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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
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

2010
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:
unhealthy
Disc. AE: Anaphylaxis...
AEs leading to
discontinuation/dose reduction:
Anaphylaxis
Sources:
AEs

AEs

AESignificanceDosePopulation
Anaphylaxis Disc. AE
50 mL single, intravesical
Recommended
Dose: 50 mL
Route: intravesical
Route: single
Dose: 50 mL
Sources:
unhealthy
PubMed

PubMed

TitleDatePubMed
Comparative in vitro percutaneous penetration of 5-aminolevulinic acid and two of its esters through excised hairless mouse skin.
2003
Photodynamic effects of 5-aminolevulinic acid and its hexylester on several cell lines.
2003 Jul
Hexyl aminolevulinate fluorescence cystoscopy: new diagnostic tool for photodiagnosis of superficial bladder cancer--a multicenter study.
2003 Jul
Hexaminolevulinate-induced fluorescence endoscopy in patients with rectal adenoma and cancer: a pilot study.
2004 Sep
Induction of apoptosis by hexaminolevulinate-mediated photodynamic therapy in human colon carcinoma cell line 320DM.
2006
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
[Fluorescence cystoscopy at bladder cancer: present trials].
2007 Nov
Protoporphyrin IX fluorescence photobleaching is a useful tool to predict the response of rat ovarian cancer following hexaminolevulinate photodynamic therapy.
2008 Jul
Preliminary results of intraoperative photodynamic therapy with 5-aminolevulinic acid in dogs with prostate carcinoma.
2008 Nov
[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
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
Blue-sky thinking about blue-light cystoscopy.
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
Hexaminolevulinate-induced fluorescence colonoscopy versus white light endoscopy for diagnosis of neoplastic lesions in the colon.
2010 Jan
Hexylaminolaevulinate fluorescence cystoscopy in patients previously treated with intravesical bacille Calmette-Guérin.
2010 Mar
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
HEXVIX
Preferred Name English
HEXAMINOLEVULINATE
MI   VANDF   WHO-DD  
Systematic Name English
HEXAMINOLEVULINATE [MI]
Common Name English
5-AMINOLEVULINIC ACID HEXYL ESTER
Common Name English
Hexaminolevulinate [WHO-DD]
Common Name English
HEXYL 5-AMINO-4-OXOPENTANOATE
Systematic Name English
HEXAMINOLEVULINATE [VANDF]
Common Name English
PENTANOIC ACID, 5-AMINO-4-OXO-, HEXYL ESTER
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 Mon Mar 31 18:06:00 GMT 2025 , Edited by admin on Mon Mar 31 18:06:00 GMT 2025
Code System Code Type Description
MERCK INDEX
m6001
Created by admin on Mon Mar 31 18:06:00 GMT 2025 , Edited by admin on Mon Mar 31 18:06:00 GMT 2025
PRIMARY Merck Index
PUBCHEM
6433083
Created by admin on Mon Mar 31 18:06:00 GMT 2025 , Edited by admin on Mon Mar 31 18:06:00 GMT 2025
PRIMARY
FDA UNII
G7H20TKI67
Created by admin on Mon Mar 31 18:06:00 GMT 2025 , Edited by admin on Mon Mar 31 18:06:00 GMT 2025
PRIMARY
CAS
140898-97-1
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PRIMARY
NCI_THESAURUS
C26654
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PRIMARY
DRUG BANK
DB06261
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PRIMARY
EPA CompTox
DTXSID40161487
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PRIMARY
MESH
C419924
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PRIMARY
DRUG CENTRAL
167
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PRIMARY
LACTMED
Hexaminolevulinate
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PRIMARY
CHEBI
356416
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PRIMARY
DAILYMED
G7H20TKI67
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PRIMARY
CHEBI
17549
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PRIMARY
EVMPD
SUB38545
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PRIMARY
SMS_ID
100000129373
Created by admin on Mon Mar 31 18:06:00 GMT 2025 , Edited by admin on Mon Mar 31 18:06:00 GMT 2025
PRIMARY