Lanreotide
{{Short description|Pharmaceutical drug}}
{{Use dmy dates|date=October 2022}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 459830563
| image = Lanreotide.svg
| alt =
| JAN = Lanreotide acetate
| USAN = Lanreotide acetate
| tradename = Somatuline
| Drugs.com = {{drugs.com|monograph|lanreotide}}
| DailyMedID = Lanreotide
| licence_US = Lanreotide
| pregnancy_AU = C
| routes_of_administration = Intramuscular, subcutaneous
| ATC_prefix = H01
| ATC_suffix = CB03
| legal_AU = S4
| legal_UK = POM
| legal_US = Rx-only
| bioavailability = Approximately 80%
| protein_bound = 78%
| metabolism = In GI tract
| elimination_half-life = 2 hours (immediate release)
5 days (sustained release)
| excretion = Mostly bile duct
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 108736-35-2
| CAS_supplemental =
| PubChem = 71349
| IUPHAR_ligand = 2031
| DrugBank_Ref =
| DrugBank = DB06791
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 64450
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0G3DE8943Y
| KEGG = D04666
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201185
| IUPAC_name = 3-(2-naphthyl)-D-alanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-L-threoninamide (2->7)-disulfide
| C=54 | H=69 | N=11 | O=10 | S=2
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| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
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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.{{cite press release | url = https://www.fda.gov/bbs/topics/NEWS/2007/NEW01692.html | title = FDA Approves New Drug to Treat Rare Disease, Acromegaly | date = August 30, 2007 | accessdate = 2007-09-06 | publisher = U.S. Food and Drug Administration | archive-date = 10 April 2021 | archive-url = https://web.archive.org/web/20210410232102/http://www.fda.gov/bbs/topics/NEWS/2007/NEW01692.html | url-status = dead }}
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,{{cite web | url = http://emc.medicines.org.uk/emc/assets/c/html/displaydoc.asp?documentid=877 | title = Somatuline LA | date = September 17, 2003 | accessdate = 2007-03-02 | publisher = electronic Medicines Compendium | archive-url = https://web.archive.org/web/20060924182805/http://emc.medicines.org.uk/emc/assets/c/html/displaydoc.asp?documentid=877 | archive-date = September 24, 2006 | url-status = dead }} 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.{{cite journal |vauthors=Kvols L, Woltering E |title=Role of somatostatin analogs in the clinical management of non-neuroendocrine solid tumors |journal=Anticancer Drugs |volume=17 |issue=6 |pages=601–8 |year=2006 |pmid=16917205 |doi=10.1097/01.cad.0000210335.95828.ed}}{{cite journal |vauthors=Susini C, Buscail L |title=Rationale for the use of somatostatin analogs as antitumor agents |journal=Ann Oncol |volume=17 |issue=12 |pages=1733–42 |year=2006 |pmid=16801334 |doi=10.1093/annonc/mdl105|doi-access=free }}
In December 2014, the US FDA approved lanreotide for the treatment of people with unresectable, well or moderately differentiated, locally advanced or metastatic gastroenteropancreatic neuroendocrine tumors (GEP-NETs).{{cite web |url=http://www.cancernetwork.com/gastrointestinal-cancer/fda-approves-lanreotide-injection-gep-nets |title=FDA Approves Lanreotide Injection for GEP-NETs |year=2014 |access-date=29 April 2023 |archive-date=26 June 2019 |archive-url=https://web.archive.org/web/20190626091016/https://www.cancernetwork.com/gastrointestinal-cancer/fda-approves-lanreotide-injection-gep-nets |url-status=dead }}
It is used for polycystic liver disease.{{medcn|date=October 2022}} It has also been shown that it reduces the volume by 264mls on average.{{medcn|date=October 2022}}
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.
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),{{cite journal |vauthors=Rens-Domiano S, Reisine T |title=Biochemical and functional properties of somatostatin receptors |journal=J Neurochem |volume=58 |issue=6 |pages=1987–96 |year=1992 |pmid=1315373 |doi=10.1111/j.1471-4159.1992.tb10938.x|s2cid=36873846 }} lanreotide has a much longer half-life, and produces far more prolonged effects.{{medcn|date=October 2022}}
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, and an extended release formulation (UK trade name 'Somatuline Autogel', or 'Somatuline Depot' in the US), which is administered subcutaneously once a month.{{cite web | url = http://emc.medicines.org.uk/emc/assets/c/html/displaydoc.asp?documentid=8203 | title = Somatuline Autogel | date = April 12, 2007 | accessdate = 2007-04-19 | publisher = electronic Medicines Compendium | archive-url = https://web.archive.org/web/20070928060402/http://emc.medicines.org.uk/emc/assets/c/html/displaydoc.asp?documentid=8203 | archive-date = September 28, 2007 | url-status = dead }}
Self-assembling properties
Lanreotide has been shown to spontaneously self-assemble into monodisperse nanotubes of 24.4 nm diameter{{cite journal |vauthors=Valéry C, Paternostre M, Robert B, Gulik-Krzywicki T, Narayanan T, Dedieu JC, Keller G, Torres ML, Cherif-Cheikh R, Calvo P, Artzner F |title=Biomimetic organization: Octapeptide self-assembly into nanotubes of viral capsid-like dimension |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=100 |issue=18 |pages=10258–62 |year=2003 |pmid= 12930900|doi=10.1073/pnas.1730609100 |pmc=193548|bibcode=2003PNAS..10010258V |doi-access=free }} and has been thereafter used as a fruitful and versatile model system in several biophysical studies.{{cn|date=October 2022}}
References
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Category:Somatostatin inhibitors