MedKoo Cat#: 202334 | Name: PRLX-93936
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Description:

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

PRLX 93936 is a structural analogue of erastin with potential antineoplastic activity. Erastin analogue PRLX 93936 appears to inhibit mitochondrial outer membrane protein VDACs (voltage-dependent anion channels) 2 and 3, resulting in an oxidative, non-apoptotic cell death. Erastin analogue PRLX 93936 exhibits greater lethality in cell lines harboring mutations in the GTPase protein oncogenes HRAS and KRAS or the serine-threonine protein kinase oncogene BRAF than in non-tumorigenic cell lines. VDACs 2 and 3 are up-regulated in a wide variety of tumor cell lines.

Chemical Structure

PRLX-93936
CAS#903499-49-0

Theoretical Analysis

MedKoo Cat#: 202334

Name: PRLX-93936

CAS#: 903499-49-0

Chemical Formula: C21H24N4O2

Exact Mass: 364.1899

Molecular Weight: 364.45

Elemental Analysis: C, 69.21; H, 6.64; N, 15.37; O, 8.78

Price and Availability

Size Price Availability Quantity
5mg USD 370.00
10mg USD 630.00
25mg USD 1,180.00
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Synonym
PRLX93936; PRLX 93936; PRLX-93936;
IUPAC/Chemical Name
3-(2-ethoxyphenyl)-2-(piperazin-1-ylmethyl)quinazolin-4(3H)-one
InChi Key
OBWOSMGNXYUDFB-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H24N4O2/c1-2-27-19-10-6-5-9-18(19)25-20(15-24-13-11-22-12-14-24)23-17-8-4-3-7-16(17)21(25)26/h3-10,22H,2,11-15H2,1H3
SMILES Code
O=C1N(C2=CC=CC=C2OCC)C(CN3CCNCC3)=NC4=C1C=CC=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 soluble in water.
Shelf Life
>5 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
PRLX 93936 is a product of extensive SAR work originating from a small molecule identified in a synthetic lethal screen against isogenic cell lines engineered to differentially express several genes including activated RasV12. Preclinical pharmacodynamic and toxicological studies, suggest that PRLX 93936 has great therapeutic potential and therefore, Prolexys initiated a Phase I clinical trial in August, 2007. Note: Structure was from http://www.chemspider.com/Chemical-Structure.9734401.html (5/31/2016).      
Product Data
Certificate of Analysis
Safety Data Sheet (SDS)
Biological target:
PRLX 93936 is a structural analogue of erastin with potential antineoplastic activity. Erastin analogue PRLX 93936 appears to inhibit mitochondrial outer membrane protein VDACs (voltage-dependent anion channels) 2 and 3, resulting in an oxidative, non-apoptotic cell death.
In vitro activity:
Cotreatment with cisplatin and PRLX93936 induced ferroptosis, as evidenced by the upregulation of ROS, lipid peroxidation and Fe2+. Further investigation revealed that cotreatment with cisplatin and PRLX93936 inhibited GPX4 and that overexpression of GPX4 prevented cell death. Moreover, the Nrf2/Keap1 pathway also regulated the sensitivity to cisplatin and PRLX93936 in NSCLC cells. Reference: Biochem Biophys Res Commun. 2021 Sep 10;569:79-85. https://pubmed.ncbi.nlm.nih.gov/34237431/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 364.45 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:
Liang Z, Zhao W, Li X, Wang L, Meng L, Yu R. Cisplatin synergizes with PRLX93936 to induce ferroptosis in non-small cell lung cancer cells. Biochem Biophys Res Commun. 2021 Sep 10;569:79-85. doi: 10.1016/j.bbrc.2021.06.088. Epub 2021 Jul 5. PMID: 34237431.
In vitro protocol:
Liang Z, Zhao W, Li X, Wang L, Meng L, Yu R. Cisplatin synergizes with PRLX93936 to induce ferroptosis in non-small cell lung cancer cells. Biochem Biophys Res Commun. 2021 Sep 10;569:79-85. doi: 10.1016/j.bbrc.2021.06.088. Epub 2021 Jul 5. PMID: 34237431.
In vivo protocol:
TBD
 Voorhees, P. M., Schlossman, R. L., Gasparetto, C. J., Berdeja, J. G., Morris, J., Jacobstein, D. A., ... & Richardson, P. G. (2014). An open-label, dose escalation, multi-center phase 1 study of PRLX 93936, an agent synthetically active against the activated ras pathway, in the treatment of relapsed or relapsed and refractory multiple myeloma. Blood, 124(21), 2140. Ramanathan, R. K., Rosen, P. J., Wagner, A. J., Sahasrabudhe, S., Weiss, G. J., Lee, P., ... & Von Hoff, D. D. (2010). A phase I pharmacodynamic and pharmacokinetic study of a Ras inhibitor, PRLX 93936, in patients with advanced solid tumors. Journal of Clinical Oncology, 28(15_suppl), e13042-e13042. Sahasrabudhe, S. R., Lai, S., Pierce, M., Clemens, C., Venkat, R., Rebentisch, M., ... & Robbins, P. B. (2008). Selective in vitro and in vivo anti-tumor activity of PRLX 93936 in biological models of melanoma and ovarian cancer. Journal of Clinical Oncology, 26(15_suppl), 14586-14586. Robbins, P., Pierce, M., Clemens, C., Venkat, R. G., Lai, S., Rebentisch, M., ... & Sahasrabudhe, S. (2009). Abstract# 4693: A novel small molecule, PRLX 93936, displays antitumor activity in vitro and in vivo against multiple models of melanoma. Cancer Research, 69(9_Supplement), 4693-4693. Sahasrabudhe, S., Robbins, P., Erkkila, T., Becklin, R., Pierce, M., Savage, J., & Stockwell, B. (2008). From genotype-selective small molecules to novel clinical candidates and novel drug targets in cancer: Chemi-proteomics approach. Clinical Cancer Research, 14(15_Supplement), A1-A1. Becklin, R., von Rechenberg, M., Stockwell, B., Zhen, Y., Chepanoske, C. L., Askovich, P., ... & Robbins, P. (2008). Target deconvolution using chemiproteomics. Cancer Research, 68(9_Supplement), 4755-4755.