Motexafin gadolinium

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MedKoo CAT#: 201940

CAS#: 246252-06-2

Description: Motexafin gadolinium, also known as PCI 0120, is a synthetic metallotexaphyrin with radiosensitizing and chemosensitizing properties. Motexafin gadolinium accumulates in tumor cells preferentially due to their increased rates of metabolism, generating reactive oxygen species (ROS) intracellularly and lowering the tumor cell apoptotic threshold to ionizing radiation and chemotherapy.


Chemical Structure

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Motexafin gadolinium
CAS# 246252-06-2

Theoretical Analysis

MedKoo Cat#: 201940
Name: Motexafin gadolinium
CAS#: 246252-06-2
Chemical Formula: C52H72GdN5O14
Exact Mass:
Molecular Weight: 1148.419
Elemental Analysis: C, 54.39; H, 6.32; Gd, 13.69; N, 6.10; O, 19.50

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Synonym: PCI 0120; PCI-0120; PCI0120; API-GP 3; Gd texaphyrin; Gd-Texgadolinium; texaphyrin; Gd (III) Texaphryin. US brand name: Xcytrin. Abbreviation: GdTex.

IUPAC/Chemical Name: Gadolinium, bis(acetato-kappaO)(9,10-diethyl-20,21-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4,15-dimethyl-8,11-imino-3,6:16,13-dinitrilo-1,18-benzodiazacycloeicosine-5,14-dipropanolato-kappaN1,kappaN18,kappaN23,kappaN24,kappaN25)-, (PB-7-11-233'2'4)-

InChi Key: LAUAZTXAMPOVHP-WRIGXHCHSA-L, VAZLWPAHMORDGR-WRIGXHCHSA-L

InChi Code: InChI=1S/C48H66N5O10.2C2H4O2.Gd/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+;;;

SMILES Code: CCC1=C(N2[Gd-4]3456(OC(C)=O)OC(C)=O)C=C7[N+]4=C(C=[N+]6C8=CC(OCCOCCOCCOC)=C(OCCOCCOCCOC)C=C8[N+]5=CC(C(C)=C9CCCO)=[N+]3C9=CC2=C1CC)C(C)=C7CCCO

Appearance: Solid powder

Purity: >98%

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 1148.419 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: McHaffie DR, Chabot P, Dagnault A, Suh JH, Fortin MA, Chang E, Timmerman R, Souhami L, Grecula J, Nabid A, Schultz C, Werner-Wasik M, Gaspar LE, Brachman D, Mody T, Mehta MP. Safety and feasibility of motexafin gadolinium administration with whole brain radiation therapy and stereotactic radiosurgery boost in the treatment of ≤ 6 brain metastases: a multi-institutional phase II trial. J Neurooncol. 2011 Nov;105(2):301-8. Epub 2011 Apr 27. PubMed PMID: 21523486.

2: Berndt C, Kurz T, Bannenberg S, Jacob R, Holmgren A, Brunk UT. Ascorbate and endocytosed Motexafin gadolinium induce lysosomal rupture. Cancer Lett. 2011 Aug 28;307(2):119-23. Epub 2011 Apr 13. PubMed PMID: 21492999.

3: Edelman MJ, Otterson G, Leach J, Malpass T, Salgia R, Jones D, Mody TD, Govindan R. Multicenter phase II trial of Motexafin gadolinium and pemetrexed for second-line treatment in patients with non-small cell lung cancer. J Thorac Oncol. 2011 Apr;6(4):786-9. PubMed PMID: 21289521.

4: Singh AT, Evens AM, Prachand SN, Gordon LI. Motexafin gadolinium enhances p53-Mdm2 interactions, reducing p53 and downstream targets in lymphoma cell lines. Anticancer Res. 2010 Apr;30(4):1131-6. PubMed PMID: 20530418.

5: Traynor AM, Thomas JP, Ramanathan RK, Mody TD, Alberti D, Wilding G, Bailey HH. Phase I trial of motexafin gadolinium and doxorubicin in the treatment of advanced malignancies. Invest New Drugs. 2011 Apr;29(2):316-22. Epub 2009 Dec 9. PubMed PMID: 19997959; PubMed Central PMCID: PMC3038176.

