Lemuteporfin

Identification

Generic Name
Lemuteporfin
DrugBank Accession Number
DB04980
Background

Lemuteporfin, under development by QLT Incorporated, is a benzoporphyrin-derived chlorin-like photosensitizer. It is intended for the treatment of beign prostatic hyperplasia.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 792.886
Monoisotopic: 792.337043762
Chemical Formula
C44H48N4O10
Synonyms
  • Lemuteporfin
External IDs
  • EA 6
  • QLT 0074
  • QLT-0074
  • QLT0074

Pharmacology

Indication

Intended for the treatment of benign prostatic hyperplasia and prostrate disorders.

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Pharmacodynamics

Trial data accumulated thus far indicate a generally positive tollerability profile and preliminary efficacy.

Mechanism of action

Lemuteporfin is transported in the plasma primarily by lipoproteins. Once lemuteporfin is activated by light in the presence of oxygen, highly reactive, short-lived singlet oxygen and reactive oxygen radicals are generated. Light activation of lemuteporfin results in local damage to neovascular endothelium, resulting in vessel occlusion. Damaged endothelium is known to release procoagulant and vasoactive factors through the lipo-oxygenase (leukotriene) and cyclo-oxygenase (eicosanoids such as thromboxane) pathways, resulting in platelet aggregation, fibrin clot formation and vasoconstriction.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
EZ109VJ012
CAS number
215808-49-4
InChI Key
PUTVMYIZBFOAFU-MTVFQPQZSA-N
InChI
InChI=1S/C44H48N4O10/c1-8-26-23(2)32-20-37-30-12-9-29(42(53)55-6)41(43(54)56-7)44(30,5)38(48-37)22-33-25(4)28(11-14-40(52)58-18-16-50)36(47-33)21-35-27(10-13-39(51)57-17-15-49)24(3)31(46-35)19-34(26)45-32/h8-9,12,19-22,41,46,48-50H,1,10-11,13-18H2,2-7H3/b34-19-,36-21-,37-20-,38-22-
IUPAC Name
20,21-dimethyl 5-ethenyl-10,14-bis[3-(2-hydroxyethoxy)-3-oxopropyl]-4,9,15,19-tetramethyl-25,26,27,28-tetraazahexacyclo[16.6.1.1^{3,6}.1^{8,11}.1^{13,16}.0^{19,24}]octacosa-1,3(28),4,6,8,10,12,14,16(26),17,21,23-dodecaene-20,21-dicarboxylate
SMILES
COC(=O)C1C(=CC=C2\C3=C\C4=N\C(=C/C5=C(C)C(CCC(=O)OCCO)=C(N5)\C=C5/N=C(/C=C(\N3)C12C)C(C)=C5CCC(=O)OCCO)\C(C=C)=C4C)C(=O)OC

References

General References
  1. Boch R, Canaan AJ, Cho A, Dolphin DD, Hong L, Jain AK, North JR, Richter AM, Smits C, Sternberg ED: Cellular and antitumor activity of a new diethylene glycol benzoporphyrin derivative (lemuteporfin). Photochem Photobiol. 2006 Jan-Feb;82(1):219-24. [Article]
PubChem Substance
347909872
ChemSpider
34990361

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentProstatic Hyperplasia1
1, 2CompletedTreatmentAcne1
1, 2CompletedTreatmentBenign Prostatic Hyperplasia (BPH)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0214 mg/mLALOGPS
logP4.5ALOGPS
logP5.85Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)11.81Chemaxon
pKa (Strongest Basic)4.98Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area203.02 Å2Chemaxon
Rotatable Bond Count17Chemaxon
Refractivity216.44 m3·mol-1Chemaxon
Polarizability90.31 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dr-0000006900-0d37286cf796f0467b5d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ug0-0000002900-e30f4d6ba22ef9eb74ff
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0000009200-c9b9f639070dffb74954
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0k9i-1000006900-a27a69afd443d145e590
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000009200-c34091ff1928ffeeac80
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052u-0000017900-1a9b63e69672443eb4d7
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at October 21, 2007 22:23 / Updated at March 26, 2021 03:54