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Octreotide acetate

Octreotide acetate
Octreotide acetate structure
CAS No.
83150-76-9
Chemical Name:
Octreotide acetate
Synonyms
ctreotide;DARAMONOL;GMP(CFDA);OXTREOTIDE;Longastatin;Octreotide acetate;Octreotode Acetate;Ocetreotide, Acetate;32) Octreotide Acetate;APIOC OCTREOTIDE ACETATE
CBNumber:
CB2138033
Molecular Formula:
C49H66N10O10S2
Formula Weight:
1019.24
MOL File:
83150-76-9.mol

Octreotide acetate Properties

Boiling point:
1447.2±65.0 °C(Predicted)
Density 
1.39±0.1 g/cm3(Predicted)
storage temp. 
−20°C
solubility 
H2O: soluble
pka
12.60±0.70(Predicted)
InChIKey
DEQANNDTNATYII-MEUDYGGUSA-N
CAS DataBase Reference
83150-76-9
FDA UNII
75R0U2568I
SAFETY
  • Risk and Safety Statements
WGK Germany  3

Octreotide acetate price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich O1014 Octreotide ≥98% (HPLC) 83150-76-9 500ug $231 2020-08-18 Buy
Sigma-Aldrich PHR1880 Octreotide Acetate Pharmaceutical Secondary Standard; Certified Reference Material 10 mg $256 2021-03-22 Buy
Sigma-Aldrich O1014 Octreotide ≥98% (HPLC) 83150-76-9 1mg $338 2020-08-18 Buy
Sigma-Aldrich 1477604 Octreotide acetate United States Pharmacopeia (USP) Reference Standard 4.37 mg $1300 2021-03-22 Buy

Octreotide acetate Chemical Properties,Uses,Production

Description

Octreotide is a long-acting somatostatin analog indicated for symptomatic control in acromegaly and gastroenteropancreatic tumors. Other potential uses under investigation include diabetes, psoriasis and Alzheimer's disease.

Originator

Sandoz (Switzerland)

Uses

Antisecretory (gastric).

Indications

Octreotide acetate (Sandostatin) is a synthetic peptide analogue of the hormone somatostatin. Its actions include inhibition of the pituitary secretion of growth hormone and an inhibition of pancreatic islet cell secretion of insulin and glucagon. Unlike somatostatin, which has a plasma half-life of a few minutes, octreotide has a plasma elimination half-life of 1 to 2 hours. Excretion of the drug is primarily renal.

Manufacturing Process

Synthesis of octreotide and derivative thereof can be carried out by two methods. The first method is synthesized initially by fragment condensation solution phase procedures. The synthetic process of octreotide has been described by Bauer et al. (1). The second method is the synthese by solidphase procedures. Edward et al. (2) isolated side chain protected octreotide with a total yield of 14% by cleaving the protected peptide from the resin with threoninol. Arano et al. (3) carried out another solid phase method for octreotide. and produced it in overall 31.8% yield based on the starting FmocThr(tBu)-ol-resin. The basic difference from the other procedures already described is that the introduction of the threoninol is carried out upon the protected peptidic structure (resin-free), which, when appropriately activated, leads quantitatively and without needing to make temporary protections upon the threoninol, to the protected precursor of octreotide, which in turn, with a simple acid treatment leads to octreotide with very high yields.
At first the Fmoc-Cys-Cl-trityl-resin was prepared. The incorporation of the Fmoc-Cys(trt)-OH residue upon 2Cl-Trt resin is accomplished with an excess of 1 eq. of Fmoc-Cys(Trt) and 2.5 eq. of N,N'-diisopropylethylamine (DIEA).
2.93 g (5.0 mmol) of Fmoc-Cys(Trt) are incorporated upon 5 g of resin (f = 1.28 mmol/g of resin, 6.4 mmol). The resin and the amino acid are weighed in separate containers and left to dry in a vacuum with KOH, for a minimum of two hours. A 1/1 solution of DIEA and CH2Cl2 (DCM) (dry on a 4A sieve) is prepared. The already dry amino acid is dissolved with dry DCM at a concentration of 0.1 g of resin per ml, adding the minimum quantity of dry DMF to complete the dissolution. 1/3 of the 1.8 ml (12.5 mmol) DIEA solution is added to this transparent solution in 1.8 ml of DCM. This is thoroughly homogenized and added to the dry resin. It is subjected to vigorous magnetic agitation for five minutes and the rest of the DIEA is added to the reaction; the mixture is allowed to react for forty minutes more. Then, 4 ml of dry MeOH are added and allowed to react for 10 minutes, after which the resin is filtered and the washings described below are carried out.

brand name

Sandostatin (Novartis).

