Lanreotide

Lanreotide
Names
Pronunciationlan ree' oh tide[1]
Trade namesSomatuline
Other namesLanreotide acetate
IUPAC name
  • 3-(2-naphthyl)-D-alanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-L-threoninamide (2->7)-disulfide
Clinical data
Drug classSomatostatin analogue[2]
Main usesAcromegaly, neuroendocrine tumors such as carcinoid, thyroid tumors[2]
Side effectsDiarrhea, abdominal pain, nausea, gallstones, joint pain, pain at the site of injection[3]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • AU: C
  • US: C (Risk not ruled out)
    Routes of
    use    		Intramuscular, subcutaneous
    External links
    AHFS/Drugs.comMonograph
    Legal
    License data
    Legal status
    Pharmacokinetics
    BioavailabilityApproximately 80%
    Protein binding78%
    MetabolismIn GI tract
    Elimination half-life2 hours (immediate release)
    5 days (sustained release)
    ExcretionMostly biliary
    Chemical and physical data
    FormulaC54H69N11O10S2
    Molar mass1096.33 g/mol
    1156.380 g/mol (acetate) g·mol−1
    3D model (JSmol)
    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)Cc2c[nH]c3c2cccc3)Cc4ccc(cc4)O)NC(=O)[C@@H](Cc5ccc6ccccc6c5)N)O
    InChI
    • InChI=1S/C54H69N11O10S2/c1-29(2)45-54(75)63-44(53(74)65-46(30(3)66)47(57)68)28-77-76-27-43(62-48(69)38(56)23-32-15-18-33-10-4-5-11-34(33)22-32)52(73)60-41(24-31-16-19-36(67)20-17-31)50(71)61-42(25-35-26-58-39-13-7-6-12-37(35)39)51(72)59-40(49(70)64-45)14-8-9-21-55/h4-7,10-13,15-20,22,26,29-30,38,40-46,58,66-67H,8-9,14,21,23-25,27-28,55-56H2,1-3H3,(H2,57,68)(H,59,72)(H,60,73)(H,61,71)(H,62,69)(H,63,75)(H,64,70)(H,65,74)/t30-,38-,40+,41+,42-,43+,44+,45+,46+/m1/s1 ☒N
    • Key:PUDHBTGHUJUUFI-SCTWWAJVSA-N ☒N

    Lanreotide, sold under the brand name Somatuline, is a medication used to treat acromegaly, neuroendocrine tumors such as carcinoid, and thyroid tumors.[2] In acromegaly it is used when other treatments are not effective.[3] It is given by injection under the skin or into a muscle.[2]

    Common side effects include diarrhea, abdominal pain, nausea, gallstones, joint pain, and pain at the site of injection.[3] Other side effects may include pancreatitis, high blood sugar, low blood sugar, and liver problems.[1] It is a somatostatin analogue and works by decreasing levels of growth hormone, insulin, and glucagon.[2][1]

    Lanreotide was approved for medical use in the United States in 2007.[3] In the United Kingdom it costs the NHS about £550 at a dose of 60 mg per month as of 2021.[2] This amount in the United States costs about 6,100 USD.[4]

    Medical uses

    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 States and Canada, lanreotide is only indicated for the treatment of acromegaly. In the United Kingdom, it is also indicated in the treatment of thyrotrophic adenoma,[5] a rare tumor of the pituitary gland which secretes TSH.

    Lanreotide also shows activity against non-endocrine tumors, and, along with other somatostatin analogues, is being studied as a possible general antitumor agent.[6][7]

    In Dec 2014 the US FDA approved lanreotide for the treatment of patients with unresectable, well or moderately differentiated, locally advanced or metastatic gastroenteropancreatic neuroendocrine tumors (GEP-NETs).[8]

    Formulations

    Lanreotide is available in two formulations: a sustained release formulation (sold under the trade name "Somatuline LA"), which is injected intramuscularly every ten or fourteen days,[5] and an extended release formulation (UK trade name "Somatuline Autogel", or "Somatuline Depot" in the US), which is administered subcutaneously once a month.[9]

    Somatuline autogel is given at a dose of 60 to 120 mg every 4 weeks.[2] Somatuline LA is given at a dose of 30 mg every 7 to 14 days.[2]

    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.[5]

    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),[10] 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.

    Chemistry

    Lanreotide has been shown to spontaneously self-assemble into monodisperse nanotubes of 24.4 nm diameter[11] and has been thereafter used as a fruitful and versatile model system in several biophysical studies.

    Its sequence is H-D-2Nal-Cys(1)-Tyr-D-Trp-Lys-Val-Cys(1)-Thr-NH2.

    References

    1. 1 2 3 "Lanreotide". LiverTox: Clinical and Research Information on Drug-Induced Liver Injury. National Institute of Diabetes and Digestive and Kidney Diseases. 2012. Archived from the original on 20 November 2021. Retrieved 20 November 2021.
    2. 1 2 3 4 5 6 7 8 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 993. ISBN 978-0857114105.
    3. 1 2 3 4 "Lanreotide Monograph for Professionals". Drugs.com. Archived from the original on 24 January 2021. Retrieved 20 November 2021.
    4. ↑ "Somatuline Depot Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 17 April 2021. Retrieved 20 November 2021.
    5. 1 2 3 "Somatuline LA". electronic Medicines Compendium. September 17, 2003. Archived from the original on September 24, 2006. Retrieved 2007-03-02.
    6. ↑ Kvols L, Woltering E (2006). "Role of somatostatin analogs in the clinical management of non-neuroendocrine solid tumors". Anticancer Drugs. 17 (6): 601–8. doi:10.1097/01.cad.0000210335.95828.ed. PMID 16917205.
    7. ↑ Susini C, Buscail L (2006). "Rationale for the use of somatostatin analogs as antitumor agents". Ann Oncol. 17 (12): 1733–42. doi:10.1093/annonc/mdl105. PMID 16801334.
    8. ↑ "FDA Approves Lanreotide Injection for GEP-NETs". 2014. Archived from the original on 2019-06-26. Retrieved 2021-09-26.
    9. ↑ "Somatuline Autogel". electronic Medicines Compendium. April 12, 2007. Archived from the original on September 28, 2007. Retrieved 2007-04-19.
    10. ↑ 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. S2CID 36873846.
    11. ↑ Valéry C, Paternostre M, Robert B, Gulik-Krzywicki T, Narayanan T, Dedieu JC, Keller G, Torres ML, Cherif-Cheikh R, Calvo P, Artzner F (2003). "Biomimetic organization: Octapeptide self-assembly into nanotubes of viral capsid-like dimension". Proceedings of the National Academy of Sciences of the United States of America. 100 (18): 10258–62. Bibcode:2003PNAS..10010258V. doi:10.1073/pnas.1730609100. PMC 193548. PMID 12930900.
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