R-1663

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

MedKoo CAT#: 528205

CAS#: 865451-66-7

Description: R-1663 is a factor Xa inhibitor potentially for the treatment of thrombosis. R-1663 prolonged clotting times, inhibited thrombin generation (peak height and endogenous thrombin potential [ETP]) and anti-factor Xa activity in a concentration-dependent manner without increasing bleeding time. Pharmacodynamic parameters were strongly correlated to R-1663 plasma concentrations. The inhibition was more pronounced on peak height (IC₅₀ = 194 ng/ml) than on ETP (2790 ng/ml). Pharmacokinetics and pharmacodynamics of R-1663 appeared not to be substantially affected by age or gender but remained to be confirmed in larger clinical trials including older patients.


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R-1663 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 528205
Name: R-1663
CAS#: 865451-66-7
Chemical Formula: C22H23ClN4O5
Exact Mass: 458.1357
Molecular Weight: 458.899
Elemental Analysis: C, 57.58; H, 5.05; Cl, 7.73; N, 12.21; O, 17.43


Synonym: R-1663; R 1663; R1663

IUPAC/Chemical Name: (2R,4R)-N1-(4-chlorophenyl)-4-hydroxy-N2-(4-(3-oxomorpholino)phenyl)pyrrolidine-1,2-dicarboxamide

InChi Key: DMYZJLOWGSRVKP-RTBURBONSA-N

InChi Code: InChI=1S/C22H23ClN4O5/c23-14-1-3-16(4-2-14)25-22(31)27-12-18(28)11-19(27)21(30)24-15-5-7-17(8-6-15)26-9-10-32-13-20(26)29/h1-8,18-19,28H,9-13H2,(H,24,30)(H,25,31)/t18-,19-/m1/s1

SMILES Code: O=C(N1[C@@H](C(NC2=CC=C(N3C(COCC3)=O)C=C2)=O)C[C@@H](O)C1)NC4=CC=C(Cl)C=C4


Technical Data

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).

Harmonized System Code:
293490


References

1: Schmitt C, Pannier A, McIntyre C, Zandt H, Ciorciaro C, Winters K, Pepper T. Crossover dose escalation study to assess safety, pharmacokinetics, and pharmacodynamics of single doses of R1663, an oral factor Xa inhibitor, in healthy male volunteers. J Clin Pharmacol. 2012 Apr;52(4):499-510. doi: 10.1177/0091270011401621. PubMed PMID: 21566199.

2: Schmitt C, Charoin-Pannier A, McIntyre C, Zandt H, Ciorciaro C, Zweigler L, Winters K, Pepper T. Effect of food on the pharmacokinetics and pharmacodynamics of R1663, an oral factor Xa inhibitor, in healthy male volunteers. Int J Clin Pharmacol Ther. 2012 Aug;50(8):566-72. doi: 10.5414/CP201697. PubMed PMID: 22735461.

3: Schmitt C, Charoin-Pannier A, McIntyre C, Zandt H, Ciorciaro C, Winters K, Pepper T. Safety, pharmacokinetics and pharmacodynamics of multiple ascending doses of R1663, an oral factor Xa inhibitor, in healthy young subjects coupled with exploration of influence of gender and age. Thromb Haemost. 2012 Jul;108(1):54-64. doi: 10.1160/TH12-01-0023. PubMed PMID: 22552265.

4: Farhy LS, Bowers CY, Veldhuis JD. Model-projected mechanistic bases for sex differences in growth hormone regulation in humans. Am J Physiol Regul Integr Comp Physiol. 2007 Apr;292(4):R1577-93. PubMed PMID: 17185408.

5: Nemet D, Eliakim A, Zaldivar F, Cooper DM. Effect of rhIL-6 infusion on GH-->IGF-I axis mediators in humans. Am J Physiol Regul Integr Comp Physiol. 2006 Dec;291(6):R1663-8. PubMed PMID: 16840657.

6: Anselm L, Banner DW, Benz J, Zbinden KG, Himber J, Hilpert H, Huber W, Kuhn B, Mary JL, Otteneder MB, Panday N, Ricklin F, Stahl M, Thomi S, Haap W. Discovery of a factor Xa inhibitor (3R,4R)-1-(2,2-difluoro-ethyl)-pyrrolidine-3,4-dicarboxylic acid 3-[(5-chloro-pyridin-2-yl)-amide] 4-[[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide] as a clinical candidate. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5313-9. doi: 10.1016/j.bmcl.2010.06.126. PubMed PMID: 20650636.

7: Imeri L, Bianchi S, Mancia M. Muramyl dipeptide and IL-1 effects on sleep and brain temperature after inhibition of serotonin synthesis. Am J Physiol. 1997 Nov;273(5 Pt 2):R1663-8. PubMed PMID: 9374807.

8: Braga AN, da Silva Lemos M, da Silva JR, Fontes WR, dos Santos RA. Effects of angiotensins on day-night fluctuations and stress-induced changes in blood pressure. Am J Physiol Regul Integr Comp Physiol. 2002 Jun;282(6):R1663-71. PubMed PMID: 12010748.