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MedKoo Cat#: 205533 | Name: Methyl aminolevulinate HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Methyl aminolevulinate HCl
Methyl aminolevulinate HCl
CAS# 79416-27-6 (HCl salt)

Theoretical Analysis

MedKoo Cat#: 205533

Name: Methyl aminolevulinate HCl

CAS#: 79416-27-6 (HCl salt)

Chemical Formula: C6H12ClNO3

Exact Mass: 0.0000

Molecular Weight: 181.62

Elemental Analysis: C, 39.68; H, 6.66; Cl, 19.52; N, 7.71; O, 26.43

Price and Availability

Size Price Availability Quantity
250mg USD 250.00 2 weeks
1g USD 450.00 2 weeks
5g USD 950.00 2 weeks
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Related CAS #
No Data
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
More Info
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.          
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methyl aminolevulinate hydrochloride is an agent used as a sensitizer in photodynamic therapy (PDT).
In vitro activity:
This study has identified the mitotic catastrophe (MC) process after MAL-PDT (methyl-aminolevulinate) in HeLa human carcinoma cells. The mitotic blockage induced by MAL-PDT resembled that induced by two compounds used in chemotherapy, taxol and nocodazole, both targeting microtubules. The alterations in tumoral cells provided evidence of MC induced by MAL-PDT, resolving mainly by apoptosis, directly or through the formation of multinucleate cells. Reference: Int J Mol Sci. 2019 Mar 11;20(5):1229. https://pubmed.ncbi.nlm.nih.gov/30862116/
In vivo activity:
All mice in four groups of female C3.Cg/TifBomTac hairless immunocompetent mice (N = 100) were irradiated with three standard erythema doses of solar-simulated ultraviolet radiation (UVR) thrice weekly. The PDT treatments consisted of topical administration of 16% MAL (methyl aminolevulinate), 20% MB (methylene blue), or 20% RF (riboflavin), and subsequent illumination that matched the photosensitizers' absorption spectra. The median times until the first, second, and third skin tumors developed in mice given MAL-PDT were significantly delayed, compared with control mice (256, 265, and 272 vs. 215, 222, and 230 days, respectively; p < 0.001). Reference: Pharmaceuticals (Basel). 2021 May 5;14(5):433. https://pubmed.ncbi.nlm.nih.gov/34063120/
Solvent mg/mL mM
Solubility
DMSO 68.0 374.42
Water 100.0 550.61
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Mascaraque M, Delgado-Wicke P, Damian A, Lucena SR, Carrasco E, Juarranz Á. Mitotic Catastrophe Induced in HeLa Tumor Cells by Photodynamic Therapy with Methyl-aminolevulinate. Int J Mol Sci. 2019 Mar 11;20(5):1229. doi: 10.3390/ijms20051229. PMID: 30862116; PMCID: PMC6429057. 2. Osman-Ponchet H, Gaborit A, Sevin K, Bianchi C, Linget JM, Wilson CE, Bouvier G. Pretreatment of skin using an abrasive skin preparation pad, a microneedling device or iontophoresis improves absorption of methyl aminolevulinate in ex vivo human skin. Photodiagnosis Photodyn Ther. 2017 Dec;20:130-136. doi: 10.1016/j.pdpdt.2017.09.006. Epub 2017 Sep 12. PMID: 28919324. 3. Wulf HC, Al-Chaer RN, Glud M, Philipsen PA, Lerche CM. A Skin Cancer Prophylaxis Study in Hairless Mice Using Methylene Blue, Riboflavin, and Methyl Aminolevulinate as Photosensitizing Agents in Photodynamic Therapy. Pharmaceuticals (Basel). 2021 May 5;14(5):433. doi: 10.3390/ph14050433. PMID: 34063120; PMCID: PMC8148192. 4. Sharfaei S, Juzenas P, Moan J, Bissonnette R. Weekly topical application of methyl aminolevulinate followed by light exposure delays the appearance of UV-induced skin tumours in mice. Arch Dermatol Res. 2002 Jul;294(5):237-42. doi: 10.1007/s00403-002-0320-4. Epub 2002 Jun 26. PMID: 12115027.
In vitro protocol:
1. Mascaraque M, Delgado-Wicke P, Damian A, Lucena SR, Carrasco E, Juarranz Á. Mitotic Catastrophe Induced in HeLa Tumor Cells by Photodynamic Therapy with Methyl-aminolevulinate. Int J Mol Sci. 2019 Mar 11;20(5):1229. doi: 10.3390/ijms20051229. PMID: 30862116; PMCID: PMC6429057. 2. Osman-Ponchet H, Gaborit A, Sevin K, Bianchi C, Linget JM, Wilson CE, Bouvier G. Pretreatment of skin using an abrasive skin preparation pad, a microneedling device or iontophoresis improves absorption of methyl aminolevulinate in ex vivo human skin. Photodiagnosis Photodyn Ther. 2017 Dec;20:130-136. doi: 10.1016/j.pdpdt.2017.09.006. Epub 2017 Sep 12. PMID: 28919324.
In vivo protocol:
1. Wulf HC, Al-Chaer RN, Glud M, Philipsen PA, Lerche CM. A Skin Cancer Prophylaxis Study in Hairless Mice Using Methylene Blue, Riboflavin, and Methyl Aminolevulinate as Photosensitizing Agents in Photodynamic Therapy. Pharmaceuticals (Basel). 2021 May 5;14(5):433. doi: 10.3390/ph14050433. PMID: 34063120; PMCID: PMC8148192. 2. Sharfaei S, Juzenas P, Moan J, Bissonnette R. Weekly topical application of methyl aminolevulinate followed by light exposure delays the appearance of UV-induced skin tumours in mice. Arch Dermatol Res. 2002 Jul;294(5):237-42. doi: 10.1007/s00403-002-0320-4. Epub 2002 Jun 26. PMID: 12115027.
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.