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MedKoo Cat#: 584279 | Name: Bropirimine
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Description:

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

Bropirimine is an immunostimulant that has an antitumor effect on superficial transitional cell carcinoma of the bladder.

Chemical Structure

Bropirimine
Bropirimine
CAS#56741-95-8

Theoretical Analysis

MedKoo Cat#: 584279

Name: Bropirimine

CAS#: 56741-95-8

Chemical Formula: C10H8BrN3O

Exact Mass: 264.9851

Molecular Weight: 266.10

Elemental Analysis: C, 45.14; H, 3.03; Br, 30.03; N, 15.79; O, 6.01

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
50mg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
Bropirimine; ABPP; NSC 149027; NSC-149027; NSC149027; PNU 54461; PNU54461; PNU-54461; U-54461; U54461; U 54461;
IUPAC/Chemical Name
4(1H)-Pyrimidinone, 2-amino-5-bromo-6-phenyl-
InChi Key
CIUUIPMOFZIWIZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H8BrN3O/c11-7-8(6-4-2-1-3-5-6)13-10(12)14-9(7)15/h1-5H,(H3,12,13,14,15)
SMILES Code
O=C1N=C(N)NC(C2=CC=CC=C2)=C1Br
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

Preparing Stock Solutions

The following data is based on the product molecular weight 266.10 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.

