Ridaforolimus

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Structural formula
Structural formula of Ridaforolimus
General
Non-proprietary name Ridaforolimus
other names
  • Dimethyl- (1 R , 2 R , 4 S ) -4 - {(2 R ) -2 - [(1 R , 9 S , 12 S , 15 R , 16 E , 18 R , 19 R , 21 R , 23 S , 24 E , 26 E , 28 E , 30 S , 32 S , 35 R ) -1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3 , 10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo [30.3.1.0 4,9 ] hexatriaconta-16,24,26,28-tetraen-12-yl] propyl} -2-methoxycyclohexylphosphinate ( IUPAC )
  • Deforolimus ( USAN )
  • AP23573
  • MK-8669
  • 42-dimethylphosphinic acid rapamycin
Molecular formula C 53 H 84 NO 14 P
Brief description

crystalline powder

External identifiers / databases
CAS number 572924-54-0
EC number 682-462-9
ECHA InfoCard 100.207.749
PubChem 11520894
ChemSpider 24597928
DrugBank DB06233
Wikidata Q2151796
Drug information
Drug class

Immunosuppressants

properties
Molar mass 990.21 g mol −1
solubility
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ridaforolimus (also Deforolimus , AP23573 or MK-8669 , trade name: Jenzyl) is an experimental immunosuppressant with a macrolide structure (macrocyclic lactone) and belongs to the phosphinic acid ester class . It was developed by Merck in collaboration with ARIAD Pharmaceuticals and was in the test phase until the end of 2012. It has a close structural relationship to sirolimus ( rapamycin ) and tacrolimus ( FK-506 ).

presentation

The rapamycin obtained from the bacterium Streptomyces hygroscopicus serves as the basis for the representation of Ridaforolimus . The hydroxy group of the cyclohexane ring of rapamycin is esterified with dimethylphosphinic acid chloride .

effect

Ridaforolimus, like the similar rapamycin, inhibits the protein mTOR ( mammalian target of rapamycin ). mTOR is one of the protein kinases that influence cell growth by regulating various cellular processes, including protein biosynthesis and autophagocytosis . This interferes with cell proliferation , metabolism and angiogenesis of cancer cells. It was used experimentally until 2012 in the treatment of patients with metastatic soft tissue sarcoma or bone sarcoma ( bone cancer ) in chemotherapy .

marketing

In November 2012, the application for marketing authorization, which was filed on June 25, 2011, was withdrawn by Merck . The application was withdrawn because the Committee for Medicinal Products for Human Use ( CHMP ) made hints that the research results may not be sufficient to enable market entry.

administration

ARIAD Pharmaceuticals, the original manufacturer and researcher, considered developing ridaforolimus in such a way that a stent could be coated with the same drug and thus connected to an angioplasty , while at the same time preventing possible restenosis .

Web links

  • Sant Chawla, Kamalesh Sankhala, Monica Mita, Anthony Tolcher: AP23573: A Review of Recent Results. In: ESUN. Liddy Shriver Sarcoma Initiative, April 2005, accessed November 23, 2017 .

Individual evidence

  1. ↑ a b c MSDS . (PDF; 127 kB) Santa Cruz Biotechnology; Retrieved August 4, 2011.
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ Clinical study (phase III): Ridaforolimus in Treatment of Sarcoma-SUCCEED (Sarcoma Multi-Center Clinical Eval. Of the Efficacy of Ridaforolimus) (8669-011) at Clinicaltrials.gov of the NIH .
  4. ↑ Ridaforolimus (Jenzyl). In: Arznei-News. Retrieved August 25, 2019 .
  5. ↑ Ridaforolimus . In: Drugs RD , November 27, 2012 (English) PMC 3586089 (free full text)