Seclidemstat | SP-2577 | CAS#1423715-37-0 | antineoplastic

MedKoo Cat#: 561864 | Name: Seclidemstat

Description:

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

Seclidemstat, also known as SP2577, is an orally active, reversible, noncompetitive inhibitor of lysine-specific demethylase 1 (LSD1, or KDM1A), with potential antineoplastic activity. Seclidemstat suppresses the expression of target genes by converting the di- and mono-methylated forms of lysine at position 4 of histone 3 (H3K4) to mono- and unmethylated H3K4, respectively.

Chemical Structure

Seclidemstat

CAS#1423715-37-0

Theoretical Analysis

MedKoo Cat#: 561864

Name: Seclidemstat

CAS#: 1423715-37-0

Chemical Formula: C20H23ClN4O4S

Exact Mass: 450.1129

Molecular Weight: 450.93

Elemental Analysis: C, 53.27; H, 5.14; Cl, 7.86; N, 12.42; O, 14.19; S, 7.11

Price and Availability

Size	Price	Availability
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 3,850.00	Ready to ship
2g	USD 6,350.00	Ready to ship

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Synonym

Seclidemstat; SP-2577; SP 2577; SP2577;

IUPAC/Chemical Name

N'-[(1E)-1-(5-chloro-2-hydroxyphenyl)ethylidene]-3-(4-methylpiperazine-1-sulfonyl)benzohydrazide

InChi Key

MVSQDUZRRVBYLA-HYARGMPZSA-N

InChi Code

InChI=1S/C20H23ClN4O4S/c1-14(18-13-16(21)6-7-19(18)26)22-23-20(27)15-4-3-5-17(12-15)30(28,29)25-10-8-24(2)9-11-25/h3-7,12-13,26H,8-11H2,1-2H3,(H,23,27)/b22-14+

SMILES Code

O=C(N/N=C(C1=CC(Cl)=CC=C1O)\C)C2=CC=CC(S(=O)(N3CCN(C)CC3)=O)=C2

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

>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

More Info

LSD1 inhibition enhances H3K4 methylation and increases the expression of tumor suppressor genes. This may lead to an inhibition of cell growth in LSD1-overexpressing tumor cells. In addition, LSD1 demethylates mono- or di-methylated H3K9 which increases gene expression of tumor promoting genes; inhibition of LSD1 promotes H3K9 methylation and decreases transcription of these genes.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T9D07P18

QC Data

View QC data: current batch, Lot#T9D07P18

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Seclidemstat is a potent noncompetitive and reversible LSD1 inhibitor (Ki=31 nM, IC50=13 nM). Seclidemstat promotes antitumor immunity in switch/sucrose nonfermentable complex mutated ovarian cancer, as well as inhibit virus production, viral DNA replication, and late gene expression.

In vitro activity:

Combination therapy of seclidemstat with checkpoint inhibitors may induce or augment immunogenic responses of SWI/SNF-mutated ovarian cancers. Seclidemstat stimulated interferon-dependent anti-tumor immunity in small cell carcinoma of the ovary hypercalcemic type (SCCOHT) and promoted the expression of PD-L1 in both SCCOHT and ovarian clear cell carcinomas. Reference: PLoS One. 2020 Jul 10;15(7):e0235705. https://pubmed.ncbi.nlm.nih.gov/32649682/

In vivo activity:

Seclidemstat has limited activity against tested pediatric sarcoma models at the dose and schedule evaluated. Seclidemstat significantly inhibited the growth of three of eight Ewing sarcoma, four of five rhabdomyosarcoma, and four of six osteosarcoma xenografts. Reference: Pediatr Blood Cancer. 2021 Nov;68(11):e29304. https://pubmed.ncbi.nlm.nih.gov/34453478/

	Solvent	mg/mL	mM
Solubility
	DMSO	90.0	199.58

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 450.93 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. Soldi R, Ghosh Halder T, Weston A, Thode T, Drenner K, Lewis R, Kaadige MR, Srivastava S, Daniel Ampanattu S, Rodriguez Del Villar R, Lang J, Vankayalapati H, Weissman B, Trent JM, Hendricks WPD, Sharma S. The novel reversible LSD1 inhibitor SP-2577 promotes anti-tumor immunity in SWItch/Sucrose-NonFermentable (SWI/SNF) complex mutated ovarian cancer. PLoS One. 2020 Jul 10;15(7):e0235705. doi: 10.1371/journal.pone.0235705. PMID: 32649682; PMCID: PMC7351179. 2. Kurmasheva RT, Erickson SW, Han R, Teicher BA, Smith MA, Roth M, Gorlick R, Houghton PJ. In vivo evaluation of the lysine-specific demethylase (KDM1A/LSD1) inhibitor SP-2577 (Seclidemstat) against pediatric sarcoma preclinical models: A report from the Pediatric Preclinical Testing Consortium (PPTC). Pediatr Blood Cancer. 2021 Nov;68(11):e29304. doi: 10.1002/pbc.29304. Epub 2021 Aug 28. PMID: 34453478; PMCID: PMC10338045. 3. Zhang C, Wang Z, Shi Y, Yu B, Song Y. Recent advances of LSD1/KDM1A inhibitors for disease therapy. Bioorg Chem. 2023 May;134:106443. doi: 10.1016/j.bioorg.2023.106443. Epub 2023 Feb 24. PMID: 36857932.

