MK-0731

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 201910

CAS#: 845256-65-7

Description: MK-0731 is a synthetic small molecule with potential antineoplastic activity. MK0731 selectively inhibits kinesin spindle protein (KSP), which may result in the inhibition of mitotic spindle assembly, induction of cell cycle arrest during the mitotic phase, and apoptosis in tumor cells that overexpress KSP. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)


Chemical Structure

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MK-0731
CAS# 845256-65-7

Theoretical Analysis

MedKoo Cat#: 201910
Name: MK-0731
CAS#: 845256-65-7
Chemical Formula: C25H28F3N3O2
Exact Mass: 459.21336
Molecular Weight: 459.5
Elemental Analysis: C, 65.35; H, 6.14; F, 12.40; N, 9.14; O, 6.96

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Synonym: MK0731, MK-0731, MK 0731

IUPAC/Chemical Name: (S)-4-(2,5-difluorophenyl)-N-((3R,4S)-3-fluoro-1-methylpiperidin-4-yl)-2-(hydroxymethyl)-N-methyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide.

InChi Key: MYBGWENAVMIGMM-GIFXNVAJSA-N

InChi Code: InChI=1S/C25H28F3N3O2/c1-29-11-10-23(22(28)15-29)30(2)24(33)31-14-17(20-12-19(26)8-9-21(20)27)13-25(31,16-32)18-6-4-3-5-7-18/h3-9,12-13,22-23,32H,10-11,14-16H2,1-2H3/t22-,23+,25-/m1/s1

SMILES Code: O=C(N1[C@@](C2=CC=CC=C2)(CO)C=C(C3=CC(F)=CC=C3F)C1)N([C@@H]4[C@H](F)CN(C)CC4)C

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 459.5 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. Matthieu, Michel; Dubois, Vincent; Tranchant, Isabelle; Kearsey, Jonathan. Preparation of peptide prodrugs modified with a 1,2,3,4-cyclobutanetetracarboxylic acid derived moiety useful in treatment and diagnosis of tumors and inflammatory diseases. PCT Int. Appl. (2008), 96pp. CODEN: PIXXD2 WO 2008120098 A2 20081009 CAN 149:448733 AN 2008:1210491

2. Matthieu, Michel; Dubois, Vincent; Tranchant, Isabelle; Kearsey, Jonathan. Preparation of peptide prodrugs modified with a 1,2,3,4-cyclobutanetetracarboxylic acid derived moiety useful in treatment and diagnosis of tumors and inflammatory diseases. Eur. Pat. Appl. (2008), 31pp. CODEN: EPXXDW EP 1977765 A1 20081008 CAN 149:448732 AN 2008:1205912

3. Cox, Christopher D.; Coleman, Paul J.; Breslin, Michael J.; Whitman, David B.; Garbaccio, Robert M.; Fraley, Mark E.; Buser, Carolyn A.; Walsh, Eileen S.; Hamilton, Kelly; Schaber, Michael D.; Lobell, Robert B.; Tao, Weikang; Davide, Joseph P.; Diehl, Ronald E.; Abrams, Marc T.; South, Vicki J.; Huber, Hans E.; Torrent, Maricel; Prueksaritanont, Thomayant; Li, Chunze; Slaughter, Donald E.; Mahan, Elizabeth; Fernandez-Metzler, Carmen; Yan, Youwei; Kuo, Lawrence C.; Kohl, Nancy E.; Hartman, George D. Kinesin Spindle Protein (KSP) Inhibitors. 9. Discovery of (2S)-4-(2,5-Difluorophenyl)-N-[(3R,4S)-3-fluoro-1-methylpiperidin-4-yl]-2-(hydroxymethyl)-N-methyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide (MK-0731) for the Treatment of Taxane-Refractory Cancer. Journal of Medicinal Chemistry (2008), 51(14), 4239-4252. CODEN: JMCMAR ISSN:0022-2623. CAN 149:191278 AN 2008:779815

4. Javadi, Gary; Karady, Sandor; Maeda, Kenji; Miller, Ross A.; Szumigala, Ronald H. A process for the preparation of 2,2-disubstituted pyrroles. PCT Int. Appl. (2005), 48 pp. CODEN: PIXXD2 WO 2005102996 A2 20051103 CAN 143:440255 AN 2005:1171050

5. Coleman, Paul J.; Cox, Christopher D.; Garbaccio, Robert M.; Hartman, George D. Preparation of dihydropyrrolecarboxamides as mitotic kinesin inhibitors for treating cancer. PCT Int. Appl. (2005), 187 pp. CODEN: PIXXD2 WO 2005019206 A1 20050303 CAN 142:280064 AN 2005:182653

6. Coleman, Paul J.; Cox, Christopher D.; Garbaccio, Robert M.; Hartman, George D. A preparation of pyrrolecarboxamide derivatives, useful as mitotic kinesin inhibitors. U.S. Pat. Appl. Publ. (2005), 52 pp. CODEN: USXXCO US 2005038074 A1 20050217 CAN 142:240324 AN 2005:140806

MK-0731

10.0mg / Not available


Additional Information

 MK-0731 is a potent inhibitor of KSP, with an IC50 of 2.2 nM, and >20,000 fold selectivity against other kinesins. MK-0731 causes mitotic arrest with an EC50 in several tumor cell lines of 3-5 nM.