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Details

Stereochemistry ACHIRAL
Molecular Formula C11H21NO3
Molecular Weight 215.2893
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HEXAMINOLEVULINATE

SMILES

CCCCCCOC(=O)CCC(=O)CN

InChI

InChIKey=RYQOILLJDKPETL-UHFFFAOYSA-N
InChI=1S/C11H21NO3/c1-2-3-4-5-8-15-11(14)7-6-10(13)9-12/h2-9,12H2,1H3

HIDE SMILES / InChI

Molecular Formula C11H21NO3
Molecular Weight 215.2893
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Hexaminolevulinate is an optical imaging drug. In solution form, it is instilled intravesically for use with photodynamic blue light cystoscopy as an adjunct to white light cystoscopy. After bladder instillation, hexaminolevulinate enters the bladder mucosa and is proposed to enter the intracellular space of mucosal cells where it is used as a precursor in the formation of the photoactive intermediate protoporphyrin IX (PpIX) and other photoactive porphyrins (PAPs). PpIX and PAPs are reported to accumulate preferentially in neoplastic cells as compared to normal urothelium, partly due to altered enzymatic activity in the neoplastic cells. In 2010, FDA granted approval for hexaminolevulinate hydrochloride as an optical imaging agent for cystoscopic detection of non-muscle invasive papillary cancer of the bladder for patients suspected or known to have lesion(s) on the basis of a prior cystoscopy.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
CYSVIEW KIT

Cmax

ValueDoseCo-administeredAnalytePopulation
343 ng/mL
100 mg single, intravesical
HEXAMINOLEVULINATE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
76 h
100 mg single, intravesical
HEXAMINOLEVULINATE plasma
Homo sapiens

Doses

AEs

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
50 mL of a reconstituted solution of hexaminolevulinate (final concentration 2mg/mL) is slowly instilled via an intravesical catheter into the emptied bladder; catheter may be a straight or intermittent urethral catheter with a proximal funnel opening to accommodate a luer lock adapter.
Route of Administration: Other
In Vitro Use Guide
Porcine bladder was excised and stored at 4C in Tyrode solution. The urothelium was microdissected from the bladder wall using fine scissors, and 7x7 mm fragments were mounted in a transparent culture chamber designed for epithelia. The chamber was fixed on the plate of an epi-illumination microscope and thermostabilized at 36 C. Solution of hexaminolevulinate (HALA) was injected as a single dose into the upper chamber in phosphate buffer. Accumulation of the protoporphyrin IX was measured by fluorimetric microscopy.
Substance Class Chemical
Record UNII
G7H20TKI67
Record Status Validated (UNII)
Record Version