Meclinertant | SR-48692 | CAS#146362-70-1 | neurotensin antagonist

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

MedKoo CAT#: 319617

CAS#: 146362-70-1

Description: Meclinertant, also known as SR-48692, is a neurotensin antagonist. SR 48692 counteracts neurotensin induced cell proliferation in human pancreatic ductal carcinoma cell line PANC-1. SR 48692 could inhibit the growth of MIA PaCa-2 cells in a neurotensin mediated fashion, and neurotensin could overcome this inhibition or stimulate proliferation.

Chemical Structure

Meclinertant

CAS# 146362-70-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319617
Name: Meclinertant
CAS#: 146362-70-1
Chemical Formula: C32H31ClN4O5
Exact Mass: 586.20
Molecular Weight: 587.073
Elemental Analysis: C, 65.47; H, 5.32; Cl, 6.04; N, 9.54; O, 13.63

Price and Availability

Size	Price	Availability
5mg	USD 350	2 weeks
10mg	USD 650	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: SR-48692; SR 48692; SR48692; Meclinertant

IUPAC/Chemical Name: (1r,3r,5r,7r)-2-(1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxamido)adamantane-2-carboxylic acid

InChi Key: DYLJVOXRWLXDIG-SHXBVJGHSA-N

InChi Code: InChI=1S/C32H31ClN4O5/c1-41-27-4-3-5-28(42-2)29(27)26-16-24(36-37(26)25-8-9-34-23-15-21(33)6-7-22(23)25)30(38)35-32(31(39)40)19-11-17-10-18(13-19)14-20(32)12-17/h3-9,15-20H,10-14H2,1-2H3,(H,35,38)(H,39,40)/t17-,18+,19-,20+,32?

SMILES Code: O=C(NC1(C(O)=O)[C@H]2C[C@@H]3C[C@@H](C[C@H]1C3)C2)C4=NN(C5=CC=NC6=CC(Cl)=CC=C56)C(C7=C(OC)C=CC=C7OC)=C4

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

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	SR 48692 is a neurotensin antagonist; selective for NTS1 over NTS2 (apparent affinity, Ke, is 36 nM for NTS1).
In vitro activity:	Using Calu3, NCI-H358, or NCI-H441 cells, the effects of NTS on HER3 transactivation were investigated. NTSR1 regulation of HER3 transactivation was impaired by SR48692 (NTSR1 antagonist) or monoclonal antibody (mAb)3481 (HER3 blocker). Reference: Peptides. 2022 Oct;156:170858. https://pubmed.ncbi.nlm.nih.gov/35932909/
In vivo activity:	Moreover, the treatment with SR48692, a selective NTSR1 antagonist, suppressed the activation of the MAPK and NF-κB signaling pathways and induction of target genes in pancreatic cancer cells in vitro, while the administration of SR48692 attenuated the tumorigenicity of pancreatic cancer cells in vivo. These findings suggest that NTSR1 may be a prognostic marker and a molecular target for pancreatic cancer treatment. Reference: Mol Oncol. 2021 Jan;15(1):151-166. https://pubmed.ncbi.nlm.nih.gov/33034134/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	11.7	20.00

Preparing Stock Solutions

The following data is based on the product molecular weight 587.07 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.

