| Identification | Back Directory | [Name]
CarbaMiMidothioic acid, 3-cyanopropyl ester, hydrochloride (1:1) | [CAS]
66592-89-0 | [Synonyms]
Kevetrin HCl
KEVETRIN, NSC 525990
Kevetrin (hydrochloride)
Thioureidobutyronitrile HCl
Kevetrin hydrochloride, >98%
3-cyanopropyl carbamimidothioate
Kevetrin hydrochloride >=98% (HPLC)
Thioureidobutyronitrile hydrochloride
4-Isothioureidobutyronitrile hydrochloride
3-cyanopropyl carbamimidothioate,hydrochloride
3-Cyanopropyl carbamimidothioate hydrochloride (1:1)
CarbaMiMidothioic acid, 3-cyanopropyl ester, hydrochloride (1
Carbamimidothioic acid, 3-cyanopropyl ester, monohydrochloride
CarbaMiMidothioic acid, 3-cyanopropyl ester, hydrochloride (1:1) | [Molecular Formula]
C5H10ClN3S | [MDL Number]
MFCD22572767 | [MOL File]
66592-89-0.mol | [Molecular Weight]
179.67 |
| Chemical Properties | Back Directory | [Melting point ]
125-127 °C | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [solubility ]
DMSO:38.0(Max Conc. mg/mL);211.5(Max Conc. mM)
Water:36.0(Max Conc. mg/mL);200.37(Max Conc. mM)
Ethanol:21.0(Max Conc. mg/mL);116.88(Max Conc. mM)
PBS (pH 7.2):10.0(Max Conc. mg/mL);55.66(Max Conc. mM) | [form ]
A crystalline solid | [color ]
White to off-white | [Water Solubility ]
H2O: 2mg/mL, clear |
| Hazard Information | Back Directory | [Uses]
4-Isothioureidobutyronitrile-13C2, 15N3 Hydrochloride acts as a reagent in the synthesis of nitrile derivatives and their pharmaceutical uses and compositions. | [Biological Activity]
Kevetrin is an activator/stabilizer of wild type p53 tumor suppressor protein in human lung carcinoma and ovarian cancer cells th at induces cell cycle arrest and apoptosis. Additionally Kevetrin down-regulates oncogenic mutant p53 in OVCAR-3 ovarian cancer cells. Kevetrin inhibits tumor growth in xenograft model of ovarian cancer. | [Synthesis]
General procedure for the synthesis of 3-cyanopropylisothiourea hydrochloride from 4-chlorobutanenitrile and thiourea: γ-chlorobutanenitrile (50 g, 48±3 mmol) and thiourea (4.04 g, 53.1 mmol) were dissolved in 40 mL of water. The reaction mixture was heated to reflux for 3 to 4 hours. After completion of the reaction, the water was removed by evaporation, 20 mL of ethanol was added and evaporated again, and this operation was repeated three times. Subsequently, 10 mL of methanol and 30 mL of acetone were added to the residue and the mixture was stirred for 1 hour. The crystalline product was collected by filtration and dried under high vacuum overnight. A final 5.44 g (30.3 mmol, yield 62 ± 7%) of white crystalline product was obtained with a melting point of 134-135 °C and a purity greater than 97%. The product was confirmed by 1H NMR (300 MHz, d6-DMSO): δ 1.89 (m, 2H), 2.63 (t, 2H, J = 7.2 Hz), 3.23 (t, 2H, J = 7.2 Hz), 3.38 (s, 3H). 13C NMR (75 MHz, d6-DMSO) δ 15.3, 25.0, 28.8, 119.8 , 169.7. molecular formula C5H10ClN3S, exact mass 179.03. mass spectral analysis showed m/z 179.03 (100.0%), 181.03 (32.1%), 180.03 (7.4%), 181.02 (4.5%), 182.03 (2.0%), 183.02 (1.5%). Elemental analysis calculated values (%): C 33.42, H 5.61, Cl 19.73, N 23.39, S 17.85; measured values: C 33.44, H 5.48, N 23.40, S 18.31. | [in vivo]
Kevetrin hydrochloride (150-200 mg/kg; i.p.; 20 d) induces ~40% cell death in OV-90 or OVCAR-3 xenograft tumors, also inhibits tumor growth and extents survival time of mice with tumor xenograft mode[2].
| Animal Model: | A2780 xenograft tumor model in nude mice[2] | | Dosage: | 200 mg/kg | | Administration: | Intraperitoneal injection; 3 times per week, for 20 days | | Result: | Inhibited tumor growth and suppressed the tumor volume. |
| Animal Model: | SKOV-3 xenograft ascites model in mice[2] | | Dosage: | 150 mg/kg | | Administration: | Intraperitoneal injection | | Result: | Prolonged the survival time of mice, and maintained 100% survival rate more over 35 days. |
| [References]
[1] Patent: WO2010/135170, 2010, A2. Location in patent: Page/Page column 20-21 |
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| Company Name: |
SPIRO PHARMA
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| Tel: |
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| Website: |
www.spiropharma.com.cn |
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