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Octreotide (pamoate)

CAT: 0804-HY-P0036BSize: 1 EachDry Ice: NoHazardous: No
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Description
Octreotide (SMS 201-995) pamoate is a somatostatin receptor agonist and synthetic octapeptide endogenous somatostatin analogue. Octreotide pamoate can bind to the somatostatin receptors which are mainly subtypes 2, 3 and 5. Octreotide pamoate increases Gi activity and reduces intracellular cAMP production. Octreotide pamoate has antitumor activity, mediates apoptosis and may also be used in disease studies in acromegaly[1][2].
CAS Number
135467-16-2
Product Name Alternative
SMS 201-995 (pamoate)
UNSPSC
12352209
Target
Apoptosis; Somatostatin Receptor
Type
Peptides
Related Pathways
Apoptosis; GPCR/G Protein; Neuronal Signaling
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Cancer; Endocrinology; Inflammation/Immunology; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/octreotide-pamoate.html
Solubility
10 mM in DMSO
Smiles
OC(C1=CC(C=CC=C2)=C2C(CC3=C(O)C(C(O)=O)=CC4=C3C=CC=C4)=C1O)=O.O=C([C@@H](NC([C@H](CSSC[C@H](NC([C@](NC([C@@H](NC5=O)CCCCN)=O)([H])[C@H](O)C)=O)C(N[C@H](CO)[C@H](O)C)=O)NC([C@H](N)CC6=CC=CC=C6)=O)=O)CC7=CC=CC=C7)N[C@@H]5CC8=CNC9=CC=CC=C89.[x]
Molecular Formula
C49H66N10O10S2.xC23H16O6
References & Citations
[1]G. Weckbecker, et al. Indirect antiproliferative effect of the somatostatin analog octreotide on MIA PaCa-2 human pancreatic carcinoma in nude mice. Yale J Biol Med. 1997 Sep-Dec;70 (5-6) :549-54.|[2] Chand Khanna, et al. A randomized controlled trial of octreotide pamoate long-acting release and carboplatin versus carboplatin alone in dogs with naturally occurring osteosarcoma: evaluation of insulin-like growth factor suppression and chemotherapy. Clin Cancer Res. 2002 Jul;8 (7) :2406-12|[3]Xiao-Xia Wang, et al. Effects of octreotide on hepatic glycogenesis in rats with high fat diet‑induced obesity. Mol Med Rep. 2017 Jul;16 (1) :109-118.
Shipping Conditions
Room temperature
Scientific Category
Peptides
Clinical Information
Launched
Isoform
SSTR2; SSTR3; SSTR5

Chemical Information

Octreotide pamoate

Octreotide Pamoate is a synthetic long-acting octapeptide analogue of endogenous somatostatin. Octreotide pamoate binds to somatostatin receptors expressed by some neuroendocrine and non-neuroendocrine tumor cells, thereby initiating somatostatin receptor-mediated apoptosis. Other possible antineoplastic activities of this agent include suppression of tumor angiogenesis and tumor growth-promoting insulin-like growth factor 1 (IGF-1). (NCI04)

CAS Number135467-16-2
PubChem CID44194024
IUPAC Name(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-19-[[(2R)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-[(1R)-1-hydroxyethyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide;4-[(3-carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid
Molecular FormulaC72H82N10O16S2
Molecular Weight1407.6
Topological Polar Surface Area498
Hydrogen Bond Donor Count17
Hydrogen Bond Acceptor Count20
Rotatable Bond Count21
Heavy Atom Count100
Formal Charge0
Complexity2310
SMILES
C[C@H]([C@H]1C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=CC=C4)NC(=O)[C@@H](CC5=CC=CC=C5)N)C(=O)N[C@H](CO)[C@@H](C)O)O.C1=CC=C2C(=C1)C=C(C(=C2CC3=C(C(=CC4=CC=CC=C43)C(=O)O)O)O)C(=O)O
InChI
InChI=1S/C49H66N10O10S2.C23H16O6/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;24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/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);1-10,24-25H,11H2,(H,26,27)(H,28,29)/t28-,29-,34-,36+,37+,38-,39-,40+,41+,42+;/m1./s1
InChIKey
KFWJVABDRRDUHY-XJQYZYIXSA-N
Chemical Structure
2D Structure
2D structure of Octreotide pamoate
CAS: 135467-16-2
CID: 44194024
Formula: C72H82N10O16S2
MW: 1407.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1407.6
Hydrogen Bond Donor Count17
Hydrogen Bond Acceptor Count20
Rotatable Bond Count21
Exact Mass1406.53516891
Monoisotopic Mass1406.53516891
Topological Polar Surface Area498 Ų
Heavy Atom Count100
Formal Charge0
Complexity2310
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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