Lanreotide acetate
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MedKoo CAT#: 100488

CAS#: 127984-74-1 (acetate)

Description: Lanreotide is a a synthetic cyclic octapeptide analogue of somatostatin. Lanreotide inhibits the secretion of growth hormone (GH) by binding to pituitary somatostatin receptors, and may inhibit the release of various other hormones, including thyroid stimulating hormone (TSH) and the gastroenteropancreatic hormones insulin, glucagon and gastrin. This agent also decreases circulating total and free insulin-like growth factor 1 (IGF-I). Lanreotide exhibits a high binding affinity for somatostatin receptor 2 (SSTR-2) and a lesser binding affinity for SSTR-5. However, compared to octreotide, this agent is less potent in inhibiting the release of growth hormone from the pituitary gland. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)


Chemical Structure

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Lanreotide acetate
CAS# 127984-74-1 (acetate)

Theoretical Analysis

MedKoo Cat#: 100488
Name: Lanreotide acetate
CAS#: 127984-74-1 (acetate)
Chemical Formula: C54H69N11O10S2
Exact Mass: 1095.46703
Molecular Weight: 1096.32
Elemental Analysis: C, 59.16; H, 6.34; N, 14.05; O, 14.59; S, 5.85 Lanreotide acetate

Price and Availability

Size Price Availability Quantity
5.0mg USD 250.0 2 Weeks
25.0mg USD 640.0 2 Weeks
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Related CAS #: 108736-35-2 (free base)   127984-74-1 (acetate)    

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

IUPAC/Chemical Name: (4S,7S,10S,13R,16S,19S)-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 acetate

InChi Key: LKOFLENOEWIRAG-NSBHJRQQSA-N

InChi Code: InChI=1S/C56H71N11O11S2/c1-30(2)47-56(77)65-46(55(76)67-48(31(3)68)49(59)70)29-80-79-28-45(64-50(71)40(58)24-34-16-19-35-11-5-6-12-36(35)23-34)54(75)62-43(25-33-17-20-38(21-18-33)78-32(4)69)52(73)63-44(26-37-27-60-41-14-8-7-13-39(37)41)53(74)61-42(51(72)66-47)15-9-10-22-57/h5-8,11-14,16-21,23,27,30-31,40,42-48,60,68H,9-10,15,22,24-26,28-29,57-58H2,1-4H3,(H2,59,70)(H,61,74)(H,62,75)(H,63,73)(H,64,71)(H,65,77)(H,66,72)(H,67,76)/t31-,40-,42+,43+,44-,45-,46-,47+,48+/m1/s1

SMILES Code: O=C([C@H](NC([C@H](C(C)C)NC([C@H](CCCCN)NC([C@@H](CC1=CNC2=C1C=CC=C2)NC([C@H](CC3=CC=C(OC(C)=O)C=C3)N4)=O)=O)=O)=O)CSSC[C@@H](NC([C@H](N)CC5=CC=C6C=CC=CC6=C5)=O)C4=O)N[C@@H]([C@H](O)C)C(N)=O

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, not in water

Shelf Life: >2 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: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 1096.32 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

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Additional Information

Lanreotide (INN) is a medication used in the management of acromegaly and symptoms caused by neuroendocrine tumors, most notably carcinoid syndrome. It is a long-acting analogue of somatostatin, like octreotide. Lanreotide (as lanreotide acetate) is manufactured by Ipsen, and marketed under the trade name Somatuline. It is available in several countries, including the United Kingdom, Australia and Canada, and was approved for sale in the United States by the Food and Drug Administration (FDA) on August 30, 2007.
 
Lanreotide is available in two formulations: a sustained release formulation (sold under the trade name Somatuline LA), which is injected intramuscularly every ten or fourteen days,[4] and an extended release formulation (UK trade name Somatuline Autogel, or Somatuline Depot in the U.S.), which is administered subcutaneously once a month.
 
Lanreotide is used in the treatment of acromegaly, due to both pituitary and non-pituitary growth hormone-secreting tumors, and the management of symptoms caused by neuroendocrine tumors, particularly carcinoid tumors and VIPomas. In the United States and Canada, lanreotide is only indicated for the treatment of acromegaly. In the United Kingdom, it is also indicated in the treatment of thyrotrophic adenoma, a rare tumor of the pituitary gland which secretes TSH. Interestingly, lanreotide also shows activity against non-endocrine tumors, and, along with other somatostatin analogues, is being studied as a possible general antitumor agent.