Methyl aminolevulinate

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	APRD01105
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, 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)