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SML0015

Sigma-Aldrich

SR 142948A

≥98% (HPLC)

Synonym(s):

2-[[5-(2,6-dimethoxyphenyl)-1-(4-(N-(3-dimethylaminopropyl)-N-methylcarbamoyl)-2-isopropylphenyl)-1H-pyrazole3-carbonyl]amino] adamantane-2-carboxylic acid hydrochloride, SR 142948 hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C39H51N5O6·HCl
CAS Number:
184162-21-8
Molecular Weight:
722.31
MDL number:
MFCD03106502
UNSPSC Code:
12352200
PubChem Substance ID:
329825090
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: ≥2 mg/mL at warmed to 60 °C

originator

Sanofi Aventis

storage temp.

2-8°C

SMILES string

Cl.COc1cccc(OC)c1-c2cc(nn2-c3ccc(cc3C(C)C)C(=O)N(C)CCCN(C)C)C(=O)NC4([C@@H]5C[C@H]6C[C@@H](C5)C[C@@H]4C6)C(O)=O

InChI

1S/C39H51N5O6.ClH/c1-23(2)29-21-26(37(46)43(5)15-9-14-42(3)4)12-13-31(29)44-32(35-33(49-6)10-8-11-34(35)50-7)22-30(41-44)36(45)40-39(38(47)48)27-17-24-16-25(19-27)20-28(39)18-24;/h8,10-13,21-25,27-28H,9,14-20H2,1-7H3,(H,40,45)(H,47,48);1H/t24-,25+,27-,28+,39?;

InChI key

CUYNEHGBVHUQQW-BVJGGMLGSA-N

Application

SR 142948A was used to study the role of neurotensin signaling in intracellular alkanization and expression of IL-8 in human pancreatic cancer cells.

Biochem/physiol Actions

SR 142948A is a non-peptide Neurotensin receptor antagonist
SR 142948A is a potent neurotensin receptor antagonist that affects the expression of c-Fos and has properties of antipsychotic agent. It blocks hypothermia and analgesia induced by neurotensin. It blocks the increase in the concentration of Ca+2 induced by the activation of phospholipase C in CHO cell model.

Features and Benefits

This compound is featured on the Neurotensin Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Elisabeth B Binder et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 29(12), 2200-2207 (2004-08-26)
Antipsychotic drugs (APDs) have previously been shown to alter Fos expression in a regionally specific manner. Increases in Fos expression in the nucleus accumbens (NAcc) are common to all clinically effective APDs. In contrast, APD-induced Fos expression increases in the
D Gully et al.
The Journal of pharmacology and experimental therapeutics, 280(2), 802-812 (1997-02-01)
SR 142948A, 2-[[5-(2,6-dimethoxyphenyl)-1-(4-(N-(3-dimethylaminopropyl)-N-methylc arbamoyl)-2-isopropylphenyl)-1H-pyrazole3-carbonyl]amino] adamantane-2-carboxylic acid, hydrochloride, a new and extremely potent neurotensin (NT) receptor antagonist, has been characterized in comparison with SR 48692. This selective compound possesses nanomolar affinities for NT receptors, recognizes the two binding sites described for
Ulrike Olszewski et al.
Molecular oncology, 3(3), 204-213 (2009-04-28)
Pancreatic adenocarcinomas express neurotensin receptors in up to 90% of cases, however, their role in tumor biology and as a drug target is not clear. In the present study, a stable neurotensin (NT) analog induced intracellular calcium release and intracellular

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