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Upamostat (WX-671; Mesupron; WX671) is a novel and potent serine protease inhibitor with anticancer activity. It is an orally bioavailable prodrug of WX-UK1, which is a urokinase plasminogen activator (uPA) inhibitor.
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| ln Vitro |
Upamostat is a urokinase plasminogen activator (uPA) inhibitor. Upamostat is an oral prodrug for the active metabolite WX-UK1, a novel uPA inhibitor [1]. Upamostat inhibits the urokinase-type plasminogen activator (uPA) system, which is involved in tumor invasion and metastasis. Upamostat is the orally available amidoxime (i.e., hydroxyamidine) prodrug of the pharmacologically active form, WX-UK1[2].
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| ln Vivo |
Rat Upamostat (Mesupron) pharmacokinetics are assessed using the validation method. Five rats get a single intravenous injection of 2 mg/kg of Upamostat, and the mean plasma concentrations of the drug are determined. The material has a terminal half-life of 0.5 hours, a monophasic decay pattern, a 2.0 L/kg volume of distribution, and a clearance of roughly 2.7 L/h/kg[3].
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| Additional Infomation |
Upamostat has been used in trials studying the treatment of Pancreatic Cancer.
Upamostat is an orally bioavailable, 3-amidinophenylalanine-derived, second generation serine protease inhibitor prodrug targeting the human urokinase plasminogen activator (uPA) system with potential antineoplastic and antimetastatic activities. After oral administration, upamostat is converted to the active N alpha-(2,4,6-triisopropylphenylsulfonyl)-3-amidino-(L)-phenylalanine-4-ethoxycarbonylpiperazide (WX-UK1), which inhibits several serine proteases, particularly uPA; inhibition of uPA may result in the inhibition of tumor growth and metastasis. uPA is a serine protease involved in degradation of the extracellular matrix and tumor cell migration and proliferation. |
| Molecular Formula |
C₃₂H₄₇N₅O₆S
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|---|---|
| Molecular Weight |
629.81
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| Exact Mass |
629.325
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| CAS # |
590368-25-5
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| Related CAS # |
590368-25-5
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| PubChem CID |
9852201
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| Appearance |
White to off-white solid powder
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| Density |
1.25
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| LogP |
6.298
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
12
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| Heavy Atom Count |
44
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| Complexity |
1070
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CCOC(=O)N1CCN(CC1)C(=O)[C@H](CC2=CC(=CC=C2)/C(=N/O)/N)NS(=O)(=O)C3=C(C=C(C=C3C(C)C)C(C)C)C(C)C
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| InChi Key |
HUASEDVYRABWCV-NDEPHWFRSA-N
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| InChi Code |
InChI=1S/C32H47N5O6S/c1-8-43-32(39)37-14-12-36(13-15-37)31(38)28(17-23-10-9-11-24(16-23)30(33)34-40)35-44(41,42)29-26(21(4)5)18-25(20(2)3)19-27(29)22(6)7/h9-11,16,18-22,28,35,40H,8,12-15,17H2,1-7H3,(H2,33,34)/t28-/m0/s1
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| Chemical Name |
ethyl 4-[(2S)-3-[3-[(Z)-N'-hydroxycarbamimidoyl]phenyl]-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]propanoyl]piperazine-1-carboxylate
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| Synonyms |
WX-671WX 671Mesupron WX671
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 250 mg/mL (~396.95 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.30 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.5878 mL | 7.9389 mL | 15.8778 mL | |
| 5 mM | 0.3176 mL | 1.5878 mL | 3.1756 mL | |
| 10 mM | 0.1588 mL | 0.7939 mL | 1.5878 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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