6: Lin TS, Naumovski L, Lecane PS, Lucas MS, Moran ME, Cheney C, Lucas DM, Phan SC, Miller RA, Byrd JC. Effects of motexafin gadolinium in a phase II trial in refractory chronic lymphocytic leukemia. Leuk Lymphoma. 2009 Dec;50(12):1977-82. PubMed PMID: 19860624.

7: Evens AM, Spies WG, Helenowski IB, Patton D, Spies S, Jovanovic BD, Miyata S, Hamilton E, Variakojis D, Chen J, Naumovski L, Rosen ST, Winter JN, Miller RA, Gordon LI. The novel expanded porphyrin, motexafin gadolinium, combined with [90Y]ibritumomab tiuxetan for relapsed/refractory non-Hodgkin's lymphoma: preclinical findings and results of a phase I trial. Clin Cancer Res. 2009 Oct 15;15(20):6462-71. Epub 2009 Oct 13. PubMed PMID: 19825958; PubMed Central PMCID: PMC2763343.

8: Francis D, Richards GM, Forouzannia A, Mehta MP, Khuntia D. Motexafin gadolinium: a novel radiosensitizer for brain tumors. Expert Opin Pharmacother. 2009 Sep;10(13):2171-80. PubMed PMID: 19640206.

9: Kanick SC, Eiseman JL, Parker RS. Pharmacokinetic modeling of motexafin gadolinium disposition in mouse tissues using optical pharmacokinetic system measurements. Photodiagnosis Photodyn Ther. 2008 Dec;5(4):276-84. Epub 2009 Jan 23. PubMed PMID: 19356671.

10: Zahedi Avval F, Berndt C, Pramanik A, Holmgren A. Mechanism of inhibition of ribonucleotide reductase with motexafin gadolinium (MGd). Biochem Biophys Res Commun. 2009 Feb 13;379(3):775-9. Epub 2009 Jan 1. PubMed PMID: 19121624.

11: Mehta MP, Shapiro WR, Phan SC, Gervais R, Carrie C, Chabot P, Patchell RA, Glantz MJ, Recht L, Langer C, Sur RK, Roa WH, Mahe MA, Fortin A, Nieder C, Meyers CA, Smith JA, Miller RA, Renschler MF. Motexafin gadolinium combined with prompt whole brain radiotherapy prolongs time to neurologic progression in non-small-cell lung cancer patients with brain metastases: results of a phase III trial. Int J Radiat Oncol Biol Phys. 2009 Mar 15;73(4):1069-76. Epub 2008 Oct 30. PubMed PMID: 18977094.

12: Amato RJ, Jac J, Hernandez-McClain J. Motexafin gadolinium for the treatment of metastatic renal cell carcinoma: phase II study results. Clin Genitourin Cancer. 2008 Sep;6(2):73-8. PubMed PMID: 18824428.



Additional Information

 
Phase I trials of  Motexafin gadolinium (MTG): Fifteen patients received 37 cycles of treatment, for a median of 2 cycles per patient (range 0-6 cycles). Three patients (20%) completed 6 cycles of therapy. The MTD was identified as MGd, 2 mg/kg/day and doxorubicin, 30 mg/m². Dose limiting toxicities included grade 3 hypertension, pneumonia, bacteremia, and elevated GGT. Serious adverse events also included pulmonary embolism and urinary tract infection requiring hospitalization. There was no exacerbation of cardiac toxicity. No patients attained a response to treatment. Six patients (54%) had stable disease. The median time to disease progression, or to last assessment, was 49 days (range 8-195 days). CONCLUSIONS:  The combination of MGd and doxorubicin was fairly well tolerated. However, due to emerging preclinical data suggesting that MGd inhibits ribonucleotide reductase, further development of the combination of MGd plus doxorubicin is not recommended. (source: Invest New Drugs. 2011 Apr;29(2):316-22).
(MTG):