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Iniparib (SAR-240550; BSI-201; NSC-746045; IND-71677) is a novel, potent, and irreversible inhibitor of PARP1 [poly(ADP-ribose) polymerase-1] with potential anticancer activity. It was the first suspected PARP inhibitor to begin phase III clinical trials, but the trials were stopped due to disappointing outcomes. It showed high efficacy and effectiveness in triple-negative breast cancer (TNBC). When used against different types of cancer cells, including drug-resistant cell lines, iniparib exhibits broad-spectrum antiproliferative activity.
Physicochemical Properties
| Molecular Formula | C7H5IN2O3 | |
| Molecular Weight | 292.03 | |
| Exact Mass | 291.934 | |
| Elemental Analysis | C, 28.79; H, 1.73; I, 43.46; N, 9.59; O, 16.44 | |
| CAS # | 160003-66-7 | |
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| PubChem CID | 9796068 | |
| Appearance | Light yellow to yellow solid powder | |
| Density | 2.1±0.1 g/cm3 | |
| Boiling Point | 344.8±32.0 °C at 760 mmHg | |
| Flash Point | 162.3±25.1 °C | |
| Vapour Pressure | 0.0±0.8 mmHg at 25°C | |
| Index of Refraction | 1.696 | |
| LogP | 1.71 | |
| Hydrogen Bond Donor Count | 1 | |
| Hydrogen Bond Acceptor Count | 3 | |
| Rotatable Bond Count | 1 | |
| Heavy Atom Count | 13 | |
| Complexity | 228 | |
| Defined Atom Stereocenter Count | 0 | |
| SMILES | IC1C([H])=C([H])C(C(N([H])[H])=O)=C([H])C=1[N+](=O)[O-] |
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| 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) | |
| Chemical Name | 4-iodo-3-nitrobenzamide | |
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| HS Tariff Code | 2934.99.9001 | |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | PARP1 | ||
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| Cell Assay | The nine-day cell proliferation assay involves plating 2000 and 500 cells/well, respectively, in a 96-well plate for MDA-MB-436 and MDA-MB-231 cells. These cells are then treated with veliparib, cmpd-A, cmpd-C, Iniparib or Iniparib-met at 0, 0.0001, 0.01,0.1, 1 or 10 μM for nine days. A 96-well plate containing 1000 and 4000 cells/well, respectively, of MDAMB-231 and MDA-MB-436 cells is used for the five-day cell proliferation assay. The cells are treated with iniparib or iniparib-met at 0.0.1, 0.3, 1, 3, or 10 μM in the presence of 0, 1.8, 3.75, or 7.5 µM BSO for five days. In a 96-well plate, 1000 cells/well of DLD1+/+ and DLD1-/- cells are plated. The cells are then treated with TMZ at 0, 0.003, 0.01, 0.03, 0.1, 0.3, or 1 mM in the presence of 0, 0.005, 0.05, 0.5, or 5 µM veliparib or Iniparib for a period of five days. Cell titer glow is performed following treatment[1]. | ||
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| References |
[1]. Iniparib nonselectively modifies cysteine-containing proteins in tumor cells and is not a bona fide PARP inhibitor. Clin Cancer Res. 2012 Jan 15;18(2):510-23. [2]. Myc mediates cancer stem-like cells and EMT changes in triple negative breast cancers cells. PLoS One. 2017 Aug 17;12(8):e0183578. [3]. Differential effects of poly(ADP-ribose) polymerase inhibition on DNA break repair in human cells are revealed with Epstein-Barr virus. Proc Natl Acad Sci U S A. 2012 Apr 24;109(17):6590-5. |
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| Additional Infomation |
4-iodo-3-nitrobenzamide is a carbonyl compound and an organohalogen compound. Iniparib is a small molecule iodobenzamide with potential cytotoxic and antineoplastic activities. Although the mechanism of action is unknown, iniparib appears to be cytotoxic in cells with DNA alterations or DNA damage, like that found in tumor cells with mutations in the ataxia telangiectasia mutated (ATM) gene. ATM encodes a serine/threonine protein kinase and mutations of the gene are associated with ataxia telangiectasia and contribute to certain cancers such as T-cell acute lymphoblastic leukemia, B-cell chronic lymphocytic leukemia and B-cell non-Hodgkin lymphomas. |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.56 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.56 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4243 mL | 17.1215 mL | 34.2431 mL | |
| 5 mM | 0.6849 mL | 3.4243 mL | 6.8486 mL | |
| 10 mM | 0.3424 mL | 1.7122 mL | 3.4243 mL |