| Identification | Back Directory | [Name]
N-CARBAMYL-L-GLUTAMIC ACID | [CAS]
1188-38-1 | [Synonyms]
OE 312
Carbaglu
N-Cbm-Glu-OH
carglumicaci
CargluMic Acid
ureidoglutaricacid
n-carbamylglutamate
carbamylglutamicacid
N-Carbamyl-L-glutamic
N-Carbamyl-L-glutamate
carbamino-l-glutamicacid
N-CarbaMoyl L- GlutaMate
(2S)-2-ureidoglutaric acid
N-CARBAMYL-L-GLUTAMIC ACID
N-CarbaMoyl-L-glutaMic Acid
N-CarbaMoyl-S-glutaMic Acid
(S)-2-Ureidopentanedioic acid
NCG,N-carbamyl-L-glutamic acid
Acide N-carbamoyl-L-glutamique
n-(aminocarbonyl)-l-glutamicaci
N-(AMinocarbonyl)-L-glutaMic Acid
L-Glutamic acid, N-(aminocarbonyl)-
N-CARBAMYL-L-GLUTAMIC ACID USP/EP/BP
N-carbamyl-L-glutamic acid crystalline
(2S)-2-(carbamoylamino)pentanedioic acid
(2S)-2-(aminocarbonylamino)pentanedioic acid
N-(Aminocarbonyl)-L-Glutamic Acid(Carglumic Acid) | [EINECS(EC#)]
601-569-3 | [Molecular Formula]
C6H10N2O5 | [MDL Number]
MFCD00047874 | [MOL File]
1188-38-1.mol | [Molecular Weight]
190.15 |
| Chemical Properties | Back Directory | [Melting point ]
174° | [Boiling point ]
438.1±45.0 °C(Predicted) | [density ]
1.499±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
DMSO (Slightly), Methanol (Slightly, Sonicated) | [form ]
Solid | [pka]
3.71±0.10(Predicted) | [color ]
White to Off-White | [InChI]
InChI=1S/C6H10N2O5/c7-6(13)8-3(5(11)12)1-2-4(9)10/h3H,1-2H2,(H,9,10)(H,11,12)(H3,7,8,13)/t3-/m0/s1 | [InChIKey]
LCQLHJZYVOQKHU-VKHMYHEASA-N | [SMILES]
C(O)(=O)[C@H](CCC(O)=O)NC(N)=O |
| Hazard Information | Back Directory | [Uses]
carbamylphosphate synthetase activator | [Uses]
N-Carbamyl-L-glutamic Acid has been shown to have protective effects against ammonia intoxication and is used in the treatment of acute hyperammonemia. | [Definition]
ChEBI: A urea that is the N-carbamoyl derivative of L-glutamic acid. An orphan drug used to treat a deficiency in the enzyme N-acetylglutamate synthase, which leads to acute hyperammonaemia. | [Biological Activity]
N-Carbamyl-L-glutamic acid (carglumic acid) is use to study its potential as a replacement therapy for N-acetylglutamate synthetase (NAGS) deficiency and to tre at hyperammonemia. | [Synthesis]
The general procedure for the synthesis of N-carbamoyl-L-glutamic acid from potassium cyanate and L-glutamic acid was as follows: 4 mmol of L-glutamic acid was dissolved in 20 mL of water and the solution was acidified using concentrated hydrochloric acid (37 μL, v/v). Subsequently, 12 mmol of potassium thiocyanate (KOCN) was added to the acidified solution. The reaction mixture was heated to 333 K under continuous stirring and maintained at this temperature for 4 hours. Upon completion of the reaction, the solution was cooled to room temperature and transferred to a glass vial sealed with a closure film, which was perforated to promote solvent evaporation until a white solid was observed to precipitate. Crystals of (I) suitable for X-ray single crystal diffraction analysis were grown at room temperature by slow evaporation of the ethanol solution (see Scheme 1). The yield of this synthetic method was 62% and the melting points of the resulting products ranged from 170°C to 171°C. This experimental procedure is an improvement and optimization of a previously reported method. | [in vivo]
The results show that Carglumic acid, but not the vehicle control, markedly inhibits tumor growth. In the orthotopic pancreatic cancer model, tumor growth inhibition by Carglumic acid on day 21 is 80% (P<0.01). In the orthotopic triple-negative breast cancer model, tumor growth inhibition by Carglumic acid on day 20 is 82% (P<0.01). These results indicate that Carglumic acid suppresses tumor growth in pancreatic cancer and triple-negative breast cancer. On day 20, mean tumor growth inhibition in orally and intravenously treated mice is 55% and 93%, respectively, relative to untreated mice (P<0.01)[1]. | [References]
[1] Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 225 - 232
[2] Pharmaceutical Chemistry Journal, 1978, vol. 12, # 5, p. 601 - 606
[3] Khimiko-Farmatsevticheskii Zhurnal, 1978, vol. 12, # 5, p. 53 - 59 |
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