Serdemetan | JNJ-26854165 | CAS#881202-45-5

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

MedKoo CAT#: 201614

CAS#: 881202-45-5

Description: Serdemetan, also known as JNJ-26854165, is an orally bioavailable, small-molecule HDM2 antagonist with potential antineoplastic activity. Serdemetan inhibits the binding of the HDM2A–p53 complex to the proteasome, blocking the degradation of p53; p53 signaling and p53-mediated induction of tumor cell apoptosis may thus be restored. In addition to p53, degradation of other HDM2 client proteins may be inhibited.

Chemical Structure

Serdemetan

CAS# 881202-45-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 201614
Name: Serdemetan
CAS#: 881202-45-5
Chemical Formula: C21H20N4
Exact Mass: 328.17
Molecular Weight: 328.410
Elemental Analysis: C, 76.80; H, 6.14; N, 17.06

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 750
200mg	USD 1250
500mg	USD 2150
1g	USD 3750
2g	USD 4850
5g	USD 6750
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: JNJ26854165; JNJ-26854165; JNJ 26854165; Serdemetan.

IUPAC/Chemical Name: N1-(2-(1H-indol-3-yl)ethyl)-N4-(pyridin-4-yl)benzene-1,4-diamine

InChi Key: CEGSUKYESLWKJP-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H20N4/c1-2-4-21-20(3-1)16(15-24-21)9-14-23-17-5-7-18(8-6-17)25-19-10-12-22-13-11-19/h1-8,10-13,15,23-24H,9,14H2,(H,22,25)

SMILES Code: C1(NCCC2=CNC3=C2C=CC=C3)=CC=C(NC4=CC=NC=C4)C=C1

Appearance: white 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, DMF, and ethanol

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

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Product Data:

Product Data

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Biological target:	Serdemetan suppresses the growth of cancer cell lines expressing wild-type p53 (IC50 values range from 240-440 nM). It induces p53-mediated transcription culminating in apoptotic death of acute leukemia cells.
In vitro activity:	Serdemetan may function by inhibiting cholesterol transport, offering a potential treatment approach for mantle cell lymphoma (MCL) and multiple myeloma (MM). Serdemetan inhibited proliferation in both wild-type and mutant p53 cell lines, inducing S phase cell cycle arrest. Serdemetan treatment led to cholesterol accumulation in endosomes in certain cells. MM and MCL cells showed reduced cholesterol efflux and lysosomal storage disease characteristics. Reference: J Pharmacol Exp Ther. 2013 Sep;346(3):381-92. https://pubmed.ncbi.nlm.nih.gov/23820125/
In vivo activity:	Serdemetan has potential as a radiosensitizer. Serdemetan caused a greater than additive increase in tumor growth delay. The dose enhancement factor was 1.9 and 1.6 for H460 and A549 tumors, respectively. Serdemetan inhibited proliferation, capillary tube formation, and migration of HMEC-1 cells. These effects were more marked concurrently with irradiation. Reference: Cancer Lett. 2011 Dec 22;312(2):209-18. https://pubmed.ncbi.nlm.nih.gov/21937165/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	25.0	76.12
	DMSO	20.0	60.90
	Ethanol	1.0	3.04

Preparing Stock Solutions

The following data is based on the product molecular weight 328.41 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. Jones RJ, Gu D, Bjorklund CC, Kuiatse I, Remaley AT, Bashir T, Vreys V, Orlowski RZ. The novel anticancer agent JNJ-26854165 induces cell death through inhibition of cholesterol transport and degradation of ABCA1. J Pharmacol Exp Ther. 2013 Sep;346(3):381-92. doi: 10.1124/jpet.113.204958. Epub 2013 Jul 2. Erratum in: J Pharmacol Exp Ther. 2013 Nov;347(2):540. PMID: 23820125; PMCID: PMC3876782. 2. Kojima K, Burks JK, Arts J, Andreeff M. The novel tryptamine derivative JNJ-26854165 induces wild-type p53- and E2F1-mediated apoptosis in acute myeloid and lymphoid leukemias. Mol Cancer Ther. 2010 Sep;9(9):2545-57. doi: 10.1158/1535-7163.MCT-10-0337. Epub 2010 Aug 24. PMID: 20736344; PMCID: PMC2949269. 3. Chargari C, Leteur C, Angevin E, Bashir T, Schoentjes B, Arts J, Janicot M, Bourhis J, Deutsch E. Preclinical assessment of JNJ-26854165 (Serdemetan), a novel tryptamine compound with radiosensitizing activity in vitro and in tumor xenografts. Cancer Lett. 2011 Dec 22;312(2):209-18. doi: 10.1016/j.canlet.2011.08.011. Epub 2011 Aug 22. PMID: 21937165. 4. Tabernero J, Dirix L, Schöffski P, Cervantes A, Lopez-Martin JA, Capdevila J, van Beijsterveldt L, Platero S, Hall B, Yuan Z, Knoblauch R, Zhuang SH. A phase I first-in-human pharmacokinetic and pharmacodynamic study of serdemetan in patients with advanced solid tumors. Clin Cancer Res. 2011 Oct 1;17(19):6313-21. doi: 10.1158/1078-0432.CCR-11-1101. Epub 2011 Aug 10. PMID: 21831953.
In vitro protocol:	1. Jones RJ, Gu D, Bjorklund CC, Kuiatse I, Remaley AT, Bashir T, Vreys V, Orlowski RZ. The novel anticancer agent JNJ-26854165 induces cell death through inhibition of cholesterol transport and degradation of ABCA1. J Pharmacol Exp Ther. 2013 Sep;346(3):381-92. doi: 10.1124/jpet.113.204958. Epub 2013 Jul 2. Erratum in: J Pharmacol Exp Ther. 2013 Nov;347(2):540. PMID: 23820125; PMCID: PMC3876782. 2. Kojima K, Burks JK, Arts J, Andreeff M. The novel tryptamine derivative JNJ-26854165 induces wild-type p53- and E2F1-mediated apoptosis in acute myeloid and lymphoid leukemias. Mol Cancer Ther. 2010 Sep;9(9):2545-57. doi: 10.1158/1535-7163.MCT-10-0337. Epub 2010 Aug 24. PMID: 20736344; PMCID: PMC2949269.
In vivo protocol:	1. Chargari C, Leteur C, Angevin E, Bashir T, Schoentjes B, Arts J, Janicot M, Bourhis J, Deutsch E. Preclinical assessment of JNJ-26854165 (Serdemetan), a novel tryptamine compound with radiosensitizing activity in vitro and in tumor xenografts. Cancer Lett. 2011 Dec 22;312(2):209-18. doi: 10.1016/j.canlet.2011.08.011. Epub 2011 Aug 22. PMID: 21937165. 2. Tabernero J, Dirix L, Schöffski P, Cervantes A, Lopez-Martin JA, Capdevila J, van Beijsterveldt L, Platero S, Hall B, Yuan Z, Knoblauch R, Zhuang SH. A phase I first-in-human pharmacokinetic and pharmacodynamic study of serdemetan in patients with advanced solid tumors. Clin Cancer Res. 2011 Oct 1;17(19):6313-21. doi: 10.1158/1078-0432.CCR-11-1101. Epub 2011 Aug 10. PMID: 21831953.

