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SML0173

Sigma-Aldrich

Reversan

≥98% (HPLC)

Synonym(s):

CBLC4H10, N-[3-(4-Morpholinyl)propyl]-5,7-diphenyl-pyrazolo[1,5-a]pyrimidine-3-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C26H27N5O2
CAS Number:
313397-13-6
Molecular Weight:
441.52
MDL number:
MFCD01528184
UNSPSC Code:
12161501
PubChem Substance ID:
329825203
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

faintly yellow to yellow

solubility

DMSO: ≥8 mg/mL at ~60 °C

storage temp.

2-8°C

SMILES string

O=C(NCCCN1CCOCC1)c2cnn3c(cc(nc23)-c4ccccc4)-c5ccccc5

InChI

1S/C26H27N5O2/c32-26(27-12-7-13-30-14-16-33-17-15-30)22-19-28-31-24(21-10-5-2-6-11-21)18-23(29-25(22)31)20-8-3-1-4-9-20/h1-6,8-11,18-19H,7,12-17H2,(H,27,32)

InChI key

JTRXWCLQFAZHGP-UHFFFAOYSA-N

Application

Reversan may be used in cell signaling studies.

Biochem/physiol Actions

Reversan increases the efficacy of vincristine and etoposide and increases the sensitivity of murine models of neuroblastoma to conventional chemotherapy.
Reversan is a selective and nontoxic multidrug resistance-associated protein 1 (MRP1) and P-glycoprotein (P-gp) inhibitor.

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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Catherine A Burkhart et al.
Cancer research, 69(16), 6573-6580 (2009-08-06)
The multidrug resistance-associated protein 1 (MRP1) has been closely linked to poor treatment response in several cancers, most notably neuroblastoma. Homozygous deletion of the MRP1 gene in primary murine neuroblastoma tumors resulted in increased sensitivity to MRP1 substrate drugs (vincristine
Michelle J Henderson et al.
Journal of the National Cancer Institute, 103(16), 1236-1251 (2011-07-30)
Although the prognostic value of the ATP-binding cassette, subfamily C (ABCC) transporters in childhood neuroblastoma is usually attributed to their role in cytotoxic drug efflux, certain observations have suggested that these multidrug transporters might contribute to the malignant phenotype independent
Katharina Esser-Nobis et al.
Hepatology (Baltimore, Md.), 62(2), 397-408 (2015-04-14)
Hepatitis A virus (HAV) and hepatitis C virus (HCV) are two positive-strand RNA viruses sharing a similar biology, but causing opposing infection outcomes, with HAV always being cleared and HCV establishing persistence in the majority of infections. To gain deeper
Frank Loganzo et al.
Molecular cancer therapeutics, 14(4), 952-963 (2015-02-04)
Antibody-drug conjugates (ADC) are emerging as clinically effective therapy. We hypothesized that cancers treated with ADCs would acquire resistance mechanisms unique to immunoconjugate therapy and that changing ADC components may overcome resistance. Breast cancer cell lines were exposed to multiple

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