5-Aminolevulinic acid hydrochloride

Names

[ Name ]:
5-Aminolevulinic acid hydrochloride

[Synonym ]:
5-Aminolevulinic acid hydrochloride
MFCD00012869
EINECS 226-679-5

Biological Activity

[Description]:

5-Aminolevulinic acid HCl is an intermediate in heme biosynthesis in the body and the universal precursor of tetrapyrroles.Target: Others5-Aminolevulinic acid is a non-fluorescent prodrug that leads to intracellular accumulation of fluorescent porphyrins in malignant gliomas-a finding that is under investigation for intraoperative identification and resection of these tumours. Median follow-up was 35.4 months (95% CI 1.0-56.7). Contrast-enhancing tumour was resected completely in 90 (65%) of 139 patients assigned 5-aminolevulinic acid compared with 47 (36%) of 131 assigned white light (difference between groups 29% [95% CI 17-40], p<0.0001). Patients allocated 5-aminolevulinic acid had higher 6-month progression free survival than did those allocated white light (41.0% [32.8-49.2] vs 21.1% [14.0-28.2]; difference between groups 19.9% [9.1-30.7], p=0.0003, Z test) [1]. 5-ALA alone proved to be insufficient in attaining gross total resection without the danger of incurring postoperative neurological deterioration. Furthermore, in the case of functional grade III gliomas, iMRI in combination with functional neuronavigation was significantly superior to the 5-ALA resection technique [2].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Autophagy >> Mitophagy

Research Areas >> Metabolic Disease

Natural Products >> Others

[References]

[1]. Stummer, W., et al., Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial. Lancet Oncol, 2006. 7(5): p. 392-401.

[2]. Eyupoglu, I.Y., et al., Improving the extent of malignant glioma resection by dual intraoperative visualization approach. PLoS One, 2012. 7(9): p. e44885.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
311.5±27.0 °C at 760 mmHg

[ Melting Point ]:
~150 °C (dec.)

[ Molecular Formula ]:
C₅H₁₀ClNO₃

[ Molecular Weight ]:
167.59

[ Flash Point ]:
142.2±23.7 °C

[ PSA ]:
80.39000

[ LogP ]:
-0.79

[ Appearance of Characters ]:
powder

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.482

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
H2O: 50 mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OI1640000

CHEMICAL NAME :: Levulinic acid, 5-amino-, hydrochloride (8CI)

CAS REGISTRY NUMBER :: 5451-09-2

LAST UPDATED :: 199304

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C5-H9-N-O3.Cl-H

MOLECULAR WEIGHT :: 167.61

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi,Xn

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin . R66:Repeated exposure may cause skin dryness or cracking. R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .

[ Safety Phrases ]:
S26-S36/37-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
OI1640000

[ HS Code ]:
2922509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922509090

[ Summary ]:
2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Identification and Characterization of EDTA Test Strip Interfering Substances Using a Digital Color Detector.

Clin. Lab. 61 , 785-91, (2015)

Rapid test strips for ethylenediaminetetraacetic acid (EDTA) can be used to verify correct specimen types for clinical assays which require, or cannot be performed on, plasma collection tubes containi...

N-3 fatty acids improve body composition and insulin sensitivity during energy restriction in the rat.

Prostaglandins Leukot. Essent. Fatty Acids 91(5) , 203-11, (2014)

The hypothesis that n-3 polyunsaturated fatty acids (PUFA) could contribute to maintain muscle mass during energy restriction aiming to weight loss was tested in the rat, with special attention paid t...

Determination of free fatty acids in human serum by HPLC with fluorescence detection.

J. Chromatogr. Sci. 53 , 537-41, (2015)

It has been suggested that serum concentrations of polyunsaturated essential fatty acids correlate with the symptoms or severity of various diseases, including depression and Alzheimer-type dementia, ...