Identification
- Summary
Hexaminolevulinate is an optical imaging agent used to perform Blue Light Cystoscopy (BLC™) in order to detect carcinoma of the bladder.
- Brand Names
- Cysview
- Generic Name
- Hexaminolevulinate
- DrugBank Accession Number
- DB06261
- Background
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. On May 28, 2010, the U.S. Food and Drug Administration (FDA) granted approval for hexaminolevulinate hydrochloride (Cysview for Intravesical Solution, Photocure ASA), as an optical imaging agent for use in combination with the Karl Storz Photodynamic Diagnostic D-Light C (PDD) System 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. Hexaminolevulinate is manufactured under the brand Cysview® by Photocure ASA. In Europe, Hexaminolevulinate is marketed under the brand Hexvix®.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Hexaminolevulinate (DB06261)
- Weight
- Average: 215.293
Monoisotopic: 215.15214354 - Chemical Formula
- C11H21NO3
- Synonyms
- 4-Hexyloxycarbonyl-2-oxobutylammoniumchloride
- Hexaminolevulinato
- Hexyl 5-amino-4-oxopentanoate hydrochloride
- Hexyl(5-amino-4-oxopentanoat)-hydrochlorid
- Pentanoic acid, 5-amino-4-oxo-, hexyl ester, hydrochloride
- External IDs
- P-1026
Pharmacology
- Indication
Hexaminolevulinate is indicated for use in the cystoscopic detection of non-muscle invasive papillary cancer of the bladder among patients suspected or known to have lesion(s) on the basis of a prior cystoscopy.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Bladder carcinoma •••••••••••• •••••••••••• ••••••••• Diagnostic agent Carcinoma in situ of urinary bladder •••••••••••• •••••••••••• ••••••••• - Contraindications & Blackbox Warnings
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In vitro studies have shown increased porphyrin fluorescence in normal urothelium after exposure to hexaminolevulinate hydrochloride intravesical solution. In the human bladder, a greater accumulation of porphyrins is proposed in neoplastic or inflamed cells, compared to normal urothelium. After bladder instillation of hexaminolevulinate hydrochloride intravesical solution for approximately 1 hour and subsequent illumination with blue light at wavelengths 360 – 450nm, the porphyrins will fluoresce red.
- Mechanism of action
Hexaminolevulinate is an ester of the heme precursor, aminolevulinic acid. 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. After excitation with light at wavelengths between 360 and 450 nm, PpIX and other PAPs return to a lower energy level by fluorescing, which can be detected and used for cystoscopic detection of lesions. The fluorescence from tumor tissue appears bright red and demarcated, whereas the background normal tissue appears dark blue. Similar processes may occur in inflamed cells.
- Absorption
Absolute bioavailability 7% (90% confidence interval [CI]: 5%-10%)
- Volume of distribution
Not Available
- Protein binding
No evidence of significant binding.
- Metabolism
Rapid metabolism in human blood.
- Route of elimination
Not Available
- Half-life
Biphasic elimination, with an initial elimination half-life of 39 minutes, followed by a terminal half-life of approximately 76 hours.
- Clearance
Not Available
- Adverse Effects
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No studies in animals have been conducted to evaluate the carcinogenic potential of hexaminolevulinate hydrochloride.
Hexaminolevulinate hydrochloride was not mutagenic in in-vitro reverse mutation tests in bacteria, or in chromosome aberration tests in human peripheral blood lymphocytes, and was negative in an in-vivo micronucleus test in mice after intravenous injection of doses up to 45 mg/kg in the absence of light activation.
Adequate studies have not been performed to evaluate the genetic toxicity of hexaminolevulinate hydrochloride in the presence of light activation.
