Identification
- Summary
Lanreotide is a somatostatin analog used for the treatment of unresectable, well- or moderately-differentiated, locally advanced or metastatic gastroenteropancreatic neuroendocrine tumors and acromegaly.
- Brand Names
- Somatuline
- Generic Name
- Lanreotide
- DrugBank Accession Number
- DB06791
- Background
Lanreotide is a drug employed in the management of acromegaly (a hormonal condition caused by excess growth hormone) in addition to symptoms caused by neuroendocrine tumors, especially carcinoid syndrome. This drug is a long-acting analog of the drug somatostatin, a growth hormone inhibitor. Lanreotide is manufactured by the company, Ipsen Pharmaceuticals as lanreotide acetate, and marketed as Somatuline. It is approved in several countries worldwide, including the United Kingdom, Australia, and Canada. Lanreotide was first approved for use in the United States by the FDA on August 30, 2007.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Lanreotide (DB06791)
- Weight
- Average: 1096.33
Monoisotopic: 1095.467029814 - Chemical Formula
- C54H69N11O10S2
- Synonyms
- Lanreotida
- Lanreotide
- External IDs
- BIM-23014C
Pharmacology
- Indication
Lanreotide is indicated for the long-term treatment of patients with acromegaly who have had an inadequate response to, or cannot be treated with, surgery and/or radiotherapy.5 It is also indicated in the treatment of adult patients with unresectable, well- or moderately-differentiated, locally advanced or metastatic gastroenteropancreatic neuroendocrine tumors (GEP-NETs) to improve progression-free survival.5
Lanreotide is additionally indicated for the treatment of adults with carcinoid syndrome - when used, it reduces the frequency of short-acting somatostatin analog rescue therapy.5
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Acromegaly •••••••••••• •••••••••• •••••••• •• ••••• ••••••••• ••••••••• Treatment of Carcinoid syndrome •••••••••••• ••••• ••••••••• Management of Unresectable, locally advanced enteropancreatic neuroendocrine tumors •••••••••••• Treatment of Unresectable, locally advanced well- or moderately-differentiated gastroenteropancreatic neuroendocrine tumors •••••••••••• ••••• ••••••••• Management of Unresectable, metastatic enteropancreatic neuroendocrine tumors •••••••••••• - Contraindications & Blackbox Warnings
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Lanreotide exhibits antisecretory effects through cAMP suppression, and activation of ion currents such as K+ and Ca2+ which leads to hyperpolarization of the membrane and inhibition of Ca2+ mediated depolarization. Furthermore, through direct and indirect mechanisms, Lanreotide has potent antiproliferative effects.
- Mechanism of action
Lanreotide is a somatostatin analogue (SSA) and has mainly inhibitory effects which are mediated via somatostatin receptors (SSTRs) 2 and 5 and include inhibition of growth hormone release in the brain. Tumor SSTR activation induces downstream cell cycle arrest and/or apoptosis, and also results in blunted production of substances that support tumor growth as well as tumor angiogenesis. This leads to the anti-proliferative effects of Lanreotide.
Target Actions Organism USomatostatin receptor type 2 agonistHumans USomatostatin receptor type 5 agonistHumans - Absorption
Lanreotide forms a drug depot at the site of injection; therefore, there are 2 phases that describe the absorption of Lanreotide: 1. Initial rapid subcutaneous release during the first few days of treatment where drug that has not precipitated is rapidly absorbed.
2. Slow release of drug from the depot via passive diffusion. Absorption is independent of body weight, gender, and dosage.- Volume of distribution
Estimated Volume of Distribution = 15.1 L
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
<5% of lanreotide is excreted in urine, and less than 0.5% is excreted unchanged in the feces suggesting biliary excretion involvement.
- Half-life
Half-life is approximately 22 days
- Clearance
Estimated Clearance = 23.1 L/h
- Adverse Effects
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The most common adverse events are GI related, occurring in 67-84% of patients, and are typically mild to moderate. GI related effects are often transient, improve with subsequent injections, and most frequently include diarrhea and abdominal pain. Other GI symptoms such as nausea, vomiting, and abdominal distension are less common. It is not clear whether or not GI effects are dose related. Adverse effects relating to site of injection occur in 43% of patients and are more common in patients who self-inject as opposed to those who had health-care professionals administer the injection. A small number of patients report newly impaired glucose tolerance, fasting glucose or diabetes mellitus. Patients being treated for diabetes mellitus may experience hypoglycemia. After 1 year, up to 30% of patients may experience gallstone formation and the presence of sludge within the gallbladder due to inhibition of gallbladder and GI motility. This may be influenced by previous exposure to somatostatin analogues. Other adverse effects include reduction in left ventricular end-diastolic and end-systolic volumes, bradycardia, nasopharyngitis, and alopecia. Lanreotide is classified as Pregnancy Category C.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The metabolism of Abemaciclib can be decreased when combined with Lanreotide. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Lanreotide. Acarbose The therapeutic efficacy of Acarbose can be decreased when used in combination with Lanreotide. Acebutolol Acebutolol may increase the bradycardic activities of Lanreotide. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Lanreotide. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Lanreotide acetate IEU56G3J9C Not Available Not applicable - International/Other Brands
- Somatuline (Ipsen)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Lanreotide Acetate Injection 90 mg/0.3mL Subcutaneous Exelan Pharmaceuticals, Inc. 2022-06-01 Not applicable US 
Lanreotide Acetate Injection 90 mg/0.3mL Subcutaneous Cipla USA Inc. 2021-12-24 Not applicable US Lanreotide Acetate Injection 60 mg/0.2mL Subcutaneous Exelan Pharmaceuticals, Inc. 2022-06-01 Not applicable US Lanreotide Acetate Injection 60 mg/0.2mL Subcutaneous Cipla USA Inc. 2021-12-24 Not applicable US Lanreotide Acetate Injection 120 mg/0.5mL Subcutaneous Exelan Pharmaceuticals, Inc. 2022-06-01 Not applicable US
Categories
- ATC Codes
- H01CB03 — Lanreotide
- Drug Categories
- Acromegaly
- Amino Acids, Peptides, and Proteins
- Antineoplastic Agents
- Bradycardia-Causing Agents
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 Enzyme Inhibitors
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hyperglycemia-Associated Agents
- Hypoglycemia-Associated Agents
- Hypothalamic Hormones
- Nerve Tissue Proteins
- Neuropeptides
- Other Miscellaneous Therapeutic Agents
- Pancreatic Hormones
- Peptide Hormones
- Peptides
- Pituitary and Hypothalamic Hormones and Analogues
- Pituitary Hormone Release Inhibiting Hormones
- Proteins
- Somatostatin and Analogues
- Somatostatin Receptor Agonists
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Oligopeptides
- Alternative Parents
- Cyclic peptides / N-acyl-alpha amino acids and derivatives / Macrolactams / Alpha amino acid amides / 3-alkylindoles / Naphthalenes / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / Substituted pyrroles / Benzene and substituted derivatives show 13 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 3-alkylindole / Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound show 33 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 0G3DE8943Y
- CAS number
- 108736-35-2
- InChI Key
- PUDHBTGHUJUUFI-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 2-({19-[2-amino-3-(naphthalen-2-yl)propanamido]-10-(4-aminobutyl)-16-[(4-hydroxyphenyl)methyl]-13-[(1H-indol-3-yl)methyl]-6,9,12,15,18-pentaoxo-7-(propan-2-yl)-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl}formamido)-3-hydroxybutanamide
- SMILES
- [H]N([H])CCCCC1N([H])C(=O)C(CC2=CN([H])C3=CC=CC=C23)N([H])C(=O)C(CC2=CC=C(O)C=C2)N([H])C(=O)C(CSSCC(N([H])C(=O)C(N([H])C1=O)C(C)C)C(=O)N([H])C(C(C)O)C(=O)N([H])[H])N([H])C(=O)C(CC1=CC2=CC=CC=C2C=C1)N([H])[H]
References
- General References
- Troconiz IF, Cendros JM, Peraire C, Ramis J, Garrido MJ, Boscani PF, Obach R: Population pharmacokinetic analysis of lanreotide Autogel in healthy subjects : evidence for injection interval of up to 2 months. Clin Pharmacokinet. 2009;48(1):51-62. doi: 10.2165/0003088-200948010-00004. [Article]
- Giustina A, Mazziotti G, Maffezzoni F, Amoroso V, Berruti A: Investigational drugs targeting somatostatin receptors for treatment of acromegaly and neuroendocrine tumors. Expert Opin Investig Drugs. 2014 Dec;23(12):1619-35. doi: 10.1517/13543784.2014.942728. Epub 2014 Jul 25. [Article]
- Narayanan S, Kunz PL: Role of Somatostatin Analogues in the Treatment of Neuroendocrine Tumors. Hematol Oncol Clin North Am. 2016 Feb;30(1):163-77. doi: 10.1016/j.hoc.2015.09.008. [Article]
- Kyriakakis N, Chau V, Lynch J, Orme SM, Murray RD: Lanreotide autogel in acromegaly - a decade on. Expert Opin Pharmacother. 2014 Dec;15(18):2681-92. doi: 10.1517/14656566.2014.970173. Epub 2014 Oct 11. [Article]
- FDA Approved Drug Products: Somatuline Depot (lanreotide) for subcutaneous injection [Link]
- External Links
- KEGG Drug
- D04666
- PubChem Compound
- 71349
- PubChem Substance
- 310264887
- ChemSpider
- 64450
- 68092
- ChEMBL
- CHEMBL1201185
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Lanreotide
- FDA label
- Download (418 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Diagnostic Neuroendocrine Tumors 1 4 Completed Treatment Acromegaly 5 4 Completed Treatment Neuroendocrine Tumors 1 4 Completed Treatment Neuroendocrine Tumour (NET) With Carcinoid Syndrome 1 4 Recruiting Treatment Gastroenteropancreatic Neuroendocrine Tumors 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for suspension, extended release Intramuscular 30 mg/2mL Injection, solution Intramuscular 60 mg Injection, solution Intramuscular 90 mg Injection, suspension, extended release Intramuscular 120 mg Injection, suspension, extended release Intramuscular 60 mg Injection, powder, for suspension Intramuscular Powder Not applicable 1 g/1g Injection, solution 120 MG Injection, solution 60 MG Injection, solution 90 MG Solution Subcutaneous 60 mg Injection, solution 24.6 mg/100mg Solution Subcutaneous 60.000 mg Solution, gel forming, extended release Subcutaneous 120 mg / syr Solution, gel forming, extended release Subcutaneous 60 mg / syr Solution, gel forming, extended release Subcutaneous 90 mg / syr Injection, solution Parenteral Injection, solution Parenteral 120 mg Solution Subcutaneous Injection, solution Parenteral 60 mg Injection Subcutaneous 60 mg/0.5ml Injection, solution Parenteral 90 mg Injection Subcutaneous 90 mg/0.5ml Injection, solution Subcutaneous 120 mg Injection, solution Subcutaneous 60 mg Injection, solution Subcutaneous 90 mg Injection Subcutaneous 120 mg/0.5mL Injection Subcutaneous 60 mg/0.2mL Injection Subcutaneous 90 mg/0.3mL - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5595760 No 1997-01-21 2020-03-08 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00496 mg/mL ALOGPS logP 1.87 ALOGPS logP -0.33 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 9.43 Chemaxon pKa (Strongest Basic) 10.26 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 13 Chemaxon Polar Surface Area 355.08 Å2 Chemaxon Rotatable Bond Count 17 Chemaxon Refractivity 292.92 m3·mol-1 Chemaxon Polarizability 114.68 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 312.30148 predictedDeepCCS 1.0 (2019) [M+H]+ 313.9864 predictedDeepCCS 1.0 (2019) [M+Na]+ 320.14322 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Somatostatin receptor activity
- Specific Function
- Receptor for somatostatin-14 and -28. This receptor is coupled via pertussis toxin sensitive G proteins to inhibition of adenylyl cyclase. In addition it stimulates phosphotyrosine phosphatase and ...
- Gene Name
- SSTR2
- Uniprot ID
- P30874
- Uniprot Name
- Somatostatin receptor type 2
- Molecular Weight
- 41332.37 Da
References
- Buil-Bruna N, Garrido MJ, Dehez M, Manon A, Nguyen TX, Gomez-Panzani EL, Troconiz IF: Population Pharmacokinetic Analysis of Lanreotide Autogel((R))/Depot in the Treatment of Neuroendocrine Tumors: Pooled Analysis of Four Clinical Trials. Clin Pharmacokinet. 2016 Apr;55(4):461-73. doi: 10.1007/s40262-015-0329-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Somatostatin receptor activity
- Specific Function
- Receptor for somatostatin 28 and to a lesser extent for somatostatin-14. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase. Increases cell growth inhibition act...
- Gene Name
- SSTR5
- Uniprot ID
- P35346
- Uniprot Name
- Somatostatin receptor type 5
- Molecular Weight
- 39201.925 Da
References
- Buil-Bruna N, Garrido MJ, Dehez M, Manon A, Nguyen TX, Gomez-Panzani EL, Troconiz IF: Population Pharmacokinetic Analysis of Lanreotide Autogel((R))/Depot in the Treatment of Neuroendocrine Tumors: Pooled Analysis of Four Clinical Trials. Clin Pharmacokinet. 2016 Apr;55(4):461-73. doi: 10.1007/s40262-015-0329-4. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
Drug created at September 14, 2010 16:21 / Updated at February 02, 2024 22:52