Piritrexim isethionate | CAS# 79483-69-5 (isethionate) | inhibitor of dihydrofolate reductase

MedKoo Cat#: 412168 | Name: Piritrexim isethionate

Description:

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

Piritrexim isethionate is a lipid-soluble inhibitor of dihydrofolate reductase (DHFR) that appears to be an active agent in patients with metastatic urothelial cancer when administered as a 5-day, low-dose oral schedule.

Chemical Structure

Piritrexim isethionate

CAS#79483-69-5 (isethionate)

Theoretical Analysis

MedKoo Cat#: 412168

Name: Piritrexim isethionate

CAS#: 79483-69-5 (isethionate)

Chemical Formula: C19H25N5O6S

Exact Mass: 451.1526

Molecular Weight: 451.49

Elemental Analysis: C, 50.54; H, 5.58; N, 15.51; O, 21.26; S, 7.10

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

79483-69-5 (isethionate) 72732-56-0 (free base)

Synonym

Piritrexim isethionate; BW301U isethionate; BW-301U isethionate; BW 301U isethionate

IUPAC/Chemical Name

Pyrido(2,3-d)pyrimidine-2,4-diamine, 6-((2,5-dimethoxyphenyl)methyl)-5-methyl-, mono(2-hydroxyethanesulfonate)

InChi Key

IOEMETRLOWNXGW-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H19N5O2.C2H6O4S/c1-9-11(6-10-7-12(23-2)4-5-13(10)24-3)8-20-16-14(9)15(18)21-17(19)22-16;3-1-2-7(4,5)6/h4-5,7-8H,6H2,1-3H3,(H4,18,19,20,21,22);3H,1-2H2,(H,4,5,6)

SMILES Code

NC1=NC(N)=C(C(C)=C(CC2=CC(OC)=CC=C2OC)C=N3)C3=N1.OCCS(=O)(O)=O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 451.49 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

