Lanreotide

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MedKoo CAT#: 597968

CAS#: 108736-35-2 (free base)

Description: Lanreotide is a somatostatin analogue that suppresses GH/IGF-I hypersecretion in acromegaly patients and used to manage neuroendocrine tumours.


Price and Availability

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Pricing updated 2020-08-10. Prices are subject to change without notice.

Lanreotide is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 597968
Name: Lanreotide
CAS#: 108736-35-2 (free base)
Chemical Formula: C54H69N11O10S2
Exact Mass: 1095.467
Molecular Weight: 1096.33
Elemental Analysis: C, 59.16; H, 6.34; N, 14.05; O, 14.59; S, 5.85


Related CAS #: 108736-35-2 (free base)   127984-74-1 (acetate)    

Synonym: Somatuline; Lanreotide; Ipstyl; BIM 23014; Somatulin; Lanreotide Autogel.

IUPAC/Chemical Name: (4R,7S,10S,13R,16S,19R)-13-((1H-indol-3-yl)methyl)-19-((R)-2-amino-3-(naphthalen-2-yl)propanamido)-N-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)-10-(4-aminobutyl)-16-(4-hydroxybenzyl)-7-isopropyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide

InChi Key: PUDHBTGHUJUUFI-SCTWWAJVSA-N

InChi Code: 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

SMILES Code: CC([C@@H]1NC([C@@H](NC([C@H](NC([C@@H](NC([C@@H](NC([C@@H](Cc(cc2)cc3c2cccc3)N)=O)CSSC[C@@H](C(N[C@H](C(N)=O)[C@H](O)C)=O)NC1=O)=O)Cc4ccc(O)cc4)=O)Cc(c[nH]5)c6c5cccc6)=O)CCCCN)=O)C


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.03.00


References

1: Caplin ME, Pavel M, Ćwikła JB, Phan AT, Raderer M, Sedláčková E, Cadiot G, Wolin EM, Capdevila J, Wall L, Rindi G, Langley A, Martinez S, Blumberg J, Ruszniewski P; CLARINET Investigators. Lanreotide in metastatic enteropancreatic neuroendocrine tumors. N Engl J Med. 2014 Jul 17;371(3):224-33. doi: 10.1056/NEJMoa1316158. PubMed PMID: 25014687.

2: Burness CB, Dhillon S, Keam SJ. Lanreotide autogel(®): a review of its use in the treatment of patients with acromegaly. Drugs. 2014 Sep;74(14):1673-91. doi: 10.1007/s40265-014-0283-8. Review. PubMed PMID: 25193626.

3: Capdevila J, Sevilla I, Alonso V, Antón Aparicio L, Jiménez Fonseca P, Grande E, Reina JJ, Manzano JL, Alonso Lájara JD, Barriuso J, Castellano D, Medina J, López C, Segura Á, Carrera S, Crespo G, Fuster J, Munarriz J, García Alfonso P. Evaluation of the efficacy and safety of lanreotide in combination with targeted therapies in patients with neuroendocrine tumours in clinical practice: a retrospective cross-sectional analysis. BMC Cancer. 2015 Jul 4;15:495. doi: 10.1186/s12885-015-1512-6. PubMed PMID: 26138480; PubMed Central PMCID: PMC4490650.

4: Zheng N, Dai W, Zhang H, Wang X, Wang J, Zhang X, Wang K, Li J, Zhang Q. Lanreotide-conjugated PEG-DSPE micelles: an efficient nanocarrier targeting to somatostatin receptor positive tumors. J Drug Target. 2015 Jan;23(1):67-78. doi: 10.3109/1061186X.2014.954118. Epub 2014 Nov 4. PubMed PMID: 25366085.

5: Gadelha MR, Bronstein MD, Brue T, Coculescu M, Fleseriu M, Guitelman M, Pronin V, Raverot G, Shimon I, Lievre KK, Fleck J, Aout M, Pedroncelli AM, Colao A; Pasireotide C2402 Study Group. Pasireotide versus continued treatment with octreotide or lanreotide in patients with inadequately controlled acromegaly (PAOLA): a randomised, phase 3 trial. Lancet Diabetes Endocrinol. 2014 Nov;2(11):875-84. doi: 10.1016/S2213-8587(14)70169-X. Epub 2014 Sep 24. PubMed PMID: 25260838.

6: Gevers TJ, Hol JC, Monshouwer R, Dekker HM, Wetzels JF, Drenth JP. Effect of lanreotide on polycystic liver and kidneys in autosomal dominant polycystic kidney disease: an observational trial. Liver Int. 2015 May;35(5):1607-14. doi: 10.1111/liv.12726. Epub 2014 Dec 1. PubMed PMID: 25369108.

7: Temmerman F, Ho TA, Vanslembrouck R, Coudyzer W, Billen J, Dobbels F, van Pelt J, Bammens B, Pirson Y, Nevens F. Lanreotide Reduces Liver Volume, But Might Not Improve Muscle Wasting or Weight Loss, in Patients With Symptomatic Polycystic Liver Disease. Clin Gastroenterol Hepatol. 2015 Dec;13(13):2353-9.e1. doi: 10.1016/j.cgh.2015.05.039. Epub 2015 Jun 12. PubMed PMID: 26073493.

