Identification
- Generic Name
- Motexafin lutetium
- DrugBank Accession Number
- DB05296
- Background
Motexafin lutetium (MLu) is a second-generation photosensitizer for photodynamic therapy (PDT) of cancer. It belongs to the family of drugs called metallotexaphyrins. Also called lutetium texaphyrin. Motexafin lutetium is a pentadentate aromatic metallotexaphyrin with photosensitizing properties.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Motexafin lutetium (DB05296)
- Weight
- Average: 1166.136
Monoisotopic: 1165.44836 - Chemical Formula
- C52H72LuN5O14
- Synonyms
- Lutetium texaphyrin anhydrous
- Motexafin lutetium anhydrous
Pharmacology
- Indication
Investigated for use/treatment in brain cancer, breast cancer, cervical dysplasia/cancer, prostate cancer, cancer/tumors (unspecified), coronary artery disease, macular degeneration, and peripheral vascular disease.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Motexafin lutetium has the potential to combine the features of selective localization, ability to be activated by deeply penetrating far-red light, low incidence of skin photosensitization and water solubility. The product is in clinical development as a treatment for several types of solid tumors (as Lutrin), age-related macular degeneration (as Optrin), atherosclerosis and prevention of restenosis (as Antrin). Motexafin lutetium preferentially accumulates in tumor cells due to their increased rates of metabolism and absorbs light, forming an extended high energy conformational state that produces high quantum yields of singlet oxygen, resulting in local cytotoxic effects.
- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwarePadeliporfin Motexafin lutetium may increase the photosensitizing activities of Padeliporfin. Porfimer sodium Motexafin lutetium may increase the photosensitizing activities of Porfimer sodium. Tretinoin The risk or severity of adverse effects can be increased when Tretinoin is combined with Motexafin lutetium. Verteporfin Motexafin lutetium may increase the photosensitizing activities of Verteporfin. - Food Interactions
- Not Available
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 Motexafin lutetium hydrate 0A85BJ22L6 156436-90-7 WIQKYZYFTAEWBF-IOYKFIIZSA-L - International/Other Brands
- Antrin / Lutrin / Optrin
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 0V38NF6N89
- CAS number
- 246252-04-0
- InChI Key
- ZCISRIHHEXSWIR-WRIGXHCHSA-L
- InChI
- InChI=1S/C48H66N5O10.2C2H4O2.Lu/c1-7-35-36(8-2)40-28-42-38(12-10-14-55)34(4)46(53-42)32-50-44-30-48(63-26-24-61-22-20-59-18-16-57-6)47(62-25-23-60-21-19-58-17-15-56-5)29-43(44)49-31-45-33(3)37(11-9-13-54)41(52-45)27-39(35)51-40;2*1-2(3)4;/h27-32,54-55H,7-26H2,1-6H3;2*1H3,(H,3,4);/q-1;;;+3/p-2/b39-27-,40-28-,41-27-,42-28-,45-31-,46-32-,49-31+,49-43+,50-32+,50-44+;;;
- IUPAC Name
- lutetium(3+) 4,5-diethyl-9,24-bis(3-hydroxypropyl)-16,17-bis({2-[2-(2-methoxyethoxy)ethoxy]ethoxy})-10,23-dimethyl-13,20,25,26,27-pentaazapentacyclo[20.2.1.1^{3,6}.1^{8,11}.0^{14,19}]heptacosa-1,3,5,7,9,11(26),12,14,16,18,20,22(25),23-tridecaen-27-ide diacetate
- SMILES
- [Lu+3].CC([O-])=O.CC([O-])=O.CCC1=C2[N-]C(\C=C3/N=C(/C=N/C4=CC(OCCOCCOCCOC)=C(OCCOCCOCCOC)C=C4\N=C\C4=N\C(=C/2)\C(CCCO)=C4C)C(C)=C3CCCO)=C1CC
References
- General References
- Chen Z, Woodburn KW, Shi C, Adelman DC, Rogers C, Simon DI: Photodynamic therapy with motexafin lutetium induces redox-sensitive apoptosis of vascular cells. Arterioscler Thromb Vasc Biol. 2001 May;21(5):759-64. [Article]
- Ross HM, Smelstoys JA, Davis GJ, Kapatkin AS, Del Piero F, Reineke E, Wang H, Zhu TC, Busch TM, Yodh AG, Hahn SM: Photodynamic therapy with motexafin lutetium for rectal cancer: a preclinical model in the dog. J Surg Res. 2006 Oct;135(2):323-30. Epub 2006 May 2. [Article]
- External Links
- PubChem Compound
- 3081907
- PubChem Substance
- 175426971
- ChemSpider
- 8095581
- Wikipedia
- Motexafin_lutetium
Clinical Trials
- Clinical Trials
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
Property Value Source Water Solubility 0.00532 mg/mL ALOGPS logP 4.99 ALOGPS logP 6.76 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 15.62 Chemaxon pKa (Strongest Basic) 2.45 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 15 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 178.75 Å2 Chemaxon Rotatable Bond Count 28 Chemaxon Refractivity 243.08 m3·mol-1 Chemaxon Polarizability 106.08 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8734 Blood Brain Barrier - 0.7339 Caco-2 permeable - 0.6221 P-glycoprotein substrate Substrate 0.8853 P-glycoprotein inhibitor I Non-inhibitor 0.5372 P-glycoprotein inhibitor II Non-inhibitor 0.8542 Renal organic cation transporter Non-inhibitor 0.757 CYP450 2C9 substrate Non-substrate 0.8583 CYP450 2D6 substrate Non-substrate 0.8056 CYP450 3A4 substrate Substrate 0.5944 CYP450 1A2 substrate Non-inhibitor 0.5684 CYP450 2C9 inhibitor Non-inhibitor 0.676 CYP450 2D6 inhibitor Non-inhibitor 0.8557 CYP450 2C19 inhibitor Non-inhibitor 0.7248 CYP450 3A4 inhibitor Non-inhibitor 0.5218 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8409 Ames test Non AMES toxic 0.6034 Carcinogenicity Non-carcinogens 0.9072 Biodegradation Not ready biodegradable 0.9768 Rat acute toxicity 2.5917 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8781 hERG inhibition (predictor II) Non-inhibitor 0.6777
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Drug created at November 18, 2007 18:23 / Updated at June 12, 2020 16:52