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Revision as of 17:41, 9 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').← Previous edit Latest revision as of 22:55, 10 August 2024 edit undoGraeme Bartlett (talk | contribs)Administrators250,106 edits added Category:Octapeptides using HotCat 
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{{Short description|Pharmaceutical drug}}
{{Use dmy dates|date=October 2022}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 414308121 | verifiedrevid = 459830563
| IUPAC_name = (4''S'',7''S'',10''S'',13''R'',16''S'',19''S'')-10-(4-aminobutyl)-19-<br><nowiki>amino]-<br>''N''--16-<br>-13-(1''H''-indol-3-ylmethyl)-<br>6,9,12,15,18-pentaoxo-7-propan-2-yl-1,2-dithia-5,8,<br>11,14,17-pentazacycloicosane-4-carboxamide
| image = Lanreotide.svg | image = Lanreotide.svg
| alt =
| JAN = Lanreotide acetate
| USAN = Lanreotide acetate


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Somatuline
| Drugs.com = {{drugs.com|monograph|lanreotide-acetate}} | Drugs.com = {{drugs.com|monograph|lanreotide}}
| DailyMedID = Lanreotide
| licence_US = Lanreotide | licence_US = Lanreotide
| pregnancy_AU = C | pregnancy_AU = C
⚫ | routes_of_administration = ], ]
| pregnancy_US = C
⚫ | ATC_prefix = H01
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 -->
⚫ | ATC_suffix = CB03

| legal_AU = S4
| legal_AU_comment = <ref>{{cite web | title=Mytolac (Amdipharm Mercury Australia Pty Ltd) | website=Therapeutic Goods Administration (TGA) | date=28 September 2022 | url=https://www.tga.gov.au/resources/prescription-medicines-registrations/mytolac-amdipharm-mercury-australia-pty-ltd | access-date=29 April 2023 | archive-date=13 November 2022 | archive-url=https://web.archive.org/web/20221113202945/https://www.tga.gov.au/resources/prescription-medicines-registrations/mytolac-amdipharm-mercury-australia-pty-ltd | url-status=live }}</ref>
| legal_UK = POM | legal_UK = POM
| legal_US = Rx-only | legal_US = Rx-only
⚫ | routes_of_administration = ], ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = Approximately 80%
| bioavailability = Approximately 80%<ref name="BIAM">{{fr icon}} {{cite web | url = http://www.biam2.org/www/Sub5041.html | title = Lanreotide Acetate | date = March 5, 2001 | accessdate = 2007-03-02 | publisher = BIAM}}</ref>
| protein_bound = 78%<ref name="BIAM"/> | protein_bound = 78%
| metabolism = In ] | metabolism = In ]
| elimination_half-life = 2 hours (immediate release)<br>5 days (sustained release) | elimination_half-life = 2 hours (immediate release)<br />5 days (sustained release)
| excretion = Mostly biliary | excretion = Mostly bile duct


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 108736-35-2 --> | CAS_number = 108736-35-2
| CAS_supplemental = {{CAS|127984-74-1}} | CAS_supplemental =
⚫ | ATC_prefix = H01
⚫ | ATC_suffix = CB03
| PubChem = 71349 | PubChem = 71349
| IUPHAR_ligand = 2031
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank_Ref =
| DrugBank = DB06791
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 64450 | ChemSpiderID = 64450
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0G3DE8943Y | UNII = 0G3DE8943Y
| KEGG = D04666
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1201185 --> | ChEMBL = 1201185

<!--Chemical data-->
| 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 | C=54 | H=69 | N=11 | O=10 | S=2
| smiles = C((C(=O)N)NC(=O)1CSSC(C(=O)N(C(=O)N(C(=O)N(C(=O)N(C(=O)N1)C(C)C)CCCCN)Cc2cc3c2cccc3)Cc4ccc(cc4)O)NC(=O)(Cc5ccc6ccccc6c5)N)O
| molecular_weight = 1096.33 g/mol<br>1156.380 g/mol (acetate)
⚫ | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| smiles = O=C(N)C(NC(=O)C3NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(N)Cc2cc1ccccc1cc2)CSSC3)Cc4ccc(O)cc4)Cc6c5ccccc5nc6)CCCCN)C(C)C)C(O)C
⚫ | 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
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫ | 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)
⚫ | StdInChIKey = PUDHBTGHUJUUFI-SCTWWAJVSA-N
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = PUDHBTGHUJUUFI-UHFFFAOYSA-N
}} }}
'''Lanreotide''' (]) is a medication used in the management of ] and symptoms caused by ], most notably ]. It is a long-acting ] of ], like ]. '''Lanreotide''', sold under the brand name '''Somatuline''' among others, is a ] used in the management of ] and symptoms caused by ]s, most notably ]. It is a long-acting ] of ], like ].


