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 (JSmol)	Interactive image;
ChEMBL	ChEMBL25263 ;
ChemSpider	111662 ;
ECHA InfoCard	100.262.818
IUPHAR/BPS	8256;
PubChem CID	125516;
UNII	WO97N24A47 ;
CompTox Dashboard (EPA)	DTXSID00176996 ;
	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

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.
Pharmaceutical Formulations for the Treatment of Alzheimer's Disease WO 2008014232
Reducing the Supply of Amyloid Fibril Precursor Proteins, MedScape Today

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[pmid12015594-1] 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] Pharmaceutical Formulations for the Treatment of Alzheimer's Disease WO 2008014232

[3] Reducing the Supply of Amyloid Fibril Precursor Proteins, MedScape Today