3-aminobenzamide

• ChemBase编号: 72529
• 分子式: C7H8N2O
• 平均质量: 136.15122
• 单一同位素质量: 136.06366289
• SMILES: c1ccc(cc1C(=O)N)N
• Canonical SMILES: Nc1cccc(c1)C(=O)N
• InChI: InChI=1S/C7H8N2O/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,8H2,(H2,9,10)
• InChIKey: GSCPDZHWVNUUFI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-aminobenzamide
• IUPAC传统名: 3-aminobenzamide; benzamide, 3-amino-
• 别名: 3-氨基苯甲酰胺; meta-Aminobenzamide; -AB; 3-ABA; 3-AB; 3-Aminobenzamide; INO-1001; 3-Aminobenzamide; PARP Inhibitor

登记号

• CAS号: 3544-24-9
• EC号: 222-586-9
• MDL号: MFCD00007989
• Beilstein号: 2802373
• PubChem SID: 24855089; 24278206; 162037454
• PubChem CID: 1645
• CHEBI ID: 64042
• Chemspider ID: 1583
• 维基百科标题: 3-Aminobenzamide

理论计算性质

• Acid pKa: 14.705779
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): -0.0073407255
• LogD (pH = 7.4): -0.005068868
• Log P: -0.0050398437
• 摩尔折射率: 39.8368 cm^3
• 极化性: 14.303061 Å^3
• 极化表面积: 69.11 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; DMSO: soluble; ethanol: soluble50 mg/mL, clear, faintly yellow; H2O: soluble (may require gentle heating)
• 外观: Off-white powder; white to off-white powder
• 熔点: 111-115°C; 115 - 116°C; 115-116 °C(lit.); 115-116°C; 116 - 118°C
• 沸点: 329°C
• 密度: 1.233g/cm^3
• 分配系数: 0.33
• 疏水性(logP): -0.252

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• 保存注意事项: Harmful/Irritant/Light Sensitive/Store under inert gas
• RTECS编号: CU8992000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38; R36/37/38
• 安全公开号: 26-36; 26-37; R
• TSCA收录: 否
• GHS危险品标识: GHS exclamation mark; GHS07
• GHS警示词: DANGER; Warning
• NFPA704:
  

  0

  2

  0
• 半数致死量: 1000mg/kg (oral, bird)
• GHS危险声明: 302, 315, 319, 335; H302-H315-H319-H335
• GHS警示性声明: 351, 338; P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 作用靶点: PARP
• 相关基因信息: mouse ... Parp1(11545)

产品相关信息

• 纯度: ≥99% (TLC); 95%; 97%; 98%
• 成盐信息: Free Base
• 线性分子式: H2NC6H4CONH2

详细说明

MP Biomedicals - 02159028

Purity: 97%
Endogenous poly-ADP-ribosyltransferase inhibitor.

Selleck Chemicals - S1132

Research Area

• Description: Reperfusion injury, Malignant melanoma

Biological Activity

• Description: INO-1001 is a potent inhibitor of PARP with IC50 of 50 nM and a mediator of oxidant-induced myocyte dysfunction during reperfusion.
• Targets: PARP
• IC50: 50 nM ^[1]
• In Vitro: INO-1001 (>1 μM) leads to more than 95% inhibition of PARP activity without significant cellular toxicity. In addition, INO-1001 significantly sensitizes CHO cells by blocking most of the DNA repair occurring between radiation fractions. ^[1] Inhibition of PARP activity by INO-1001 significantly improves endothelial function by enhancing the acetylcholine-induced, endothelium-dependent, nitric oxide mediated vasorelaxation after exposure with 400 μM H₂O₂. ^[2]
• In Vivo: In a db/db (Lepr_db/db) mouse model, INO-1001 ameliorates diabetes-induced albumin excretion and mesangial expansion, and also decreases diabetes-induced podocyte depletion. ^[3] Treatment with INO-1001 (1.6 mg/kg via intracerebral injection) prevents NAD+ depletion and improves water maze performance after controlled cortical impact (CCI) in mice. ^[4]
• Clinical Trials: INO-1001 is currently in Phase II clinical trials in patients with Acute Myocardial Infarction.

Combination Therapy

• Description: In a mismatch repair (MMR)-deficient xenograft, INO-1001 prior to isolated limb infusion (ILI) significantly increased the efficacy of temozolomide (TMZ) and reduces the increase in tumor volume of advanced extremity malignant melanoma than TMZ-ILI alone. ^[5]

Protocol

• Protocol: Kinase Assay ^[1]
• PARP enzyme activity: PARP activity is measured with a PARP Activity Assay Kit. This method measures relative PARP activity by determining the level of incorporation of ₃H-NAD into trichloroacetic acid (TCA) precipitable material in the presence of sheared genomic DNA, which activates PARP. The reaction mixture is added directly to washed cultures in 12-well culture plates and the reaction is allowed to proceed for 60 minutes at 37 °C before the cells are removed mechanically, transferred to a microcentrifuge tube, and precipitated with ice-cold 5% TCA.
• Protocol: Animal Study ^[3]
• Animal Models: Male db/db (Lepr_db/db) mice.
• Formulation: INO-1001 is dissolved in water.
• Doses: ≤60 mg/kg
• Administration: Administered via p.o.

References

• References: [1] Brock WA, et al. Cancer Lett. 2004, 205(2), 155-160.
• References: [2] Radovits T, et al. Eur J Pharmacol. 2007, 564(1-3), 158-166.
• References: [3] Szabó C, et al. Diabetes. 2006, 55(11), 3004-3012.
• References: [4] Clark RS, et al. J Neurotrauma. 2007, 24(8), 1399-1405.
• References: [5] Toshimitsu H, et al. Ann Surg Oncol. 2010, 17(8), 2247-2254.

Sigma Aldrich - A0788

Biochem/physiol Actions
3-Aminobenzamide is an inhibitor of poly (ADP-ribose) polymerase (PARP).

参考文献

• Kozak, K.R. and Ross, I.A., Biochem. Biophys. Res. Commun. , 179 : 1225, (1991).
• Toshimitsu H, et al. Ann Surg Oncol. 2010, 17(8), 2247-2254.
• Brock WA, et al. Cancer Lett. 2004, 205(2), 155-160.
• Radovits T, et al. Eur J Pharmacol. 2007, 564(1-3), 158-166.
• Szabó C, et al. Diabetes. 2006, 55(11), 3004-3012.
• Clark RS, et al. J Neurotrauma. 2007, 24(8), 1399-1405.