AMG-837 calcium hydrate

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

MedKoo CAT#: 510210

CAS#: 1259389-38-2 (calium hydrate)

Description: AMG-837 is a potent, orally bioavailable GPR40 agonist. AMG 837 was a potent partial agonist in the calcium flux assay on the GPR40 receptor and potentiated glucose stimulated insulin secretion in vitro and in vivo. Acute administration of AMG 837 lowered glucose excursions and increased glucose stimulated insulin secretion during glucose tolerance tests in both normal and Zucker fatty rats. The improvement in glucose excursions persisted following daily dosing of AMG 837 for 21-days in Zucker fatty rats. Preclinical studies demonstrated that AMG 837 was a potent GPR40 partial agonist which lowered post-prandial glucose levels. These studies support the potential utility of AMG 837 for the treatment of type 2 diabetes.

Chemical Structure

AMG-837 calcium hydrate
CAS# 1259389-38-2 (calium hydrate)

Theoretical Analysis

MedKoo Cat#: 510210
Name: AMG-837 calcium hydrate
CAS#: 1259389-38-2 (calium hydrate)
Chemical Formula: C52H42CaF6O7
Exact Mass:
Molecular Weight: 932.9694
Elemental Analysis: C, 66.94; H, 4.54; Ca, 4.30; F, 12.22; O, 12.00

Price and Availability

Size Price Availability Quantity
5.0mg USD 150.0 2 Weeks
10.0mg USD 250.0 2 Weeks
25.0mg USD 450.0 2 Weeks
50.0mg USD 650.0 2 Weeks
100.0mg USD 950.0 2 Weeks
200.0mg USD 1450.0 2 Weeks
500.0mg USD 2450.0 2 Weeks
1.0g USD 3450.0 2 Weeks
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Related CAS #: 865231-45-4 (sodium)   865231-46-5 (free acid)   1259389-38-2 (calium hydrate)   1291087-14-3 (hemicalcium salt)    

Synonym: AMG837; AMG-837; AMG 837; AMG 837 hemicalcium salt; AMG 837 hemicalcium hydrate.

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


InChi Code: InChI=1S/2C26H21F3O3.Ca.H2O/c2*1-2-4-21(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;;/h2*3,5-15,21H,16-17H2,1H3,(H,30,31);;1H2/q;;+2;/p-2/t2*21-;;/m00../s1

SMILES Code: CC#C[C@@H](CC([O-])=O)C1=CC=C(C=C1)OCC2=CC(C3=CC=C(C=C3)C(F)(F)F)=CC=C2.CC#C[C@@H](CC([O-])=O)C4=CC=C(C=C4)OCC5=CC(C6=CC=C(C=C6)C(F)(F)F)=CC=C5.[H]O[H].[Ca+2]

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

Preparing Stock Solutions

The following data is based on the product molecular weight 932.9694 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.

Additional Information

1259389-38-2 (AMG-837 calcium salt hydrate)
865231-46-5 (AMG-837 free acid)
865231-45-4 (AMG-837 sodium salt).