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Details

Stereochemistry ACHIRAL
Molecular Formula C11H21NO3
Molecular Weight 215.2898
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
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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
CYSVIEW KIT

Approved Use

Cysview 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 Date

1.27500485E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
343 ng/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
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
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
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
Flexible cystoscopy: a revolution in urological practice.
2009 Oct
[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
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
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
Hexylaminolaevulinate fluorescence cystoscopy in patients previously treated with intravesical bacille Calmette-Guérin.
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.
Name Type Language
HEXAMINOLEVULINATE
MI   VANDF   WHO-DD  
Systematic Name English
HEXAMINOLEVULINATE [MI]
Common Name English
5-AMINOLEVULINIC ACID HEXYL ESTER
Common Name English
HEXYL 5-AMINO-4-OXOPENTANOATE
Systematic Name English
HEXVIX
Brand Name English
HEXAMINOLEVULINATE [VANDF]
Common Name English
PENTANOIC ACID, 5-AMINO-4-OXO-, HEXYL ESTER
Common Name English
HEXAMINOLEVULINATE [WHO-DD]
Common Name English
5-AMINO-4-OXOPENTANOIC ACID HEXYL ESTER
Systematic Name English
5-AMINOLEVULINATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1420
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
Code System Code Type Description
MERCK INDEX
M6001
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
PRIMARY Merck Index
PUBCHEM
6433083
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
PRIMARY
FDA UNII
G7H20TKI67
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
PRIMARY
CAS
140898-97-1
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
PRIMARY
NCI_THESAURUS
C26654
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
PRIMARY
DRUG BANK
DB06261
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
PRIMARY
EPA CompTox
140898-97-1
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
PRIMARY
MESH
C419924
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
PRIMARY
DRUG CENTRAL
167
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
PRIMARY
LACTMED
Hexaminolevulinate
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
PRIMARY
EVMPD
SUB38545
Created by admin on Sat Jun 26 03:42:36 UTC 2021 , Edited by admin on Sat Jun 26 03:42:36 UTC 2021
PRIMARY