CAS 396091-73-9|pasireotide

Introduction：Basic information about CAS 396091-73-9|pasireotide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. pasireotide BiologicalActivity
3. Chemical & Physical Properties
4. Synonyms

Common Name	pasireotide
CAS Number	396091-73-9	Molecular Weight	1047.206
Density	1.4±0.1 g/cm3	Boiling Point	1351.4±65.0 °C at 760 mmHg
Molecular Formula	C₅₈H₆₆N₁₀O₉	Melting Point	/
MSDS	/	Flash Point	771.1±34.3 °C

Names

Name	pasireotide
Synonym	More Synonyms

pasireotide BiologicalActivity

Description	Pasireotide(SOM 230) is a stable cyclohexapeptide somatostatin mimic that exhibits unique high-affinity binding to human somatostatin receptors (subtypes sst1/2/3/4/5, pKi=8.2/9.0/9.1/<7.0/9.9 respectively).IC50 value: 8.2/9.0/9.1/<7.0/9.9(pKi, sst1/2/3/4/5) [1]in vitro: SOM230 showed a lower potency of GH release inhibition (IC(50), 0.5 nM), compared with OCT (IC(50), 0.02 nM) and SRIF-14 (IC(50), 0.02 nM). A positive correlation was found between sst(2) but not sst(5) mRNA levels in the adenoma cells and the inhibitory potency of OCT on GH release in vivo and in vitro, and the effects of SOM230 and SRIF-14 in vitro [2]. In cultures of human fetal pituitary cells, SOM230 inhibited GH secretion by 42 +/- 9% (P = 0.002) but had no effect on TSH release. SOM230 inhibited GH release from GH-secreting adenoma cultures by 34 +/- 8% (P = 0.002), PRL by 35 +/- 4% from PRL-secreting adenomas (P = 0.01), and alpha-subunit secretion from nonfunctioning pituitary adenomas by 46 +/- 18% (P = 0.34) [3].in vivo: On day 7, there was a decrease in serum insulin levels from 1.06 ± 0.28 μg/L to 0.37 ± 0.17 μg/L (P = .0128) and a significant increase in serum glucose from 4.2 ± 0.45 mmol/L to 7.12 ± 1.06 mmol/L (P = .0075) in the treatment group but no change in the control group [4]. In wild-type mice, both octreotide and pasireotide significantly attenuated knee joint swelling and histopathologic manifestations of arthritis to an extent comparable to that of dexamethasone. In SSTR2(-/-) mice, the antiinflammatory effects of both octreotide and pasireotide were completely abrogated [5].
Related Catalog	Signaling Pathways >>GPCR/G Protein >>Somatostatin ReceptorResearch Areas >>Endocrinology
References	[1]. Lewis I, et al. A novel somatostatin mimic with broad somatotropin release inhibitory factor receptor binding and superior therapeutic potential. J Med Chem. 2003 Jun 5;46(12):2334-44. [2]. Hofland LJ, et al. The novel somatostatin analog SOM230 is a potent inhibitor of hormone release by growth hormone- and prolactin-secreting pituitary adenomas in vitro. J Clin Endocrinol Metab. 2004 Apr;89(4):1577-85. [3]. Murray RD, et al. The novel somatostatin ligand (SOM230) regulates human and rat anterior pituitary hormone secretion. J Clin Endocrinol Metab. 2004 Jun;89(6):3027-32. [4]. Quinn TJ, et al. Pasireotide (SOM230) is effective for the treatment of pancreatic neuroendocrine tumors (PNETs) in a multiple endocrine neoplasia type 1 (MEN1) conditional knockout mouse model. Surgery. 2012 Dec;152(6):1068-77. [5]. Imhof AK, et al. Differential antiinflammatory and antinociceptive effects of the somatostatin analogs octreotide and pasireotide in a mouse model of immune-mediated arthritis. Arthritis Rheum. 2011 Aug;63(8):2352-62.

