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 Date1.27500485E12 |
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 |
|---|---|---|
| Comparison of 5-aminolevulinic acid and its hexylester mediated photodynamic action on human hepatoma cells. | 2002 Sep |
|
| Protoporphyrin IX-accumulation in human tumor cells following topical ALA- and h-ALA-application in vivo. | 2003 Dec 8 |
|
| Hexyl aminolevulinate: 5-ALA hexylester, 5-ALA hexylesther, aminolevulinic acid hexyl ester, hexaminolevulinate, hexyl 5-aminolevulinate, P 1206. | 2005 |
|
| Spectroscopic measurements of photoinduced processes in human skin after topical application of the hexyl ester of 5-aminolevulinic acid. | 2006 |
|
| Microbiological effect of photodynamic therapy (PDT) in healthy volunteers: a comparative study using methyl aminolaevulinate and hexyl aminolaevulinate cream. | 2007 Nov |
|
| The role of hexaminolevulinate fluorescence cystoscopy in bladder cancer. | 2007 Oct |
|
| Recent developments in fluorescence cystoscopy: do novel agents bring a benefit? | 2007 Sep |
|
| Early detection of premalignant conditions in the colon by fluorescence endoscopy using local sensitization with hexaminolevulinate. | 2008 Feb |
|
| [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 |
|
| 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 |
|
| Fluorescence cystoscopy with high-resolution optical coherence tomography imaging as an adjunct reduces false-positive findings in the diagnosis of urothelial carcinoma of the bladder. | 2009 Dec |
|
| Hexaminolevulinate fluorescence cystoscopy and transurethral resection of the bladder in noninvasive bladder tumors. | 2009 Jun |
|
| [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 |
|
| 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 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 |
|
| 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 |
|
| [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
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on
Edited
Fri Dec 15 15:42:06 UTC 2023
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Fri Dec 15 15:42:06 UTC 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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