MedKoo Biosciences

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

MedKoo CAT#: 561690

CAS#: 63208-82-2

Description: Pifithrin-alpha is a p53 inactivator. It also has neuroprotective activity against strokes.

Chemical Structure

Pifithrin-alpha

CAS# 63208-82-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 561690
Name: Pifithrin-alpha
CAS#: 63208-82-2
Chemical Formula: C16H19BrN2OS
Exact Mass: 366.04
Molecular Weight: 367.305
Elemental Analysis: C, 52.32; H, 5.21; Br, 21.75; N, 7.63; O, 4.36; S, 8.73

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 450
200mg	USD 750
500mg	USD 1450
1g	USD 2450
2g	USD 4250
5g	USD 6950
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: Pifithrin-alpha; Pifithrin alpha; PFT-alpha; PFTalpha; PFT alpha;

IUPAC/Chemical Name: 2-(2-Imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3-yl)-1-(4-methylphenyl)ethanone;hydrobromide

InChi Key: HAGVCKULCLQGRF-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H18N2OS.BrH/c1-11-6-8-12(9-7-11)14(19)10-18-13-4-2-3-5-15(13)20-16(18)17;/h6-9,17H,2-5,10H2,1H3;1H

SMILES Code: CC1=CC=C(C(CN2C(SC3=C2CCCC3)=N)=O)C=C1.[H]Br

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

Product Data:

Product Data

Instruction:

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Biological target:	Pifithrin-α hydrobromide is a p53 inhibitor which blocks its transcriptional activity and prevents cells from apoptosis. Pifithrin-α hydrobromide is also an aryl hydrocarbon receptor (AhR) agonist.
In vitro activity:	This study investigated the effect of pifithrin (PFT)-α, an inhibitor of p53-dependent transcriptional activation, on self-renewal of ES cells. These results revealed that treatment of ES cells with PFT-α resulted in the inhibition of ES cell propagation in a dose-dependent manner, as indicated by a marked reduction in the cell number and colony size. Also, PFT-α caused a cell cycle arrest and significant reduction in DNA synthesis. Reference: Biochem Biophys Res Commun. 2012 Apr 13;420(3):605-10. https://pubmed.ncbi.nlm.nih.gov/22445757/
In vivo activity:	Chemotherapy and radiation therapy for cancer often have severe side effects that limit their efficacy. Because these effects are in part determined by p53-mediated apoptosis, temporary suppression of p53 has been suggested as a therapeutic strategy to prevent damage of normal tissues during treatment of p53-deficient tumors. To test this possibility, a small molecule was isolated for its ability to reversibly block p53-dependent transcriptional activation and apoptosis. This compound, pifithrin-alpha, protected mice from the lethal genotoxic stress associated with anticancer treatment without promoting the formation of tumors. Reference: Science. 1999 Sep 10;285(5434):1733-7. https://pubmed.ncbi.nlm.nih.gov/10481009/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	1.0	2.72
	DMSO	40.2	109.40
	DMSO:PBS (pH 7.2) (1:10)	0.1	0.27
	Water	1.3	3.40

