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MedKoo Cat#: 530401 | Name: AMG-221

Description:

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

AMG-221, BVT-83370, is a potent and selective 11β-HSD1 inhibitor. AMG-221 decreased fed blood glucose and insulin levels and reduced body weight in diet-induced obesity mice. AMG 221 potently blocked 11β-HSD1 activity, producing sustained inhibition for the 24-hour study duration as measured in ex vivo adipose samples. Early characterization of concentration-response relationships can support rational selection of dose and regimen for future studies.

Chemical Structure

AMG-221
AMG-221
CAS#1095565-81-3

Theoretical Analysis

MedKoo Cat#: 530401

Name: AMG-221

CAS#: 1095565-81-3

Chemical Formula: C14H22N2OS

Exact Mass: 266.1453

Molecular Weight: 266.40

Elemental Analysis: C, 63.12; H, 8.32; N, 10.52; O, 6.01; S, 12.03

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
AMG-221; AMG 221; AMG221; BVT-83370; BVT83370; BVT 83370;
IUPAC/Chemical Name
(5S)-2-[[(1R,3S,4S)-3-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one
InChi Key
YCNCXQNUXCHRRX-ZHPDPMBESA-N
InChi Code
InChI=1S/C14H22N2OS/c1-8(2)14(3)12(17)16-13(18-14)15-11-7-9-4-5-10(11)6-9/h8-11H,4-7H2,1-3H3,(H,15,16,17)/t9-,10+,11+,14+/m1/s1
SMILES Code
O=C1N=C(N[C@H]2C[C@]3([H])CC[C@@]2([H])C3)S[C@@]1(C)C(C)C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 266.40 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
1: Gao Q, Kimura RE, Zhang X, Nam J, Amore BM, Hickman D, Greg Slatter J, Emery MG. Intestinal and hepatic first-pass extraction of the 11β-HSD1 inhibitor AMG 221 in rats with chronic vascular catheters. Xenobiotica. 2014 Mar;44(3):264-9. doi: 10.3109/00498254.2013.769074. PubMed PMID: 23517558. 2: Zhu X, Slatter JG, Emery MG, Deane MR, Akrami A, Zhang X, Hickman D, Skiles GL, Subramanian R. Activity-based exposure comparisons among humans and nonclinical safety testing species in an extensively metabolized drug candidate. Xenobiotica. 2013 Jul;43(7):617-27. doi: 10.3109/00498254.2012.747711. PubMed PMID: 23244593. 3: Greene RJ, Davis JA, Subramanian R, Deane MR, Emery MG, Slatter JG. Regiospecific and stereospecific triangulation of the structures of metabolites formed by sequential metabolism at multiple prochiral centers. Drug Metab Dispos. 2012 May;40(5):928-42. doi: 10.1124/dmd.111.043166. PubMed PMID: 22328582. 4: Li A, Yuan CC, Chow D, Chen M, Emery MG, Hale C, Zhang X, Subramanian R, St Jean DJ Jr, Komorowski R, Véniant M, Wang M, Fotsch C. Synthesis and Evaluation of the Metabolites of AMG 221, a Clinical Candidate for the Treatment of Type 2 Diabetes. ACS Med Chem Lett. 2011 Sep 13;2(11):824-7. doi: 10.1021/ml2001467. PubMed PMID: 24900270; PubMed Central PMCID: PMC4018091. 5: Gibbs JP, Emery MG, McCaffery I, Smith B, Gibbs MA, Akrami A, Rossi J, Paweletz K, Gastonguay MR, Bautista E, Wang M, Perfetti R, Daniels O. Population pharmacokinetic/pharmacodynamic model of subcutaneous adipose 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) activity after oral administration of AMG 221, a selective 11β-HSD1 inhibitor. J Clin Pharmacol. 2011 Jun;51(6):830-41. doi: 10.1177/0091270010374470. PubMed PMID: 20663992. 6: Véniant MM, Hale C, Hungate RW, Gahm K, Emery MG, Jona J, Joseph S, Adams J, Hague A, Moniz G, Zhang J, Bartberger MD, Li V, Syed R, Jordan S, Komorowski R, Chen MM, Cupples R, Kim KW, St Jean DJ Jr, Johansson L, Henriksson MA, Williams M, Vallgårda J, Fotsch C, Wang M. Discovery of a potent, orally active 11beta-hydroxysteroid dehydrogenase type 1 inhibitor for clinical study: identification of (S)-2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-isopropyl-5-methylthiazol-4(5 H)-one (AMG 221). J Med Chem. 2010 Jun 10;53(11):4481-7. doi: 10.1021/jm100242d. PubMed PMID: 20465278. 7: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Dec;31(10):661-700. PubMed PMID: 20140276. 8: Caille S, Cui S, Hwang TL, Wang X, Faul MM. Two asymmetric syntheses of AMG 221, an inhibitor of 11beta-hydroxysteroid dehydrogenase type 1. J Org Chem. 2009 May 15;74(10):3833-42. doi: 10.1021/jo900287b. PubMed PMID: 19391575.