Octreotide Acetate
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Octreotide Acetate

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Octreotide acetate is a long-acting octapeptide with pharmacologic actions similars to the natural hormone somatostatin. It is a more potent inhibitor of growth hormone, glucagon, and insulin than the natural hormone. It was approved as an injectable depot formulation used for acromegaly, gigantism, thyrotropinoma, diarrhea and flushing episodes associated with carcinoid syndrome, and diarrhea in patients with vasoactive intestinal peptide-secreting tumors. It is a gastric antisecretory agent andcould inhibit the secretion of insulin and glucagon. It reduces production of IGF-1 and IGF-2 by the liver by modulation of growth-hormone secretion from the pituitary gland. It decreased the urinary excretion of uric acid as well as the plasma concentrations of glucagon and insulin. It decreased the urinary excretion of sodium and chloride without significiant influence on creatinine clearance, while the concentrations of lactic acid, pyruvic acid in blood, and cyclic AMP in plasma were not changed. It was first synthesized in 1979 by the chemist Wilfried Bauer and was developed by Novartis Pharmaceuticals.

Category
Peptide Inhibitors
Catalog number
BAT-010766
CAS number
79517-01-4
Molecular Formula
C49H66N10O10S2.xC2H4O2
Molecular Weight
1019.25 (free base)
Octreotide Acetate
IUPAC Name
acetic acid;1-[(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-19-[[(2R)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-4-[[(2R,3R)-1,3-dihydroxybutan-2-yl]carbamoyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicos-7-yl]ethyl acetate
Synonyms
L-Cysteinamide, D-phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]-, cyclic (2→7)-disulfide, acetate (1:x); H-D-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr-ol.xCH3CO2H (Disulfide Bridge between Cys2-Cys7); D-phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-L-cysteinyl-L-threoninol (2->7)-disulfide acetic acid; L-Cysteinamide, D-phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]-, cyclic (2→7)-disulfide, acetate (salt); L-Cysteinamide, D-phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threonyl-N-[2-hydroxy-1-(hydroxymethyl)propyl]-, cyclic (2→7)-disulfide, [R-(R*,R*)]-, acetate (salt); Mycapssa; Octreotide LAR; Sandostatin; Sandostatin LAR; Sandostatin LAR Depot; SMS 201-995ac
Related CAS
83150-76-9 (free base) 622838-44-2 (diacetate)
Appearance
White to Off-White Solid
Purity
>98%
Melting Point
>140°C (dec.)
Sequence
fCFwKTCT-ol.CH3CO2H (Disulfide bridge: Cys2-Cys7)
Storage
Store at -20°C
Solubility
Soluble in Acetic Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)
Application
Antineoplastic Agents, Hormonal
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
InChI Key
XQEJFZYLWPSJOV-XJQYZYIXSA-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.CC(=O)O
1.Patient-Reported Symptom Experiences in Patients With Carcinoid Syndrome After Participation in a Study of Telotristat Etiprate: A Qualitative Interview Approach.
Gelhorn HL1, Kulke MH2, O'Dorisio T3, Yang QM4, Jackson J4, Jackson S4, Boehm KA4, Law L4, Kostelec J1, Auguste P1, Lapuerta P5. Clin Ther. 2016 Mar 31. pii: S0149-2918(16)30122-9. doi: 10.1016/j.clinthera.2016.03.002. [Epub ahead of print]
PURPOSE: Telotristat etiprate, a tryptophan hydroxylase inhibitor, was previously evaluated in a Phase II randomized, placebo-controlled clinical trial in patients with carcinoid syndrome (CS) and diarrhea not adequately controlled by octreotide. The objective of the current study was to characterize the symptom experiences of patients participating in that trial.
2.Quantitative ELISA-Like Immunohistochemistry of Fibroblast Growth Factor 23 in Diagnosis of Tumor-Induced Osteomalacia and Clinical Characteristics of the Disease.
Hu F1, Jiang C2, Zhang Q3, Shi H4, Wei L4, Wang Y3. Dis Markers. 2016;2016:3176978. doi: 10.1155/2016/3176978. Epub 2016 Mar 13.
Tumor-induced osteomalacia (TIO) is a rare acquired paraneoplastic disorder and fibroblast growth factor 23 (FGF23) plays a key role in its pathogenesis. This study was conducted to describe a novel FGF23 detecting procedure and describe clinical features of the disease. Fourteen TIO cases were retrieved and FGF23 expression was measured by quantitative ELISA-like immunohistochemistry using formalin-fixed and paraffin-embedded tissues. As summarized from 14 TIO cases, clinical features of TIO were long-standing history of osteomalacia, hypophosphatemia, and urinary phosphate wasting. The associated tumors were mostly benign phosphaturic mesenchymal tumors mixed connective tissue variant (PMTMCT) which could be located anywhere on the body, and most of them could be localized by conventional examinations and octreotide scanning. By quantitative ELISA-like immunohistochemistry, all the 14 TIO cases had high FGF23 expression (median 0.69, 25%-75% interquartile 0.
3.[A Case of Rectal Carcinoid with Liver and Lymph Node Metastases Treated by a Two-Stage Operation].
Moriyama H1, Denno R, Kida A, Usui Y. Gan To Kagaku Ryoho. 2016 Feb;43(2):255-7.
A 77-year-old woman was admitted to our hospital with the chief complaint of chest pain. CT showed a liver tumor that was 45mm in diameter. A colonoscopic examination revealed a submucosal tumor in the lower rectum, which was diagnosed by histopathology as a neuroendocrine tumor(NET), grade 2. Liver biopsy confirmed the diagnosis of a liver metastasis from a rectal carcinoid. Considering surgical stress and possible complications, we first performed hepatectomy followed by low anterior rectal resection in a two-stage operation. Histopathological examination revealed that the rectal carcinoid was 14 mm in diameter with four lymph node metastases. After surgery, treatment with an octreotide LAR was initiated. The patient remained disease-free for 1 year 8 months after surgery.
4.Reports of 17 Chinese patients with tumor-induced osteomalacia.
Yu WJ1, He JW1, Fu WZ1, Wang C2, Zhang ZL3. J Bone Miner Metab. 2016 Apr 16. [Epub ahead of print]
Tumor-induced osteomalacia (TIO) is a rare acquired form of hypophosphatemic osteomalacia, which is usually attributed to the overproduction of fibroblast growth factor 23 (FGF-23) by benign mesenchymal neoplasms. Localization and thereafter surgical resection of tumors lead to a cure. The present study aimed to investigate the clinical data, diagnostic methods, and follow-up after tumor resection at one medical center in Shanghai to characterize the profile of this rare disorder and to share our successful experience in diagnosis and treatment. Twenty-three patients with adult-onset hypophosphatemia osteomalacia seen in Shanghai Sixth People's Hospital from 2009 to 2014 and 95 normal individuals were enrolled. After taking a medical history and performing a physical examination, we analyzed the laboratory results (including the serum FGF-23 levels) and localized the tumors by 18F-fluorodeoxyglucose positron emission tomography and computed tomography (18F-FDG PET/CT), 99mTc-octreotide (99mTc-OCT) scintigraphy, and magnetic resonance imaging (MRI).
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