Pyrazoloacridine | CAS#99009-20-8

MedKoo Cat#: 526067 | Name: Pyrazoloacridine

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Description:

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

Pyrazoloacridine is an investigational nucleic acid binding agent that inhibits the activity of topoisomerases 1 and 2. Pyrazoloacridine was a phase II clinical study to determine the efficacy and toxicities of PZA in patients with metastatic breast cancer (MBC)Pyrazoloacridine appears to intercalate into DNA and inhibit RNA synthesis, DNA synthesis, and the activities of topoisomerases I and II, thereby causing cytotoxicity.

Chemical Structure

Pyrazoloacridine

CAS#99009-20-8

Theoretical Analysis

MedKoo Cat#: 526067

Name: Pyrazoloacridine

CAS#: 99009-20-8

Chemical Formula: C19H21N5O3

Exact Mass: 367.1644

Molecular Weight: 367.41

Elemental Analysis: C, 62.11; H, 5.76; N, 19.06; O, 13.06

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 290.00

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Synonym

Pyrazoloacridine; PD 115934; PD-115934;NSC 366140; NSC-366140; PD 115,934.

IUPAC/Chemical Name

N,N-Dimethyl-9-methoxy-5-nitropyrazolo(3,4,5-kl)acridine-2(6H)-propanamine

InChi Key

HZCWPKGYTCJSEB-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H21N5O3/c1-22(2)9-4-10-23-15-7-8-16(24(25)26)19-17(15)18(21-23)13-11-12(27-3)5-6-14(13)20-19/h5-8,11,20H,4,9-10H2,1-3H3

SMILES Code

O=[N+](C1=CC=C2C3=C1NC4=CC=C(OC)C=C4C3=NN2CCCN(C)C)[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

>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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 367.41 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