Recalculate based on batch purity %
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: Suzuki H, Mochizuki A, Yoshimura K, Miyamoto Y, Kaneko K, Inoue T, Chikazu D, Takami M, Kamijo R. Bropirimine inhibits osteoclast differentiation through production of interferon-β. Biochem Biophys Res Commun. 2015 Nov 6;467(1):146-51. doi: 10.1016/j.bbrc.2015.09.092. Epub 2015 Sep 21. PubMed PMID: 26399683. 2: Dammermann W, Bochmann D, Bentzien F, Komorowski L, Steinhagen K, Ullrich S, van Lunzen J, Lüth S. CMV specific cytokine release assay in whole blood is optimized by combining synthetic CMV peptides and toll like receptor agonists. J Immunol Methods. 2014 Dec 1;414:82-90. doi: 10.1016/j.jim.2014.10.011. Epub 2014 Oct 30. PubMed PMID: 25450001. 3: Dammermann W, Wollenberg L, Bentzien F, Lohse A, Lüth S. Toll like receptor 2 agonists lipoteichoic acid and peptidoglycan are able to enhance antigen specific IFNγ release in whole blood during recall antigen responses. J Immunol Methods. 2013 Oct 31;396(1-2):107-15. doi: 10.1016/j.jim.2013.08.004. Epub 2013 Aug 15. PubMed PMID: 23954282. 4: Sarosdy MF, Tangen CM, Weiss GR, Nestok BR, Benson MC, Schellhammer PF, Sagalowsky AI, Wood DP Jr, Crawford ED. A phase II clinical trial of oral bropirimine in combination with intravesical bacillus Calmette-Guérin for carcinoma in situ of the bladder: a Southwest Oncology Group Study. Urol Oncol. 2005 Nov-Dec;23(6):386-9. PubMed PMID: 16301114; PubMed Central PMCID: PMC3632328. 5: Kassouf W, Kamat AM. Current state of immunotherapy for bladder cancer. Expert Rev Anticancer Ther. 2004 Dec;4(6):1037-46. Review. PubMed PMID: 15606331. 6: Perabo FG, Müller SC. Current and new strategies in immunotherapy for superficial bladder cancer. Urology. 2004 Sep;64(3):409-21. Review. PubMed PMID: 15351555. 7: Schenkman E, Lamm DL. Superficial bladder cancer therapy. ScientificWorldJournal. 2004 Jun 28;4 Suppl 1:387-99. Review. PubMed PMID: 15349563. 8: Wynalda MA, Wynalda KM, Amore BM, Fagerness PE, Wienkers LC. Characterization of bropirimine O-glucuronidation in human liver microsomes. Xenobiotica. 2003 Oct;33(10):999-1011. PubMed PMID: 14555337. 9: Vroegop SM, Chapman DL, Decker DE, Galinet LA, Brideau RJ, Ready KA, Dunn CJ, Buxser SE. Pharmacokinetic properties, induction of interferon, and efficacy of selected 5-halo-6-phenyl pyrimidinones, bropirimine analogues, in a model of severe experimental autoimmune encephalomyelitis. Int J Immunopharmacol. 1999 Oct;21(10):647-62. PubMed PMID: 12609460. 10: Akira S, Hemmi H. Recognition of pathogen-associated molecular patterns by TLR family. Immunol Lett. 2003 Jan 22;85(2):85-95. Review. PubMed PMID: 12527213. 11: Tei Y, Matsuyama H, Wada T, Kurisu H, Tahara M, Naito K. In vitro antitumor activity of bropirimine against urinary bladder tumor cells. Anticancer Res. 2002 May-Jun;22(3):1667-71. PubMed PMID: 12168852. 12: Kamat AM, Lamm DL. Immunotherapy for bladder cancer. Curr Urol Rep. 2001 Feb;2(1):62-9. Review. PubMed PMID: 12084297. 13: Yamazaki S, Hayashi M, Toth LN, Ozawa N. Lack of interaction between bropirimine and 5-fluorouracil on human dihydropyrimidine dehydrogenase. Xenobiotica. 2001 Jan;31(1):25-31. PubMed PMID: 11334264. 14: Ríos González E, Martínez-Piñeiro Lorenzo L, Martínez-Piñeiro Caramés JA, de la Peña Barthel JJ. [Immunotherapy in superficial bladder carcinoma]. Arch Esp Urol. 2000 Dec;53(10):879-92. Review. Spanish. PubMed PMID: 11213392. 15: Kim JC, Steinberg GD. The limits of bacillus Calmette-Guerin for carcinoma in situ of the bladder. J Urol. 2001 Mar;165(3):745-56. Review. PubMed PMID: 11176460. 16: Zlotta AR, Schulman CC. Biological response modifiers for the treatment of superficial bladder tumors. Eur Urol. 2000;37 Suppl 3:10-5. Review. PubMed PMID: 10828682. 17: Hannah DR, Sherer EC, Davies RV, Titman RB, Laughton CA, Stevens MF. Structural studies on bioactive compounds. Part 29: palladium catalysed arylations and alkynylations of sterically hindered immunomodulatory 2-amino-5-halo-4,6-(disubstituted)pyrimidines. Bioorg Med Chem. 2000 Apr;8(4):739-50. PubMed PMID: 10819163. 18: Echezarreta-López M, Torres-Labandeira JJ, Castiñeiras-Seijo L, Santana-Penín L, Vila-Jato JL. Complexation of the interferon inducer, bropirimine, with hydroxypropyl-beta-cyclodextrin. Eur J Pharm Sci. 2000 Feb;9(4):381-6. PubMed PMID: 10664478. 19: Akaza H, Shimazaki J, Tashiro K, Kotake T, Okajima E, Kagawa S, Machida T. [Late phase II clinical study for bropirimine (U-54461S) in situ carcinoma of the bladder: follow-up investigation. Bropirimine Study Group]. Gan To Kagaku Ryoho. 1999 Nov;26(13):2049-53. Japanese. PubMed PMID: 10584570. 20: Witjes WP, König M, Boeminghaus FP, Hall RR, Schulman CC, Zurlo M, Fittipaldo A, Riggi M, Debruyne FM. Results of a European comparative randomized study comparing oral bropirimine versus intravesical BCG treatment in BCG-naive patients with carcinoma in situ of the urinary bladder. European Bropirimine Study Group. Eur Urol. 1999 Dec;36(6):576-81. PubMed PMID: 10559611.