NAV

Ridaforolimus

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Ridaforolimus
DrugBank Accession Number
DB06233
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 990.222
Monoisotopic: 989.562943387
Chemical Formula
C53H84NO14P
Synonyms
  • Deforolimus
  • Ridaforolimus
External IDs
  • AP 23573
  • AP-23573
  • AP23573
  • MK-8669
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Pharmacology

Indication

Investigated for use/treatment in solid tumors, sarcoma, cancer/tumors (unspecified), endometrial cancer, prostate cancer, and bone metastases.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Deforolimus inhibits the mammalian target of rapamycin (mTOR), a serine kinase of the phosphatidylinositol-3-kinase (PI3K) family that regulates protein synthesis, affecting cell growth and proliferation. mTOR is a downstream effector of the phosphatidylinositol 3-kinase/Akt and nutrient-sensing pathways which cancer cells need to proliferate.

TargetActionsOrganism
ASerine/threonine-protein kinase mTOR
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Ridaforolimus.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with Ridaforolimus.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Ridaforolimus.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Ridaforolimus.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Ridaforolimus.
Food Interactions
Not Available

Categories

ATC Codes
L01EG03 — Ridaforolimus
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolide lactams
Sub Class
Not Available
Direct Parent
Macrolide lactams
Alternative Parents
Alpha amino acid esters / Macrolides and analogues / Piperidines / Oxanes / Tertiary carboxylic acid amides / Secondary alcohols / Carboxylic acid esters / Cyclic ketones / Hemiacetals / Lactams
show 10 more
Substituents
Alcohol / Aliphatic heteropolycyclic compound / Alpha-amino acid ester / Alpha-amino acid or derivatives / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone
show 24 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
lactam, macrolide (CHEBI:79700)
Affected organisms
Not Available

Chemical Identifiers

UNII
48Z35KB15K
CAS number
572924-54-0
InChI Key
BUROJSBIWGDYCN-GAUTUEMISA-N
InChI
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
IUPAC Name
(1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,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[30.3.1.0^{4,9}]hexatriaconta-16,24,26,28-tetraen-12-yl]propyl]-2-methoxycyclohexyl dimethylphosphinate
SMILES
CO[C@@H]1C[C@H](C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N3CCCC[C@H]3C(=O)O2)OC)CC[C@H]1OP(C)(C)=O

References

General References
  1. Mita MM, Mita AC, Chu QS, Rowinsky EK, Fetterly GJ, Goldston M, Patnaik A, Mathews L, Ricart AD, Mays T, Knowles H, Rivera VM, Kreisberg J, Bedrosian CL, Tolcher AW: Phase I trial of the novel mammalian target of rapamycin inhibitor deforolimus (AP23573; MK-8669) administered intravenously daily for 5 days every 2 weeks to patients with advanced malignancies. J Clin Oncol. 2008 Jan 20;26(3):361-7. doi: 10.1200/JCO.2007.12.0345. [Article]
  2. Rizzieri DA, Feldman E, Dipersio JF, Gabrail N, Stock W, Strair R, Rivera VM, Albitar M, Bedrosian CL, Giles FJ: A phase 2 clinical trial of deforolimus (AP23573, MK-8669), a novel mammalian target of rapamycin inhibitor, in patients with relapsed or refractory hematologic malignancies. Clin Cancer Res. 2008 May 1;14(9):2756-62. doi: 10.1158/1078-0432.CCR-07-1372. [Article]
KEGG Compound
C15183
ChemSpider
24597928
ChEBI
79700
ChEMBL
CHEMBL2103839
ZINC
ZINC000169677038
Wikipedia
Deforolimus

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentMetastatic Bone Sarcomas / Metastatic Soft Tissue Sarcoma1
2CompletedTreatmentBreast Cancer1
2CompletedTreatmentBreast Cancer / Breast Neoplasms1
2CompletedTreatmentBreast Neoplasms1
2CompletedTreatmentEndometrial Cancer3

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000805 mg/mLALOGPS
logP4.84ALOGPS
logP7.25Chemaxon
logS-6.1ALOGPS
pKa (Strongest Acidic)9.96Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area201.5 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity267.98 m3·mol-1Chemaxon
Polarizability107.25 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0000000009-45460f3dff3a23e65c65
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0000000009-8bfeb7ae2558c792f0c2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0100000039-e6d5694ce0913a8e33c0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01p9-4000000009-28fb8f03bb7447f094c1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0o94-2600000293-c4d9cf3f20719bee2161
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002o-5000000907-d07da7231201a22960e6
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-300.1784
predicted
DeepCCS 1.0 (2019)
[M+H]+301.90213
predicted
DeepCCS 1.0 (2019)
[M+Na]+308.21368
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Serine/threonine-protein kinase mTOR
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Tfiiic-class transcription factor binding
Specific Function
Serine/threonine protein kinase which is a central regulator of cellular metabolism, growth and survival in response to hormones, growth factors, nutrients, energy and stress signals. MTOR directly...
Gene Name
MTOR
Uniprot ID
P42345
Uniprot Name
Serine/threonine-protein kinase mTOR
Molecular Weight
288889.05 Da
References
  1. Bachegowda L, Gligich O, Mantzaris I, Schinke C, Wyville D, Carrillo T, Braunschweig I, Steidl U, Verma A: Signal transduction inhibitors in treatment of myelodysplastic syndromes. J Hematol Oncol. 2013 Jul 10;6:50. doi: 10.1186/1756-8722-6-50. [Article]
  2. Piha-Paul SA, Munster PN, Hollebecque A, Argiles G, Dajani O, Cheng JD, Wang R, Swift A, Tosolini A, Gupta S: Results of a phase 1 trial combining ridaforolimus and MK-0752 in patients with advanced solid tumours. Eur J Cancer. 2015 Sep;51(14):1865-73. doi: 10.1016/j.ejca.2015.06.115. Epub 2015 Jul 18. [Article]
  3. Brana I, Berger R, Golan T, Haluska P, Edenfield J, Fiorica J, Stephenson J, Martin LP, Westin S, Hanjani P, Jones MB, Almhanna K, Wenham RM, Sullivan DM, Dalton WS, Gunchenko A, Cheng JD, Siu LL, Gray JE: A parallel-arm phase I trial of the humanised anti-IGF-1R antibody dalotuzumab in combination with the AKT inhibitor MK-2206, the mTOR inhibitor ridaforolimus, or the NOTCH inhibitor MK-0752, in patients with advanced solid tumours. Br J Cancer. 2014 Nov 11;111(10):1932-44. doi: 10.1038/bjc.2014.497. Epub 2014 Oct 7. [Article]

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kuper JI, D'Aprile M: Drug-Drug interactions of clinical significance in the treatment of patients with Mycobacterium avium complex disease. Clin Pharmacokinet. 2000 Sep;39(3):203-14. doi: 10.2165/00003088-200039030-00003. [Article]

Drug created at March 19, 2008 16:18 / Updated at May 05, 2022 22:52