Structure via PubChem · Public domain (PubChem)
lanreotide
Sign in to saveAlso known as Somatuline, Lanreotide acetate, BIM 23014, DC 13-116
Lanreotide, sold under the brand name Somatuline among others, is a medication used in the management of acromegaly and symptoms caused by neuroendocrine tumors, most notably carcinoid syndrome. It is a long-acting analogue of somatostatin, like octreotide.
Chemical data
- Formula
- C54H69N11O10S2
- Molecular weight
- 1096.3 g/mol
- IUPAC name
- (4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-N-[(2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]-19-[[(2R)-2-amino-3-naphthalen-2-ylpropanoyl]amino]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-propan-2-yl-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide
- SMILES
- C[C@H]([C@@H](C(=O)N)NC(=O)[C@@H]1CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C(C)C)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)[C@@H](CC5=CC6=CC=CC=C6C=C5)N)O
- InChIKey
- PUDHBTGHUJUUFI-SCTWWAJVSA-N
- XLogP
- 2.5
- Polar surface area
- 406 Ų
- H-bond donors
- 13
- H-bond acceptors
- 14
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Protein
- First approval
- 2007
- Admin. routes
- parenteral
- Indications
- neoplasm, acromegaly, carcinoid syndrome, peptic esophagitis
via ChEMBL · EBI
Research
1,538 papers- Lanreotide in metastatic enteropancreatic neuroendocrine tumors.The New England journal of medicine · 2014
- Lanreotide autogel/depot in advanced enteropancreatic neuroendocrine tumours: final results of the CLARINET open-label extension study.Endocrine · 2021
- The safety of lanreotide for neuroendocrine tumor.Expert opinion on drug safety · 2019
- Lanreotide for the treatment of acromegaly.Advances in therapy · 2009
- Lanreotide Depot: An Antineoplastic Treatment of Carcinoid or Neuroendocrine Tumors.Journal of gastrointestinal cancer · 2016
via PubMed
Wikidata facts
- Mass
- 1095.467
- Has use
- medication
Show 5 more facts
- chemical formula
- C₅₄H₆₉N₁₁O₁₀S₂
- canonical SMILES
- CC(C)C1C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)C(CC5=CC6=CC=CC=C6C=C5)N)C(=O)NC(C(C)O)C(=O)N
- isomeric SMILES
- C[C@H]([C@@H](C(=O)N)NC(=O)[C@@H]1CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C(C)C)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)[C@@H](CC5=CC6=CC=CC=C6C=C5)N)O
- defined daily dose
- 3
- subject has role
- antineoplastic
Sources (6)
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Medical uses
- Side effects
- Pharmacology
- Formulations
- Self-assembling properties
- References
Lanreotide, sold under the brand name Somatuline among others, is a medication used in the management of acromegaly and symptoms caused by neuroendocrine tumors, most notably carcinoid syndrome. It is a long-acting analogue of somatostatin, like octreotide.
Lanreotide (as lanreotide acetate) is manufactured by Ipsen. It is available in several countries, including the United Kingdom, Australia and Canada, and was approved for sale in the United States by the Food and Drug Administration (FDA) on August 30, 2007.
Excerpted from Wikipedia’s “lanreotide” article, available under the CC BY-SA 4.0 licence.