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

Formulation protocol:	1. Moody TW, Ramos-Alvarez I, Jensen RT. Adding of neurotensin to non-small cell lung cancer cells increases tyrosine phosphorylation of HER3. Peptides. 2022 Oct;156:170858. doi: 10.1016/j.peptides.2022.170858. Epub 2022 Aug 3. PMID: 35932909; PMCID: PMC9529830. 2. Tokumoto H, Setoguchi T, Saitoh Y, Sasaki H, Nagano S, Maeda S, Tanimoto A, Taniguchi N. Neurotensin receptor 1 is a new therapeutic target for human undifferentiated pleomorphic sarcoma growth. Mol Carcinog. 2019 Dec;58(12):2230-2240. doi: 10.1002/mc.23111. Epub 2019 Sep 3. PMID: 31478563. 3. Takahashi K, Ehata S, Miyauchi K, Morishita Y, Miyazawa K, Miyazono K. Neurotensin receptor 1 signaling promotes pancreatic cancer progression. Mol Oncol. 2021 Jan;15(1):151-166. doi: 10.1002/1878-0261.12815. Epub 2020 Nov 20. PMID: 33034134; PMCID: PMC7782081. 4. Yin M, Kim YO, Choi JI, Jeong S, Yang SH, Bae HB, Yoon MH. Antinociceptive role of neurotensin receptor 1 in rats with chemotherapy-induced peripheral neuropathy. Korean J Pain. 2020 Oct 1;33(4):318-325. doi: 10.3344/kjp.2020.33.4.318. PMID: 32989196; PMCID: PMC7532295.
In vitro protocol:	1. Moody TW, Ramos-Alvarez I, Jensen RT. Adding of neurotensin to non-small cell lung cancer cells increases tyrosine phosphorylation of HER3. Peptides. 2022 Oct;156:170858. doi: 10.1016/j.peptides.2022.170858. Epub 2022 Aug 3. PMID: 35932909; PMCID: PMC9529830. 2. Tokumoto H, Setoguchi T, Saitoh Y, Sasaki H, Nagano S, Maeda S, Tanimoto A, Taniguchi N. Neurotensin receptor 1 is a new therapeutic target for human undifferentiated pleomorphic sarcoma growth. Mol Carcinog. 2019 Dec;58(12):2230-2240. doi: 10.1002/mc.23111. Epub 2019 Sep 3. PMID: 31478563.
In vivo protocol:	1. Takahashi K, Ehata S, Miyauchi K, Morishita Y, Miyazawa K, Miyazono K. Neurotensin receptor 1 signaling promotes pancreatic cancer progression. Mol Oncol. 2021 Jan;15(1):151-166. doi: 10.1002/1878-0261.12815. Epub 2020 Nov 20. PMID: 33034134; PMCID: PMC7782081. 2. Yin M, Kim YO, Choi JI, Jeong S, Yang SH, Bae HB, Yoon MH. Antinociceptive role of neurotensin receptor 1 in rats with chemotherapy-induced peripheral neuropathy. Korean J Pain. 2020 Oct 1;33(4):318-325. doi: 10.3344/kjp.2020.33.4.318. PMID: 32989196; PMCID: PMC7532295.

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1: Baxendale IR, Cheung S, Kitching MO, Ley SV, Shearman JW. The synthesis of neurotensin antagonist SR 48692 for prostate cancer research. Bioorg Med Chem. 2013 Jul 15;21(14):4378-87. doi: 10.1016/j.bmc.2013.04.075. Epub 2013 May 6. PubMed PMID: 23721919.

2: Wang JG, Li NN, Li HN, Cui L, Wang P. Pancreatic cancer bears overexpression of neurotensin and neurotensin receptor subtype-1 and SR 48692 counteracts neurotensin induced cell proliferation in human pancreatic ductal carcinoma cell line PANC-1. Neuropeptides. 2011 Apr;45(2):151-6. doi: 10.1016/j.npep.2011.01.002. Epub 2011 Jan 26. PubMed PMID: 21272935.

3: Tirado-Santiago G, Lázaro-Muñoz G, Rodríguez-González V, Maldonado-Vlaar CS. Microinfusions of neurotensin antagonist SR 48692 within the nucleus accumbens core impair spatial learning in rats. Behav Neurosci. 2006 Oct;120(5):1093-102. PubMed PMID: 17014260.

4: Zerbib F, Piche T, Charles F, Galmiche JP, Bruley des Varannes S. SR 48692, a specific neurotensin receptor antagonist, has no effect on oesophageal motility in humans. Aliment Pharmacol Ther. 2004 Apr 15;19(8):931-9. PubMed PMID: 15080855.

5: Corley KC, Phan TH, Daugherty WP, Boadle-Biber MC. Stress-induced activation of median raphe serotonergic neurons in rats is potentiated by the neurotensin antagonist, SR 48692. Neurosci Lett. 2002 Feb 8;319(1):1-4. PubMed PMID: 11814639.

6: Fadel J, Dobner PR, Deutch AY. The neurotensin antagonist SR 48692 attenuates haloperidol-induced striatal Fos expression in the rat. Neurosci Lett. 2001 Apr 27;303(1):17-20. PubMed PMID: 11297813.

7: Lépée-Lorgeoux I, Betancur C, Souazé F, Rostène W, Bérod A, Pélaprat D. Regulation of the neurotensin NT(1) receptor in the developing rat brain following chronic treatment with the antagonist SR 48692. J Neurosci Res. 2000 May 1;60(3):362-9. PubMed PMID: 10797539; PubMed Central PMCID: PMC2556440.

