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
| Molecular Formula | C11H21NO3 |
| Molecular Weight | 215.2893 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Gateways to clinical trials. | 2007 Nov |
|
| [Fluorescence diagnosis and photodynamic therapy in urology]. | 2007 Nov |
|
| Microbiological effect of photodynamic therapy (PDT) in healthy volunteers: a comparative study using methyl aminolaevulinate and hexyl aminolaevulinate cream. | 2007 Nov |
|
| ["... The better to see you with"--phothodynamic diagnostic in superficial bladder cancer]. | 2007 Oct 17 |
|
| Comparison of ALA- and ALA hexyl-ester-induced PpIX depth distribution in human skin carcinoma. | 2008 Dec 11 |
|
| Early detection of premalignant conditions in the colon by fluorescence endoscopy using local sensitization with hexaminolevulinate. | 2008 Feb |
|
| Gateways to clinical trials. | 2008 Jan-Feb |
|
| Protoporphyrin IX fluorescence photobleaching is a useful tool to predict the response of rat ovarian cancer following hexaminolevulinate photodynamic therapy. | 2008 Jul |
|
| The economic benefit of photodynamic diagnosis in non-muscle invasive bladder cancer. | 2008 Jun |
|
| 5-Aminolaevulinic acid peptide prodrugs enhance photosensitization for photodynamic therapy. | 2008 Jun |
|
| [Initial experience in the diagnosis and treatment of superficial bladder tumors with Hexvix]. | 2008 May |
|
| Photodynamic therapy of cervical intraepithelial neoplasia with hexaminolevulinate. | 2008 Nov |
|
| Comparison of continuous and fractionated illumination during hexaminolaevulinate-photodynamic therapy. | 2008 Sep |
|
| Changes in human skin after topical PDT with hexyl aminolevulinate. | 2008 Sep |
|
| 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 |
|
| Effects of photoactivated 5-aminolevulinic acid hexyl ester on MDR1 over-expressing human uterine sarcoma cells. | 2008 Sep |
|
| Fluorescence-guided transurethral resection of bladder cancer using hexaminolevulinate: analysis of health economic impact in Sweden. | 2009 |
|
| HAL fluorescence cystoscopy and TURB one year of Romanian experience. | 2009 Apr-Jun |
|
| Hexyl aminolevulinate fluorescence cystoscopy in bladder cancer. | 2009 Aug |
|
| Editorial comment on: A new generation of optical diagnostics for bladder cancer: technology, diagnostic accuracy, and future applications. | 2009 Aug |
|
| Editorial comment. | 2009 Dec |
|
| Hexaminolevulinate is equal to 5-aminolevulinic acid concerning residual tumor and recurrence rate following photodynamic diagnostic assisted transurethral resection of bladder tumors. | 2009 Dec |
|
| 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 |
|
| Hexylaminolevulinate photodynamic diagnosis for multifocal recurrent nonmuscle invasive bladder cancer. | 2009 Jun |
|
| Hexylaminolaevulinate 'blue light' fluorescence cystoscopy in the investigation of clinically unconfirmed positive urine cytology. | 2009 May |
|
| [Photodynamic diagnosis (PDD) in non-muscle invasive bladder cancer. Literature review]. | 2009 Oct |
|
| Synergistic increase in osteosarcoma cell sensitivity to photodynamic therapy with aminolevulinic acid hexyl ester in the presence of hyperthermia. | 2009 Oct |
|
| Blue-sky thinking about blue-light cystoscopy. | 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 |
|
| Pharmacokinetic of ALA and h-ALA induced porphyrins in the models Mycobacterium phlei and Mycobacterium smegmatis. | 2009 Oct 6 |
|
| 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 |
|
| Photodynamic diagnosis in non-muscle-invasive bladder cancer: a systematic review and cumulative analysis of prospective studies. | 2010 Apr |
|
| 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 |
|
| Photodynamic therapy with topical methyl- and hexylaminolevulinate for prophylaxis and treatment of UV-induced SCC in hairless mice. | 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 |
|
| The role of hexylaminolaevulinate in the diagnosis and follow-up of non-muscle-invasive bladder cancer. | 2010 Feb |
|
| Hexaminolevulinate-induced fluorescence colonoscopy versus white light endoscopy for diagnosis of neoplastic lesions in the colon. | 2010 Jan |
|
| 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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:42:06 GMT 2023
by
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on
Fri Dec 15 15:42:06 GMT 2023
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| Record UNII |
G7H20TKI67
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| Record Status |
Validated (UNII)
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| Record Version |
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C1420
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