CPHPC

CPHPC ((R)-1-{6-[(R)-2-carboxypyrrolidin-1-yl]-6-oxohexanoyl}pyrrolidine-2-carboxylic acid) is a proline-derived small molecule able to strip amyloid P (AP) from deposits by reducing levels of circulating serum amyloid P (SAP). The SAP-amyloid association has also been identified as a possible drug target for anti-amyloid therapy, with the recent development and first stage clinical trials of CPHPC for amyloidosis.[1]

CPHPC
Names
Preferred IUPAC name
(2R,2′R)-1,1′-Hexanedioyldi(pyrrolidine-2-carboxylic acid)
Other names
Ro 63-8695
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.262.818
UNII
  • InChI=1S/C16H24N2O6/c19-13(17-9-3-5-11(17)15(21)22)7-1-2-8-14(20)18-10-4-6-12(18)16(23)24/h11-12H,1-10H2,(H,21,22)(H,23,24)/t11-,12-/m1/s1 checkY
    Key: HZLAWYIBLZNRFZ-VXGBXAGGSA-N checkY
  • InChI=1/C16H24N2O6/c19-13(17-9-3-5-11(17)15(21)22)7-1-2-8-14(20)18-10-4-6-12(18)16(23)24/h11-12H,1-10H2,(H,21,22)(H,23,24)/t11-,12-/m1/s1
    Key: HZLAWYIBLZNRFZ-VXGBXAGGBC
  • O=C(O)[C@@H]2N(C(=O)CCCCC(=O)N1[C@@H](C(=O)O)CCC1)CCC2
Properties
C16H24N2O6
Molar mass 340.37 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

CPHPC has also been patented for possible treatment of Alzheimer's disease.[2]

Mechanism

The symmetrical nature of CPHPC allows it to bind to two molecules of AP (the SAP subunits). This allows five molecules of CPHPC to bind two SAP pentamers together by the B/binding face blocking the binding on to existing amyloid deposits.[3]

References
  1. Pepys MB, Herbert J, Hutchinson WL, Tennent GA, Lachmann HJ, Gallimore JR, Lovat LB, Bartfai T, Alanine A, Hertel C, Hoffmann T, Jakob-Roetne R, Norcross RD, Kemp JA, Yamamura K, Suzuki M, Taylor GW, Murray S, Thompson D, Purvis A, Kolstoe S, Wood SP, Hawkins PN (2002). "Targeted pharmacological depletion of serum amyloid P component for treatment of human amyloidosis". Nature. 417 (6886): 254–9. Bibcode:2002Natur.417..254P. doi:10.1038/417254a. PMID 12015594. S2CID 733818.
  2. WO 2008014232, Dinh, Steven & Shevchuk, Ihor, "Pharmaceutical Formulations for the Treatment of Alzheimer's Disease", assigned to Emisphere Technologies Inc.
  3. Reducing the Supply of Amyloid Fibril Precursor Proteins, MedScape Today
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