Therapeutic Function

Antiulcer, Growth hormone inhibitor

Biological Functions

Octreotide acetate, a long-acting octapeptide analogue of somatostatin, has a half-life of approximately 100 minutes. A comparison of the primary structures of octreotide and somatostatin suggests little similarity, but from earlier work at the Salk Institute it was known that not all the residues in somatostatin were necessary to elicit its full biological activity. Other studies suggested that the essential fragment for its activity was the tetrapeptide Phe7-Trp8- Lys9-Thr10. These earlier studies helped in the design of the potent drug now known as octreotide acetate. This drug suppresses the secretion of gastroenteropancreatic peptides, such as gastrin, vasoactive intestinal peptide (VIP), insulin, and glucagon, as well as pituitary GH. Furthermore, it is more potent than natural somatostatin in inhibiting the release of glucagon, insulin, and GH.

Clinical Use

Octreotide acetate is used by SC injection in the palliative treatment of patients with metastatic carcinoid tumors, which are tumors of the endocrine system, GI tract, and lung (gastroenteropancreatic). Carcinoid tumors secrete increasing amounts of vasoactive substances, including histamine, serotonin, bradykinin, and prostaglandins. Octreotide acetate inhibits or suppresses the release of these vasoactive substances and, thus, is useful in treating the severe diarrhea, facial flushing, and wheezing episodes that accompany carcinoid tumors. In addition, it finds use in the palliative management of VIP-secreting tumors (VIPomas, usually pancreatic tumors). Patients with VIPomas suffer a profuse, watery diarrhea syndrome, and octreotide acetate is able to help by decreasing the release of damaging intestinal tumor cell secretions. Octreotide also helps to reduce hypokalemia by correcting electrolyte imbalances.
An excessive secretion of GH from the pituitary can cause the disorder known as acromegaly, which is characterized by a progressive enlargement of the head, face, hands, feet, and thorax. Inasmuch as octreotide acetate is able to decrease the secretion of GH from the pituitary, it is used in treating patients with acromegaly who are unresponsive to previous pituitary radiation therapy or surgery. It is used in the treatment of acromegaly, because it reduces the blood levels of both GH and insulin-like growth factor-I (IGF-I). The long-acting repository form of octreotide acetate also is used in treating acromegaly, carcinoid tumors, and VIPomas, but in monthly depot injections.
Octreotide for IV injection is used in the treatment of acute bleeding from esophageal varices. Variceal bleeding occurs in about half the patients with cirrhosis of the liver and is responsible for about one-third of deaths in these patients. Octreotide is a potent vasoconstrictor that reduces portal and collateral blood flow by constricting visceral vessels, which leads to reduced portal blood pressure and decreases the bleeding.

Veterinary Drugs and Treatments

Octreotide may be useful in the adjunctive treatment of hyperinsulinemia in patients with insulinomas (especially dogs, ferrets). Response is variable, presumably dependent on whether the tumor cells have receptors for somatostatin. Octreotide may also be useful in the diagnosis and symptomatic treatment of gastrinomas in dogs or cats. It may be of use in the treatment of acute pancreatitis, but more research is needed before it can be recommended for this use in veterinary patients.

Octreotide acetate Preparation Products And Raw materials

Raw materials

Preparation Products


Octreotide acetate Suppliers

Global( 271)Suppliers
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Cellmano Biotech Limited
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View Lastest Price from Octreotide acetate manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-06-03 Octreotide acetate
83150-76-9
US $0.00-0.00 / KG 1g 98%min 1 KG WUHAN FORTUNA CHEMICAL CO., LTD
2021-02-25 Octreotide acetate
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-04-16 Octreotide
83150-76-9
US $10.00 / Kg/Bag 1Kg/Bag 99%min 2000 Wuhan Monad Medicine Tech Co.,LTD

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