octreotide

Also known as SMS995, octrotide

Octreotide, sold under the brand name Sandostatin among others, 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 and binds predominantly to the somatostatin receptors SSTR2 and SSTR5.

In the Vinony graph

Vinony's link graph records 874 inbound references to octreotide, and connects out to growth hormone, intravenous infusion and defusion and ghrelin.

It is catalogued under topics including Chemical articles with multiple CAS registry numbers, Chemical articles with multiple PubChem CIDs and Chemicals using indexlabels.

Vinony links it to 28 Wikipedia language editions.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 458287873
Drug.image: Octreotide.svg
Drug.image_class: skin-invert-image
Drug.image2: Octreotride PDB-6vc1.png
Drug.image_class2: bg-transparent
Drug.caption: 3D structure of octreotide.
Drug.tradename: Sandostatin, Bynfezia Pen, Mycapssa, others
Drug.MedlinePlus: a693049
Drug.DailyMedID: Octreotide
Drug.pregnancy_AU: C
Drug.routes_of_administration: Subcutaneous, intramuscular, intravenous, by mouth
Drug.ATC_prefix: H01
Drug.ATC_suffix: CB02
Drug.legal_AU: S4
Drug.legal_CA: Rx-only
Drug.legal_UK: POM

via Wikipedia infobox

Chemical data

Formula: C49H66N10O10S2
Molecular weight: 1019.2 g/mol
IUPAC name: (4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-19-[[(2R)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-[(1R)-1-hydroxyethyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide
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)CC2=CNC3=CC=CC=C32)CC4=CC=CC=C4)NC(=O)[C@@H](CC5=CC=CC=C5)N)C(=O)N[C@H](CO)[C@@H](C)O)O
InChIKey: DEQANNDTNATYII-OULOTJBUSA-N
XLogP: 1
Polar surface area: 383 Å²
H-bond donors: 13
H-bond acceptors: 14
Formal charge: 0

via PubChem

Research

12,596 papers

Octreotide and Octreotide-derived delivery systems.Journal of drug targeting · 2023
Octreotide.Neonatal network : NN · 2006
Octreotide.Journal of pain and symptom management · 2010
Octreotide in hyperinsulinism.The Annals of pharmacotherapy · 1997
ANNIVERSARY REVIEW: Octreotide, 40 years later.European journal of endocrinology · 2019

via PubMed

Wikidata facts

Mass: 1018.44048
Has use: medication

Show 9 more facts

chemical formula: C₄₉H₆₆N₁₀O₁₀S₂
medical condition treated: carcinoid tumor
isomeric SMILES: C[C@@H](O)[C@@H](CO)NC(=O)[C@@H]1CSSC[C@H](NC(=O)[C@H](N)CC2=CC=CC=C2)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@H](CC4=CNC5=C4C=CC=C5)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1
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
defined daily dose: 0.7
NCI Thesaurus ID: C711
MCN code: 3003.39.25
World Health Organisation international non-proprietary name: octreotide
stylized name: SandoSTATIN

Sources (6)

via Wikidata · CC0

~11 min read

Encyclopedic overview

17 sections

Contents

Medical uses
Tumors
Bleeding esophageal varices
Radiolabeling
Acromegaly
Hypoglycemia
Contraindications
Adverse effects
Interactions
Pharmacology
Pharmacokinetics
History
Society and culture
Legal status
Research
Obesity
References

It was approved for use in the United States in 1988. Octreotide was approved for medical use in the European Union in 2022. , octreotide is the first oral somatostatin analog (SSA) approved by the FDA. It is on the World Health Organization's List of Essential Medicines.

Excerpted from Wikipedia’s “octreotide” article, available under the CC BY-SA 4.0 licence.