Iniparib
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Hodoodo CAT#: H200582

CAS#: 160003-66-7

Description: Iniparib, also known as SAR-240550; NSC-746045; BSI-201; IND-71677; NIBA; INO-2BA, is a small-molecule prodrug inhibitor of the nuclear enzyme poly(ADP-ribose) polymerase-1 (PARP-1) with potential chemosensitizing, radiosensitizing and antineoplastic activities. In vivo, PARP-1 inhibitor BSI-201 is converted to the active drug, which selectively binds to PARP-1 and inhibits PARP-1- mediated DNA repair. Consequently, this agent may enhance the cytotoxicity of DNA-damaging agents and reverse tumor cell resistance to chemotherapy and radiation therapy. In addition, PARP-1 inhibitor BSI-201 may exhibit direct antineoplastic activity against cancers defective in DNA repair.

Chemical Structure

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Iniparib
CAS# 160003-66-7
Instruction

Theoretical Analysis

Hodoodo Cat#: H200582
Name: Iniparib
CAS#: 160003-66-7
Chemical Formula: C7H5IN2O3
Exact Mass: 291.93
Molecular Weight: 292.033
Elemental Analysis: C, 28.79; H, 1.73; I, 43.46; N, 9.59; O, 16.44

Price and Availability

Size Price Availability Quantity
200mg USD 250 2 Weeks
500mg USD 450 2 Weeks
1g USD 750 2 Weeks
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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

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, 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:
In vitro activity:
In vivo activity:

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.

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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 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.