1: Chen DS, Zhou YJ, Li YL, Yao CS, Wang XS. Combinatorial synthesis of pyrazoloquinoline and pyrazoloacridine derivatives with high regioselectivity. Comb Chem High Throughput Screen. 2013 Jun 28;16(7):550-61. PubMed PMID: 23410044. 2: Ramaswamy B, Mrozek E, Kuebler JP, Bekaii-Saab T, Kraut EH. Phase II trial of pyrazoloacridine (NSC#366140) in patients with metastatic breast cancer. Invest New Drugs. 2011 Apr;29(2):347-51. doi: 10.1007/s10637-009-9338-1. Epub 2009 Oct 21. PubMed PMID: 19844661; PubMed Central PMCID: PMC3486428. 3: Galanis E, Buckner JC, Maurer MJ, Reid JM, Kuffel MJ, Ames MM, Scheithauer BW, Hammack JE, Pipoly G, Kuross SA. Phase I/II trial of pyrazoloacridine and carboplatin in patients with recurrent glioma: a North Central Cancer Treatment Group trial. Invest New Drugs. 2005 Oct;23(5):495-503. PubMed PMID: 16133802. 4: Reid JM, Walker DL, Miller JK, Benson LM, Tomlinson AJ, Naylor S, Blajeski AL, LoRusso PM, Ames MM. The metabolism of pyrazoloacridine (NSC 366140) by cytochromes p450 and flavin monooxygenase in human liver microsomes. Clin Cancer Res. 2004 Feb 15;10(4):1471-80. PubMed PMID: 14977851. 5: Hu Y, Krishan A, Nie W, Sridhar KS, Mayer LD, Bally M. Synergistic cytotoxicity of pyrazoloacridine with doxorubicin, etoposide, and topotecan in drug-resistant tumor cells. Clin Cancer Res. 2004 Feb 1;10(3):1160-9. PubMed PMID: 14871996. 6: Keshelava N, Tsao-Wei D, Reynolds CP. Pyrazoloacridine is active in multidrug-resistant neuroblastoma cell lines with nonfunctional p53. Clin Cancer Res. 2003 Aug 15;9(9):3492-502. PubMed PMID: 12960142. 7: Dees EC, Rowinsky EK, Noe DA, O'Reilly S, Adjei AA, Elza-Brown K, Donehower RC. A phase I and pharmacologic study of pyrazoloacridine and cisplatin in patients with advanced cancer. Invest New Drugs. 2003 Feb;21(1):75-84. PubMed PMID: 12795532. 8: Bastasch M, Panella TJ, Kretzschmer SL, Graham D, Mayo M, Williamson S. Phase II trial of pyrazoloacridine in advanced non-small cell carcinoma of the lung--a Kansas Cancer Institute and Thompson Cancer Survival Center Study. Invest New Drugs. 2002 Aug;20(3):339-42. PubMed PMID: 12201497. 9: Adjei AA, Reid JM, Erlichman C, Sloan JA, Pitot HC, Alberts SR, Goldberg RM, Hanson LJ, Ruben S, Boemer SA, Atherton P, Ames MM, Kaufmann SH. A phase I and pharmacologic study of pyrazoloacridine (NSC 366140) and carboplatin in patients with advanced cancer. Invest New Drugs. 2002 Aug;20(3):297-304. PubMed PMID: 12201492. 10: Plaxe SC, Blessing JA, Olt G, Husseinzadah N, Lentz SS, DeGeest K, Valea FA. A phase II trial of pyrazoloacridine (PZA) in squamous cell carcinoma of the cervix: a Gynecologic Oncology Group study. Cancer Chemother Pharmacol. 2002 Aug;50(2):151-4. Epub 2002 Jul 5. PubMed PMID: 12172981. 11: Grem JL, Harold N, Keith B, Chen AP, Kao V, Takimoto CH, Hamilton JM, Pang J, Pace M, Jasser GB, Quinn MG, Monahan BP. A phase I pharmacologic and pharmacodynamic study of pyrazoloacridine given as a weekly 24-hour continuous intravenous infusion in adult cancer patients. Clin Cancer Res. 2002 Jul;8(7):2149-56. PubMed PMID: 12114415. 12: Plaxe SC, Blessing JA, Morgan MA, Carlson J; Gynecologic Oncology Group. Phase II trial of pyrazoloacridine in recurrent platinum-resistant ovarian cancer: a Gynecologic Oncology Group study. Am J Clin Oncol. 2002 Feb;25(1):45-7. PubMed PMID: 11823695. 13: Plaxe SC, Blessing JA, Husseinzadeh N, Webster KD, Rader JS, Dunton CJ. Phase II trial of pyrazoloacridine in patients with persistent or recurrent endometrial carcinoma: a Gynecologic Oncology Group Study. Gynecol Oncol. 2002 Feb;84(2):241-4. PubMed PMID: 11812081. 14: Plaxe SC, Blessing JA, Bookman MA, Creasman WT. Phase II trial of pyrazoloacridine in recurrent platinum-sensitive ovarian cancer: a Gynecologic Oncology Group study. Gynecol Oncol. 2002 Jan;84(1):32-5. PubMed PMID: 11748972. 15: Kuebler JP, King GW, Triozzi P, Moore T, Kraut EH. Phase II study of pyrazoloacridine in metastatic renal cell carcinoma. Invest New Drugs. 2001;19(4):327-8. PubMed PMID: 11561693. 16: Plaxe SC, Blessing JA, Lucci JA, Hurteau JA. A phase II trial of pyrazoloacridine (PZA) in squamous carcinoma of the cervix--a Gynecologic Oncology Group Study. Invest New Drugs. 2001;19(1):77-80. PubMed PMID: 11291835. 17: Berg SL, Blaney SM, Sullivan J, Bernstein M, Dubowy R, Harris MB; Pediatric Oncology Group. Phase II trial of pyrazoloacridine in children with solid tumors: a Pediatric Oncology Group phase II study. J Pediatr Hematol Oncol. 2000 Nov-Dec;22(6):506-9. PubMed PMID: 11132217; PubMed Central PMCID: PMC4008246. 18: Pelley R, Ganapathi R, Wood L, Rybicki L, McLain D, Budd GT, Peereboom D, Olencki T, Bukowski RM. A phase II pharmacodynamic study of pyrazoloacridine in patients with metastatic colorectal cancer. Cancer Chemother Pharmacol. 2000;46(3):251-4. PubMed PMID: 11021744. 19: Vuky J, McCaffrey J, Ginsberg M, Mariani T, Bajorin DF, Bosl GJ, Motzer RJ. Phase II trial of pyrazoloacridine in patients with cisplatin-refractory germ cell tumors. Invest New Drugs. 2000 Aug;18(3):265-7. PubMed PMID: 10958596. 20: Dodd PM, McCaffrey JA, Mazumdar M, Icasiano E, Higgins G, Herr H, Bajorin DF. Phase II trial of pyrazoloacridine as second-line therapy for patients with unresectable or metastatic transitional cell carcinoma. Invest New Drugs. 2000 Aug;18(3):247-51. PubMed PMID: 10958593.

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