Basic information Safety Supplier Related

(S)-2-(4-(piperidin-3-yl)phenyl)-2H-indazole-7-carboxaMide

Basic information Safety Supplier Related

(S)-2-(4-(piperidin-3-yl)phenyl)-2H-indazole-7-carboxaMide Basic information

Product Name:
(S)-2-(4-(piperidin-3-yl)phenyl)-2H-indazole-7-carboxaMide
Synonyms:
  • MK-4827 (HCl)
  • MK-4827 (hydrochloride)
  • CS-787
  • Niraparib(MK4827) hydrochloride
  • 2-[4-[(3S)-piperidin-3-yl]phenyl]indazole-7-carboxamide,hydrochloride
  • Zejula
  • Niraparib hydrochloride
  • 2H-Indazole-7-carboxamide, 2-[4-(3S)-3-piperidinylphenyl]-, hydrochloride (1:1)
CAS:
1038915-64-8
MF:
C19H20N4O
MW:
320.3883
Product Categories:
  • API
Mol File:
1038915-64-8.mol
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(S)-2-(4-(piperidin-3-yl)phenyl)-2H-indazole-7-carboxaMide Chemical Properties

Melting point:
144 °C
storage temp. 
Store at -20°C
solubility 
Soluble in DMSO
form 
Solid
color 
White to light yellow
InChI
InChI=1/C19H20N4O/c20-19(24)17-5-1-3-15-12-23(22-18(15)17)16-8-6-13(7-9-16)14-4-2-10-21-11-14/h1,3,5-9,12,14,21H,2,4,10-11H2,(H2,20,24)/t14-/s3
InChIKey
PCHKPVIQAHNQLW-WDHUHKLTNA-N
SMILES
N1=C2C(C=CC=C2C(N)=O)=CN1C1=CC=C([C@@H]2CCCNC2)C=C1 |&1:16,r|
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(S)-2-(4-(piperidin-3-yl)phenyl)-2H-indazole-7-carboxaMide Usage And Synthesis

Uses

Niraparib hydrochloride (MK-4827 hydrochloride) is a highly potent and orally bioavailable PARP1 and PARP2 inhibitor with IC50s of 3.8 and 2.1 nM, respectively. Niraparib hydrochloride leads to inhibition of repair of DNA damage, activates apoptosis and shows anti-tumor activity[1][2][3].

in vivo

Niraparib is well tolerated and demonstrates efficacy as a single agent in a xenograft model of BRCA-1 deficient cancer. Niraparib is well tolerated in vivo and demonstrates efficacy as a single agent in a xenograft model of BRCA-1 deficient cancer. Niraparib is characterized by acceptable pharmacokinetics in rats with plasma clearance of 28 (mL/min)/kg, very high volume of distribution (Vdss=6.9 L/kg), long terminal half-life (t1/2=3.4 h), and excellent bioavailability, F = 65%[1]. Niraparib enhances radiation response of p53 mutant Calu-6 tumor in both cases, with the single daily dose of 50 mg/kg being more effective than 25 mg/kg given twice daily[3].

IC 50

PARP-2: 2.1 nM (IC50); PARP-1: 3.8 nM (IC50); V-PARP: 330 nM (IC50); TANK-1: 570 nM (IC50); PARP-3: 1300 nM (IC50)

References

[1] Jones P, et al. Discovery of 2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (MK-4827): a novel oral poly(ADP-ribose)polymerase (PARP) inhibitor efficacious in BRCA-1 and -2 mutant tumors. J Med Chem. 2009 Nov 26;52(22):7170-85. DOI:10.1021/jm901188v
[2] Bridges KA, et al. Niraparib (MK-4827), a novel poly(ADP-Ribose) polymerase inhibitor, radiosensitizes human lung and breast cancer cells. Oncotarget. 2014 Jul 15;5(13):5076-86. DOI:10.18632/oncotarget.2083
[3] Wang L, et al. MK-4827, a PARP-1/-2 inhibitor, strongly enhances response of human lung and breast cancer xenografts to radiation. Invest New Drugs. 2012 Dec;30(6):2113-20. DOI:10.1007/s10637-011-9770-x
[4] Mirza MR, et al. Niraparib Maintenance Therapy in Platinum-Sensitive, Recurrent Ovarian Cancer. N Engl J Med. 2016 Dec 1;375(22):2154-2164. DOI:10.1056/NEJMoa1611310

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