Preparing Stock Solutions

The following data is based on the product molecular weight 367.305000000000000000000000000000 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. Yu H, Han Y, Cui C, Li G, Zhang B. Loss of SV2A promotes human neural stem cell apoptosis via p53 signaling. Neurosci Lett. 2023 Mar 13;800:137125. doi: 10.1016/j.neulet.2023.137125. Epub 2023 Feb 11. PMID: 36780942. 2. Abdelalim EM, Tooyama I. The p53 inhibitor, pifithrin-α, suppresses self-renewal of embryonic stem cells. Biochem Biophys Res Commun. 2012 Apr 13;420(3):605-10. doi: 10.1016/j.bbrc.2012.03.041. Epub 2012 Mar 16. PMID: 22445757. 3. Culmsee C, Zhu X, Yu QS, Chan SL, Camandola S, Guo Z, Greig NH, Mattson MP. A synthetic inhibitor of p53 protects neurons against death induced by ischemic and excitotoxic insults, and amyloid beta-peptide. J Neurochem. 2001 Apr;77(1):220-8. doi: 10.1046/j.1471-4159.2001.t01-1-00220.x. PMID: 11279278. 4. Komarov PG, Komarova EA, Kondratov RV, Christov-Tselkov K, Coon JS, Chernov MV, Gudkov AV. A chemical inhibitor of p53 that protects mice from the side effects of cancer therapy. Science. 1999 Sep 10;285(5434):1733-7. doi: 10.1126/science.285.5434.1733. PMID: 10481009.
In vitro protocol:	1. Yu H, Han Y, Cui C, Li G, Zhang B. Loss of SV2A promotes human neural stem cell apoptosis via p53 signaling. Neurosci Lett. 2023 Mar 13;800:137125. doi: 10.1016/j.neulet.2023.137125. Epub 2023 Feb 11. PMID: 36780942. 2. Abdelalim EM, Tooyama I. The p53 inhibitor, pifithrin-α, suppresses self-renewal of embryonic stem cells. Biochem Biophys Res Commun. 2012 Apr 13;420(3):605-10. doi: 10.1016/j.bbrc.2012.03.041. Epub 2012 Mar 16. PMID: 22445757.
In vivo protocol:	1. Culmsee C, Zhu X, Yu QS, Chan SL, Camandola S, Guo Z, Greig NH, Mattson MP. A synthetic inhibitor of p53 protects neurons against death induced by ischemic and excitotoxic insults, and amyloid beta-peptide. J Neurochem. 2001 Apr;77(1):220-8. doi: 10.1046/j.1471-4159.2001.t01-1-00220.x. PMID: 11279278. 2. Komarov PG, Komarova EA, Kondratov RV, Christov-Tselkov K, Coon JS, Chernov MV, Gudkov AV. A chemical inhibitor of p53 that protects mice from the side effects of cancer therapy. Science. 1999 Sep 10;285(5434):1733-7. doi: 10.1126/science.285.5434.1733. PMID: 10481009.

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1: Higgins SP, Tang Y, Higgins CE, Mian B, Zhang W, Czekay RP, Samarakoon R, Conti DJ, Higgins PJ. TGF-β1/p53 signaling in renal fibrogenesis. Cell Signal. 2017 Nov 28;43:1-10. doi: 10.1016/j.cellsig.2017.11.005. [Epub ahead of print] Review. PubMed PMID: 29191563. 2: Asjad HMM, Nasrollahi-Shirazi S, Sucic S, Freissmuth M, Nanoff C. Relax, Cool Down and Scaffold: How to Restore Surface Expression of Folding-Deficient Mutant GPCRs and SLC6 Transporters. Int J Mol Sci. 2017 Nov 14;18(11). pii: E2416. doi: 10.3390/ijms18112416. Review. PubMed PMID: 29135937; PubMed Central PMCID: PMC5713384. 3: Vávrová J, Rezáčová M. Importance of proapoptotic protein PUMA in cell radioresistance. Folia Biol (Praha). 2014;60(2):53-6. Review. PubMed PMID: 24785107. 4: Ding D, Allman BL, Salvi R. Review: ototoxic characteristics of platinum antitumor drugs. Anat Rec (Hoboken). 2012 Nov;295(11):1851-67. doi: 10.1002/ar.22577. Epub 2012 Oct 8. Review. PubMed PMID: 23044998. 5: Esposito E, Cuzzocrea S. New therapeutic strategy for Parkinson's and Alzheimer's disease. Curr Med Chem. 2010;17(25):2764-74. Review. PubMed PMID: 20586718. 6: Gudkov AV, Komarova EA. Dangerous habits of a security guard: the two faces of p53 as a drug target. Hum Mol Genet. 2007 Apr 15;16 Spec No 1:R67-72. Review. PubMed PMID: 17613549. 7: Bowen JM, Gibson RJ, Cummins AG, Keefe DM. Intestinal mucositis: the role of the Bcl-2 family, p53 and caspases in chemotherapy-induced damage. Support Care Cancer. 2006 Jul;14(7):713-31. Epub 2006 Feb 2. Review. PubMed PMID: 16453135. 8: Gudkov AV, Komarova EA. Prospective therapeutic applications of p53 inhibitors. Biochem Biophys Res Commun. 2005 Jun 10;331(3):726-36. Review. PubMed PMID: 15865929. 9: Dagher PC. Apoptosis in ischemic renal injury: roles of GTP depletion and p53. Kidney Int. 2004 Aug;66(2):506-9. Review. PubMed PMID: 15253698. 10: Howell SB. Resistance to apoptosis in prostate cancer cells. Mol Urol. 2000 Fall;4(3):225-9;discussion 231. Review. PubMed PMID: 11062378. 11: Komarova EA, Gudkov AV. Suppression of p53: a new approach to overcome side effects of antitumor therapy. Biochemistry (Mosc). 2000 Jan;65(1):41-8. Review. PubMed PMID: 10702639.

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