Synonym
R-138727; R 138727; R138727; Prasugrel active metabolite.
IUPAC/Chemical Name
(2Z)-2-[1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic acid
InChi Key
ZWUQVNSJSJHFPS-XFXZXTDPSA-N
InChi Code
InChI=1S/C18H20FNO3S/c19-14-4-2-1-3-13(14)17(18(23)11-5-6-11)20-8-7-15(24)12(10-20)9-16(21)22/h1-4,9,11,15,17,24H,5-8,10H2,(H,21,22)/b12-9-
SMILES Code
O=C(O)/C=C1CN(C(C2=CC=CC=C2F)C(C3CC3)=O)CCC/1S
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
349.42
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.
| 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: Sugidachi A, Mizuno M, Ohno K, Jakubowski JA, Tomizawa A. The active metabolite of prasugrel, R-138727, improves cerebral blood flow and reduces cerebral infarction and neurologic deficits in a non-human primate model of acute ischaemic stroke. Eur J Pharmacol. 2016 Oct 5;788:132-139. doi: 10.1016/j.ejphar.2016.06.023. Epub 2016 Jun 16. PMID: 27318323.
2: Kakarla S, Datla PV, Kodali G, Seru G. Analysis of prasugrel active metabolite R-138727 in human plasma: a sensitive, highly selective and fast LC- MS/MS method. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 May 1;1020:103-10. doi: 10.1016/j.jchromb.2016.03.035. Epub 2016 Mar 24. PMID: 27038402.
3: Lukram O, Zarapkar M, Kumar Jha C, Parmar S, Tomar KS, Hande A. Electrospray ionization LC-MS/MS validated method for the determination of the active metabolite (R-138727) of prasugrel in human plasma and its application to a bioequivalence study. Drug Test Anal. 2012 Feb;4(2):158-66. doi: 10.1002/dta.264. Epub 2011 Mar 25. PMID: 21438161.
4: Algaier I, Jakubowski JA, Asai F, von Kügelgen I. Interaction of the active metabolite of prasugrel, R-138727, with cysteine 97 and cysteine 175 of the human P2Y12 receptor. J Thromb Haemost. 2008 Nov;6(11):1908-14. doi: 10.1111/j.1538-7836.2008.03136.x. Epub 2008 Aug 22. PMID: 18752581.
5: Hasegawa M, Sugidachi A, Ogawa T, Isobe T, Jakubowski JA, Asai F. Stereoselective inhibition of human platelet aggregation by R-138727, the active metabolite of CS-747 (prasugrel, LY640315), a novel P2Y12 receptor inhibitor. Thromb Haemost. 2005 Sep;94(3):593-8. doi: 10.1160/TH05-03-0208. PMID: 16268477.
