Lanreotide

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Lanreotide
Systematic (IUPAC) name
(4S,7S,10S,13R,16S,19S)-10-(4-aminobutyl)-19- [[(2R)-2-amino-3-naphthalen-2-yl-propanoyl]amino]- N-[(1S,2R)-1-carbamoyl-2-hydroxy-propyl]-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
Identifiers
CAS number	108736-35-2 127984-74-1
ATC code	H01CB03
PubChem	71349
Chemical data
Formula	C₅₄H₆₉N₁₁O₁₀S₂
Mol. mass	1096.33 g/mol 1156.380 g/mol (acetate)
Pharmacokinetic data
Bioavailability	Approximately 80%^[1]
Protein binding	78%^[1]
Metabolism	?
Half life	2 hours (immediate release) 5 days (sustained release)
Excretion	?
Therapeutic considerations
Pregnancy cat.	C(AU)
Legal status	POM(UK)
Routes	Intramuscular

Lanreotide (INN) 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, and marketed under the trade name Somatuline. It is available in several countries, including the United Kingdom, Australia and Canada, but not in the United States.

1 Pharmacology
2 Indications
3 Side effects
4 Formulations
5 References

[edit] Pharmacology

Lanreotide is a synthetic analogue of somatostatin, a naturally-occurring inhibitory hormone which blocks the release of several other hormones, including growth hormone, thyroid-stimulating hormone (TSH), insulin and glucagon. Lanreotide binds to the same receptors as somatostatin, although with higher affinity to peripheral receptors, and has similar activity. However, while somatostatin is quickly broken down in the body (within minutes),^[2] lanreotide has a much longer half-life, and produces far more prolonged effects.

The efficacy of lanreotide has not been extensively studied, and results differ greatly between trials and formulations.

[edit] Indications

Lanreotide is used in the treatment of acromegaly, due to both pituitary and non-pituitary growth hormone-secreting tumors, and the management of symptoms caused by neuroendocrine tumors, particularly carcinoid tumors and VIPomas. In the United Kingdom, it is also indicated in the treatment of thyrotrophic adenoma,^[3] a rare tumor of the pituitary gland which secretes TSH.

Interestingly, lanreotide also shows activity against non-endocrine tumors, and, along with other somatostatin analogues, is being studied as a possible general antitumor agent.^[4]^[5]

[edit] Side effects

The main side effects of lanreotide treatment are mild to moderate pain at the injection site and gastrointestinal disturbances, such as diarrhea, nausea and vomiting. Isolated cases of gallstone formation have been associated with use of lanreotide, particularly over long periods of time.^[1]^[3]

[edit] Formulations

Lanreotide is available in two formulations: a sustained release formulation (sold under the trade name Somatuline LA), which is administered every ten or fourteen days, and an extended release formulation (trade name Somatuline Autogel), which is injected intramuscularly once a month.

[edit] References

^ ^a ^b ^c (French) Lanreotide Acetate. BIAM (March 5, 2001). Retrieved on 2007-03-02.
^ Rens-Domiano S, Reisine T (1992). "Biochemical and functional properties of somatostatin receptors". J Neurochem 58 (6): 1987–96. DOI:10.1111/j.1471-4159.1992.tb10938.x. PMID 1315373.
^ ^a ^b Somatuline LA. electronic Medicines Compendium (September 17, 2003). Retrieved on 2007-03-02.
^ Kvols L, Woltering E (2006). "Role of somatostatin analogs in the clinical management of non-neuroendocrine solid tumors". Anticancer Drugs 17 (6): 601–8. PMID 16917205.
^ Susini C, Buscail L (2006). "Rationale for the use of somatostatin analogs as antitumor agents". Ann Oncol 17 (12): 1733–42. PMID 16801334.