Octreotide acetateProduct ingredient for Octreotide

Name
Octreotide acetate
Drug Entry
Octreotide

Acromegaly is a disorder caused by excess growth hormone (GH), increasing the growth of body tissues and causing metabolic dysfunction.6 In most cases, it results from an anterior pituitary growth hormone-releasing tumor. Typically, the feet, hands, and face grow abnormally large; organomegaly and insulin resistance may also occur. Acromegaly is a life-threatening disease requiring life-long management.6

Octreotide is a long-acting drug with pharmacologic activities that mimic those of the natural hormone, somatostatin, which inhibits the secretion of growth hormone.8 Additionally, it is used for the treatment of acromegaly and symptoms arising from various tumors, including carcinoid tumors and vasoactive intestinal tumors (VIPomas).8 In the past, octreotide has been administered solely by injection. On June 26, 2020, the first approved delayed-release oral somatostatin analog, Mycapssa, received FDA approval for the long term maintenance treatment of acromegaly. This drug was developed by Chiasma Inc.5,7,10

Accession Number
DBSALT000130
Structure
Synonyms
Octreotide (as acetate)
External IDs
SMS 201-995 AC / SMS-201995-AC
UNII
75R0U2568I
CAS Number
79517-01-4
Weight
Average: 1079.3
Monoisotopic: 1078.461610082
Chemical Formula
C51H70N10O12S2
InChI Key
XQEJFZYLWPSJOV-XJQYZYIXSA-N
InChI
InChI=1S/C49H66N10O10S2.C2H4O2/c1-28(61)39(25-60)56-48(68)41-27-71-70-26-40(57-43(63)34(51)21-30-13-5-3-6-14-30)47(67)54-37(22-31-15-7-4-8-16-31)45(65)55-38(23-32-24-52-35-18-10-9-17-33(32)35)46(66)53-36(19-11-12-20-50)44(64)59-42(29(2)62)49(69)58-41;1-2(3)4/h3-10,13-18,24,28-29,34,36-42,52,60-62H,11-12,19-23,25-27,50-51H2,1-2H3,(H,53,66)(H,54,67)(H,55,65)(H,56,68)(H,57,63)(H,58,69)(H,59,64);1H3,(H,3,4)/t28-,29-,34-,36+,37+,38-,39-,40+,41+,42+;/m1./s1
IUPAC Name
(4R,7S,10S,13R,16S,19R)-19-[(2R)-2-amino-3-phenylpropanamido]-10-(4-aminobutyl)-16-benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-[(1R)-1-hydroxyethyl]-13-[(1H-indol-3-yl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide; acetic acid
SMILES
CC(O)=O.[H][C@]1(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](CSSC[C@H](NC1=O)C(=O)N[C@H](CO)[C@@H](C)O)NC(=O)[C@H](N)CC1=CC=CC=C1)[C@@H](C)O
PubChem Compound
66524450
ChemSpider
5293182
ChEMBL
CHEMBL1200480
Wikipedia
Octreotide
Predicted Properties
PropertyValueSource
Water Solubility0.0122 mg/mLALOGPS
logP0.42ALOGPS
logP-1.4Chemaxon
logS-4.9ALOGPS
pKa (Strongest Acidic)11.4Chemaxon
pKa (Strongest Basic)10.17Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count13Chemaxon
Polar Surface Area332.22 Å2Chemaxon
Rotatable Bond Count17Chemaxon
Refractivity269.77 m3·mol-1Chemaxon
Polarizability107.65 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon