Lanreotide

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
Thumb
Weight
Average: 1096.33
Monoisotopic: 1095.467029814
Chemical Formula
C54H69N11O10S2
Synonyms
  • Lanreotida
  • Lanreotide
External IDs
  • BIM-23014C

Pharmacology

Indication

Lanreotide is a somatostatin analog approved for treatment of neuroendocrine tumours and acromegaly.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

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.

TargetActionsOrganism
USomatostatin receptor type 2
agonist
Humans
USomatostatin receptor type 5
agonist
Humans
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
Adverseeffects
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Toxicity

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
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Lanreotide.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Lanreotide.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Lanreotide.
AcebutololAcebutolol may increase the bradycardic activities of Lanreotide.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Lanreotide.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Lanreotide.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Lanreotide.
AlbiglutideThe therapeutic efficacy of Albiglutide can be decreased when used in combination with Lanreotide.
AlectinibThe metabolism of Alectinib can be decreased when combined with Lanreotide.
AlfentanilAlfentanil may increase the bradycardic activities of Lanreotide.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Lanreotide acetateIEU56G3J9CNot AvailableNot applicable
International/Other Brands
Somatuline (Ipsen)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Somatuline AutogelSolution, gel forming, extended release120 mg / syrSubcutaneousIpsen Biopharmaceuticals Canada Inc2007-02-22Not applicableCanada flag
Somatuline AutogelSolution, gel forming, extended release90 mg / syrSubcutaneousIpsen Biopharmaceuticals Canada Inc2007-02-22Not applicableCanada flag
Somatuline AutogelSolution, gel forming, extended release60 mg / syrSubcutaneousIpsen Biopharmaceuticals Canada Inc2007-02-22Not applicableCanada flag
Somatuline DepotInjection60 mg/0.2mLSubcutaneousIpsen Biopharmaceuticals, Inc.2007-11-142016-08-31US flag
Somatuline DepotInjection120 mg/0.5mLSubcutaneousIpsen Biopharmaceuticals, Inc.2007-11-14Not applicableUS flag
Somatuline DepotInjection120 mg/0.5mLSubcutaneousIpsen Biopharmaceuticals, Inc.2007-11-142016-08-31US flag
Somatuline DepotInjection90 mg/0.3mLSubcutaneousIpsen Biopharmaceuticals, Inc.2007-11-14Not applicableUS flag
Somatuline DepotInjection90 mg/0.3mLSubcutaneousIpsen Biopharmaceuticals, Inc.2007-11-142016-08-31US flag
Somatuline DepotInjection60 mg/0.2mLSubcutaneousIpsen Biopharmaceuticals, Inc.2007-11-14Not applicableUS flag

Categories

ATC Codes
H01CB03 — Lanreotide
Drug Categories
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
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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
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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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
KEGG Drug
D04666
PubChem Compound
71349
PubChem Substance
310264887
ChemSpider
64450
RxNav
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
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentNeuroendocrine Tumours (NETs)1
4CompletedDiagnosticNeuroendocrine Tumours (NETs)1
4CompletedTreatmentAcromegaly5
4CompletedTreatmentNeuroendocrine Tumour With Carcinoid Symptoms1
4RecruitingTreatmentNeuroendocrine Tumours (NETs)1
4TerminatedTreatmentAcromegaly1
4Unknown StatusTreatmentCongenital Hyperinsulinism (CHI)1
4Unknown StatusTreatmentDumping Syndrome1
3Active Not RecruitingTreatmentAcromegaly1
3CompletedPreventionLymphoceles1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, for suspension, extended releaseIntramuscular30 mg/2mL
Injection, solutionIntramuscular60 mg
Injection, solutionIntramuscular90 mg
Injection, suspension, extended releaseIntramuscular120 mg
Injection, suspension, extended releaseIntramuscular60 mg
Injection, powder, for suspensionIntramuscular
PowderNot applicable1 g/1g
SolutionSubcutaneous60 mg
Injection, solution24.6 mg/100mg
Solution, gel forming, extended releaseSubcutaneous120 mg / syr
Solution, gel forming, extended releaseSubcutaneous60 mg / syr
Solution, gel forming, extended releaseSubcutaneous90 mg / syr
Injection, solutionParenteral
InjectionSubcutaneous
SolutionSubcutaneous
Injection, solutionSubcutaneous120 mg
Injection, solutionSubcutaneous60 mg
Injection, solutionSubcutaneous90 mg
InjectionSubcutaneous120 mg/0.5mL
InjectionSubcutaneous60 mg/0.2mL
InjectionSubcutaneous90 mg/0.3mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5595760No1997-01-212020-03-08US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00496 mg/mLALOGPS
logP1.87ALOGPS
logP-0.33ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)9.43ChemAxon
pKa (Strongest Basic)10.26ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area355.08 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity292.92 m3·mol-1ChemAxon
Polarizability114.68 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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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
  1. 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
  1. 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 on September 14, 2010 16:21 / Updated on October 24, 2021 16:00