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    Technical details about AM022465, learn more about the structure, uses, toxicity, action, side effects and more

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    AM022465

    DOSSIERs // Finished Dosage Forms

    GLOBAL SALES INFORMATION

    PharmaCompass

    Phyton is a World Leader in Plant Cell Fermentation Technology and Commercial Manufacturing.

    Athena Pharmaceutiques is a Partner of Choice for Drug Delivery & Life Cycle Management.

    2D Structure
    1. Also known as: Metvix, 33320-16-0, Methyl 5-aminolevulinate, Methyl 5-amino-4-oxopentanoate, Aminolevulinic acid methyl ester, 5-aminolevulinic acid methyl ester
    Molecular Formula
    C6H11NO3
    Molecular Weight
    145.16  g/mol
    InChI Key
    YUUAYBAIHCDHHD-UHFFFAOYSA-N
    FDA UNII
    585NM85KYM
    Methyl aminolevulinate is a prodrug that is metabolised to Protoporphyrin IX (a photosensitizer) used in photodynamic therapy.
    Methyl aminolevulinate is a Porphyrin Precursor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl 5-amino-4-oxopentanoate
    2.1.2 InChI
    InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3
    2.1.3 InChI Key
    YUUAYBAIHCDHHD-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    COC(=O)CCC(=O)CN
    2.2 Other Identifiers
    2.2.1 UNII
    585NM85KYM
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Maop Cpd

    2. Methyl 5-aminolevulinate

    3. Methyl Aminolaevulinate

    4. Metvix

    2.3.2 Depositor-Supplied Synonyms

    1. Metvix

    2. 33320-16-0

    3. Methyl 5-aminolevulinate

    4. Methyl 5-amino-4-oxopentanoate

    5. Aminolevulinic Acid Methyl Ester

    6. 5-aminolevulinic Acid Methyl Ester

    7. Methyl Aminolaevulinate

    8. Methyl Delta-aminolevulinate

    9. Pentanoic Acid, 5-amino-4-oxo-, Methyl Ester

    10. D-aminolevulinicacidmethylesterhydrochloride

    11. 585nm85kym

    12. Chebi:724125

    13. Maop Cpd

    14. Ncgc00018251-03

    15. Unii-585nm85kym

    16. Levulinic Acid, 5-amino-, Methyl Ester

    17. Methyl5-amino-4-oxopentanoate

    18. Methylaminolevulinate

    19. Methyl-aminolevulinate

    20. Methyl-5-aminolevulinate

    21. Schembl8521

    22. 5-aminolavulinsauremethylester

    23. Chembl1096562

    24. Dtxsid3048570

    25. Methyl Aminolevulinate [mi]

    26. Hy-a0169

    27. Zinc1909090

    28. Methyl Aminolevulinate [vandf]

    29. Akos006220489

    30. Db00992

    31. Methyl Aminolevulinate [who-dd]

    32. Ncgc00018251-01

    33. Ncgc00018251-02

    34. Ncgc00018251-04

    35. Ncgc00018251-05

    36. Da-06782

    37. 5-amino-4-oxo-pentanoic Acid Methyl Ester

    38. Cs-0017508

    39. Ft-0760150

    40. D08204

    41. Q619603

    2.4 Create Date
    2005-06-29
    3 Chemical and Physical Properties
    Molecular Weight 145.16 g/mol
    Molecular Formula C6H11NO3
    XLogP3-1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass145.07389321 g/mol
    Monoisotopic Mass145.07389321 g/mol
    Topological Polar Surface Area69.4 Ų
    Heavy Atom Count10
    Formal Charge0
    Complexity133
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For topical use, in combination with 570 to 670 nm wavelength red light illumination, in the treatment of non-hyperkeratotic actinic keratoses of the face and scalp in immunocompetent patients when used in conjunction with lesion preparation (debridement using a sharp dermal curette).

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    After topical application of methyl aminolevulinate, porphyrins will accumulate intracellularly in the treated skin lesions. The intracellular porphyrins (including PpIX) are photoactive, fluorescing compounds and, upon light activation in the presence of oxygen, singlet oxygen is formed which causes damage to cellular compartments, in particular the mitochondria. Light activation of accumulated porphyrins leads to a photochemical reaction and thereby phototoxicity to the light-exposed target cells.

    5.2 MeSH Pharmacological Classification

    Photosensitizing Agents

    Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms. (See all compounds classified as Photosensitizing Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    METHYL AMINOLEVULINATE
    5.3.2 FDA UNII
    585NM85KYM
    5.3.3 Pharmacological Classes
    Chemical Structure [CS] - Porphyrinogens
    5.4 ATC Code

    L01XD03

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01X - Other antineoplastic agents

    L01XD - Sensitizers used in photodynamic/radiation therapy

    L01XD03 - Methyl aminolevulinate

    5.5 Absorption, Distribution and Excretion

    Absorption

    In vitro, after 24 hours the mean cumulative absorption through human skin was 0.26% of the administered dose.

    5.6 Mechanism of Action

    Photosensitization following application of methyl aminolevulinate cream occurs through the metabolic conversion of methyl aminolevulinate (prodrug) to photoactive porphyrins (PAP), which accumulates in the skin lesions to which the cream has been applied. When exposed to light of appropriate wavelength and energy, the accumulated photoactive porphyrins produce a photodynamic reaction, resulting in a cytotoxic process dependent upon the simultaneous presence of oxygen. The absorption of light results in an excited state of porphyrin molecules, and subsequent spin transfer from photoactive porphyrins to molecular oxygen generates singlet oxygen, which can further react to form superoxide and hydroxyl radicals.

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