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Chemistry

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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
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

Methyl Aminolevulinate

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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Methyl Aminolevulinate manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Methyl Aminolevulinate API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Methyl Aminolevulinate manufacturer or Methyl Aminolevulinate supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Methyl Aminolevulinate manufacturer or Methyl Aminolevulinate supplier.

PharmaCompass also assists you with knowing the Methyl Aminolevulinate API Price utilized in the formulation of products. Methyl Aminolevulinate API Price is not always fixed or binding as the Methyl Aminolevulinate Price is obtained through a variety of data sources. The Methyl Aminolevulinate Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Methyl Aminolevulinate

Synonyms

Metvix, 33320-16-0, Methyl 5-aminolevulinate, Methyl 5-amino-4-oxopentanoate, Aminolevulinic acid methyl ester, 5-aminolevulinic acid methyl ester

Cas Number

33320-16-0

Unique Ingredient Identifier (UNII)

585NM85KYM

About Methyl Aminolevulinate

Methyl aminolevulinate is a prodrug that is metabolised to Protoporphyrin IX (a photosensitizer) used in photodynamic therapy.

Methyl Aminolevulinate Manufacturers

A Methyl Aminolevulinate manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Methyl Aminolevulinate, including repackagers and relabelers. The FDA regulates Methyl Aminolevulinate manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Methyl Aminolevulinate API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Methyl Aminolevulinate Suppliers

A Methyl Aminolevulinate supplier is an individual or a company that provides Methyl Aminolevulinate active pharmaceutical ingredient (API) or Methyl Aminolevulinate finished formulations upon request. The Methyl Aminolevulinate suppliers may include Methyl Aminolevulinate API manufacturers, exporters, distributors and traders.

Methyl Aminolevulinate GMP

Methyl Aminolevulinate Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Methyl Aminolevulinate GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Methyl Aminolevulinate GMP manufacturer or Methyl Aminolevulinate GMP API supplier for your needs.

Methyl Aminolevulinate CoA

A Methyl Aminolevulinate CoA (Certificate of Analysis) is a formal document that attests to Methyl Aminolevulinate's compliance with Methyl Aminolevulinate specifications and serves as a tool for batch-level quality control.

Methyl Aminolevulinate CoA mostly includes findings from lab analyses of a specific batch. For each Methyl Aminolevulinate CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Methyl Aminolevulinate may be tested according to a variety of international standards, such as European Pharmacopoeia (Methyl Aminolevulinate EP), Methyl Aminolevulinate JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Methyl Aminolevulinate USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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