Octreotide

Octreotide

Clinical data
Trade names	Sandostatin
AHFS/Drugs.com	Monograph
Pregnancy category	AU: C US: B (No risk in non-human studies)
Routes of administration	Subcutaneous, intramuscular, intravenous
ATC code	H01CB02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	60% (IM), 100% (SC)
Protein binding	40–65%
Metabolism	Hepatic
Biological half-life	1.7–1.9 hours
Excretion	Urine (32%)
Identifiers
IUPAC name (4R,7S,10S,13R,16S,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
CAS Number	83150-76-9 Y
PubChem CID	448601
IUPHAR/BPS	2055
DrugBank	DB00104 Y
ChemSpider	395352 N
UNII	RWM8CCW8GP
KEGG	D00442 N
ChEMBL	CHEMBL1680 N
Chemical and physical data
Formula	C49H66N10O10S2
Molar mass	1019.24 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@H]([C@H]1C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CCCCN)Cc2c[nH]c3c2cccc3)Cc4ccccc4)NC(=O)[C@@H](Cc5ccccc5)N)C(=O)N[C@H](CO)[C@@H](C)O)O
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 N Key:DEQANNDTNATYII-OULOTJBUSA-N N
NY (what is this?)

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.

Octreotide is used for the treatment of growth hormone producing tumors (acromegaly and gigantism), pituitary tumors that secrete thyroid stimulating hormone (thyrotropinoma), diarrhea and flushing episodes associated with carcinoid syndrome, and diarrhea in people with vasoactive intestinal peptide-secreting tumors (VIPomas).

Octreotide is often given as an infusion for management of acute haemorrhage from esophageal varices in liver cirrhosis on the basis that it reduces portal venous pressure, though current evidence suggests that this effect is transient and does not improve survival.

Octreotide is used in nuclear medicine imaging by labelling with indium-111 (Octreoscan) to noninvasively image neuroendocrine and other tumours expressing somatostatin receptors. More recently, it has been radiolabelled with carbon-11 as well as gallium-68, enabling imaging with positron emission tomography (PET), which provides higher resolution and sensitivity.