OCTREOTIDE ACETATE

Synonyms. Octreotide acetate; D-Phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L- threonyl-L- cysteinyl- L-threoninol cyclic (2-7)- disulfide acetate; Longastatin; Octreotida; Octreotide-LAR; Octreotidum; Sandostatin; Sandostatin LAR; 7-(4-Aminobutyl)-16-[(2-amino-3-phenyl propanoyl) amino]-13-benzyl-N- (1,3- dihydroxybutan -2-yl)- 4-(1-hydroxyethyl)-10-(1H-indol-3-ylmethyl) -3,6,9,12,15-pentaoxo-18,19- dithia- 2,5,8,11,14-pentazacycloicosane-1-carboxamide acetic acid; Phe-Cys-Phe-Trp-Lys-Thr-Cys-Thr-ol [Disulfide bridge: 2-7];

OCTREOTIDE ACETATE

 

PRODUCT IDENTIFICATION

CAS RN

83150-76-9(parent), 79517-01-4 (acetate)

EINECS RN

FORMULA

C51H70N10O12S2

MOLE WEIGHT

1079.29

H.S CODE

 2933.99.7900

SMILES

 C(c1ccccc1)[C@@H]1NC(=O)[C@@H] (NC([C@@H](N)Cc2ccccc2)=O)CSSC[C@@H](NC([C@@H](NC([C@@H] (NC ([C@@H](NC1=O)Cc1c[nH]c2c1cccc2)=O)CCCCN)=O)[C@@H](O )C)=O) C(N[C@H](CO)[C@H](O)C)=O.CC(O)=O.CC(O)=O

CLASSIFICATION

Antineoplastic, Antisecretory, Gastrointestinal agent

EXTRA NOTES

 A potent, long-acting synthetic SOMATOSTATIN octapeptide analog that inhibits secretion of growth hormone and is used to treat hormone-secreting tumors; diabetes mellitus; hypotension, orthostatic; hyperinsulinism; hypergastrinemia; and small bowel fistula.
Somatostatin analog that is 3-times more potent than the native hormone in inhibiting the secretion of growth hormone.

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

white powder

MELTING POINT

 

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

Soluble (Soluble in acetic acid)

VAPOR DENSITY

 

log P(octanol-water)

  

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pH

 

REFRACTIVE INDEX

 

FLASH POINT

 

 
STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong acids, Strong bases

POLYMERIZATION

Has not been reported

NFPA RATINGS

Health: 0,Flammability:0, Reactivity: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Octreotide is a hormone that occurs naturally in the body. It is used to treat carcinoid syndrome, which is seen in patients with carcinoid or neuroendocrine tumors. These tumors cause the body to overproduce certain hormones, and these hormones in turn can lead to symptoms collectively known as "carcinoid syndrome". Common symptoms include: flushing (90% of patients), diarrhea (75%), abdominal cramping (51%), and abnormalities of the heart valves (53%) possibly leading to right heart failure. Octreotide works to reduce the production of these hormones and thereby decrease the symptoms.

  • Octreotide is available in two forms, a fast/short-acting form called Sandostatin, and a long-acting form called Sandostatin LAR.
  • Octreotide is used to control symptoms in gastro-entero-pancreatic (GEP) endocrine tumors, such as insulinoma, gastrinoma, VIPoma, glucagonoma, somatostatinoma, and carcinoid tumors.
  • Octreotide is also used to treat acromegaly, also known as gigantism, and chemotherapy induced diarrhea. (http://www.oncolink.com/treatment/)

Octreotide is a synthetic octapeptide analogue with a similar pharmacologic action to that of somatostatin, but with a prolonged duration of action. It has a half-life of 100 minutes after subcutaneous administration. Its effects include the inhibition of the release of pituitary growth hormone and secretion of peptides (for example, insulin, glucagon, gastrin, and other peptides) and serotonin produced in the gastroenteropancreatic (GEP) endocrine system. It alters gastrointestinal motility, splanchnic blood flow, and gastrointestinal absorption. Somatostatin analogues have also been used in an attempt to suppress tumour growth through the inhibition of cell proliferation, stimulation of apoptosis, inhibition of the release of circulating tumour growthpromoting humoral effectors, and reduction in the blood supply to tumours. (http://www.cadth.ca/media/pdf/)

 

The effect of Octreotide (SMS 201-995), synthetic somatostatin analogue on small intestinal and colonic fluid secretion induced respectively by cholera toxin (CT) and deoxycholic acid (DCA) was investigated in rabbits using in vivo isolated loops. After exposure to CT and DCA, marked fluid accumulation was observed in the small intestinal and colonic loops, along with elevation of jejunal and colonic mucosal cyclic AMP concentrations. Octreotide inhibited CT and DCA induced small intestinal and colonic secretion, dose-dependently. This anti-secretory effect was observed after both intramuscular and oral administration of octreotide. In contrast, octreotide did not affect the elevated mucosal cyclic AMP concentrations. These results suggest that octreotide inhibits CT and DCA induced intestinal secretion, and this anti-secretory effect is produced by affecting processes beyond cyclic AMP formation.(http://www.ncbi.nlm.nih.gov/)

Gastric Antisecretory Agents

Product

CAS RN.

Deprostil

33813-84-2
Arbaprostil 55028-70-1
Fenoctimine sulfate 69365-66-8
Fenoctimine 69365-65-7
15-Acetyltrimoprostil 81397-66-2
Trimoprostil 69900-72-7
Rioprostil 77287-05-9
Octreotide acetate 79517-01-4
Octreotide 83150-76-9
Omeprazole sodium 95510-70-6
Omeprazole 73590-58-6
Ufiprazole 73590-85-9
Lanreotide 108736-35-2

 

SALES SPECIFICATION

APPEARANCE

 white to slightly yellowish powder
IDENTIFICATION

pass (HPLC)

PURITY

98.0% min
AMINO ACID ±10% (theoretical Composition)

RELATED SUBSTANCES

2.0% max (total impurity), 1.0% max (Individual impurity)
PEPTIDE CONTENT
80.0% min (N determination)
ACETATE CONTENT

15.0% max
WATER CONTENT 8.0% max
OPTICAL ROTATION -45.0° ~ -55.0°(c=0.5, 95% HAc)
BACTERIAL ENDOTOXINS 5EU/mg max

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

Not known

HAZARD CLASS

  
PACKING GROUP  

 

SAFETY INFORMATION

HAZARD OVERVIEW

Not known

HAZARD CODES

 

RISK PHRASES

 36

SAFETY PHRASES

 26

 

PACKING