SEGLITIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C44H56N8O7
Molecular Weight	808.9648
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC2=CNC3=CC=CC=C23)NC(=O)[C@H](CC4=CC=C(O)C=C4)NC(=O)[C@H](C)N(C)C(=O)[C@H](CC5=CC=CC=C5)NC1=O

InChI

InChIKey=NPJIOCBFOAHEDO-AVWFULIKSA-N

InChI=1S/C44H56N8O7/c1-26(2)38-43(58)50-37(23-28-12-6-5-7-13-28)44(59)52(4)27(3)39(54)48-35(22-29-17-19-31(53)20-18-29)41(56)49-36(24-30-25-46-33-15-9-8-14-32(30)33)42(57)47-34(40(55)51-38)16-10-11-21-45/h5-9,12-15,17-20,25-27,34-38,46,53H,10-11,16,21-24,45H2,1-4H3,(H,47,57)(H,48,54)(H,49,56)(H,50,58)(H,51,55)/t27-,34-,35-,36+,37-,38-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2858052 | https://www.ncbi.nlm.nih.gov/pubmed/2900206 | https://www.ncbi.nlm.nih.gov/pubmed/1680212 | https://adisinsight.springer.com/drugs/800000642

Seglitide (previously known as L363,586 or MK-678), a cyclic, hexapeptide analog of somatostatin-14, is a somatostatin receptor 2 (SSTR2) agonist. This compound was studied in Alzheimer's disease. Besides, it possessed inhibitory actions on rat growth hormone (GH) release and thus could have a role in the treatment of acromegaly. Intravenous and intranasal administration of seglitide to diabetic subjects was effective in reducing both fasting and postprandial hyperglycemia. Thus, this compound could be useful in the control of unstable diabetes. In addition, preclinical studies have shown that seglitide had potential as a treatment for diabetic retinopathy and macular degeneration. However, the further studied of this compound were discontinued.

Approval Year

PubMed

Title	Date	PubMed
Cloned somatostatin receptors: identification of subtype-selective peptides and demonstration of high affinity binding of linear peptides.	1993 Jun	8100350
Subtype selectivity of peptide analogs for all five cloned human somatostatin receptors (hsstr 1-5).	1994 Dec	7988476
Binding properties of somatostatin receptor subtypes.	1996 Aug	8769372
The elucidation of somatostatin receptor functions: a current view.	1998	9600011
[125I]Tyr10-cortistatin14 labels all five somatostatin receptors.	1998 May	9650799
[125I][Tyr3]octreotide labels human somatostatin sst2 and sst5 receptors.	1998 May 8	9652348
Synthesis and biological activities of potent peptidomimetics selective for somatostatin receptor subtype 2.	1998 Sep 1	9724791
Characterisation of human recombinant somatostatin receptors. 1. Radioligand binding studies.	1999 Nov	10598788
Cloning, expression and pharmacological characterisation of the mouse somatostatin sst(5) receptor.	2000 Jun 8	10818261

Patents

Name

Type

Language

SEGLITIDE

Official Name

English

L-363586

Code

English

CYCLO(N-METHYL-L-ALANYL-L-TYROSYL-D-TRYPTOPHYL-L-LYSYL-L-VALYL-L-PHENYLALANYL)

Common Name

English

seglitide [INN]

Common Name

English

MK-678

Code

English

CYCLO(N-METHYL-ALA-TYR-D-TRP-LYS-VAL-PHE)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C62799