Description

Pasireotide(SOM 230) is a stable cyclohexapeptide somatostatin mimic that exhibits unique high-affinity binding to human somatostatin receptors (subtypes sst1/2/3/4/5, pKi=8.2/9.0/9.1/<7.0/9.9 respectively).IC50 value: 8.2/9.0/9.1/<7.0/9.9(pKi, sst1/2/3/4/5) [1]in vitro: SOM230 showed a lower potency of GH release inhibition (IC(50), 0.5 nM), compared with OCT (IC(50), 0.02 nM) and SRIF-14 (IC(50), 0.02 nM). A positive correlation was found between sst(2) but not sst(5) mRNA levels in the adenoma cells and the inhibitory potency of OCT on GH release in vivo and in vitro, and the effects of SOM230 and SRIF-14 in vitro [2]. In cultures of human fetal pituitary cells, SOM230 inhibited GH secretion by 42 +/- 9% (P = 0.002) but had no effect on TSH release. SOM230 inhibited GH release from GH-secreting adenoma cultures by 34 +/- 8% (P = 0.002), PRL by 35 +/- 4% from PRL-secreting adenomas (P = 0.01), and alpha-subunit secretion from nonfunctioning pituitary adenomas by 46 +/- 18% (P = 0.34) [3].in vivo: On day 7, there was a decrease in serum insulin levels from 1.06 ± 0.28 μg/L to 0.37 ± 0.17 μg/L (P = .0128) and a significant increase in serum glucose from 4.2 ± 0.45 mmol/L to 7.12 ± 1.06 mmol/L (P = .0075) in the treatment group but no change in the control group [4]. In wild-type mice, both octreotide and pasireotide significantly attenuated knee joint swelling and histopathologic manifestations of arthritis to an extent comparable to that of dexamethasone. In SSTR2(-/-) mice, the antiinflammatory effects of both octreotide and pasireotide were completely abrogated [5].

Related Catalog

Signaling Pathways >>GPCR/G Protein >>Somatostatin ReceptorResearch Areas >>Endocrinology

References

[1]. Lewis I, et al. A novel somatostatin mimic with broad somatotropin release inhibitory factor receptor binding and superior therapeutic potential. J Med Chem. 2003 Jun 5;46(12):2334-44.

[2]. Hofland LJ, et al. The novel somatostatin analog SOM230 is a potent inhibitor of hormone release by growth hormone- and prolactin-secreting pituitary adenomas in vitro. J Clin Endocrinol Metab. 2004 Apr;89(4):1577-85.

[3]. Murray RD, et al. The novel somatostatin ligand (SOM230) regulates human and rat anterior pituitary hormone secretion. J Clin Endocrinol Metab. 2004 Jun;89(6):3027-32.

[4]. Quinn TJ, et al. Pasireotide (SOM230) is effective for the treatment of pancreatic neuroendocrine tumors (PNETs) in a multiple endocrine neoplasia type 1 (MEN1) conditional knockout mouse model. Surgery. 2012 Dec;152(6):1068-77.

[5]. Imhof AK, et al. Differential antiinflammatory and antinociceptive effects of the somatostatin analogs octreotide and pasireotide in a mouse model of immune-mediated arthritis. Arthritis Rheum. 2011 Aug;63(8):2352-62.

Chemical & Physical Properties

Density	1.4±0.1 g/cm3
Boiling Point	1351.4±65.0 °C at 760 mmHg
Molecular Formula	C₅₈H₆₆N₁₀O₉
Molecular Weight	1047.206
Flash Point	771.1±34.3 °C
Exact Mass	1046.501465
PSA	281.20000
LogP	2.79
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.680
InChIKey	REVVFYZEISKUMT-QKXVGOHISA-N
SMILES	NCCCCC1NC(=O)C(Cc2c[nH]c3ccccc23)NC(=O)C(c2ccccc2)NC(=O)C2CC(OC(=O)NCCN)CN2C(=O)C(Cc2ccccc2)NC(=O)C(Cc2ccc(OCc3ccccc3)cc2)NC1=O.O=C(O)C(F)(F)F
Storage condition	2-8℃

Synonyms

SOM 230

SOM230

Cyclo[(2S)-2-phenylglycyl-D-tryptophyl-L-lysyl-O-(phenylmethyl)-L-tyrosyl-L-phenylalanyl-(4R)-4-[[[(2-aminoethyl)amino]carbonyl]oxy]-L-prolyl]

SOM-230

pasireotide

cyclo((4R)-4-(2-aminoethylcarbamoyloxy)-L-prolyl-L-phenylglycyl-D-tryptophyl-L-lysyl-4-O-benzyl-L-tyrosyl-L- phenylalanyl-)

Cyclo[(2S)-2-phenylglycyl-D-tryptophyl-L-lysyl-O-benzyl-L-tyrosyl-L-phenylalanyl-(4R)-4-{[(2-aminoethyl)carbamoyl]oxy}-L-prolyl]

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