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Aminolevulinic acid hydrochloride

Aminolevulinic acid hydrochloride structure

CAS No:
5451-09-2
Formula:
C5H9NO3.ClH
Chemical Name:
Aminolevulinic acid hydrochloride
Synonyms:
Pentanoic acid,5-amino-4-oxo-,hydrochloride (1:1);Levulinic acid,5-amino-,hydrochloride;Pentanoic acid,5-amino-4-oxo-,hydrochloride;δ-Aminolevulinic acid hydrochloride;5-Aminolevulinic acid hydrochloride;Aminolevulinic acid hydrochloride;5-Amino-4-oxopentanoic acid hydrochloride;5-Aminolaevulinic acid hydrochloride;Levulan Kerastick;Ameluz;Gliolan
Categories:
Biochemical Engineering > Amino Acids and Derivatives

Description

5-Aminolevulinic acid HCl is an intermediate in heme biosynthesis in the body and the universal precursor of tetrapyrroles.Target: Others5-Aminolevulinic acid is a non-fluorescent prodrug that leads to intracellular accumulation of fluorescent porphyrins in malignant gliomas-a finding that is under investigation for intraoperative identification and resection of these tumours. Median follow-up was 35.4 months (95% CI 1.0-56.7). Contrast-enhancing tumour was resected completely in 90 (65%

5-aminolevulinic acid hydrochloride is a hydrochloride that is the monohydrochloride of 5-aminolevulinic acid. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp. It has a role as an antineoplastic agent, a photosensitizing agent, a dermatologic drug and a prodrug. It contains a 5-ammoniolevulinic acid.|Aminolevulinic Acid Hydrochloride is the hydrochloride salt form of aminolevulinic acid, an aminoketone, used for local photosensitizing therapy. Aminolevulinic acid (ALA) is a metabolic pro-drug that is converted into the photosensitizer protoporphyrin IX (PpIX), which accumulates intracellularly. Upon exposure to light of appropriate wavelength (red, or blue), PpIX catalyzes oxygen to singlet oxygen, an intracellular toxin, which can further react to form superoxide and hydroxyl radicals. This leads to cellular cytotoxic effects.|A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.

Aminolevulinic acid hydrochloride Basic Attributes

Molecular Weight：

167.59

Exact Mass：

167.035

BRN：

3690651

EC Number：

226-679-5

UNII：

V35KBM8JGR

NSC Number：

758687|18509

DSSTox ID：

DTXSID5045914

NCI Thesaurus Code：

C1849

ATC Code：

L01XD04

HScode：

29224999

Characteristics

PSA：

80.39000

XLogP3：

-0.79

Appearance：

White to pale yellow powder

Density：

1.2±0.1 g/cm3

Melting Point：

145 °C

Boiling Point：

311.5±27.0 °C at 760 mmHg

Flash Point：

155-157°C

Refractive Index：

1.482

Water Solubility：

soluble in dimethyl sulfoxide, methanol and water.

Storage Conditions：

2-8°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-66-20/21/22-36/38

safety instructions：

26-36/37-37/39-36

RTECS Number：

OI1640000

Marks：

Xi,Xn

Hazard note：

Irritant

Precautionary statement(s)：

P305 + P351 + P338

Hazard Statements：

H315-H319

Drug Information

Drug Indication：

Treatment of actinic keratosis of mild to moderate severity on the face and scalp (Olsen grade 1 to 2; see section 5.1) and of field cancerization in adults.Treatment of superficial and/or nodular basal cell carcinoma unsuitable for surgical treatment due to possible treatment-related morbidity and/or poor cosmetic outcome in adults.|Gliolan is indicated in adult patients for visualisation of malignant tissue during surgery for malignant glioma (World Health Organization grade III and IV).|Drug: Aminolevulinicacid

MeSH：

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.)

MeSH Entry Terms：

5 Aminolaevulinate

Aminolevulinic acid hydrochloride Use and Manufacturing

Uses

Naturally occurring amino acid; precursor of tetrapyrroles in the biosynthesis of chlorophyll and heme. Antineoplastic (photosensitizer).

Use Classification：

Human drugs -> Ameluz -> EMA Drug Category|Antineoplastic agents -> Human pharmacotherapeutic group|Human drugs -> Gliolan -> EMA Drug Category|Human drugs -> Rare disease (orphan)|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:167.59
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:167.0349209
Monoisotopic Mass:167.0349209
Topological Polar Surface Area:80.4
Heavy Atom Count:10
Complexity:121
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Aminolevulinic acid (ALA) is the first step in the biochemical pathway of heme synthesis in the human body. It is not a photosensitizer itself but a metabolic precursor of the photosensitizer protoporphyrin IX (PpIX). Exogenous ALA leads to the accumulation of PpIX, which is converted into PpIX and accumulates to produce photosensitivity after skin application. Under light, the accumulated PpIX produces a photodynamic effect, generating singlet oxygen and free radicals through light- and oxygen-dependent cytotoxicity, which is the basis of ALA photodynamic therapy.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Aminolevulinic acid hydrochloride powder for external use
Ingredients	The main ingredient of this product is aminolevulinic acid hydrochloride.
Indication	There are no formal studies on the interaction of this product with other drugs, and no specific drug interactions have been mentioned in any clinical trials. However, concomitant use with some known photosensitizing drugs such as griseofulvin, thiazide diuretics, sulfonylureas, phenothiazines, sulfonamides and tetracyclines may increase the local photosensitivity reaction of the affected area to photodynamic therapy with this product.
Specifications	118mg

Aminolevulinic acid hydrochloride powder for external use
Ingredients	The main ingredient of this product is aminolevulinic acid hydrochloride.
Indication	See instructions for details.
Specifications	118mg/bottle

Aminolevulinic acid hydrochloride

Registered Holders

HERAEUS PRECIOUS METALS GMBH AND CO KG

United States
Active
日本理化学薬品株式会社

Japan
Active
Heraeus Precious Metals GmbH & Co. KG

Germany
Active

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Guide of Aminolevulinic acid hydrochloride

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Drug Function and Efficacy
Related Drugs
Registered Holders
Recommended Suppliers
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