3-Aminobenzamide

Names

[ Name ]:
3-Aminobenzamide

[Synonym ]:
meta-aminobenzoylamine
m-Aminobenzamide
3-Aminobenzimide
Benzamide,m-amino
Benzamide, 3-amino-
3-Aminobenzamide
3-Amino-benzamide
MFCD00007989
EINECS 222-586-9
Benzamide,3-amino
INO1001
meta-aminobenzamide
3-NH2-Ph-CO-NH2
5-amino-benzamide
INO-1001

Biological Activity

[Description]:

3-Aminobenzamide is a potent inhibitor of PARP with IC50 of appr 50 nM in CHO cells, and acts as a mediator of oxidant-induced myocyte dysfunction during reperfusion.

[Related Catalog]:

Research Areas >> Cancer

[Target]

PARP:50 nM (IC50)

[In Vitro]

3-Aminobenzamide (>1 μM) causes more than 95% inhibition of PARP activity without significant cellular toxicity. INO-1001 significantly sensitizes CHO cells by blocking most of the DNA repair occurring between radiation fractions[1]. 3-Aminobenzamide 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 (Leprdb/db) mouse model, 3-Aminobenzamide ameliorates diabetes-induced albumin excretion and mesangial expansion, and also decreases diabetes-induced podocyte depletion[3]. 3-Aminobenzamide (1.6 mg/kg via intracerebral injection) prevents NAD+ depletion and improves water maze performance after controlled cortical impact (CCI) in mice[4].

[Kinase Assay]

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.

[Animal admin]

Male db/db (Leprdb/db) mice, together with nondiabetic control db/m mice on C57BLKs/J background, are used. INO-1001 and PJ-34 treatment are initiated at 5 weeks of age. In sterile water that is sweetened with NutraSweet, 4.8 g/L 3-Aminobenzamide and 2.4 g/L PJ-34 is dissolved. Control animals receive sweetened water only. The average inhibitor consumption is 60 mg/kg 3-Aminobenzamide and 30 mg/kg PJ-34.

[References]

[1]. Brock WA, et al. Radiosensitization of human and rodent cell lines by INO-1001, a novel inhibitor of poly(ADP-ribose) polymerase. Cancer Lett. 2004 Mar 18;205(2):155-60.

[2]. Radovits T, et al. Poly(ADP-ribose) polymerase inhibition improves endothelial dysfunction induced by reactive oxidant hydrogen peroxide in vitro. Eur J Pharmacol. 2007 Jun 14;564(1-3):158-66.

[3]. Szabo C, et al. Poly(ADP-ribose) polymerase inhibitors ameliorate nephropathy of type 2 diabetic Leprdb/db mice. Diabetes. 2006 Nov;55(11):3004-12.

[4]. Clark RS, et al. Local administration of the poly(ADP-ribose) polymerase inhibitor INO-1001 prevents NAD+ depletion and improves water maze performance after traumatic brain injury in mice. J Neurotrauma. 2007 Aug;24(8):1399-405.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
329.6±25.0 °C at 760 mmHg

[ Melting Point ]:
115-116 °C(lit.)

[ Molecular Formula ]:
C₇H₈N₂O

[ Molecular Weight ]:
136.151

[ Flash Point ]:
153.2±23.2 °C

[ Exact Mass ]:
136.063660

[ PSA ]:
69.11000

[ LogP ]:
0.33

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.633

[ Water Solubility ]:
ethanol: 50 mg/mL, clear, faintly yellow

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CU8992000

CHEMICAL NAME :: Benzamide, m-amino-

CAS REGISTRY NUMBER :: 3544-24-9

BEILSTEIN REFERENCE NO. :: 2802373

LAST UPDATED :: 199612

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C7-H8-N2-O

MOLECULAR WEIGHT :: 136.17

WISWESSER LINE NOTATION :: ZVR CZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - wild bird species

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Mammal - species unspecified Fibroblast

DOSE/DURATION :: 1 mmol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 254,13,1991

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P280-P301 + P312 + P330-P304 + P340 + P312-P305 + P351 + P338-P337 + P313

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
CU8992000

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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