In vitro protocol:

In vivo protocol:

1. Kurmasheva RT, Erickson SW, Han R, Teicher BA, Smith MA, Roth M, Gorlick R, Houghton PJ. In vivo evaluation of the lysine-specific demethylase (KDM1A/LSD1) inhibitor SP-2577 (Seclidemstat) against pediatric sarcoma preclinical models: A report from the Pediatric Preclinical Testing Consortium (PPTC). Pediatr Blood Cancer. 2021 Nov;68(11):e29304. doi: 10.1002/pbc.29304. Epub 2021 Aug 28. PMID: 34453478; PMCID: PMC10338045. 2. Zhang C, Wang Z, Shi Y, Yu B, Song Y. Recent advances of LSD1/KDM1A inhibitors for disease therapy. Bioorg Chem. 2023 May;134:106443. doi: 10.1016/j.bioorg.2023.106443. Epub 2023 Feb 24. PMID: 36857932.

1: Rask GC, Taslim C, Bayanjargal A, Cannon MV, Selich-Anderson J, Crow JC, Duncan A, Theisen ER. Seclidemstat blocks the transcriptional function of multiple FET-fusion oncoproteins. bioRxiv [Preprint]. 2024 May 21:2024.05.19.594897. doi: 10.1101/2024.05.19.594897. PMID: 38826330; PMCID: PMC11142045. 2: Baby S, Shinde SD, Kulkarni N, Sahu B. Lysine-Specific Demethylase 1 (LSD1) Inhibitors: Peptides as an Emerging Class of Therapeutics. ACS Chem Biol. 2023 Oct 20;18(10):2144-2155. doi: 10.1021/acschembio.3c00386. Epub 2023 Oct 9. PMID: 37812385. 3: Noce B, Di Bello E, Fioravanti R, Mai A. LSD1 inhibitors for cancer treatment: Focus on multi-target agents and compounds in clinical trials. Front Pharmacol. 2023 Feb 2;14:1120911. doi: 10.3389/fphar.2023.1120911. PMID: 36817147; PMCID: PMC9932783. 4: Bazinet A, Bravo GM. New Approaches to Myelodysplastic Syndrome Treatment. Curr Treat Options Oncol. 2022 May;23(5):668-687. doi: 10.1007/s11864-022-00965-1. Epub 2022 Mar 23. PMID: 35320468. 5: Sacilotto N, Dessanti P, Lufino MMP, Ortega A, Rodríguez-Gimeno A, Salas J, Maes T, Buesa C, Mascaró C, Soliva R. Comprehensive in Vitro Characterization of the LSD1 Small Molecule Inhibitor Class in Oncology. ACS Pharmacol Transl Sci. 2021 Nov 12;4(6):1818-1834. doi: 10.1021/acsptsci.1c00223. PMID: 34927013; PMCID: PMC8669716. 6: Kurmasheva RT, Erickson SW, Han R, Teicher BA, Smith MA, Roth M, Gorlick R, Houghton PJ. In vivo evaluation of the lysine-specific demethylase (KDM1A/LSD1) inhibitor SP-2577 (Seclidemstat) against pediatric sarcoma preclinical models: A report from the Pediatric Preclinical Testing Consortium (PPTC). Pediatr Blood Cancer. 2021 Nov;68(11):e29304. doi: 10.1002/pbc.29304. Epub 2021 Aug 28. PMID: 34453478; PMCID: PMC10338045. 7: Bailey CP, Figueroa M, Gangadharan A, Lee DA, Chandra J. Scaffolding LSD1 Inhibitors Impair NK Cell Metabolism and Cytotoxic Function Through Depletion of Glutathione. Front Immunol. 2020 Sep 17;11:2196. doi: 10.3389/fimmu.2020.02196. PMID: 33042135; PMCID: PMC7527493. 8: Soldi R, Ghosh Halder T, Weston A, Thode T, Drenner K, Lewis R, Kaadige MR, Srivastava S, Daniel Ampanattu S, Rodriguez Del Villar R, Lang J, Vankayalapati H, Weissman B, Trent JM, Hendricks WPD, Sharma S. The novel reversible LSD1 inhibitor SP-2577 promotes anti-tumor immunity in SWItch/Sucrose-NonFermentable (SWI/SNF) complex mutated ovarian cancer. PLoS One. 2020 Jul 10;15(7):e0235705. doi: 10.1371/journal.pone.0235705. PMID: 32649682; PMCID: PMC7351179.