Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H21NO3.ClH |
| Molecular Weight | 251.75 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCCCCCOC(=O)CCC(=O)CN
InChI
InChIKey=LZYXPFZBAZTOCH-UHFFFAOYSA-N
InChI=1S/C11H21NO3.ClH/c1-2-3-4-5-8-15-11(14)7-6-10(13)9-12;/h2-9,12H2,1H3;1H
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 |
|---|---|---|---|---|
| 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 |
|---|---|---|---|---|
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cystoscopic detection of non-muscle invasive papillary cancer of the bladder Sources: Page: p.1 |
Disc. AE: Anaphylaxis... AEs leading to discontinuation/dose reduction: Anaphylaxis Sources: Page: p.1 |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Anaphylaxis | Disc. AE | 50 mL single, intravesical Recommended Dose: 50 mL Route: intravesical Route: single Dose: 50 mL Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cystoscopic detection of non-muscle invasive papillary cancer of the bladder Sources: Page: p.1 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of protoporphyrin IX production, phototoxicity and cell death pathway induced by hexylester of 5-aminolevulinic acid in Reh and HPB-ALL cells. | 2001 Aug 10 |
|
| ALA and ALA hexyl ester-induced porphyrin synthesis in chemically induced skin tumours: the role of different vehicles on improving photosensitization. | 2001 Nov 30 |
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| ALA and ALA hexyl ester induction of porphyrins after their systemic administration to tumour bearing mice. | 2002 Sep 23 |
|
| Hexyl aminolevulinate fluorescence cystoscopy: new diagnostic tool for photodiagnosis of superficial bladder cancer--a multicenter study. | 2003 Jul |
|
| Spectroscopic measurements of photoinduced processes in human skin after topical application of the hexyl ester of 5-aminolevulinic acid. | 2006 |
|
| Induction of apoptosis by hexaminolevulinate-mediated photodynamic therapy in human colon carcinoma cell line 320DM. | 2006 |
|
| Pharmacokinetics of the photosensitizers aminolevulinic acid and aminolevulinic acid hexylester in oro-facial tumors embedded in the chorioallantois membrane of a hen's egg. | 2006 Dec |
|
| Involvement of both caspase-dependent and -independent pathways in apoptotic induction by hexaminolevulinate-mediated photodynamic therapy in human lymphoma cells. | 2006 Nov |
|
| Detection of urinary bladder cancer with flow cytometry and hexaminolevulinate in urine samples. | 2007 Apr |
|
| Comparison of aminolevulinic acid- and hexylester aminolevulinate-induced protoporphyrin IX fluorescence for the detection of ovarian cancer in a rat model. | 2007 Aug |
|
| Mapping of oxidative stress responses of human tumor cells following photodynamic therapy using hexaminolevulinate. | 2007 Aug 13 |
|
| 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 |
|
| A phase III, multicenter comparison of hexaminolevulinate fluorescence cystoscopy and white light cystoscopy for the detection of superficial papillary lesions in patients with bladder cancer. | 2007 Jul |
|
| Gateways to clinical trials. | 2007 Nov |
|
| The role of hexaminolevulinate fluorescence cystoscopy in bladder cancer. | 2007 Oct |
|
| Gateways to clinical trials. | 2008 Jan-Feb |
|
| Analysis of differential PDT effect in rat bladder tumor models according to concentrations of intravesical hexyl-aminolevulinate. | 2008 Sep |
|
| [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 |
|
| Fluorescence-guided transurethral resection of bladder cancer using hexaminolevulinate: analysis of health economic impact in Sweden. | 2009 |
|
| Hexyl aminolevulinate fluorescence cystoscopy in bladder cancer. | 2009 Aug |
|
| Photodynamic therapy inhibits P-glycoprotein mediated multidrug resistance via JNK activation in human hepatocellular carcinoma using the photosensitizer pheophorbide a. | 2009 Jul 31 |
|
| Hexaminolevulinate fluorescence cystoscopy and transurethral resection of the bladder in noninvasive bladder tumors. | 2009 Jun |
|
| Flexible cystoscopy: a revolution in urological practice. | 2009 Oct |
|
| Improved detection and reduced early recurrence of non-muscle-invasive bladder cancer using hexaminolaevulinate fluorescence cystoscopy: results of a multicentre prospective randomized study (PC B305). | 2009 Oct |
|
| Photodynamic diagnosis in patients with T1G3 bladder cancer: influence on recurrence rate. | 2010 Aug |
|
| Hexyl aminolaevulinate is a more effective topical photosensitiser precursor than methyl aminolaevulinate and 5-aminolaevulinic acids when applied in equimolar doses. | 2010 Aug |
|
| Continuous or fractionated photodynamic therapy? Comparison of three PDT schemes for ovarian peritoneal micrometastasis treatment in a rat model. | 2010 Dec |
|
| Reflectance spectroscopy and fluorescein angiography applied to assess photodynamic response in healthy mouse skin treated with topical hexylaminolevulinate. | 2010 Dec |
|
| New bladder cancer removal technique reduces recurrence. | 2010 Feb |
|
| The role of hexylaminolaevulinate in the diagnosis and follow-up of non-muscle-invasive bladder cancer. | 2010 Feb |
|
| Photodynamic therapy with hexenyl ester of 5-aminolevulinic acid induces necrotic cell death in salivary gland adenocarcinoma cells. | 2010 Jul |
|
| Augmented cecal mucosa appears pink under hexylaminolevulinate "blue light" fluorescence cystoscopy. | 2010 Jun |
|
| [Hexaminolevulinate fluorescence cystoscopy in 2009]. | 2010 Mar |
|
| [Fluorescence diagnosis in patients with non-muscle invasive bladder cancer: results of a metaanalysis]. | 2010 May |
|
| [Photodynamic diagnosis (cystoscopy with hexaminolevulinate) in the surveillance of urothelial lesions managed with conservative treatment]. | 2010 Nov |
|
| Effects of photodynamic therapy using topical applied hexylaminolevulinate and methylaminolevulinate upon the integrity of cervical epithelium. | 2010 Nov |
|
| Hexaminolevulinate guided fluorescence cystoscopy reduces recurrence in patients with nonmuscle invasive bladder cancer. | 2010 Nov |
|
| Hexaminolevulinate-mediated photodynamic purging of leukemia cells from BM. | 2010 Oct |
|
| HAL blue-light cystoscopy in high-risk nonmuscle-invasive bladder cancer--re-TURBT recurrence rates in a prospective, randomized study. | 2010 Sep |
Patents
Sample Use Guides
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
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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C1937
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ACTIVE MOIETY
SUBSTANCE RECORD
