Lanreotide

DCTPepD ID  DCTPepD0005

Active Ingredients   Lanreotide

Description  A synthetic cyclic octapeptide analogue of somatostatin. Lanreotide binds to somatostatin receptors (SSTR), specifically SSTR-2 and also to SSTR-5 with a lesser affinity. However, compare with octreotide, this agent is less potent in inhibiting the release of growth hormone from the pituitary gland. Furthermore, lanreotide has an acute effect on decreasing circulating total and free insulin-like growth factor 1 (IGF-I). This agent is usually given as a prolonged-release microparticle or Autogel formulation for the treatment of acromegaly and to relieve the symptoms of neuroendocrine tumors.

Synonyms  Abarelix; Plenaxis; Angiopeptin; BIM-23014; DC 13116; Dermopeptin; Ipstyl; L-Threoninamide, 3-(2-naphthalenyl)-D-alanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-, cyclic (2-7)-disulfide; Nal-cyclo(cys-tyr-trp-lys-val-cys)-thr-NH2; Somatulina; Somatuline; Lanreotide

Disease  Gastroenteropancreatic neuroendocrine tumors, Acromegaly

Classification

  

Somatostatin and analogues Peptide and derivative Hormone and analogue

Structure Information


Molecular Formula  C54H69N11O10S2

Molecular Weight  1096.333

Active Sequence  XCYWKVCX

Sequence Length  8

Modification  X(1)=2Nal, X(8)=xiThr, N-terminal NH2

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  3-(2-naphthyl)-D-alanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-L-threoninamide (2->7)-disulfide

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)

InChI_Key PUDHBTGHUJUUFI-UHFFFAOYSA-N

SMILES  CC(C1NC(C(NC(C(NC(C(NC(C(CSSCC(NC1=O)C(NC(C(O)C)C(N)=O)=O)NC(C(CC2=CC=C3C=CC=CC3=C2)N)=O)=O)CC4=CC=C(C=C4)O)=O)CC5=CNC6=CC=CC=C56)=O)CCCCN)=O)C

External Codes


PubChem CID  6918011

DrugBank Accession Number  DB06791

NCI Thesaurus Code  C1523  

UNII  0G3DE8943Y   GSRS

CAS  108736-35-2



Drug approval


Drug 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. 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.
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.

Drug Name Strength Dosage Form/Route Company Marketing Status Drug ID Approval year
Somatuline Depot eq 60mg base/0.2ml; eq 90mg base/0.3ml; eq 120mg base/0.5ml Solution; Subcutaneous Ipsen Pharma Prescription NDA: 022074 2007
Somatuline Autogel 60 mg/syr Solution; Subcutaneous Ipsen Biopharm Limited Prescription DIN: 02283395 2007
Somatuline Autogel 90 mg/syr Solution; Subcutaneous Ipsen Biopharm Limited Prescription DIN: 02283409 2007
Somatuline Autogel 120 mg/syr Solution; Subcutaneous Ipsen Biopharm Limited Prescription DIN: 02283417 2007

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT03946527 Exploratory Phase II Study of LAnreotide in Metastatic Pheochromocytoma/PARAganglioma (LAMPARA) Paraganglioma; Pheochromocytoma Phase 2 Treatment
NCT04427787 A Phase II Trial Aiming to Assess the Safety and Activity of the Combination of Cabozantinib Plus Lanreotide in Gastroenteropancreatic (GEP) and Thoracic Neuroendocrine Tumor (NET): The LOLA Trial Metastatic Well Differentiated Neuroendocrine Neoplasm; Neuroendocrine Tumors Phase 2 Treatment
NCT02651987 Efficacy and Safety of Lanreotide Autogel® 120 mg Administered Every 14 Days in Well Differentiated, Metastatic or Locally Advanced, Unresectable Pancreatic or Midgut Neuroendocrine Tumours Having Progressed Radiologically While Previously Treated With Lanreotide Autogel® 120 mg Administered Every 28 Days Pancreatic Tumours; Midgut Neuroendocrine Tumours Phase 2 Treatment
NCT03043664 Phase Ib/II Study of Pembrolizumab With Lanreotide Depot for Gastroenteropancreatic Neuroendocrine Tumors Gastroenteropancreatic Neuroendocrine Tumors Phase 1/2 Treatment
NCT00842348 Open Label Extension Study of Lanreotide Autogel 120 mg in Patients With Non-functioning Entero-pancreatic Endocrine Tumour Non Functioning Entero-pancreatic Endocrine Tumour Phase 3 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





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