Somatostatin acetateProduct ingredient for Somatostatin

Name
Somatostatin acetate
Drug Entry
Somatostatin

Somatostatin, also known as growth hormone-inhibiting hormone, is a naturally-occurring peptide hormone of 14 or 28 amino acid residues 9 that regulates the endocrine system. It is secreted by the D cells of the islets to inhibit the release of insulin and glucagon, and is also generated in the hypothalamus, where it inhibits the release of growth hormone and thyroid-stimulating hormones from the anterior pituitary 9. Somatostatin is initially secreted as a 116 amino acid precursor, preprosomatostatin, which undergoes endoproteolytic cleavage to prosomastatin. Prosomastatin is further process into two active forms, somatostatin-14 (SST-14) and somatostatin-28 (SST-28), an extended SST-14 sequence to the N-terminus 1. The actions of somatostatin are mediated via signalling pathways of G protein-coupled somatostatin receptors.

Antineoplastic effects and potential uses of somatostatin on various tumours, including pituitary adenomas, GEP-NETs, paragangliomas, carcinoids, breast cancers, malignant lymphoma and small-cell lung cancers, have been extensively investigated 1. Somatostatin has been used in the clinical setting for the diagnosis of acromegaly and gastrointestinal tract tumours. Its analogues have been developed to achieve more favourable kinetics for efficiency use in the management of acute conditions, such as esophageal varices. Octreotide is a long-acting analogue of somatostatin that inhibits the release of a number of hormones, and is clinically used to relieve symptoms of uncommon gastroenteropancreatic endocrine tumours, as well as treat acromegaly 9.

Accession Number
DBSALT001156
Structure
Synonyms
Not Available
UNII
F6R2N217HS
CAS Number
54472-66-1
Weight
Average: 1697.95
Monoisotopic: 1696.737784918
Chemical Formula
C78H108N18O21S2
InChI Key
GFYNCDIZASLOMM-HMAILDBGSA-N
InChI
InChI=1S/C76H104N18O19S2.C2H4O2/c1-41(79)64(100)82-37-61(99)83-58-39-114-115-40-59(76(112)113)92-72(108)57(38-95)91-75(111)63(43(3)97)94-71(107)54(33-46-23-11-6-12-24-46)90-74(110)62(42(2)96)93-66(102)51(28-16-18-30-78)84-69(105)55(34-47-36-81-49-26-14-13-25-48(47)49)88-68(104)53(32-45-21-9-5-10-22-45)86-67(103)52(31-44-19-7-4-8-20-44)87-70(106)56(35-60(80)98)89-65(101)50(85-73(58)109)27-15-17-29-77;1-2(3)4/h4-14,19-26,36,41-43,50-59,62-63,81,95-97H,15-18,27-35,37-40,77-79H2,1-3H3,(H2,80,98)(H,82,100)(H,83,99)(H,84,105)(H,85,109)(H,86,103)(H,87,106)(H,88,104)(H,89,101)(H,90,110)(H,91,111)(H,92,108)(H,93,102)(H,94,107)(H,112,113);1H3,(H,3,4)/t41-,42+,43+,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,62-,63-;/m0./s1
IUPAC Name
(4R,7S,10S,13S,16S,19S,22S,25S,28S,31S,34S,37R)-19,34-bis(4-aminobutyl)-37-{2-[(2S)-2-aminopropanamido]acetamido}-13,25,28-tribenzyl-31-(carbamoylmethyl)-10,16-bis[(1R)-1-hydroxyethyl]-7-(hydroxymethyl)-22-[(1H-indol-3-yl)methyl]-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontane-4-carboxylic acid; acetic acid
SMILES
CC(O)=O.C[C@@H](O)[C@@H]1NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC2=CNC3=C2C=CC=C3)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@H](CO)NC1=O)C(O)=O)NC(=O)CNC(=O)[C@H](C)N)[C@@H](C)O
ChemSpider
77431691
Predicted Properties
PropertyValueSource
Water Solubility0.0205 mg/mLALOGPS
logP-1.8ALOGPS
logP-8.2Chemaxon
logS-4.9ALOGPS
pKa (Strongest Acidic)2.88Chemaxon
pKa (Strongest Basic)10.47Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count22Chemaxon
Hydrogen Donor Count22Chemaxon
Polar Surface Area613.23 Å2Chemaxon
Rotatable Bond Count26Chemaxon
Refractivity420.26 m3·mol-1Chemaxon
Polarizability166.08 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon