WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 205533
CAS#: 79416-27-6 (HCl salt)
Description: Methyl-5-aminolevulinate hydrochloride cream is a topical cream formulation containing the hydrochloride salt of methyl-5-aminolevulinate, a lipophilic methyl ester of 5-aminolevulinic acid, with photosensitizer prodrug activity. Upon topical administration, methyl-5-aminolevulinate in the cream is selectively absorbed by tumor cells where it is converted to the photosensitizer protoporphyrin IX (PpIX). Upon photoirradiation, PpIX is activated and transfers energy to oxygen, generating singlet oxygen and superoxide and hydroxyl radicals, which may result in free-radical-mediated DNA damage and cell death.
MedKoo Cat#: 205533
Name: Methyl aminolevulinate HCl
CAS#: 79416-27-6 (HCl salt)
Chemical Formula: C6H12ClNO3
Exact Mass:
Molecular Weight: 181.62
Elemental Analysis: C, 39.68; H, 6.66; Cl, 19.52; N, 7.71; O, 26.43
Synonym: LS-187769; LS 187769; LS187769; MAL; 5-Aminolevulinic acid methyl ester; Aminolevulinic acid methyl ester; methyl 5-amino-4-oxopentanoate; methyl 5-aminolevulinate; Methyl aminolevulinate hydrochloride. brand name: Metvix.
IUPAC/Chemical Name: methyl 5-amino-4-oxo-pentanoate hydrochloride
InChi Key: UJYSYPVQHFNBML-UHFFFAOYSA-N
InChi Code: InChI=1S/C6H11NO3.ClH/c1-10-6(9)3-2-5(8)4-7;/h2-4,7H2,1H3;1H
SMILES Code: O=C(OC)CCC(CN)=O.[H]Cl
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 181.62 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Devirgiliis V, Panasiti V, Fioriti D, Anzivino E, Bellizzi A, Cimillo M, Curzio M, Melis L, Roberti V, Gobbi S, Liteo P, Richetta AG, Calvieri S, Chiarini F, Nicosia R, Pietropaolo V. Antibacterial activity of methyl aminolevulinate photodynamic therapy in the treatment of a cutaneous ulcer. Int J Immunopathol Pharmacol. 2011 Jul-Sep;24(3):793-5. PubMed PMID: 21978711.
2: Haedersdal M, Katsnelson J, Sakamoto FH, Farinelli WA, Doukas AG, Tam J, Anderson RR. Enhanced uptake and photoactivation of topical methyl aminolevulinate after fractional CO2 laser pretreatment. Lasers Surg Med. 2011 Sep;43(8):804-13. doi: 10.1002/lsm.21096. PubMed PMID: 21956628.
3: Fai D, Romano I, Cassano N, Vena GA. Methyl-aminolevulinate photodynamic therapy for the treatment of erythroplasia of Queyrat in 23 patients. J Dermatolog Treat. 2011 Sep 4. [Epub ahead of print] PubMed PMID: 21888568.
4: Antonia Pastor-Nieto M, Olivares M, Sánchez-Herreros C, Belmar P, De Eusebio E. Occupational allergic contact dermatitis from methyl aminolevulinate. Dermatitis. 2011 Aug 1;22(4):216-9. PubMed PMID: 21781638.
5: Pauwels C, Mazereeuw-Hautier J, Basset-Seguin N, Livideanu C, Viraben R, Paul C, Meyer N. Topical methyl aminolevulinate photodynamic therapy for management of basal cell carcinomas in patients with basal cell nevus syndrome improves patient's satisfaction and reduces the need for surgical procedures. J Eur Acad Dermatol Venereol. 2011 Jul;25(7):861-4. doi: 10.1111/j.1468-3083.2010.03854.x. Epub 2010 Oct 3. PubMed PMID: 21668511.
6: Kitagawa KH, Bogner P, Zeitouni NC. Photodynamic therapy with methyl-aminolevulinate for the treatment of double extramammary Paget's disease. Dermatol Surg. 2011 Jul;37(7):1043-6. doi: 10.1111/j.1524-4725.2011.02039.x. Epub 2011 Jun 1. PubMed PMID: 21631634.
7: Tierney E, Petersen J, Hanke CW. Photodynamic diagnosis of tumor margins using methyl aminolevulinate before Mohs micrographic surgery. J Am Acad Dermatol. 2011 May;64(5):911-8. PubMed PMID: 21496702.
8: Lee JW, Lee HI, Kim MN, Kim BJ, Chun YJ, Kim D. Topical photodynamic therapy with methyl aminolevulinate may be an alternative therapeutic option for the recalcitrant Malassezia folliculitis. Int J Dermatol. 2011 Apr;50(4):488-90. doi: 10.1111/j.1365-4632.2009.04377.x. PubMed PMID: 21413966.
9: Tyrrell J, Campbell SM, Curnow A. Monitoring the accumulation and dissipation of the photosensitizer protoporphyrin IX during standard dermatological methyl-aminolevulinate photodynamic therapy utilizing non-invasive fluorescence imaging and quantification. Photodiagnosis Photodyn Ther. 2011 Mar;8(1):30-8. Epub 2010 Dec 17. PubMed PMID: 21333932.
10: Ballester I, Belinchón I, Guijarro J, Oltra F, Toledo F, Cuesta L. Photodynamic therapy of vulvar intraepithelial neoplasia using methyl aminolevulinate. J Dermatolog Treat. 2011 Jan 22. [Epub ahead of print] PubMed PMID: 21254852.
Related CAS#
79416-27-6 (HCl salt); 33320-16-0 (free base)
Methyl aminolevulinate (MAL) is a prodrug that is metabolised to Protoporphyrin IX (sensitizer) used in photodynamic therapy. It is marketed as Metvix. Metvix cream is applied topically and some time later the skin is illuminated with a proprietary red light (630 nm) source (medical lamp 'Aktilite') to activate the photosensitiser. Metvix is developed by Photocure and Galderma has bought all rights to Metvix. Methyl aminolevulinate was approved in New Zealand for treatment of basal cell carcinoma, It is now approved in many countries and has been used to treat non-melanoma skin cancer (including basal cell carcinoma). It has some advantages over Levulan (source: http://en.wikipedia.org/wiki/Methyl_aminolevulinate).
Metvixia (methyl aminolevulinate cream) Cream is an oil in water emulsion. Metvixia (methyl aminolevulinate cream) Cream contains methyl aminolevulinate hydrochloride equivalent to168 mg/g of methyl aminolevulinate. Methyl aminolevulinate hydrochloride is a white to slightly yellow powder that is freely soluble in water and methanol, soluble in ethanol and practically insoluble in most organic solvents.