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1: Lehman JA, Hauck PM, Gendron JM, Batuello CN, Eitel JA, Albig A, Kadakia MP, Mayo LD. Serdemetan antagonizes the Mdm2-HIF1α axis leading to decreased levels of glycolytic enzymes. PLoS One. 2013 Sep 6;8(9):e74741. doi: 10.1371/journal.pone.0074741. eCollection 2013. PubMed PMID: 24040331; PubMed Central PMCID: PMC3765416.

2: Jones RJ, Gu D, Bjorklund CC, Kuiatse I, Remaley AT, Bashir T, Vreys V, Orlowski RZ. The novel anticancer agent JNJ-26854165 induces cell death through inhibition of cholesterol transport and degradation of ABCA1. J Pharmacol Exp Ther. 2013 Sep;346(3):381-92. doi: 10.1124/jpet.113.204958. Epub 2013 Jul 2. Erratum in: J Pharmacol Exp Ther. 2013 Nov;347(2):540. PubMed PMID: 23820125; PubMed Central PMCID: PMC3876782.

3: Chargari C, Leteur C, Angevin E, Bashir T, Schoentjes B, Arts J, Janicot M, Bourhis J, Deutsch E. Preclinical assessment of JNJ-26854165 (Serdemetan), a novel tryptamine compound with radiosensitizing activity in vitro and in tumor xenografts. Cancer Lett. 2011 Dec 22;312(2):209-18. doi: 10.1016/j.canlet.2011.08.011. Epub 2011 Aug 22. PubMed PMID: 21937165.

4: Smith MA, Gorlick R, Kolb EA, Lock R, Carol H, Maris JM, Keir ST, Morton CL, Reynolds CP, Kang MH, Arts J, Bashir T, Janicot M, Kurmasheva RT, Houghton PJ. Initial testing of JNJ-26854165 (Serdemetan) by the pediatric preclinical testing program. Pediatr Blood Cancer. 2012 Aug;59(2):329-32. doi: 10.1002/pbc.23319. Epub 2011 Sep 15. PubMed PMID: 21922647.

5: Tabernero J, Dirix L, SchÃ¶ffski P, Cervantes A, Lopez-Martin JA, Capdevila J, van Beijsterveldt L, Platero S, Hall B, Yuan Z, Knoblauch R, Zhuang SH. A phase I first-in-human pharmacokinetic and pharmacodynamic study of serdemetan in patients with advanced solid tumors. Clin Cancer Res. 2011 Oct 1;17(19):6313-21. doi: 10.1158/1078-0432.CCR-11-1101. Epub 2011 Aug 10. PubMed PMID: 21831953.

6: Yuan Y, Liao YM, Hsueh CT, Mirshahidi HR. Novel targeted therapeutics: inhibitors of MDM2, ALK and PARP. J Hematol Oncol. 2011 Apr 20;4:16. doi: 10.1186/1756-8722-4-16. Review. PubMed PMID: 21504625; PubMed Central PMCID: PMC3103487.

7: Millard M, Pathania D, Grande F, Xu S, Neamati N. Small-molecule inhibitors of p53-MDM2 interaction: the 2006-2010 update. Curr Pharm Des. 2011;17(6):536-59. Review. PubMed PMID: 21391905.

8: Kojima K, Burks JK, Arts J, Andreeff M. The novel tryptamine derivative JNJ-26854165 induces wild-type p53- and E2F1-mediated apoptosis in acute myeloid and lymphoid leukemias. Mol Cancer Ther. 2010 Sep;9(9):2545-57. doi: 10.1158/1535-7163.MCT-10-0337. Epub 2010 Aug 24. PubMed PMID: 20736344; PubMed Central PMCID: PMC2949269.

9: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Apr;31(3):183-226. PubMed PMID: 19536362.

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