CPHPC

CPHPC

Names
IUPAC name (2R)-1-[6-[(2R)-2-Carboxypyrrolidin-1-yl]-6-oxohexanoyl]pyrrolidine-2-carboxylic acid
Other names Ro 63-8695
Identifiers
CAS Number	224624-80-0
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL25263
ChemSpider	111662
IUPHAR/BPS	8256
PubChem	125516
UNII	WO97N24A47
InChI 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 Key: HZLAWYIBLZNRFZ-VXGBXAGGSA-N 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
SMILES O=C(O)[C@@H]2N(C(=O)CCCCC(=O)N1[C@@H](C(=O)O)CCC1)CCC2
Properties
Chemical formula	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).
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Infobox references

CPHPC (R-1-[6-[R-2-carboxy-pyrrolidin-1-yl]-6-oxo-hexanoyl] 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 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. doi:10.1038/417254a. PMID 12015594.
2. Pharmaceutical Formulations for the Treatment of Alzheimer's Disease WO 2008014232 
3. Reducing the Supply of Amyloid Fibril Precursor Proteins, MedScape Today