Methyl aminolevulinate

Methyl aminolevulinate
Clinical data

AHFS/Drugs.com	Multum Consumer Information
ATC code	L01XD03 (WHO)
Identifiers
IUPAC name Methyl 5-amino-4-oxopentanoate
CAS Number	33320-16-0^Y
PubChem (CID)	16052023
DrugBank	DB00992^Y
ChemSpider	13180320^Y
ChEMBL	CHEMBL1096562^N
Chemical and physical data
Formula	C₆H₁₁NO₃
Molar mass	145.156 g/mol
3D model (Jmol)	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

Interim result of phototherapy for actinic keratosis with Metvix one week after exposure. Patient has light skin and blue eyes.

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

↑ 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
↑ http://www.abc.net.au/news/2013-11-16/concerns-raised-over-side-effects-of-skin-cancer-cream/5096496

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) Nelarabine Thiopurine (Thioguanine^# Mercaptopurine^#)

Pyrimidine	Thymidylate synthase inhibitor (Fluorouracil^# Capecitabine Tegafur (+gimeracil/oteracil) 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 Cositecan^† Belotecan Gimatecan Exatecan Irinotecan Lurtotecan^‡ Silatecan^§ Topotecan Rubitecan^‡)

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

Platinum-based	Carboplatin Cisplatin Dicycloplatin Nedaplatin Oxaliplatin Satraplatin

Nonclassical	Hydrazines (Procarbazine^#) Triazenes (Dacarbazine^# Temozolomide) Altretamine Mitobronitol Pipobroman

Intercalation	Streptomyces (Actinomycin^# Bleomycin^# Mitomycin Plicamycin)

Photosensitizers/PDT

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Alvocidib^† Seliciclib^† Palbociclib) PrI Bortezomib Carfilzomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Olaparib) HDAC (Belinostat Panobinostat Romidepsin Vorinostat) PIKI (Idelalisib)

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 Lucanthone Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Eribulin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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