Hexaminolevulinate Hydrochloride

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Cat Number

API0232155

CAS Number

140898-91-5

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Product Detail Description Scientific Support Customer Q&A

CAS Number

140898-91-5

EINECS

646-411-4

Storage

Store at 2-8°C

Synonyms

Hexyl 5-amino-4-oxopentanoate hydrochloride; hexaminolevulinate HCl; Cysview; Hexvix; HEXYL AMINOLEVULINATE HCL; P-1206; D4F329SL1O

Molecular Formula

C11H22ClNO3

Molecular Weight

251.75

Smiles

CCCCCCOC(=O)CCC(=O)CN.Cl

Appearance

White to off-white powder

Melting Point

145-147°C

Boiling Point

313.2°C at 760 mmHg

General Description

Hexaminolevulinate hydrochloride is a hexyl ester of 5-aminolevulinic acid (ALA), designed to enhance cellular uptake and tissue penetration. The molecule consists of a 5-aminolevulinic acid core with a six-carbon aliphatic ester chain, which increases lipophilicity. The hydrochloride salt improves stability and solubility. This compound is a prodrug that induces accumulation of fluorescent porphyrins in neoplastic cells.

Mechanism of Action

Once taken up by cells, hexaminolevulinate is hydrolyzed by esterases to 5-aminolevulinic acid, which enters the heme biosynthesis pathway. Malignant cells preferentially convert ALA to protoporphyrin IX (PpIX) due to reduced ferrochelatase activity. PpIX is a fluorescent photosensitizer that emits red light (635 nm) when excited by blue-violet light (375-440 nm), allowing visualization of tumor tissue under fluorescence cystoscopy.

Application

Hexaminolevulinate is indicated as an optical imaging agent for fluorescence cystoscopy in the detection of non-muscle invasive papillary bladder cancer, including carcinoma in situ (CIS). It improves detection of lesions that may be missed under white light alone, particularly flat and small tumors.

Meta‑analysis of 16 controlled trials (154 publications screened) evaluated hexaminolevulinate (HAL) photodynamic diagnosis (PDD) for bladder cancer. HAL‑PDD increased overall tumor detection by 19% (95% CI 15.2‑23.6%), with greatest benefit for carcinoma in situ (CIS) lesions (15.7% increase). Detection of papillary Ta and T1 lesions increased by 5.9% and 1.2%, respectively. An additional tumor was seen in 15% of patients with PDD. Data on recurrence rates were insufficient for statistical analysis but showed a trend favoring HAL‑PDD. HAL‑PDD improves tumor detection, especially for CIS.

Fig. 1 Begg’s funnel plot for publication bias with the 95% confidence limits. (Di Stasi SM, et al., 2015)

References

Di Stasi SM, et al. Hexaminolevulinate hydrochloride in the detection of nonmuscle invasive cancer of the bladder. Ther Adv Urol. 2015;7(6):339-350.

Does Hexaminolevulinate Hydrochloride require protection from light and heat during storage?

Yes, it is highly sensitive to light and heat, which cause polymerization and degradation. Store in light-resistant containers at 2-8°C (refrigerated).

Is Hexaminolevulinate Hydrochloride stable in solution for intravesical use?

Reconstituted solutions degrade rapidly (within 4-6 hours at room temperature). Use immediately after preparation.

What packaging is recommended for shipping Hexaminolevulinate Hydrochloride?

Use amber glass vials with airtight closures, transported in validated cold chain packaging with temperature data loggers and light protection.

How is the impurity 5-aminolevulinic acid (de-hexylated product) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains below ICH qualification thresholds.