Chemistry:Dihexa

Short description: Chemical compound

Dihexa

Clinical data
Other names	N-(1-Oxohexyl)-l-tyrosyl-N-(6-amino-6-oxohexyl)-l-isoleucinamide
Identifiers
IUPAC name 6-[(2S,3S)-2-[(2S)-2-hexanamido-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]hexanamide
CAS Number	1401708-83-5
PubChem CID	129010512
ChemSpider	57582587
UNII	9WYX65A5C2
Chemical and physical data
Formula	C27H44N4O5
Molar mass	504.672 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCCCCCC(N)=O
InChI InChI=1S/C27H44N4O5/c1-4-6-8-12-24(34)30-22(18-20-13-15-21(32)16-14-20)26(35)31-25(19(3)5-2)27(36)29-17-10-7-9-11-23(28)33/h13-16,19,22,25,32H,4-12,17-18H2,1-3H3,(H2,28,33)(H,29,36)(H,30,34)(H,31,35)/t19-,22-,25-/m0/s1 Key:XEUVNVNAVKZSPT-JTJYXVOQSA-N

Dihexa (developmental code name PNB-0408), also known as N-hexanoic-Tyr-Ile-(6) aminohexanoic amide, is an oligopeptide drug derived from angiotensin IV that binds with high affinity to hepatocyte growth factor (HGF) and potentiates its activity at its receptor, c-Met. The compound has been found to potently improve cognitive function in animal models of Alzheimer's disease-like mental impairment. In an assay of neurotrophic activity, Dihexa was found to be seven orders of magnitude more potent than brain-derived neurotrophic factor.

According to a patent, "Short duration safety studies with Dihexa have uncovered no apparent toxicity. Of particular note is a lack of neoplastic induction, since c-Met is recognized as an oncogene. This is unsurprising since oncogenesis requires multiple mutations including both oncogene induction and tumor suppressor attenuation."

History

Dihexa was developed by Joseph Harding and his team at Washington State University. Later developments were done under "M3 Biotechnology", a company founded to commercialise Dihexa.