1: Sigel CW, Macklin AW, Woolley JL Jr, Johnson NW, Collier MA, Blum MR, Clendeninn NJ, Everitt BJ, Grebe G, Mackars A, et al. Preclinical biochemical pharmacology and toxicology of piritrexim, a lipophilic inhibitor of dihydrofolate reductase. NCI Monogr. 1987;(5):111-20. PubMed PMID: 3431588. 2: Rosowsky A, Mota CE, Wright JE, Queener SF. 2,4-Diamino-5-chloroquinazoline analogues of trimetrexate and piritrexim: synthesis and antifolate activity. J Med Chem. 1994 Dec 23;37(26):4522-8. PubMed PMID: 7799402. 3: de Vries EG, Gietema JA, Workman P, Scott JE, Crawshaw A, Dobbs HJ, Dennis I, Mulder NH, Sleijfer DT, Willemse PH. A phase II and pharmacokinetic study with oral piritrexim for metastatic breast cancer. Br J Cancer. 1993 Sep;68(3):641-4. PubMed PMID: 8353055; PubMed Central PMCID: PMC1968400. 4: Lassiter LK, Tummala MK, Hussain MH, Stadler WM, Petrylak DP, Carducci MA. Phase II open-label study of oral piritrexim in patients with advanced carcinoma of the urothelium who have experienced failure with standard chemotherapy. Clin Genitourin Cancer. 2008 Mar;6(1):31-5. doi: 10.3816/CGC.2008.n.005. PubMed PMID: 18501080. 5: Laszlo J, Brenckman WD Jr, Morgan E, Clendeninn NJ, Williams T, Currie V, Young C. Initial clinical studies of piritrexim. NCI Monogr. 1987;(5):121-5. PubMed PMID: 3323908. 6: de Wit R, Kaye SB, Roberts JT, Stoter G, Scott J, Verweij J. Oral piritrexim, an effective treatment for metastatic urothelial cancer. Br J Cancer. 1993 Feb;67(2):388-90. PubMed PMID: 8431372; PubMed Central PMCID: PMC1968166. 7: Perkins W, Williams RE, Vestey JP, Tidman MJ, Layton AM, Cunliffe WJ, Saihan EM, Klaber MR, Manna VK, Baker H, et al. A multicentre 12-week open study of a lipid-soluble folate antagonist, piritrexim in severe psoriasis. Br J Dermatol. 1993 Nov;129(5):584-9. PubMed PMID: 8251356. 8: Kovacs JA, Allegra CJ, Swan JC, Drake JC, Parrillo JE, Chabner BA, Masur H. Potent antipneumocystis and antitoxoplasma activities of piritrexim, a lipid-soluble antifolate. Antimicrob Agents Chemother. 1988 Apr;32(4):430-3. PubMed PMID: 2967669; PubMed Central PMCID: PMC172195. 9: Adamson PC, Balis FM, Miser J, Wells RJ, Bleyer WA, Williams TE, Gillespie A, Penta JS, Clendeninn NJ, Poplack DG. Pediatric phase I trial and pharmacokinetic study of piritrexim administered orally on a five-day schedule. Cancer Res. 1990 Aug 1;50(15):4464-7. PubMed PMID: 2369724. 10: Gangjee A, Zhu Y, Queener SF. 6-Substituted 2,4-diaminopyrido[3,2-d]pyrimidine analogues of piritrexim as inhibitors of dihydrofolate reductase from rat liver, Pneumocystis carinii, and Toxoplasma gondii and as antitumor agents. J Med Chem. 1998 Nov 5;41(23):4533-41. PubMed PMID: 9804692. 11: Guzzo C, Benik K, Lazarus G, Johnson J, Weinstein G. Treatment of psoriasis with piritrexim, a lipid-soluble folate antagonist. Arch Dermatol. 1991 Apr;127(4):511-4. PubMed PMID: 2006875. 12: Richards RG, Brown OE, Gillison ML, Sedwick WD. Drug concentration-dependent DNA lesions are induced by the lipid-soluble antifolate, piritrexim (BW301U). Mol Pharmacol. 1986 Dec;30(6):651-8. PubMed PMID: 3491287. 13: Woolley JL, Deangelis DV, Grace ME, Liao SH, Crouch RC, Sigel CW. The disposition and metabolism of [14C]piritrexim in dogs after intravenous and oral administration. Drug Metab Dispos. 1991 Nov-Dec;19(6):1139-46. PubMed PMID: 1687022. 14: Feun LG, Savaraj N, Benedetto P, Hanlon J, Sridhar KS, Collier M, Richman S, Liao SH, Clendeninn NJ. Phase I trial of piritrexim capsules using prolonged, low-dose oral administration for the treatment of advanced malignancies. J Natl Cancer Inst. 1991 Jan 2;83(1):51-5. PubMed PMID: 1984518. 15: Bleehen NM, Newman HV, Rampling RP, Ramsay JR, Roberts JT, Bedford P, Nethersell AB. A phase II study of oral piritrexim in recurrent high-grade (III, IV) glioma. Br J Cancer. 1995 Sep;72(3):766-8. PubMed PMID: 7669591; PubMed Central PMCID: PMC2033879. 16: Woolley JL, Deangelis DV, Crouch RC, Shockcor JP, Sigel CW. The disposition and metabolism of [14C]piritrexim in rats after intravenous and oral administration. Drug Metab Dispos. 1991 May-Jun;19(3):600-8. PubMed PMID: 1680625. 17: Chan DC, Rosowsky A. Synthesis of the lipophilic antifolate piritrexim via a palladium(0)-catalyzed cross-coupling reaction. J Org Chem. 2005 Feb 18;70(4):1364-8. PubMed PMID: 15704971. 18: Woolley JL Jr, Ringstad JL, Sigel CW. Competitive protein binding assay for piritrexim. J Pharm Sci. 1989 Sep;78(9):749-52. PubMed PMID: 2585269. 19: Chan DC, Fu H, Forsch RA, Queener SF, Rosowsky A. Design, synthesis, and antifolate activity of new analogues of piritrexim and other diaminopyrimidine dihydrofolate reductase inhibitors with omega-carboxyalkoxy or omega-carboxy-1-alkynyl substitution in the side chain. J Med Chem. 2005 Jun 30;48(13):4420-31. PubMed PMID: 15974594. 20: Lai JP, He XW, Chen F. Separation and determination of the antitumor drug piritrexim by molecularly imprinted microspheres in high-performance liquid chromatography. Anal Bioanal Chem. 2003 Sep;377(1):208-13. Epub 2003 Jul 4. PubMed PMID: 12845402.

View History

Description:

Chemical Structure

Theoretical Analysis

Price and Availability

Preparing Stock Solutions

View History

NT-157

Dexchlorpheniramine free base

Oxabolone cipionate

OICR766A

NSD-1024

Buscaline

Error message: