Synonym
BSI-201; BSI201; BSI 201; NSC746045; NSC-746045; NSC 746045; ND-71677; NIBA; INO-2BA; SAR-240550; Iniparib
IUPAC/Chemical Name
4-iodo-3-nitrobenzamide
InChi Key
MDOJTZQKHMAPBK-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H5IN2O3/c8-5-2-1-4(7(9)11)3-6(5)10(12)13/h1-3H,(H2,9,11)
SMILES Code
O=C(N)C1=CC=C(I)C([N+]([O-])=O)=C1
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, not soluble in water.
Shelf Life
>5 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
Iniparib (previously BSI 201) (4-iodo-3-nitrobenzamide) is a drug that acts as an irreversible inhibitor of PARP1 (hence, it is a PARP inhibitor) and possibly other enzymes through covalent modification. It is undergoing clinical trials for treatment of some types of breast cancer. It is the first PARP inhibitor to commence phase III clinical trials. The first was for breast cancer, another has started for squamous cell lung cancer. Preliminary results in June 2009 on triple-negative breast cancer were promising. Later results showed increased median survival of triple negative breast cancer patients from 7.7 to 12.2 months. However, Phase III results disclosed in January 2011 were disappointing. Since December 2009, the FDA have been fast-tracking the New Drug Application of iniparib for triple-negative breast cancer. (source: http://en.wikipedia.org/wiki/Iniparib).
Iniparib (previously BSI 201) (4-iodo-3-nitrobenzamide) is a drug that acts as an irreversible inhibitor of PARP1 (hence, it is a PARP inhibitor) and possibly other enzymes through covalent modification. It is undergoing clinical trials for treatment of some types of breast cancer. It is the first PARP inhibitor to commence phase III clinical trials. The first was for breast cancer, another has started for squamous cell lung cancer. Preliminary results in June 2009 on triple-negative breast cancer were promising. Later results showed increased median survival of triple negative breast cancer patients from 7.7 to 12.2 months. However, Phase III results disclosed in January 2011 were disappointing. Since December 2009, the FDA have been fast-tracking the New Drug Application of iniparib for triple-negative breast cancer. (source: http://en.wikipedia.org/wiki/Iniparib).
Biological target:
Iniparib (BSI-201) is an irreversible inhibitor of PARP1, used in the research of triple negative breast cancer.
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
102.73 |
| DMSO |
62.7 |
214.59 |
| DMSO:PBS (pH 7.2) (1:1) |
0.5 |
1.71 |
| Ethanol |
23.5 |
80.47 |
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
292.03
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:
TBD
1: Pal SK, Childs BH, Pegram M. Triple negative breast cancer: unmet medical needs. Breast Cancer Res Treat. 2010 Dec 15. [Epub ahead of print] PubMed PMID: 21161370.
2: Liang H, Tan AR. Iniparib, a PARP1 inhibitor for the potential treatment of cancer, including triple-negative breast cancer. IDrugs. 2010 Sep;13(9):646-56. Review. PubMed PMID: 20799148.
3: He JX, Yang CH, Miao ZH. Poly(ADP-ribose) polymerase inhibitors as promising cancer therapeutics. Acta Pharmacol Sin. 2010 Sep;31(9):1172-80. Epub 2010 Aug 2. PubMed PMID: 20676117.
4: Maxmen A. Beyond PARP inhibitors: agents in pipelines target DNA repair mechanisms. J Natl Cancer Inst. 2010 Aug 4;102(15):1110-1. Epub 2010 Jul 28. PubMed PMID: 20668266.
5: Hashimoto K, Tamura K. [Breakthrough breast cancer treatment--PARP inhibitor, BRCA, and triple negative breast cancer]. Gan To Kagaku Ryoho. 2010 Jul;37(7):1187-91. Review. Japanese. PubMed PMID: 20647696.
6: Gartner EM, Burger AM, Lorusso PM. Poly(adp-ribose) polymerase inhibitors: a novel drug class with a promising future. Cancer J. 2010 Mar-Apr;16(2):83-90. Review. PubMed PMID: 20404603.
7: Pal SK, Mortimer J. Triple-negative breast cancer: novel therapies and new directions. Maturitas. 2009 Aug 20;63(4):269-74. Epub 2009 Jul 25. Review. PubMed PMID: 19632796.
8: BiPar Sciences presents interim phase 2 results for PARP inhibitor BSI-201 at San Antonio Breast Cancer Symposium. Cancer Biol Ther. 2009 Jan;8(1):2-3. PubMed PMID: 19455741.
9: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Sep;30(7):543-88. PubMed PMID: 18985183.
10: Bauer PI, Mendeleyeva J, Kirsten E, Comstock JA, Hakam A, Buki KG, Kun E. Anti-cancer action of 4-iodo-3-nitrobenzamide in combination with buthionine sulfoximine: inactivation of poly(ADP-ribose) polymerase and tumor glycolysis and the appearance of a poly(ADP-ribose) polymerase protease. Biochem Pharmacol. 2002 Feb 1;63(3):455-62. PubMed PMID: 11853696.
11: Kirsten E, Kun E. Cancer cell selectivity of 5-iodo-6-aminobenzopyrone (INH2BP) and methyl-3,5-diiodo-4(4'-methoxyphenoxy) benzoate (DIME). Int J Mol Med. 2000 Mar;5(3):279-81. PubMed PMID: 10677569.
12: Mendeleyev J, Kirsten E, Hakam A, Buki KG, Kun E. Potential chemotherapeutic activity of 4-iodo-3-nitrobenzamide. Metabolic reduction to the 3-nitroso derivative and induction of cell death in tumor cells in culture. Biochem Pharmacol. 1995 Aug 25;50(5):705-14. PubMed PMID: 7669074.
13: Chuang AJ, Killam KF Jr, Chuang RY, Mendeleyev J, Kun E. Comparison of the cytotoxic and antiretroviral effects of 3-nitrosobenzamide and 4-iodo-3-nitrobenzamide. Proc West Pharmacol Soc. 1994;37:117-9. PubMed PMID: 7527151.
