MedKoo Cat#: 200860 Name: Ridaforolimus CAS#: 572924-54-0 Chemical Formula: C53H84NO14P Exact Mass: 989.56294 Molecular Weight: 990.21 Elemental Analysis: C, 64.29; H, 8.55; N, 1.41; O, 22.62; P, 3.13

Synonym: AP23573; AP 23573; AP-23573; MK8669; MK 8669; MK-8669; Deforolimus, Ridaforolimus

IUPAC/Chemical Name: (1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28Z,30S,32S,35R)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraen-12-yl]propyl]-2-methoxycyclohexyl dimethylphosphinate

InChi Key: BUROJSBIWGDYCN-QVXCGEACSA-N

InChi Code: InChI=1S/C53H84NO14P/c1-32-18-14-13-15-19-33(2)44(63-8)30-40-23-21-38(7)53(61,67-40)50(58)51(59)54-25-17-16-20-41(54)52(60)66-45(35(4)28-39-22-24-43(46(29-39)64-9)68-69(11,12)62)31-42(55)34(3)27-37(6)48(57)49(65-10)47(56)36(5)26-32/h13-15,18-19,27,32,34-36,38-41,43-46,48-49,57,61H,16-17,20-26,28-31H2,1-12H3/b15-13+,18-14+,33-19-,37-27+/t32-,34-,35-,36-,38-,39+,40+,41+,43-,44+,45+,46-,48-,49+,53-/m1/s1

SMILES Code: O=P(C)(C)O[C@H]1[C@H](OC)C[C@H](C[C@H]([C@H](CC([C@H](C)/C=C(C)/[C@@H](O)[C@H]2OC)=O)OC([C@]3([H])CCCCN3C(C([C@@](O4)(O)[C@H](C)CC[C@@]4([H])C[C@H](OC)/C(C)=CC=CC=C[C@@H](C)C[C@@H](C)C2=O)=O)=O)=O)C)CC1

Technical Data

Appearance: Solid powder

Purity: >97% (or refer to the Certificate of Analysis)

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 soluble 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).

Harmonized System Code: 293490

Additional Information

ridaforolimus is a small molecule and non-prodrug analogue of the lipophilic macrolide antibiotic rapamycin with potential antitumor activity. Ridaforolimus binds to and inhibits the mammalian target of rapamycin (mTOR), which may result in cell cycle arrest and,consequently, the inhibition of tumor cell growth and proliferation. Upregulated in some tumors, mTOR is a serine/threonine kinase involved in regulating cellular proliferation, motility, and survival that is located downstream of the PI3K/Akt signaling pathway. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).   Ridaforolimus (also known as AP23573 and MK-8669; formerly known as Deforolimus) is an immunosuppressant currently undergoing research for the treatment of certain cancers. It is a small-molecule inhibitor of the mammalian target of rapamycin (mTOR). Blocking mTOR creates a starvation-like effect in cancer cells by interfering with cell growth, division, metabolism, and angiogenesis. Ridaforolimus is being co-developed by Merck and ARIAD Pharmaceuticals. As of 2008, a phase III clinical trial of ridaforolimus in metastatic soft-tissue and bone sarcomas responsive to chemotherapy, SUCCEED (Sarcoma Multi-Center Clinical Evaluation of the Efficacy of Deforolimus), is recruiting patients. On May 5, 2010, Ariad Pharmaceuticals and Merck & Company announced a clinical development and marketing agreement. With this agreement, Ariad will receive an upfront payment of $50 million with an additional $19 million reimbursement for R&D expenses incurred to date in the program. Future payments are triggered upon acceptance of the NDA by the FDA with another payment when the drug receives marketing approval. There are similar milestones for acceptance and approval in both Europe and Japan. Other milestone payments are tied to revenue goals for the drug. the information was directly from: http://en.wikipedia.org/wiki/Ridaforolimus .   Current developer:    Merck and ARIAD Pharmaceuticals.    

References

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