AMG-837
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MedKoo CAT#: 573787

CAS#: 865231-46-5

Description: AMG-837 is a potent partial agonist of GPR40 (FFAR1) that is highly selective over GPR41, GPR43, and GPR120. GPR40 is a G protein-coupled free fatty acid receptor localized mainly on pancreatic islet cells that activates the Gq signaling pathway. AMG 837 increases insulin release when glucose levels are elevated, but it failed to do so in healthy volunteers during Phase I clinical trials.


Chemical Structure

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AMG-837
CAS# 865231-46-5

Theoretical Analysis

MedKoo Cat#: 573787
Name: AMG-837
CAS#: 865231-46-5
Chemical Formula: C26H21F3O3
Exact Mass: 438.1443
Molecular Weight: 438.45
Elemental Analysis: C, 71.23; H, 4.83; F, 13.00; O, 10.95

Price and Availability

Size Price Availability Quantity
1.0mg USD 210.0 2 Weeks
5.0mg USD 385.0 2 Weeks
10.0mg USD 645.0 2 Weeks
25.0mg USD 900.0 2 Weeks
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Related CAS #: 865231-45-4 (sodium)   1259389-38-2 (calium hydrate)   1291087-14-3 (hemicalcium salt)  

Synonym: AMG-837, AMG837, AMG 837

IUPAC/Chemical Name: (S)-3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)hex-4-ynoic acid

InChi Key: ZOPNBMMVVZRSGH-NRFANRHFSA-N

InChi Code: 1S/C26H21F3O3/c1-2-4-21(16-25(30)31)20-9-13-24(14-10-20)32-17-18-5-3-6-22(15-18)19-7-11-23(12-8-19)26(27,28)29/h3,5-15,21H,16-17H2,1H3,(H,30,31)/t21-/m0/s1

SMILES Code: CC#C[C@@H](CC(=O)O)c1ccc(cc1)OCc2cccc(c2)c3ccc(cc3)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: >3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 438.45 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

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1: Liu JJ, Wang Y, Ma Z, Schmitt M, Zhu L, Brown SP, Dransfield PJ, Sun Y, Sharma R, Guo Q, Zhuang R, Zhang J, Luo J, Tonn GR, Wong S, Swaminath G, Medina JC, Lin DC, Houze JB. Optimization of GPR40 Agonists for Type 2 Diabetes. ACS Med Chem Lett. 2014 Feb 6;5(5):517-21. doi: 10.1021/ml400501x. eCollection 2014 May 8. PubMed PMID: 24900872; PubMed Central PMCID: PMC4027784.

2: Wang Y, Liu JJ, Dransfield PJ, Zhu L, Wang Z, Du X, Jiao X, Su Y, Li AR, Brown SP, Kasparian A, Vimolratana M, Yu M, Pattaropong V, Houze JB, Swaminath G, Tran T, Nguyen K, Guo Q, Zhang J, Zhuang R, Li F, Miao L, Bartberger MD, Correll TL, Chow D, Wong S, Luo J, Lin DC, Medina JC. Discovery and Optimization of Potent GPR40 Full Agonists Containing Tricyclic Spirocycles. ACS Med Chem Lett. 2013 May 7;4(6):551-5. doi: 10.1021/ml300427u. eCollection 2013 Jun 13. PubMed PMID: 24900707; PubMed Central PMCID: PMC4027505.

3: Choi YJ, Shin D, Lee JY. G-protein coupled receptor 40 agonists as novel therapeutics for type 2 diabetes. Arch Pharm Res. 2014 Apr;37(4):435-9. PubMed PMID: 24234912.

4: Hamilton JY, Sarlah D, Carreira EM. Iridium-catalyzed enantioselective allylic alkynylation. Angew Chem Int Ed Engl. 2013 Jul 15;52(29):7532-5. doi: 10.1002/anie.201302731. Epub 2013 May 27. PubMed PMID: 23712914.

5: Luo J, Swaminath G, Brown SP, Zhang J, Guo Q, Chen M, Nguyen K, Tran T, Miao L, Dransfield PJ, Vimolratana M, Houze JB, Wong S, Toteva M, Shan B, Li F, Zhuang R, Lin DC. A potent class of GPR40 full agonists engages the enteroinsular axis to promote glucose control in rodents. PLoS One. 2012;7(10):e46300. doi: 10.1371/journal.pone.0046300. Epub 2012 Oct 9. PubMed PMID: 23056280; PubMed Central PMCID: PMC3467217.

6: Brown SP, Dransfield PJ, Vimolratana M, Jiao X, Zhu L, Pattaropong V, Sun Y, Liu J, Luo J, Zhang J, Wong S, Zhuang R, Guo Q, Li F, Medina JC, Swaminath G, Lin DC, Houze JB. Discovery of AM-1638: A Potent and Orally Bioavailable GPR40/FFA1 Full Agonist. ACS Med Chem Lett. 2012 Aug 15;3(9):726-30. doi: 10.1021/ml300133f. eCollection 2012 Sep 13. PubMed PMID: 24900539; PubMed Central PMCID: PMC4025659.

7: Lin DC, Guo Q, Luo J, Zhang J, Nguyen K, Chen M, Tran T, Dransfield PJ, Brown SP, Houze J, Vimolratana M, Jiao XY, Wang Y, Birdsall NJ, Swaminath G. Identification and pharmacological characterization of multiple allosteric binding sites on the free fatty acid 1 receptor. Mol Pharmacol. 2012 Nov;82(5):843-59. doi: 10.1124/mol.112.079640. Epub 2012 Aug 2. PubMed PMID: 22859723; PubMed Central PMCID: PMC3477236.

8: Houze JB, Zhu L, Sun Y, Akerman M, Qiu W, Zhang AJ, Sharma R, Schmitt M, Wang Y, Liu J, Liu J, Medina JC, Reagan JD, Luo J, Tonn G, Zhang J, Lu JY, Chen M, Lopez E, Nguyen K, Yang L, Tang L, Tian H, Shuttleworth SJ, Lin DC. AMG 837: a potent, orally bioavailable GPR40 agonist. Bioorg Med Chem Lett. 2012 Jan 15;22(2):1267-70. doi: 10.1016/j.bmcl.2011.10.118. Epub 2011 Nov 6. PubMed PMID: 22217876.

9: Lin DC, Zhang J, Zhuang R, Li F, Nguyen K, Chen M, Tran T, Lopez E, Lu JY, Li XN, Tang L, Tonn GR, Swaminath G, Reagan JD, Chen JL, Tian H, Lin YJ, Houze JB, Luo J. AMG 837: a novel GPR40/FFA1 agonist that enhances insulin secretion and lowers glucose levels in rodents. PLoS One. 2011;6(11):e27270. doi: 10.1371/journal.pone.0027270. Epub 2011 Nov 8. PubMed PMID: 22087278; PubMed Central PMCID: PMC3210765.

10: Yazaki R, Kumagai N, Shibasaki M. Cooperative activation of alkyne and thioamide functionalities; direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides. Chem Asian J. 2011 Jul 4;6(7):1778-90. doi: 10.1002/asia.201100050. Epub 2011 May 2. PubMed PMID: 21538905.

11: Yazaki R, Kumagai N, Shibasaki M. Enantioselective synthesis of a GPR40 agonist AMG 837 via catalytic asymmetric conjugate addition of terminal alkyne to α,β-unsaturated thioamide. Org Lett. 2011 Mar 4;13(5):952-5. doi: 10.1021/ol102998w. Epub 2011 Feb 3. PubMed PMID: 21291204.

AMG-837

1.0mg / USD 210.0