15-28-Somatostatin-28
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15-28-Somatostatin-28
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CAS No:
38916-34-6
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Formula:
C76H104N18O19S2
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Chemical Name:
15-28-Somatostatin-28
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Synonyms:
GROWTH HORMONE RELEASE INHIBITING FACTOR (HUMAN, OVINE, PORCINE, RAT, MOUSE);GROWTH HORMONE RELEASE INHIBITING FACTOR (HUMAN, OVINE, PORCINE, RAT, MOUSE) 2ACOH 6H2O;H-ALA-GLY-CYS-LYS-ASN-PHE-PHE-TRP-LYS-THR-PHE-THR-SER-CYS-OH;H-ALA-GLY-CYS-LYS-ASN-PHE-PHE-TRP-LYS-THR-PHE-THR-SER-CYS-OH (COUPLED TO BSA);H-ALA-GLY-CYS-LYS-ASN-PHE-PHE-TRP-LYS-THR-PHE-THR-SER-CYS-OH (COUPLED TO KLH);H-ALA-GLY-CYS-LYS-ASN-PHE-PHE-TRP-LYS-THR-PHE-THR-SER-CYS-OH, CYS3,14, CYCLIC;H-ALA-GLY-CYS-LYS-ASN-PHE-PHE-TRP-LYS-THR-PHE-THR-SER-CYS-OH (DISULFIDE BRIDGE: 3-14);GIF (HUMAN, OVINE, PORCINE, RAT, MOUSE)
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Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System
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CAS No:
Description
Cyclic somatostatin is a growth hormone-release inhibiting factor used in the treatment of severe, acute hemorrhages of gastroduodenal ulcers. Sequence: H-Ala-Gly-Cys-Lys-Asn-Phe-Phe-Trp-Lys-Thr-Phe-Thr-Ser-Cys-OH (Disulfide bridge: Cys3-Cys14).
Lanreotide is a synthetic polypeptide analogue of somatostatin that resembles the native hormone in its ability to suppress levels and activity of growth hormone, insulin, glucagon and many other gastrointestinal peptides. Because its half-life is longer than somatostatin, lanreotide can be used clinically to treat neuroendocrine tumors that secrete excessive amounts of growth hormone (acromegaly) or other active hormones or neuropeptides. Lanreotide has many side effects including suppression of gall bladder contractility and bile production, and maintenance therapy may cause cholelithiasis and pancreatitis as well accompanying liver injury.|Octreotide is a synthetic somatostatin analogue that resembles the native polypeptide in its activity in suppressing levels and activity of growth hormone, insulin, glucagon and many other gastrointestinal peptides. Because its half-life is longer than somatostatin, octreotide can be used clinically to treat neuroendocrine tumors that secrete excessive amounts of growth hormone (acromegaly) or other active hormones or neuropeptides. Octreotide has many side effects including suppression of gall bladder contractility and bile production, and maintenance therapy can cause cholelithiasis, pancreatitis as well as clinically apparent liver injury.|Pasireotide is a synthetic polypeptide analogue of somatostatin that resembles the native hormone in its ability to suppress levels and activity of growth hormone, insulin, glucagon and many other gastrointestinal peptides. Because its half-life is longer than somatostatin, pasireotide can be used clinically to treat neuroendocrine pituitary tumors that secrete excessive amounts of growth hormone causing acromegaly, or adrenocorticotropic hormone (ACTH) causing Cushing disease. Pasireotide has many side effects including suppression of gall bladder contractility and bile production, and maintenance therapy can cause cholelithiasis and accompanying elevations in serum enzymes and bilirubin.|A 14-amino acid peptide named for its ability to inhibit pituitary GROWTH HORMONE release, also called somatotropin release-inhibiting factor. It is expressed in the central and peripheral nervous systems, the gut, and other organs. SRIF can also inhibit the release of THYROID-STIMULATING HORMONE; PROLACTIN; INSULIN; and GLUCAGON besides acting as a neurotransmitter and neuromodulator. In a number of species including humans, there is an additional form of somatostatin, SRIF-28 with a 14-amino acid extension at the N-terminal.
15-28-Somatostatin-28 Basic Attributes
1637.88
1636.716675
254-186-5
DTXSID8046793
H - Systemic hormonal preparations, excl. sex hormones and insulins
Characteristics
663.83000
-4.25
powder
1.4±0.1 g/cm3
1970.9±65.0 °C at 760 mmHg
1145.7±34.3 °C
1.670
soluble in water(25,00°C 1,00 g/L),Methanol.