Adequate reproductive and developmental toxicity studies in animals have not been performed to evaluate the effects of hexaminolevulinate hydrochloride on fertility.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareBCG vaccine BCG vaccine may decrease effectiveness of Hexaminolevulinate as a diagnostic agent. Padeliporfin Hexaminolevulinate may increase the photosensitizing activities of Padeliporfin. Porfimer sodium Hexaminolevulinate may increase the photosensitizing activities of Porfimer sodium. Tretinoin The risk or severity of adverse effects can be increased when Tretinoin is combined with Hexaminolevulinate. Verteporfin Hexaminolevulinate may increase the photosensitizing activities of Verteporfin. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Hexaminolevulinate hydrochloride D4F329SL1O 140898-91-5 LZYXPFZBAZTOCH-UHFFFAOYSA-N - International/Other Brands
- Hexvix (GE Healthcare)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cysview Kit; Powder, for solution 100 mg/50mL Intravesical Photocure Inc. 2018-05-01 Not applicable US 
Cysview Kit 100 mg/50mL Intravesical Ge Healthcare 2010-09-01 2011-12-31 US Cysview Kit; Powder, for solution 100 mg / vial Intravesical Photocure Asa 2015-12-14 Not applicable Canada 
Categories
- ATC Codes
- V04CX06 — Hexaminolevulinate
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as delta amino acids and derivatives. These are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Delta amino acids and derivatives
- Alternative Parents
- Gamma-keto acids and derivatives / Fatty acid esters / Alpha-amino ketones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Alpha-aminoketone / Amine / Carbonyl group / Carboxylic acid ester / Delta amino acid or derivatives / Fatty acid ester / Fatty acyl / Gamma-keto acid / Hydrocarbon derivative
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- G7H20TKI67
- CAS number
- 140898-97-1
- InChI Key
- RYQOILLJDKPETL-UHFFFAOYSA-N
- InChI
- InChI=1S/C11H21NO3/c1-2-3-4-5-8-15-11(14)7-6-10(13)9-12/h2-9,12H2,1H3
- IUPAC Name
- hexyl 5-amino-4-oxopentanoate
- SMILES
- [H]N([H])CC(=O)CCC(=O)OCCCCCC
References
- General References
- Yang LP: Hexaminolevulinate blue light cystoscopy: a review of its use in the diagnosis of bladder cancer. Mol Diagn Ther. 2014 Feb;18(1):105-16. doi: 10.1007/s40291-013-0068-x. [Article]
- O'Brien T, Thomas K: Bladder cancer: Photodynamic diagnosis can improve surgical outcome. Nat Rev Urol. 2010 Nov;7(11):598-9. doi: 10.1038/nrurol.2010.183. [Article]
- Hillemanns P, Wang X, Hertel H, Andikyan V, Hillemanns M, Stepp H, Soergel P: Pharmacokinetics and selectivity of porphyrin synthesis after topical application of hexaminolevulinate in patients with cervical intraepithelial neoplasia. Am J Obstet Gynecol. 2008 Mar;198(3):300.e1-7. doi: 10.1016/j.ajog.2007.07.045. Epub 2008 Feb 21. [Article]
- FDA Approved Drug Products: Cysview (hexaminolevulinate hydrochloride), for Intravesical Solution For bladder instillation only [Link]
- External Links
- KEGG Drug
- D04436
- PubChem Compound
- 6433083
- PubChem Substance
- 310264865
- ChemSpider
- 4938272
- 1426872
- ChEBI
- 134892
- ChEMBL
- CHEMBL1201784
- ZINC
- ZINC000001554392
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cysview
- FDA label
- Download (194 KB)
- MSDS
- Download (60.8 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Not Yet Recruiting Treatment High Risk Non-Muscle Invasive Bladder Urothelial Carcinoma / Non-Muscle Invasive Bladder Urothelial Carcinoma / Non-Muscle-invasive Bladder Cancer (NMIBC) 1 4 Withdrawn Diagnostic Bladder Cancer 1 3 Completed Not Available Bladder Cancer 1 3 Completed Diagnostic Bladder Cancer 4 3 Completed Treatment Bladder Cancer / Pervasive Development Disorder / Recurrences 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Intravesical 100 mg/50mL Kit; powder, for solution Intravesical 100 mg / vial Kit; powder, for solution Intravesical 100 mg/50mL Powder, for solution Intravenous; Intravesical 85 MG Powder, for solution Intravesical 85 MG Solution Intravesical 85 MG Injection, powder, for solution Intravesical 85 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6034267 No 2000-03-07 2016-03-08 US US7247655 No 2007-07-24 2016-03-08 US US7530461 No 2009-05-12 2017-01-11 US US7348361 No 2008-03-25 2020-11-06 US US10556010 No 2020-02-11 2036-12-19 US US11235168 No 2018-01-04 2038-01-04 US US11311620 No 2016-12-19 2036-12-19 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.511 mg/mL ALOGPS logP 1.55 ALOGPS logP 1.37 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 16.11 Chemaxon pKa (Strongest Basic) 7.83 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 69.39 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 58.29 m3·mol-1 Chemaxon Polarizability 24.96 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-06sr-9200000000-0e60df2b518c68b3624f Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-02ti-9760000000-1bee57e57bbb80ca20f8 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-3910000000-10f08668d8f50d2a46cc Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-01p9-9400000000-6dedf74dbc1a3c8ee8e1 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0c09-9400000000-630140df89a35756baee Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0bu3-9000000000-eb89aca8b987746e549b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05fr-9100000000-a391fbd9b589de8607bd Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 166.1955583 predictedDarkChem Lite v0.1.0 [M-H]- 145.67784 predictedDeepCCS 1.0 (2019) [M+H]+ 167.0416583 predictedDarkChem Lite v0.1.0 [M+H]+ 148.0734 predictedDeepCCS 1.0 (2019) [M+Na]+ 166.4605583 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.02138 predictedDeepCCS 1.0 (2019)
Drug created at March 19, 2008 16:19 / Updated at April 23, 2024 11:38