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
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
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
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | CYSVIEW KIT Approved UseCysview is an optical imaging agent indicated for use in the cystoscopic detection of carcinoma of the bladder, including carcinoma in situ (CIS), among patients suspected or known to have lesion(s) on the basis of a prior cystoscopy, or in patients undergoing surveillance cystoscopy for carcinoma of the bladder. Cysview is used with the KARL STORZ D-Light C Photodynamic Diagnostic (PDD) system to perform Blue Light Cystoscopy (BLCTM) as an adjunct to the white light cystoscopy. Launch Date2010 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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343 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16554454/ |
100 mg single, intravesical dose: 100 mg route of administration: Intravesical experiment type: SINGLE co-administered: |
HEXAMINOLEVULINATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
76 h |
100 mg single, intravesical dose: 100 mg route of administration: Intravesical experiment type: SINGLE co-administered: |
HEXAMINOLEVULINATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
50 mL single, intravesical Recommended Dose: 50 mL Route: intravesical Route: single Dose: 50 mL Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Anaphylaxis... AEs leading to discontinuation/dose reduction: Anaphylaxis Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Anaphylaxis | Disc. AE | 50 mL single, intravesical Recommended Dose: 50 mL Route: intravesical Route: single Dose: 50 mL Sources: |
unhealthy Health Status: unhealthy Sources: |
PubMed
Title | Date | PubMed |
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Comparative in vitro percutaneous penetration of 5-aminolevulinic acid and two of its esters through excised hairless mouse skin. | 2003 |
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Photodynamic effects of 5-aminolevulinic acid and its hexylester on several cell lines. | 2003 Jul |
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Hexyl aminolevulinate fluorescence cystoscopy: new diagnostic tool for photodiagnosis of superficial bladder cancer--a multicenter study. | 2003 Jul |
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Hexaminolevulinate-induced fluorescence endoscopy in patients with rectal adenoma and cancer: a pilot study. | 2004 Sep |
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Induction of apoptosis by hexaminolevulinate-mediated photodynamic therapy in human colon carcinoma cell line 320DM. | 2006 |
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A comparison of hexaminolevulinate fluorescence cystoscopy and white light cystoscopy for the detection of carcinoma in situ in patients with bladder cancer: a phase III, multicenter study. | 2007 Jul |
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[Fluorescence cystoscopy at bladder cancer: present trials]. | 2007 Nov |
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Protoporphyrin IX fluorescence photobleaching is a useful tool to predict the response of rat ovarian cancer following hexaminolevulinate photodynamic therapy. | 2008 Jul |
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Preliminary results of intraoperative photodynamic therapy with 5-aminolevulinic acid in dogs with prostate carcinoma. | 2008 Nov |
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[Calculating the price of a new diagnostic or therapeutic option. Example of transurethral resection of bladder tumors using photodynamic diagnostics with hexaminolevulinic acid]. | 2008 Sep |
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Editorial comment. | 2009 Dec |
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Hexaminolevulinate is equal to 5-aminolevulinic acid concerning residual tumor and recurrence rate following photodynamic diagnostic assisted transurethral resection of bladder tumors. | 2009 Dec |
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Photodynamic therapy inhibits P-glycoprotein mediated multidrug resistance via JNK activation in human hepatocellular carcinoma using the photosensitizer pheophorbide a. | 2009 Jul 31 |
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Blue-sky thinking about blue-light cystoscopy. | 2009 Oct |
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Hexaminolevulinate-guided fluorescence cystoscopy in the diagnosis and follow-up of patients with non-muscle-invasive bladder cancer: review of the evidence and recommendations. | 2010 Apr |
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Hexaminolevulinate-induced fluorescence colonoscopy versus white light endoscopy for diagnosis of neoplastic lesions in the colon. | 2010 Jan |
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Hexylaminolaevulinate fluorescence cystoscopy in patients previously treated with intravesical bacille Calmette-Guérin. | 2010 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/ppa/hexaminolevulinate.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10411086
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.
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)