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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

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
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 induction of porphyrins after their systemic administration to tumour bearing mice.
2002 Sep 23
Protoporphyrin IX-accumulation in human tumor cells following topical ALA- and h-ALA-application in vivo.
2003 Dec 8
Photodynamic effects of 5-aminolevulinic acid and its hexylester on several cell lines.
2003 Jul
Gateways to clinical trials.
2004 Sep
Hexaminolevulinate-induced fluorescence endoscopy in patients with rectal adenoma and cancer: a pilot study.
2004 Sep
Light scattering from intact cells reports oxidative-stress-induced mitochondrial swelling.
2005 Apr
Hexyl aminolevulinate in the detection of bladder cancer: profile report.
2006
Hexyl aminolevulinate: in the detection of bladder cancer.
2006
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
Determination of the bioavailability of [14C]-hexaminolevulinate using accelerator mass spectrometry after intravesical administration to human volunteers.
2006 Apr
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
A case of anaphylactic shock possibly caused by intravesical Hexvix.
2006 Oct
Topical application of 5-aminolaevulinic acid, methyl 5-aminolaevulinate and hexyl 5-aminolaevulinate on normal human skin.
2006 Oct
Photodynamic effects on nasopharyngeal carcinoma (NPC) cells with 5-aminolevulinic acid or its hexyl ester.
2006 Oct 8
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
Hexyl-aminolevulinate-mediated photodynamic therapy: how to spare normal urothelium. An in vitro approach.
2007 Jan
[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
Clinical evaluation of bioadhesive hydrogels for topical delivery of hexylaminolevulinate to Barrett's esophagus.
2007 Nov 20
Recent developments in fluorescence cystoscopy: do novel agents bring a benefit?
2007 Sep
Comparison of ALA- and ALA hexyl-ester-induced PpIX depth distribution in human skin carcinoma.
2008 Dec 11
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
5-Aminolaevulinic acid peptide prodrugs enhance photosensitization for photodynamic therapy.
2008 Jun
Preliminary results of intraoperative photodynamic therapy with 5-aminolevulinic acid in dogs with prostate carcinoma.
2008 Nov
Effects of photoactivated 5-aminolevulinic acid hexyl ester on MDR1 over-expressing human uterine sarcoma cells.
2008 Sep
Editorial comment on: A new generation of optical diagnostics for bladder cancer: technology, diagnostic accuracy, and future applications.
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
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
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 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
Hexylaminolaevulinate fluorescence cystoscopy in patients previously treated with intravesical bacille Calmette-Guérin.
2010 Mar
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
Hexaminolevulinate [WHO-DD]
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
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 Fri Dec 15 15:42:06 UTC 2023 , Edited by admin on Fri Dec 15 15:42:06 UTC 2023
Code System Code Type Description
MERCK INDEX
m6001
Created by admin on Fri Dec 15 15:42:06 UTC 2023 , Edited by admin on Fri Dec 15 15:42:06 UTC 2023
PRIMARY Merck Index
PUBCHEM
6433083
Created by admin on Fri Dec 15 15:42:06 UTC 2023 , Edited by admin on Fri Dec 15 15:42:06 UTC 2023
PRIMARY
FDA UNII
G7H20TKI67
Created by admin on Fri Dec 15 15:42:06 UTC 2023 , Edited by admin on Fri Dec 15 15:42:06 UTC 2023
PRIMARY
CAS
140898-97-1
Created by admin on Fri Dec 15 15:42:06 UTC 2023 , Edited by admin on Fri Dec 15 15:42:06 UTC 2023
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
Created by admin on Fri Dec 15 15:42:06 UTC 2023 , Edited by admin on Fri Dec 15 15:42:06 UTC 2023
PRIMARY
CHEBI
356416
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PRIMARY
DAILYMED
G7H20TKI67
Created by admin on Fri Dec 15 15:42:06 UTC 2023 , Edited by admin on Fri Dec 15 15:42:06 UTC 2023
PRIMARY
CHEBI
17549
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PRIMARY
EVMPD
SUB38545
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PRIMARY
SMS_ID
100000129373
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PRIMARY