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Octreotide
Systematic (IUPAC) name
(4R,7S,10S,13R,16 S,19R)-10-(4-aminobutyl)-19-
[[(2R)-2-amino-3-phenyl-propanoyl]amino]-16-
benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-
(1-hydroxyethyl)-13-(1H-indol-3-ylmethyl)-6,9,12,
15,18-pentaoxo-1,2-dithia-5,8,11,14,17-
pentazacycloicosane-4-carboxamide
Identifiers
CAS number 83150-76-9
ATC code H01CB02
PubChem 54373
DrugBank BTD00088
Chemical data
Formula C 49H66N10O10S2  
Mol. mass 1019.24 g/mol
Pharmacokinetic data
Bioavailability 100%; I.M: 60% to 63% of subcutaneous dose
Protein binding 65%
Metabolism Hepatic
Half life 1.7-1.9 hours
Excretion  ?
Therapeutic considerations
Pregnancy cat. B(US)
Legal status
Routes Intramuscular, intravenous

Octreotide (brand name Sandostatin, Novartis Pharmaceuticals) is an octapeptide that mimics natural somatostatin pharmacologically, though it is a more potent inhibitor of growth hormone, glucagon, and insulin than the natural hormone. It was first synthesized in 1979 by the chemist Wilfried Bauer.

Contents

Pharmacological Effects

Since octreotide resembles somatostatin in physiological activities, it can:

Adverse Effects

Most Frequent Adverse Effects: Abdominal pain with cramps, bradycardia, cardiac conduction changes, gastrointestinal reactions (including nausea/vomiting and diarrhea or constipation), injection site reactions, nausea, vomiting

Less Frequent Adverse Effects: Discolored feces, dyspepsia, flatulence, hypothyroidism, steatorrhea, tenesmus

Rare Adverse Effects: Acute pancreatitis, alopecia, biliary calculi, liver failure, dizziness, edema, fatigue, fever, flushing, generalized weakness, headache, hepatitis, hyperbilirubinemia, hyperglycemia, prolonged QT interval

Uses

The Food and Drug Administration (FDA) has approved the usage of a salt form of this peptide, octreotide acetate, as an injectable depot formulation for the treatment of acromegaly, the treatment of diarrhea and flushing episodes associated with carcinoid syndrome, and treatment of diarrhea in patients with vasoactive intestinal peptide-secreting tumors (VIPomas).

Octreotide has also been used off-label for the treatment of severe, refractory diarrhea from other causes. It is used in toxicology for the treatment of prolonged recurrent hypoglycemia after sulfonylurea and possibly meglitinides overdose.

Octreotide has also been used with varying degrees of success in infants with nesidioblastosis to help decrease insulin hypersecretion.

In patients with suspected esophageal varices, octreotide can be given to help decrease bleeding.[3]

Octreotide has been investigated for patients with pain from chronic pancreatitis.[4]

Octreotide may be useful in the treatment of thymic neoplasms.

Octreotide has been used as an unlicensed drug, injected sub-cutaneously in the management of hypertrophic pulmonary osteoarthropathy (HPOA), secondary to non-small cell lung carcinoma. Although its mechanism is not known it appears to reduce the pain associated with HPOA

It has been used in the treatment of malignant bowel obstruction.[5]

Octreotide may be used in conjunction with midodrine to partially reverse peripheral vasodilation in the hepato-renal syndrome. By increasing systemic vascular resistance, these drugs reduce shunting and improve renal perfusion, prolonging survival until definitive treatment with liver transplant. [6]

In recent years, the drug has been shown to be effective in the treatment of chylothorax.[7][8]

References

  1. ^ Maurer R, Gaehwiler BH, Buescher HH, Hill RC, Roemer D. Opiate antagonistic properties of an octapeptide somatostatin analog. Proceedings of the National Academy of Sciences USA. 1982 Aug;79(15):4815-7. PMID 6126877
  2. ^ Allen MP, Blake JF, Bryce DK, Haggan ME, Liras S, McLean S, Segelstein BE. Design, synthesis and biological evaluation of 3-amino-3-phenylpropionamide derivatives as novel mu opioid receptor ligands. Bioorganic and Medicinal Chemistry Letters. 2000 Mar 20;10(6):523-6. PMID 10741545
  3. ^ Abid S, Jafri W, Hamid S, et al. (March 2009). "Terlipressin vs. octreotide in bleeding esophageal varices as an adjuvant therapy with endoscopic band ligation: a randomized double-blind placebo-controlled trial". Am. J. Gastroenterol. 104 (3): 617–23. doi:10.1038/ajg.2008.147. PMID 19223890. http://dx.doi.org/10.1038/ajg.2008.147.  
  4. ^ Uhl W, Anghelacopoulos SE, Friess H, Büchler MW (1999). "The role of octreotide and somatostatin in acute and chronic pancreatitis". Digestion 60 Suppl 2: 23–31. doi:10.1159/000051477. PMID 10207228.  
  5. ^ Shima Y, Ohtsu A, Shirao K, Sasaki Y (May 2008). "Clinical efficacy and safety of octreotide (SMS201-995) in terminally ill Japanese cancer patients with malignant bowel obstruction". Japanese journal of clinical oncology 38 (5): 354–9. doi:10.1093/jjco/hyn035. PMID 18490369. http://jjco.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=18490369.  
  6. ^ Skagen C, Einstein M, Lucey MR, Said A (Feb 2009). "Combination Treatment With Octreotide, Midodrine, and Albumin Improves Survival in Patients With Type 1 and Type 2 Hepatorenal Syndrome.". J Clin Gastroenterol.. PMID 19238094.  
  7. ^ Dalokay Kilic, MD, Ekber Sahin, MD, Oner Gulcan, MD, Bulent Bolat, MD, Riza Turkoz, MD, Ahmet Hatipoglu, MD (2005). "Octreotide for Treating Chylothorax after Cardiac Surgery". Texas Heart Institute Journal 32 (3): 437–39. http://www.pubmedcentral.nih.gov/picrender.fcgi?artid=1336729&blobtype=pdf.  
  8. ^ Marcia L. Buck, Pharm.D., FCCP (2004). "Octreotide for the Management of Chylothorax in Infants and Children". Pediatric Pharmacotherapy 10 (10). http://www.medscape.com/viewarticle/494653.  

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