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=C2C=CC=C3)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

Molecular Formula	C44H56N8O7
Molecular Weight	808.9648
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Cloning, expression and pharmacological characterisation of the mouse somatostatin sst(5) receptor.	2000-06-08	10818261
Characterisation of human recombinant somatostatin receptors. 1. Radioligand binding studies.	1999-11	10598788
Synthesis and biological activities of potent peptidomimetics selective for somatostatin receptor subtype 2.	1998-09-01	9724791
[125I][Tyr3]octreotide labels human somatostatin sst2 and sst5 receptors.	1998-05-08	9652348
[125I]Tyr10-cortistatin14 labels all five somatostatin receptors.	1998-05	9650799
The elucidation of somatostatin receptor functions: a current view.	1998	9600011
Binding properties of somatostatin receptor subtypes.	1996-08	8769372
Subtype selectivity of peptide analogs for all five cloned human somatostatin receptors (hsstr 1-5).	1994-12	7988476
Cloned somatostatin receptors: identification of subtype-selective peptides and demonstration of high affinity binding of linear peptides.	1993-06	8100350

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:26:25 GMT 2025` Edited by `admin` on `Mon Mar 31 18:26:25 GMT 2025`
Record UNII	5P57R7IR6J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SEGLITIDE

Official Name

English

L-363586

Preferred Name

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