Lanreotide (as lanreotide ]) is manufactured by ], and marketed under the trade name '''Somatuline'''. It is available in several countries, including the ], ] and ], and was approved for sale in the ] by the ] (FDA) on August 30, 2007.<ref>{{cite press release | url = http://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. ]}}</ref> Lanreotide (as lanreotide ]) is manufactured by ]. It is available in several countries, including the United Kingdom, Australia and Canada, and was approved for sale in the United States by the ] (FDA) on August 30, 2007.<ref>{{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. ] | 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 }}</ref>


==Pharmacology== ==Medical uses==
⚫ Lanreotide is used in the treatment of ], due to both ] and non-pituitary growth hormone-secreting tumors, and the management of symptoms caused by ]s, particularly ]s and ]s. 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 ] ],<ref name="eMC_LA">{{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 }}</ref> a rare tumor of the pituitary gland which secretes TSH.
⚫ Lanreotide is a synthetic analogue of ], a naturally occurring inhibitory ] which blocks the release of several other hormones, including ], ] (TSH), ] and ]. Lanreotide binds to the same ]s 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),<ref>{{cite journal |author=Rens-Domiano S, Reisine T |title=Biochemical and functional properties of somatostatin receptors |journal=J Neurochem |volume=58 |issue=6 |pages=1987&ndash;96 |year=1992 |pmid=1315373 |doi=10.1111/j.1471-4159.1992.tb10938.x}}</ref> lanreotide has a much longer half-life, and produces far more prolonged effects.


⚫ Lanreotide also shows activity against non-endocrine tumors, and, along with other ]s, is being studied as a possible general antitumor agent.<ref>{{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&ndash;8 |year=2006 |pmid=16917205 |doi=10.1097/01.cad.0000210335.95828.ed}}</ref><ref>{{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&ndash;42 |year=2006 |pmid=16801334 |doi=10.1093/annonc/mdl105|doi-access=free }}</ref>
The efficacy of lanreotide has not been extensively studied, and results differ greatly between trials and formulations.


In December 2014, the US FDA approved lanreotide for the treatment of people with unresectable, well or moderately differentiated, locally advanced or metastatic gastroenteropancreatic ]s (]s).<ref>{{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 }}</ref>
==Indications==
⚫ Lanreotide is used in the treatment of ], due to both ] and non-pituitary growth hormone-secreting tumors, and the management of symptoms caused by ], particularly ]s and ]s. 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 ] ],<ref name="eMC_LA">{{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}}</ref> a rare tumor of the pituitary gland which secretes TSH.


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}}
⚫ Interestingly, lanreotide also shows activity against non-endocrine tumors, and, along with other somatostatin analogues, is being studied as a possible general antitumor agent.<ref>{{cite journal |author=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&ndash;8 |year=2006 |pmid=16917205 |doi=10.1097/01.cad.0000210335.95828.ed}}</ref><ref>{{cite journal |author=Susini C, Buscail L |title=Rationale for the use of somatostatin analogs as antitumor agents |journal=Ann Oncol |volume=17 |issue=12 |pages=1733&ndash;42 |year=2006 |pmid=16801334 |doi=10.1093/annonc/mdl105}}</ref>


==Side effects== ==Side effects==
The main ]s of lanreotide treatment are mild to moderate pain at the injection site and ] disturbances, such as ], ] and ]. Isolated cases of ] have been associated with use of lanreotide, particularly over long periods of time.<ref name="BIAM"/><ref name="eMC_LA"/> The main ]s of lanreotide treatment are mild to moderate pain at the injection site and ] disturbances, such as ], ] and ]. Isolated cases of ] have been associated with use of lanreotide, particularly over long periods of time.<ref name="eMC_LA"/>


==Formulations== ==Pharmacology==
⚫ Lanreotide is a synthetic analogue of ], a naturally occurring inhibitory ] which blocks the release of several other hormones, including ], ] (TSH), ] and ]. Lanreotide binds to the same ]s 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),<ref>{{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&ndash;96 |year=1992 |pmid=1315373 |doi=10.1111/j.1471-4159.1992.tb10938.x|s2cid=36873846 }}</ref> lanreotide has a much longer half-life, and produces far more prolonged effects.{{medcn|date=October 2022}}
⚫ Lanreotide is available in two formulations: a sustained release formulation (sold under the trade name '''Somatuline LA'''), which is ] every ten or fourteen days,<ref name="eMC_LA"/> and an extended release formulation (UK trade name '''Somatuline Autogel''', or '''Somatuline Depot''' in the U.S.), which is administered subcutaneously once a month.<ref>{{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}}</ref>


==References== ==Formulations==
⚫ Lanreotide is available in two formulations: a sustained release formulation (sold under the trade name 'Somatuline LA'), which is ] every ten or fourteen days,<ref name="eMC_LA"/> and an extended release formulation (UK trade name 'Somatuline Autogel', or 'Somatuline ]' in the US), which is administered subcutaneously once a month.<ref>{{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 }}</ref>
{{Reflist}}


==Self-assembling properties==
== External links ==
Lanreotide has been shown to spontaneously self-assemble into monodisperse nanotubes of 24.4&nbsp;nm diameter<ref>{{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&ndash;62 |year=2003 |pmid= 12930900|doi=10.1073/pnas.1730609100 |pmc=193548|bibcode=2003PNAS..10010258V |doi-access=free }}</ref> and has been thereafter used as a fruitful and versatile model system in several biophysical studies.{{cn|date=October 2022}}
*
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* Somatuline Package insert available in PDF format.
*


== References ==
{{reflist}}


{{GH/IGF-1 axis signaling modulators}}
{{Pituitary and hypothalamic hormones and analogues}}
{{Portal bar | Medicine}}
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