Octreotide
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Octreotide

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Octreotide is an inhibitor of growth hormone, glucagon and insulin. It is also an agonist for sst2, sst3 and sst5 somatostatin receptors, hormone-secreting tumors.

Category
Peptide Inhibitors
Catalog number
BAT-010572
CAS number
83150-76-9
Molecular Formula
C49H66N10O10S2
Molecular Weight
1019.24
Octreotide
Size Price Stock Quantity
5 mg $199 In stock
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
Synonyms
SMS 201-995; Phe-Cys-Phe-Trp-Lys-Thr-Cys-Thr (Disulfide bridge: Cys2-Cys7); H-D-Phe-Cys(1)-Phe-D-Trp-Lys-Thr-Cys(1)-Thr-ol; D-phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-L-cysteinyl-L-threoninol (2->7)-disulfide; Sandostatin; Longastatin; [R-(R*,R*)]-D-Phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-N-[2-hydroxy-1-(hydroxy-methyl)propyl]-cysteinamide cyclic(2->7)-disulfide; Samilstin; SMS 201-995
Related CAS
79517-01-4 (acetate salt)
Appearance
White to Off-white Lyophilized Solid
Purity
>98%
Density
1.39±0.1 g/cm3 (Predicted)
Boiling Point
1447.2±65.0°C (Predicted)
Sequence
d-FCF-d-WKTCT (Disulfide bridge: Cys2-Cys7)
Storage
Store at -20°C
Solubility
Soluble in Water, DMSO
Application
the treatment of hormone-secreting tumors, etc.
InChI
InChI=1S/C49H66N10O10S2/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/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)/t28-,29-,34-,36+,37+,38-,39-,40+,41+,42+/m1/s1
InChI Key
DEQANNDTNATYII-OULOTJBUSA-N
Canonical SMILES
CC(C1C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=CC=C4)NC(=O)C(CC5=CC=CC=C5)N)C(=O)NC(CO)C(C)O)O
1.Pituitary apoplexy causing spontaneous remission of acromegaly following long-acting octreotide therapy: a rare drug side effect or just a coincidence.
Kumar S1, Sharma S2. Oxf Med Case Reports. 2016 Apr 26;2016(4):81-3. doi: 10.1093/omcr/omw009. eCollection 2016.
Pituitary apoplexy is characterized by abrupt onset of haemorrhage or non-haemorrhagic infarction of a pituitary adenoma. The clinical features include acute onset severe headache, visual field defects, meningeal irritation, ophthalmoplegia and hypopituitarism. The pituitary apoplexy may be clinically silent in ∼25% of patients. We report a case of acromegaly due to pituitary macroadenoma. The patient was started on long-acting octreotide therapy. On 3-month follow-up, the patient showed clinical and biochemical remission and the magnetic resonance imaging (MRI) of the brain showed subclinical haemorrhage and resolution of tumour. The octreotide therapy was stopped. On 6-month follow-up, the patient was still in remission and the MRI of brain revealed non-enhancing mixed intensities haemorrhagic and cystic areas of the pituitary gland. In our patient, whether spontaneous remission of acromegaly due to subclinical pituitary haemorrhage was coincidental or due to long-acting octreotide therapy is still a dilemma.
2.Paclitaxel-loaded solid lipid nanoparticles modified with Tyr-3-octreotide for enhanced anti-angiogenic and anti-glioma therapy.
Banerjee I1, De K2, Mukherjee D2, Dey G3, Chattopadhyay S4, Mukherjee M5, Mandal M3, Bandyopadhyay AK6, Gupta A7, Ganguly S7, Misra M8. Acta Biomater. 2016 Apr 19. pii: S1742-7061(16)30188-X. doi: 10.1016/j.actbio.2016.04.026. [Epub ahead of print]
Somatostatin receptors (SSTRs) especially subtype 2 (SSTR2) are overexpressed in glioma. By taking advantage of the specific expression of SSTR2 on both glioma neovasculature endothelial cells and glioma cells, we constructed Tyr-3-octreotide (TOC)-modified solid lipid nanoparticles (SLN) loaded with paclitaxel (PTX) to enable tumor neovasculature and tumor cells dual-targeting chemotherapy. In this work, a TOC-polyethylene glycol-lipid (TOC-PEG-lipid) was successfully synthesized and used as a targeting molecule to enhance anticancer efficacy of PTX loaded sterically stabilized lipid nanoparticles. The prepared PTX-loaded SLN modified with TOC (PSM) was characterized by standard methods. In rat C6 glioma cells, PSM improved PTX induced apoptosis. Both tube formation assay and CD31 staining of treated orthotopic glioma tissues confirmed that PSM significantly improved the antiangiogenic ability of PTX in vitro and in vivo, respectively. Radiolabelled PSM achieved a much higher and specific accumulation within the glioma as suggested by the biodistribution and imaging studies.
3.Serial follow-up of presurgical treatment using pasireotide long-acting release with or without octreotide long-acting release for naïve active acromegaly.
Chang JS1, Tseng HM2, Chang TC3. J Formos Med Assoc. 2016 Apr 22. pii: S0929-6646(16)30001-8. doi: 10.1016/j.jfma.2016.02.003. [Epub ahead of print]
The aim of the present study was to evaluate the serial changes of GH and IGF-1 in seven patients with naïve, active acromegaly following presurgical treatment of the somatostatin analog pasireotide long-acting release (LAR) and octreotide LAR. The patients were treated with pasireotide LAR with or without octreotide LAR for two years and underwent transsphenoidal adenomectomy. After treatment with the somatostatin analogs, the surgical cure rate was similar to that in patients who underwent transsphenoidal surgery alone. Diabetes insipidus was not identified in any patients after the operation. Pasireotide LAR was effective on GH as well as IGF-1 suppression and tumor size decreasing when used as the primary therapy. Future large-population studies to investigate the surgical curative rate after presurgical treatment with somatostatin analogs in patients with acromegaly and macroadenomas close to the cavernous sinus are warranted. However, that hyperglycemia developed following pre-surgical treatment with pasireotide should take into consideration.
4.Thyrotropinoma with Graves' disease detected by the fusion of indium-111 octreotide scintigraphy and pituitary magnetic resonance imaging.
Okuyucu K1, Alagoz E1, Arslan N1, Taslipinar A2, Deveci MS3, Bolu E2. Indian J Nucl Med. 2016 Apr-Jun;31(2):141-3. doi: 10.4103/0972-3919.178322.
Thyroid-stimulating hormone-secreting pituitary adenoma (TSHoma) is a rare benign endocrinological tumor which produces TSH in the pituitary gland. Herein, we presented a female patient having TSHoma with Graves' disease during and just after pregnancy that we found by indium-111 octreotide scintigraphy while investigating the patient for hyperthyroidism symptoms.
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