Drug Libraray

DCTPepD ID DCTPepD0041

Active Ingredients Tigapotide

Description A synthetic 15-mer peptide corresponding to amino acids 31-45 of the 94-amino acid isoform of human prostate secretory protein (PSP-94) with potential anti-metastasis and anti-angiogenesis activities. PSP-94-derived peptide PCK3145 may inhibit the secretion of the metastasis-related protein matrix metalloproteinase-9 (MMP-9) and its potential binding to its cell surface receptor CD44; may interfere with the vascular endothelial growth factor (VEGF) signaling pathway, resulting in an anti-angiogenesis effect; and may reduce the levels of parathyroid hormone-related protein (PTHrP), decreasing plasma calcium levels. PSP-94, one of three predominant proteins found in seminal fluid, may be down-regulated in prostate cancer, representing a potential survival mechanism for prostate cancer cells. MMP-9 is implicated in the invasion and metastasis of cancer. PTHrP may be expressed by various tumor cell types, resulting in the hypercalcemia of malignancy.

Synonyms PCK3145; Prostate-Secretory Protein-94-Derived Peptide PCK3145; Tigapotide

Disease Hormone Refractory Prostate Cancer (HRPC)

Classification

Peptide and derivative Antiangiogenesis agent

Molecular Formula C82H119N21O34S3

Molecular Weight 2039.1

Active Sequence EWQTDNXETXTXYET

Sequence Length 15

Modification X=Cys(ACM)

Structure

Show IUPAC/InChI/SMILES

IUPAC Name (4S)-5-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2R)-3-(acetamidomethylsulfanyl)-1-[[(2S)-1-[[(2S,3R)-1-[[(2R)-3-(acetamidomethylsulfanyl)-1-[[(2S,3R)-1-[[(2R)-3-(acetamidomethylsulfanyl)-1-[[(2S)-1-[[(2S)-4-carboxy-1-[[(1S,2R)-1-carboxy-2-hydroxypropyl]amino]-1-oxobutan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-amino-1,4-dioxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-5-amino-1,5-dioxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-amino-5-oxopentanoic acid

InChI InChI=1S/C82H119N21O34S3/c1-35(104)64(100-69(123)48(17-20-58(84)112)90-73(127)52(93-68(122)46(83)16-21-60(114)115)25-43-28-86-47-11-9-8-10-45(43)47)79(133)96-54(27-63(120)121)75(129)95-53(26-59(85)113)74(128)97-55(29-138-32-87-39(5)108)76(130)92-49(18-22-61(116)117)70(124)101-65(36(2)105)80(134)99-57(31-140-34-89-41(7)110)78(132)102-66(37(3)106)81(135)98-56(30-139-33-88-40(6)109)77(131)94-51(24-42-12-14-44(111)15-13-42)72(126)91-50(19-23-62(118)119)71(125)103-67(38(4)107)82(136)137/h8-15,28,35-38,46,48-57,64-67,86,104-107,111H,16-27,29-34,83H2,1-7H3,(H2,84,112)(H2,85,113)(H,87,108)(H,88,109)(H,89,110)(H,90,127)(H,91,126)(H,92,130)(H,93,122)(H,94,131)(H,95,129)(H,96,133)(H,97,128)(H,98,135)(H,99,134)(H,100,123)(H,101,124)(H,102,132)(H,103,125)(H,114,115)(H,116,117)(H,118,119)(H,120,121)(H,136,137)/t35-,36-,37-,38-,46+,48+,49+,50+,51+,52+,53+,54+,55+,56+,57+,64+,65+,66+,67+/m1/s1

InChI_Key ZRXXHPDJLAQCPC-SFJRRRFZSA-N

SMILES O=C(O)CC[C@H](N)C(N[C@@H](CC1=CNC2=C1C=CC=C2)C(N[C@@H](CCC(N)=O)C(N[C@@H]([C@H](O)C)C(N[C@@H](CC(O)=O)C(N[C@@H](CC(N)=O)C(N[C@@H](CSCNC(C)=O)C(N[C@@H](CCC(O)=O)C(N[C@@H]([C@H](O)C)C(N[C@@H](CSCNC(C)=O)C(N[C@@H]([C@H](O)C)C(N[C@@H](CSCNC(C)=O)C(N[C@@H](CC3=CC=C(O)C=C3)C(N[C@@H](CCC(O)=O)C(N[C@H](C(O)=O)[C@H](O)C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O

PubChem CID 16155604

DrugBank Accession Number DB04985

NCI Thesaurus Code C78474

UNII 1WZ6S45S94 GSRS

CAS 848084-83-3

Drug indication
For the treatment of late stage Hormone Refractory Prostate Cancer (HRPC) for which no effective therapy currently exists.

The drug is not approved.

ClinicalTrials.gov Identifier	Title	Condition or disease	Phase	Purpose
NCT00695851	A Phase I Randomized Dose-Seeking Trial of PCK3145 in Asymptomatic, Castrate Metastatic Prostate Cancer Patients.	Prostate Cancer	Phase 1	Treatment

More clinical information is obtained from ClinicalTrials.gov.