Octreotide (pamoate)

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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 Number	135467-16-2
PubChem CID	44194024
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 Formula	C72H82N10O16S2
Molecular Weight	1407.6
Topological Polar Surface Area	498
Hydrogen Bond Donor Count	17
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	21
Heavy Atom Count	100
Formal Charge	0
Complexity	2310

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

CAS: 135467-16-2

CID: 44194024

Formula: C72H82N10O16S2

MW: 1407.6

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	1407.6
Hydrogen Bond Donor Count	17
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	21
Exact Mass	1406.53516891
Monoisotopic Mass	1406.53516891
Topological Polar Surface Area	498 Å²
Heavy Atom Count	100
Formal Charge	0
Complexity	2310
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	2
Compound Is Canonicalized	Yes

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