8: Herzig MC, Chapman WG, Sheridan A, Rake JB, Woynarowski JM. Neurotensin receptor-mediated inhibition of pancreatic cancer cell growth by the neurotensin antagonist SR 48692. Anticancer Res. 1999 Jan-Feb;19(1A):213-9. PubMed PMID: 10226545.

9: Azzi M, Betancur C, Sillaber I, Spanagel R, Rostène W, Bérod A. Repeated administration of the neurotensin receptor antagonist SR 48692 differentially regulates mesocortical and mesolimbic dopaminergic systems. J Neurochem. 1998 Sep;71(3):1158-67. PubMed PMID: 9721741.

10: Portier M, Combes T, Gully D, Maffrand JP, Casellas P. Neurotensin type 1 receptor-mediated activation of krox24, c-fos and Elk-1: preventing effect of the neurotensin antagonists SR 48692 and SR 142948. FEBS Lett. 1998 Jul 31;432(1-2):88-93. PubMed PMID: 9710257.

11: Miller LA, Cochrane DE, Feldberg RS, Carraway RE. Inhibition of neurotensin-stimulated mast cell secretion and carboxypeptidase A activity by the peptide inhibitor of carboxypeptidase A and neurotensin-receptor antagonist SR 48692. Int Arch Allergy Immunol. 1998 Jun;116(2):147-53. PubMed PMID: 9652308.

12: Labbé-Jullié C, Barroso S, Nicolas-Etève D, Reversat JL, Botto JM, Mazella J, Bernassau JM, Kitabgi P. Mutagenesis and modeling of the neurotensin receptor NTR1. Identification of residues that are critical for binding SR 48692, a nonpeptide neurotensin antagonist. J Biol Chem. 1998 Jun 26;273(26):16351-7. PubMed PMID: 9632698.

13: Smith DJ, Hawranko AA, Monroe PJ, Gully D, Urban MO, Craig CR, Smith JP, Smith DL. Dose-dependent pain-facilitatory and -inhibitory actions of neurotensin are revealed by SR 48692, a nonpeptide neurotensin antagonist: influence on the antinociceptive effect of morphine. J Pharmacol Exp Ther. 1997 Aug;282(2):899-908. PubMed PMID: 9262357.

14: Croci T, Landi M, Gully D, Maffrand JP, Le Fur G, Manara L. Negative modulation of nitric oxide production by neurotensin as a putative mechanism of the diuretic action of SR 48692 in rats. Br J Pharmacol. 1997 Apr;120(7):1312-8. PubMed PMID: 9105707; PubMed Central PMCID: PMC1564587.

15: Botto JM, Guillemare E, Vincent JP, Mazella J. Effects of SR 48692 on neurotensin-induced calcium-activated chloride currents in the Xenopus oocyte expression system: agonist-like activity on the levocabastine-sensitive neurotensin receptor and absence of antagonist effect on the levocabastine insensitive neurotensin receptor. Neurosci Lett. 1997 Feb 28;223(3):193-6. PubMed PMID: 9080465.

16: Stoessl AJ, James KA, Napier BJ. The neurotensin antagonist SR 48692 fails to modify the behavioural responses to a dopamine D1 receptor agonist in the rat. Neuropharmacology. 1997 Jan;36(1):93-9. PubMed PMID: 9144645.

17: Castagliuolo I, Leeman SE, Bartolak-Suki E, Nikulasson S, Qiu B, Carraway RE, Pothoulakis C. A neurotensin antagonist, SR 48692, inhibits colonic responses to immobilization stress in rats. Proc Natl Acad Sci U S A. 1996 Oct 29;93(22):12611-5. PubMed PMID: 8901630; PubMed Central PMCID: PMC38040.

18: Chapman MA, See RE. The neurotensin receptor antagonist SR 48692 decreases extracellular striatal GABA in rats. Brain Res. 1996 Aug 5;729(1):124-6. PubMed PMID: 8874884.

19: Mulè F, Serio R, Postorino A, Vetri T, Bonvissuto F. Antagonism by SR 48692 of mechanical responses to neurotensin in rat intestine. Br J Pharmacol. 1996 Feb;117(3):488-492. PubMed PMID: 8821538; PubMed Central PMCID: PMC1909323.

20: Yamada M, Bolden-Watson C, Watson MA, Cho T, Coleman NJ, Yamada M, Richelson E. Regulation of neurotensin receptor mRNA expression by the receptor antagonist SR 48692 in the rat midbrain dopaminergic neurons. Brain Res Mol Brain Res. 1995 Nov;33(2):343-6. PubMed PMID: 8750895.

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