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Details

Stereochemistry ABSOLUTE
Molecular Formula C44H56N8O7.C2H4O2
Molecular Weight 869.0168
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SEGLITIDE ACETATE

SMILES

CC(O)=O.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=FIKSSPSBVSPVFU-WIKDFEFZSA-N
InChI=1S/C44H56N8O7.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t27-,34-,35-,36+,37-,38-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C2H4O2
Molecular Weight 60.052
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C44H56N8O7
Molecular Weight 808.9648
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Substance Class Chemical
Record UNII
URM20C99DG
Record Status Validated (UNII)
Record Version