8: Sagvand BT, Khairi S, Haghshenas A, Swearingen B, Tritos NA, Miller KK, Klibanski A, Nachtigall LB. Monotherapy with lanreotide depot for acromegaly: long-term clinical experience in a pituitary center. Pituitary. 2016 Aug;19(4):437-47. doi: 10.1007/s11102-016-0724-3. PubMed PMID: 27155600.

9: Wolin EM, Manon A, Chassaing C, Lewis A, Bertocchi L, Richard J, Phan AT. Lanreotide Depot: An Antineoplastic Treatment of Carcinoid or Neuroendocrine Tumors. J Gastrointest Cancer. 2016 Dec;47(4):366-374. Review. PubMed PMID: 27619395; PubMed Central PMCID: PMC5138269.

10: Hernández B, Coïc YM, Baron B, Kruglik SG, Pflüger F, Cohen R, Carelli C, Ghomi M. Low concentration structural dynamics of lanreotide and somatostatin-14. Biopolymers. 2014 Oct;101(10):1019-28. doi: 10.1002/bip.22491. PubMed PMID: 24729416.

11: Ryan P, Phan AT, Adelman DT, Iwasaki M. Neuroendocrine Tumors and Lanreotide Depot: Clinical Considerations and Nurse and Patient Preferences. Clin J Oncol Nurs. 2016 Dec 1;20(6):E139-E146. Review. PubMed PMID: 27857269.

12: Neggers SJ, Pronin V, Balcere I, Lee MK, Rozhinskaya L, Bronstein MD, Gadelha MR, Maisonobe P, Sert C, van der Lely AJ; LEAD Study Group. Lanreotide Autogel 120 mg at extended dosing intervals in patients with acromegaly biochemically controlled with octreotide LAR: the LEAD study. Eur J Endocrinol. 2015 Sep;173(3):313-23. doi: 10.1530/EJE-15-0215. Epub 2015 Jun 5. PubMed PMID: 26047625; PubMed Central PMCID: PMC4544680.

13: Witek P, Mucha S, Ruchała M. Patient satisfaction and preferences of lanreotide Autogel treatment in acromegaly. Endokrynol Pol. 2016;67(6):572-579. doi: 10.5603/EP.2016.0066. PubMed PMID: 28042650.

14: Shah P, Rahman SA, McElroy S, Gilbert C, Morgan K, Hinchey L, Senniappan S, Levy H, Amin R, Hussain K. Use of Long-Acting Somatostatin Analogue (Lanreotide) in an Adolescent with Diazoxide-Responsive Congenital Hyperinsulinism and Its Psychological Impact. Horm Res Paediatr. 2015;84(5):355-60. doi: 10.1159/000439131. Epub 2015 Sep 17. PubMed PMID: 26375451.

15: Puig-Domingo M, Soto A, Venegas E, Vilchez R, Blanco C, Cordido F, Lucas T, Marazuela M, Casany R, Cuatrecasas G, Fajardo C, Gálvez MÁ, Maraver S, Martín T, Romero E, Paja M, Picó A, Bernabeu I, Resmini E; ACROCOMB study group. Use of lanreotide in combination with cabergoline or pegvisomant in patients with acromegaly in the clinical practice: The ACROCOMB study. Endocrinol Nutr. 2016 Oct;63(8):397-408. doi: 10.1016/j.endonu.2016.05.010. Epub 2016 Jul 20. English, Spanish. PubMed PMID: 27448708.

16: Caplin ME, Pavel M, Ćwikła JB, Phan AT, Raderer M, Sedláčková E, Cadiot G, Wolin EM, Capdevila J, Wall L, Rindi G, Langley A, Martinez S, Gomez-Panzani E, Ruszniewski P; CLARINET Investigators. Anti-tumour effects of lanreotide for pancreatic and intestinal neuroendocrine tumours: the CLARINET open-label extension study. Endocr Relat Cancer. 2016 Mar;23(3):191-9. doi: 10.1530/ERC-15-0490. Epub 2016 Jan 7. PubMed PMID: 26743120; PubMed Central PMCID: PMC4740728.

17: Caron PJ, Bevan JS, Petersenn S, Flanagan D, Tabarin A, Prévost G, Maisonobe P, Clermont A; PRIMARYS Investigators. Tumor shrinkage with lanreotide Autogel 120 mg as primary therapy in acromegaly: results of a prospective multicenter clinical trial. J Clin Endocrinol Metab. 2014 Apr;99(4):1282-90. doi: 10.1210/jc.2013-3318. Epub 2013 Jan 1. PubMed PMID: 24423301; PubMed Central PMCID: PMC4009579.

18: 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. Review. PubMed PMID: 25307803.

19: Sun L, Yu CY, Mackey LV, Coy DH. Lanreotide and its Potential Applications in Polycystic Kidney and Liver Diseases. Curr Top Med Chem. 2015;16(2):133-40. Review. PubMed PMID: 26126910.

20: Vinik AI, Wolin EM, Liyanage N, Gomez-Panzani E, Fisher GA; ELECT Study Group *. EVALUATION OF LANREOTIDE DEPOT/AUTOGEL EFFICACY AND SAFETY AS A CARCINOID SYNDROME TREATMENT (ELECT): A RANDOMIZED, DOUBLE-BLIND, PLACEBO-CONTROLLED TRIAL. Endocr Pract. 2016 Sep;22(9):1068-80. doi: 10.4158/EP151172.OR. Epub 2016 May 23. PubMed PMID: 27214300.