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SML0132

Sigma-Aldrich

Lanreotide acetate

≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C54H69N11O10S2 · xC2H4O2
CAS Number:
127984-74-1
Molecular Weight:
1096.32 (free base basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329825182
NACRES:
NA.25

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to off-white

shipped in

wet ice

storage temp.

−20°C

SMILES string

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

InChI key

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.

Biochem/physiol Actions

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.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361

Precautionary Statements

P281

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
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
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
Shaun Coughlin et al.
World journal of surgery, 36(5), 1016-1029 (2012-03-16)
Enterocutaneous fistulas are abnormal connections between the skin and gastrointestinal tract that most commonly occur after surgery. Somatostatin analogues have been used in their treatment. The objective of the present study was to determine if somatostatin analogues shorten the time
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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