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MedKoo Cat#: 597968 | Name: Lanreotide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Chemical Structure

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

Theoretical Analysis

MedKoo Cat#: 597968

Name: Lanreotide

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

Chemical Formula: C54H69N11O10S2

Exact Mass: 1095.4670

Molecular Weight: 1096.33

Elemental Analysis: C, 59.16; H, 6.34; N, 14.05; O, 14.59; S, 5.85

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,096.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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.

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