MedKoo Cat#: 462304 | Name: Reversan
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Description:

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

Reversan is an inhibitor of multidrug resistance-associated proteins (MRPs), particularly MRP1. It enhances the efficacy of chemotherapeutic agents by blocking the efflux activity of MRP1, which is often overexpressed in cancer cells and contributes to drug resistance. Reversan has demonstrated chemosensitizing effects in preclinical models, notably improving the cytotoxicity of agents like etoposide and doxorubicin in neuroblastoma and other cancer cell lines. Unlike broad-spectrum efflux pump inhibitors, Reversan exhibits lower toxicity and greater selectivity, making it a promising candidate for overcoming drug resistance in cancer therapy.

Chemical Structure

Reversan
Reversan
CAS#313397-13-6

Theoretical Analysis

MedKoo Cat#: 462304

Name: Reversan

CAS#: 313397-13-6

Chemical Formula: C26H27N5O2

Exact Mass: 441.2165

Molecular Weight: 441.54

Elemental Analysis: C, 70.73; H, 6.16; N, 15.86; O, 7.25

Price and Availability

Size Price Availability Quantity
10mg USD 150.00 Ready to Ship
25mg USD 250.00 Ready to Ship
50mg USD 450.00 Ready to Ship
100mg USD 750.00 Ready to Ship
200mg USD 1,250.00 Ready to Ship
500mg USD 2,650.00 Ready to Ship
1g USD 4,250.00 Ready to Ship
2g USD 6,450.00 Ready to Ship
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Related CAS #
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Synonym
Reversan; CBLC4H10; CBLC 4H10; CBLC-4H10
IUPAC/Chemical Name
N-(3-morpholinopropyl)-5,7-diphenylpyrazolo[1,5-a]pyrimidine-3-carboxamide
InChi Key
JTRXWCLQFAZHGP-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(C1=C2N(C(C3=CC=CC=C3)=CC(C4=CC=CC=C4)=N2)N=C1)NCCCN5CCOCC5
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
Shelf Life
>3 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
Biological target:
Reversan increases the sensitivity of MRP1-overexpressing tumor cells (MCF7/VP) to doxorubicin, vincristine, and etoposide by 3.8-, 14.6- and 11.6-fold respectively. Reversan increases the efficacy of vincristine and etoposide in murine models of neuroblastoma in vivo. It does not sensitize MRP2, MRP3, MRP4 or MRP5 transporters to known substrates.
In vitro activity:
Reversan has demonstrated significant in vitro efficacy in reversing MRP1-mediated multidrug resistance. In HEK293 cells overexpressing MRP1, Reversan at 2 μM reduced the IC₅₀ of vincristine from 15.73 nM to 1.28 nM, doxorubicin from 46.62 nM to 16.32 nM, and etoposide from 1.29 μM to 0.27 μM. This indicates a substantial enhancement in drug sensitivity, with fold sensitization values of 11.8 for vincristine, 2.9 for doxorubicin, and 4.8 for etoposide. FEBS.ONLINELIBRARY.WILEY.COM Notably, Reversan alone exhibited minimal cytotoxicity at effective concentrations, underscoring its potential as a safe chemosensitizing agent.
In vivo activity:
Reversan increased the efficacy of both vincristine and etoposide in murine models of neuroblastoma. Reversan was not toxic by itself nor did it increase the toxicity of chemotherapeutic drug exposure in mice. Reversan may be clinically useful for the treatment of neuroblastoma and other MRP1-overexpressing drug-refractory tumors by increasing their sensitivity to conventional chemotherapy. Reference: Cancer Res. 2009 Aug 15;69(16):6573-80. https://pubmed.ncbi.nlm.nih.gov/19654298/
Solvent mg/mL mM
Solubility
DMSO 11.0 25.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 441.54 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.

Recalculate based on batch purity %
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. Kopanitsa L, Kopanitsa MV, Safitri D, Ladds G, Bailey DS. Suppression of Proliferation of Human Glioblastoma Cells by Combined Phosphodiesterase and Multidrug Resistance-Associated Protein 1 Inhibition. Int J Mol Sci. 2021 Sep 7;22(18):9665. doi: 10.3390/ijms22189665. PMID: 34575827; PMCID: PMC8471536. 2. Wen X, Iwata K, Ikuta K, Zhang X, Zhu K, Ibi M, Matsumoto M, Asaoka N, Liu J, Katsuyama M, Yabe-Nishimura C. NOX1/NADPH oxidase regulates the expression of multidrug resistance-associated protein 1 and maintains intracellular glutathione levels. FEBS J. 2019 Feb;286(4):678-687. doi: 10.1111/febs.14753. Epub 2019 Feb 6. PMID: 30653821. 3. Burkhart CA, Watt F, Murray J, Pajic M, Prokvolit A, Xue C, Flemming C, Smith J, Purmal A, Isachenko N, Komarov PG, Gurova KV, Sartorelli AC, Marshall GM, Norris MD, Gudkov AV, Haber M. Small-molecule multidrug resistance-associated protein 1 inhibitor reversan increases the therapeutic index of chemotherapy in mouse models of neuroblastoma. Cancer Res. 2009 Aug 15;69(16):6573-80. doi: 10.1158/0008-5472.CAN-09-1075. Epub 2009 Aug 4. PMID: 19654298; PMCID: PMC2746061.
In vitro protocol:
1. Kopanitsa L, Kopanitsa MV, Safitri D, Ladds G, Bailey DS. Suppression of Proliferation of Human Glioblastoma Cells by Combined Phosphodiesterase and Multidrug Resistance-Associated Protein 1 Inhibition. Int J Mol Sci. 2021 Sep 7;22(18):9665. doi: 10.3390/ijms22189665. PMID: 34575827; PMCID: PMC8471536. 2. Wen X, Iwata K, Ikuta K, Zhang X, Zhu K, Ibi M, Matsumoto M, Asaoka N, Liu J, Katsuyama M, Yabe-Nishimura C. NOX1/NADPH oxidase regulates the expression of multidrug resistance-associated protein 1 and maintains intracellular glutathione levels. FEBS J. 2019 Feb;286(4):678-687. doi: 10.1111/febs.14753. Epub 2019 Feb 6. PMID: 30653821.
In vivo protocol:
1. Burkhart CA, Watt F, Murray J, Pajic M, Prokvolit A, Xue C, Flemming C, Smith J, Purmal A, Isachenko N, Komarov PG, Gurova KV, Sartorelli AC, Marshall GM, Norris MD, Gudkov AV, Haber M. Small-molecule multidrug resistance-associated protein 1 inhibitor reversan increases the therapeutic index of chemotherapy in mouse models of neuroblastoma. Cancer Res. 2009 Aug 15;69(16):6573-80. doi: 10.1158/0008-5472.CAN-09-1075. Epub 2009 Aug 4. PMID: 19654298; PMCID: PMC2746061.
1: Tivnan A, Zakaria Z, O'Leary C, et al. Inhibition of multidrug resistance protein 1 (MRP1) improves chemotherapy drug response in primary and recurrent glioblastoma multiforme. Front Neurosci. 2015;9:218. Published 2015 Jun 16. doi:10.3389/fnins.2015.00218 2: Burkhart CA, Watt F, Murray J, et al. Small-molecule multidrug resistance-associated protein 1 inhibitor reversan increases the therapeutic index of chemotherapy in mouse models of neuroblastoma. Cancer Res. 2009;69(16):6573-6580. doi:10.1158/0008-5472.CAN-09-1075