Methyl aminolevulinate

Chemical compound

L01XD03 (WHO)

Identifiers

IUPAC name

Methyl 5-amino-4-oxopentanoate

CAS Number

33320-16-0^Y

PubChem CID

157922

DrugBank

DB00992^Y

ChemSpider

13180320^Y

UNII

585NM85KYM

ChEMBL

ChEMBL1096562^N

CompTox Dashboard (EPA)

DTXSID3048570

Chemical and physical dataFormulaC₆H₁₁NO₃Molar mass145.158 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=C(CC(N)C(=O)OC)C

InChI

InChI=1S/C6H11NO3/c1-4(8)3-5(7)6(9)10-2/h5H,3,7H2,1-2H3^Y
Key:FLQHIIVXMKXKFT-UHFFFAOYSA-N^Y

^NY (what is this?) (verify)

Methyl aminolevulinate (MAL) is a drug used as a sensitizer in photodynamic therapy. It is a prodrug that is metabolized to protoporphyrin IX. 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.^[1]

Approvals and indications

Methyl aminolevulinate is approved in New Zealand for treatment of basal cell carcinoma.^[2]

It is now approved in many countries and has been used to treat non-melanoma skin cancer (including basal cell carcinoma).^[3]

It has some advantages over Levulan.^[4]

It has been reported as controversial in some quarters, with severe pain allegedly being experienced by some patients. ^[5]

References

^ "Photocure Divests Metvix to Galderma for EUR 51 Million". Archived from the original on 2011-02-07. Retrieved 2010-09-10.
^ Ngan V (2003). "Methyl aminolevulinate photodynamic therapy (MAL PDT)". DermNet NZ.
^ "New 5 Year Metvix-PDT Data Demonstrate Long-Term Efficacy & Reliability For NM Skin Cancer Treatment". EurekAlert!. 2006.
^ O'Connor AE, Gallagher WM, Byrne AT (2009). "Porphyrin and nonporphyrin photosensitizers in oncology: preclinical and clinical advances in photodynamic therapy". Photochemistry and Photobiology. 85 (5): 1053–74. doi:10.1111/j.1751-1097.2009.00585.x. PMID 19682322. S2CID 205950773.
^ "Concerns raised over ALA skin cancer cream as patients recount 'horrendous' pain". Australian Broadcasting Corporation. 16 November 2013.

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly	Vinca alkaloids (Vinblastine^# Vincristine^# Vindesine Vinflunine^§ Vinorelbine^#)
Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel^# Larotaxel Ortataxel^† Paclitaxel^# Tesetaxel) Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Pemetrexed Raltitrexed)
Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Mercaptopurine^# Tioguanine^#)
Pyrimidine	Thymidylate synthase inhibitor (Capecitabine^# Carmofur Doxifluridine Floxuridine Fluorouracil^# Tegafur (+gimeracil/oteracil)) DNA polymerase inhibitor (Cytarabine^# +daunorubicin) Ribonucleotide reductase inhibitor (Gemcitabine^#) Hypomethylating agent (Azacitidine Decitabine)
Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide^#)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Belotecan Camptothecin Cositecan^† Etirinotecan pegol^† Exatecan Gimatecan Irinotecan^# Lurtotecan^‡ Rubitecan^‡ Silatecan^§ Topotecan)
II	Podophyllum (Etoposide^# Teniposide)
II+Intercalation	Anthracyclines (Aclarubicin Amrubicin^† Daunorubicin^# (+cytarabine) Doxorubicin^# Epirubicin Idarubicin Pirarubicin Valrubicin Zorubicin) Anthracenediones (Mitoxantrone Losoxantrone Pixantrone) Amsacrine Bisantrene Crisnatol Menogaril^§

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards: Bendamustine^# Chlormethine Cyclophosphamide^# (Ifosfamide^# Trofosfamide) Chlorambucil^# Melphalan (Melphalan flufenamide) Prednimustine Uramustine Nitrosoureas: Carmustine Fotemustine Lomustine (Semustine) Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine
Platinum-based	Carboplatin^# Cisplatin^# Dicycloplatin Nedaplatin Oxaliplatin^# Satraplatin
Nonclassical	Altretamine Hydrazines (Procarbazine^#) Etoglucid Mitobronitol Pipobroman Triazenes (Dacarbazine^# Mitozolomide^§ Temozolomide)
Intercalation	Streptomyces (Dactinomycin^# Bleomycin^# Mitomycins Plicamycin)

Photosensitizers/PDT

Aminolevulinic acid
Efaproxiral
Methyl aminolevulinate
Padeliporfin
Porphyrin derivatives (Porfimer sodium
Talaporfin
Temoporfin
Verteporfin)

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Abemaciclib Alvocidib^† Palbociclib Ribociclib Seliciclib^†) PrI Bortezomib Carfilzomib Oprozomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Niraparib +abiraterone acetate Olaparib Rucaparib) HDAC (Belinostat Entinostat Panobinostat Romidepsin Vorinostat) PIKI (Pi3K) (Alpelisib Copanlisib Duvelisib Idelalisib Umbralisib^‡)
Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)
Other/ungrouped	Adagrasib Aflibercept Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Axicabtagene ciloleucel Belzutifan Bexarotene Brexucabtagene autoleucel Celecoxib Ciltacabtagene autoleucel Demecolcine Denileukin diftitox Elesclomol^§ Elsamitrucin Enasidenib Epacadostat Eribulin Estramustine phosphate Glasdegib Idecabtagene vicleucel Ivosidenib Lifileucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Plitidepsin Retinoids (Alitretinoin Tretinoin^#) Selinexor Sitimagene ceradenovec Sotorasib Tagraxofusp Talimogene laherparepvec Tazemetostat Tebentafusp Tiazofurine Tigilanol tiglate Tisagenlecleucel Trabectedin Veliparib Venetoclax Verdinexor Vosaroxin