Methyl aminolevulinate

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Methyl aminolevulinate

Systematic (IUPAC) name
methyl 5-amino-4-oxo-pentanoate
Clinical data
AHFS/Drugs.com	Multum Consumer Information
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	33320-16-0^Y
ATC code	L01XD03
PubChem	CID 16052023
DrugBank	DB00992
ChemSpider	13180320^Y
ChEMBL	CHEMBL1096562^N
Chemical data
Formula	C₆H₁₁N O₃
Mol. mass	145.156 g/mol
SMILES	eMolecules & PubChem
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
N (what is this?) (verify)

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.^[1]

Approvals and Indications

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]

References

^ http://photocure.com/NEWS/newcontainer/Photocure-divests-Metvix-to-Galderma-for-EUR-51-million/ Photocure divests Metvix to Galderma
^ http://dermnetnz.org/procedures/metvix-pdt.html "Methyl aminolevulinate photodynamic therapy (MAL PDT)"
^ http://www.medicalnewstoday.com/articles/36953.php "New 5 Year Metvix-PDT Data Demonstrate Long-Term Efficacy & Reliability For NM Skin Cancer Treatment" 2006
^ http://findarticles.com/p/articles/mi_qa3931/is_200909/ai_n42040200/pg_13/ Porphyrin and Nonporphyrin Photosensitizers in Oncology: Preclinical and Clinical Advances in Photodynamic Therapy Photochemistry and Photobiology, Sep/Oct 2009 by O'Connor, Aisling E, Gallagher, William M, Byrne, Annette T

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly	Vinca alkaloids (Vinblastine Vincristine Vinflunine Vindesine 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 (Raltitrexed Pemetrexed)

Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Thiopurine (Thioguanine Mercaptopurine)

Pyrimidine	Thymidylate synthase inhibitor (Fluorouracil Capecitabine Tegafur Carmofur Floxuridine) DNA polymerase inhibitor (Cytarabine) Ribonucleotide reductase inhibitor (Gemcitabine) Hypomethylating agent (Azacitidine Decitabine)

Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Camptothecin Topotecan Irinotecan Rubitecan Belotecan)

II	Podophyllum (Etoposide Teniposide)

II+Intercalation	Anthracyclines (Aclarubicin Daunorubicin Doxorubicin Epirubicin Idarubicin Amrubicin Pirarubicin Valrubicin Zorubicin) Anthracenediones (Mitoxantrone Pixantrone)

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards: Mechlorethamine Cyclophosphamide (Ifosfamide Trofosfamide) Chlorambucil (Melphalan Prednimustine) Bendamustine Uramustine Estramustine Nitrosoureas: Carmustine Lomustine (Semustine) Fotemustine Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone ThioTEPA Triaziquone Triethylenemelamine

Alkylating-like	Platinum (Carboplatin Cisplatin Nedaplatin Oxaliplatin Triplatin tetranitrate Satraplatin)

Nonclassical	Hydrazines (Procarbazine) Triazenes (Dacarbazine Temozolomide) Altretamine Mitobronitol

Intercalation	Streptomyces (Actinomycin Bleomycin Pingyangmycin Mitomycin Plicamycin)

Photosensitizers/PDT

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

Other

Enzyme inhibitors	FI (Tipifarnib) CDK inhibitors (Alvocidib Seliciclib) PrI (Bortezomib) PhI (Anagrelide) IMPDI (Tiazofurine) LI (Masoprocol) PARP inhibitor (Olaparib) HDAC (Panobinostat Vorinostat Romidepsin)

Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)

Other/ungrouped	Amsacrine Trabectedin Retinoids (Alitretinoin Tretinoin) Arsenic trioxide Asparagine depleters (Asparaginase/Pegaspargase) Celecoxib Demecolcine Elesclomol Elsamitrucin Etoglucid Lonidamine HAMLET (human alpha-lactalbumin made lethal to tumor cells) Lucanthone Mitoguazone Mitotane Oblimersen Omacetaxine mepesuccinate mTOR inhibitors (Everolimus Temsirolimus)

M: NEO

tsoc, mrkr

tumr, epon, para

drug (L1i/1e/V03)

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