−20°C
Toxicity
In preregistration studies of lanreotide, serum enzyme levels did not change appreciably and there were no reports of clinically apparent acute liver injury. Pooled analyses reported that there were no overall changes in serum ALT, AST or alkaline phosphatase levels during therapy or instances of clinically meaningful elevations with treatment. Prolonged therapy with lanreotide, as with other somatostatin analogues, was associated with a high rate of biliary sludge and cholelithiasis, probably due to inhibition of gall bladder contractility and decrease in bile secretion. In long term studies, cholelithiasis developed in 20% to 33% of lanreotide treated patients. In some instances, symptomatic cholecystitis occurred which can be accompanied by mild-to-moderate elevations in serum enzymes and bilirubin. However, most lanreotide associated gallstones were asymptomatic. Unlike octreotide, lanreotide and other long acting somatostatin analogues have not been liked to cases of clinically apparent liver injury, independent of cholelithiasis or biliary sludge, although they have had more limited use and have not been used in many of the clinical situations that were treated with octreotide (portal hypertension, variceal hemorrhage and infants with congenital hyperinsulinemia).|Mild, transient, asymptomatic elevations in serum aminotransferase levels occur in a small proportion of patients receiving octreotide, and in some individuals the elevations are persistent and worsen over time and may require drug discontinuation. In addition, several instances of acute, clinically apparent liver injury attributable to octreotide have been described. The onset is generally within 1 to 6 months of starting therapy and injury may be more frequent with higher doses. Most cases of liver injury associated with octreotide therapy have been asymptomatic and anicteric, and marked by prominent elevations in serum ALT and AST with normal or near normal serum alkaline phosphatase, GGT and bilirubin. In some instances, however, jaundice has arisen, particularly with rechallenge. There have been no instances of acute liver failure or vanishing bile duct syndrome associated with octreotide, and a characteristic feature of the injury is the rapidity of improvement upon stopping the injections or infusions. Several instances of marked aminotransferase elevations with rapid improvements on stopping have been reported in newborns and infants with congenital hyperinsulinemia who were treated with continuous infusions of high doses of octreotide.|Mild, transient, asymptomatic elevations in serum aminotransferase levels occur in up to 29% of patients receiving pasireotide LAR, but elevations above 5 times the upper limit of normal are rare (
Drug Information
Lanreotide is a synthetic polypeptide analogue of somatostatin that resembles the native hormone in its ability to suppress levels and activity of growth hormone, insulin, glucagon and many other gastrointestinal peptides. Because its half-life is longer than somatostatin, lanreotide can be used clinically to treat neuroendocrine tumors that secrete excessive amounts of growth hormone (acromegaly) or other active hormones or neuropeptides. Lanreotide has many side effects including suppression of gall bladder contractility and bile production, and maintenance therapy may cause cholelithiasis and pancreatitis as well accompanying liver injury.|Octreotide is a synthetic somatostatin analogue that resembles the native polypeptide in its activity in suppressing levels and activity of growth hormone, insulin, glucagon and many other gastrointestinal peptides. Because its half-life is longer than somatostatin, octreotide can be used clinically to treat neuroendocrine tumors that secrete excessive amounts of growth hormone (acromegaly) or other active hormones or neuropeptides. Octreotide has many side effects including suppression of gall bladder contractility and bile production, and maintenance therapy can cause cholelithiasis, pancreatitis as well as clinically apparent liver injury.|Pasireotide is a synthetic polypeptide analogue of somatostatin that resembles the native hormone in its ability to suppress levels and activity of growth hormone, insulin, glucagon and many other gastrointestinal peptides. Because its half-life is longer than somatostatin, pasireotide can be used clinically to treat neuroendocrine pituitary tumors that secrete excessive amounts of growth hormone causing acromegaly, or adrenocorticotropic hormone (ACTH) causing Cushing disease. Pasireotide has many side effects including suppression of gall bladder contractility and bile production, and maintenance therapy can cause cholelithiasis and accompanying elevations in serum enzymes and bilirubin.
Hormonal Agents
Chemical substances having a specific regulatory effect on the activity of a certain organ or organs. The term was originally applied to substances secreted by various ENDOCRINE GLANDS and transported in the bloodstream to the target organs. It is sometimes extended to include those substances that are not produced by the endocrine glands but that have similar effects. (See all compounds classified as Hormones.)
Cyclic Somatostatin
15-28-Somatostatin-28 Use and Manufacturing
Growth hormone-release inhibiting factor; treatment of severe, acute hemorrhage of gastroduodenal ulcers; experimental antidiabetic
Computed Properties
Molecular Weight:1637.9
XLogP3:-3.1
Hydrogen Bond Donor Count:22
Hydrogen Bond Acceptor Count:24
Rotatable Bond Count:26
Exact Mass:1636.71665551
Monoisotopic Mass:1636.71665551
Topological Polar Surface Area:664
Heavy Atom Count:115
Complexity:3240
Undefined Atom Stereocenter Count:15
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
1. It can inhibit the secretion of growth hormone, thyroid stimulating hormone, insulin, and glucagon; 2. It can inhibit the secretion of gastric acid stimulated by the test meal and pentagastrin, and inhibit the release of pepsin and gastrin; 3. It can significantly reduce visceral blood flow, reduce portal vein pressure, reduce collateral circulation blood flow and pressure, and reduce liver blood flow; 4. It can reduce the endocrine secretion of the pancreas, the secretion of the stomach, small intestine, and gallbladder, reduce enzyme activity, and have a protective effect on pancreatic cells; 5. It can inhibit the secretion of glucagon; 6. It can affect gastrointestinal absorption and nutritional function.
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