=C(N2[C@@H](C#CC)CN(S(=O)(C3=CC=C(N)N=C3)=O)CC2)C=C1)C(F)(F)F

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 191.4

Preparing Stock Solutions

The following data is based on the product molecular weight 522.4664 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

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1: Bourbeau MP, Ashton KS, Yan J, St Jean DJ Jr. Nonracemic synthesis of GK-GKRP disruptor AMG-3969. J Org Chem. 2014 Apr 18;79(8):3684-7. doi: 10.1021/jo500336e. Epub 2014 Apr 10. PubMed PMID: 24678849.

2: Nishimura N, Norman MH, Liu L, Yang KC, Ashton KS, Bartberger MD, Chmait S, Chen J, Cupples R, Fotsch C, Helmering J, Jordan SR, Kunz RK, Pennington LD, Poon SF, Siegmund A, Sivits G, Lloyd DJ, Hale C, St Jean DJ Jr. Small molecule disruptors of the glucokinase-glucokinase regulatory protein interaction: 3. Structure-activity relationships within the aryl carbinol region of the N-arylsulfonamido-N'-arylpiperazine series. J Med Chem. 2014 Apr 10;57(7):3094-116. doi: 10.1021/jm5000497. Epub 2014 Mar 31. PubMed PMID: 24611879.

3: St Jean DJ Jr, Ashton KS, Bartberger MD, Chen J, Chmait S, Cupples R, Galbreath E, Helmering J, Hong FT, Jordan SR, Liu L, Kunz RK, Michelsen K, Nishimura N, Pennington LD, Poon SF, Reid D, Sivits G, Stec MM, Tadesse S, Tamayo N, Van G, Yang KC, Zhang J, Norman MH, Fotsch C, Lloyd DJ, Hale C. Small molecule disruptors of the glucokinase-glucokinase regulatory protein interaction: 2. Leveraging structure-based drug design to identify analogues with improved pharmacokinetic profiles. J Med Chem. 2014 Jan 23;57(2):325-38. doi: 10.1021/jm4016747. Epub 2014 Jan 9. PubMed PMID: 24405213.

4: Lloyd DJ, St Jean DJ Jr, Kurzeja RJ, Wahl RC, Michelsen K, Cupples R, Chen M, Wu J, Sivits G, Helmering J, Komorowski R, Ashton KS, Pennington LD, Fotsch C, Vazir M, Chen K, Chmait S, Zhang J, Liu L, Norman MH, Andrews KL, Bartberger MD, Van G, Galbreath EJ, Vonderfecht SL, Wang M, Jordan SR, Véniant MM, Hale C. Antidiabetic effects of glucokinase regulatory protein small-molecule disruptors. Nature. 2013 Dec 19;504(7480):437-40. doi: 10.1038/nature12724. Epub 2013 Nov 13. PubMed PMID: 24226772.



Additional Information

Glucose homeostasis is a vital and complex process, and its disruption can cause hyperglycaemia and type II diabetes mellitus. Glucokinase (GK), a key enzyme that regulates glucose homeostasis, converts glucose to glucose-6-phosphate in pancreatic β-cells, liver hepatocytes, specific hypothalamic neurons, and gut enterocytes. In hepatocytes, GK regulates glucose uptake and glycogen synthesis, suppresses glucose production, and is subject to the endogenous inhibitor GK regulatory protein (GKRP). During fasting, GKRP binds, inactivates and sequesters GK in the nucleus, which removes GK from the gluconeogenic process and prevents a futile cycle of glucose phosphorylation. Compounds that directly hyperactivate GK (GK activators) lower blood glucose levels and are being evaluated clinically as potential therapeutics for the treatment of type II diabetes mellitus.