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SML0132

Sigma-Aldrich

Lanreotide acetate

≥98% (HPLC)

Synonyme(s) :

3-(2-Naphthalenyl)-D-alanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-L-threoninamide cyclic (2→7)-disulfide acetate, Angiopeptin acetate, BIM-23014C

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About This Item

Formule empirique (notation de Hill):
C54H69N11O10S2 · xC2H4O2
Numéro CAS:
127984-74-1
Poids moléculaire :
1096.32 (free base basis)
Code UNSPSC :
12352200
ID de substance PubChem :
329825182
Nomenclature NACRES :
NA.25

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to off-white

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

CC(O)=O.CC(C)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc4ccc(O)cc4)NC(=O)[C@H](CSSC[C@H](NC1=O)C(=O)N[C@@H]([C@@H](C)O)C(N)=O)NC(=O)[C@H](N)Cc5ccc6ccccc6c5

InChI

1S/C54H69N11O10S2.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t30-,38-,40+,41+,42-,43+,44?,45+,46+;/m1./s1

Clé InChI

DEXPIBGCLCPUHE-HPDHVNDUSA-N

Application

Lanreotide acetate has been used as an inhibitor to test the plasticity of hydrogen sulfide modulation by growth hormone/thyroid hormone signaling in wild-type mice.

Actions biochimiques/physiologiques

Lanreotide acetate is a somatostatin analog, a selective agonist for the SRIF-1 sst2 subtype of somatostatin receptor with a binding affinity of 0.8 nM for sst2 compared to 5.2 nM for sst5, 100 nM for sst3 and more than 1000 nM for the SRIF-2 subtypes, sst1 and sst4 receptors. It is used clinically in the management of acromegaly and symptoms caused by neuroendocrine tumors, and in recent studies can also inhibit tumor growth and has shown activity against non-endocrine tumors.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Warning

Mentions de danger

H361

Conseils de prudence

P281

Classification des risques

Repr. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Philippe J Caron et al.
The Journal of clinical endocrinology and metabolism, 99(4), 1282-1290 (2014-01-16)
Methodological shortcomings often compromise investigations into the effects of primary somatostatin-analog treatment on tumor size in acromegaly. There are also limited data for the long-acting lanreotide formulation. The aim of the study was to better characterize the effects of primary
Ivan Borbath et al.
Acta gastro-enterologica Belgica, 75(2), 270-273 (2012-08-09)
We describe the case of a 54 years old woman, with hepatitis B, in whom the diagnosis of a 6 cm hepatocellular carcinoma (HCC) in the left liver was made in 2001. Alpha-foeto-protein (AFP) was 63 ng/mL (NI < 10
Maxime Palazzo et al.
European journal of gastroenterology & hepatology, 25(2), 232-238 (2012-10-31)
An antiproliferative effect of somatostatin analogs was recently demonstrated. To identify factors associated with tumor control in a group of patients with well-differentiated malignant digestive neuroendocrine tumors treated with lanreotide. A retrospective study was conducted in 68 patients treated with
S L Gans et al.
The British journal of surgery, 99(6), 754-760 (2012-03-21)
Somatostatin analogues are used for the treatment of pancreatic fistula, with the aim of achieving fistula closure or reduction of output. MEDLINE, Embase and Cochrane databases were searched systematically for relevant articles followed by hand-searching of reference lists. Data on
Nan Zheng et al.
Molecular pharmaceutics, 9(5), 1175-1188 (2012-03-23)
Many tumor cells specifically overexpress somatostatin receptors, in particular, subtype 2 (SSTR2). Lanreotide, a somatostatin analogue with high affinity for SSTR2, can be exploited as a ligand for tumor targeted therapy. In this study, lanreotide was first conjugated to poly(ethylene
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