Epothilone D
Identification
- Name
- Epothilone D
- Accession Number
- DB01873
- Description
- Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Epothilone D (DB01873)
- Weight
- Average: 491.683
Monoisotopic: 491.270544117 - Chemical Formula
- C27H41NO5S
- Synonyms
- (-)-desoxyepothilone B
- 12,13-desoxyepothilone B
- Desoxyepothilone B
- External IDs
- KOS-862
- NSC-703147
- R-1492
- R1492
Pharmacology
- Indication
Investigated for use/treatment in colorectal cancer, lung cancer, breast cancer, solid tumors, and prostate cancer.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
The principal mechanism of the epothilone class is inhibition of microtubule function. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing.
Target Actions Organism UTubulin alpha-3C/D chain Not Available Humans UTubulin beta chain Not Available Humans UTubulin beta-1 chain Not Available Humans UTubulin beta-4B chain Not Available Humans UTubulin beta-4A chain Not Available Humans UTubulin alpha-4A chain Not Available Humans UTubulin beta-3 chain Not Available Humans UTubulin alpha-1C chain Not Available Humans UTubulin alpha-8 chain Not Available Humans UTubulin alpha-1B chain Not Available Humans UTubulin alpha-1A chain Not Available 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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.
Drug Interaction Unlock Additional DataAbiraterone The metabolism of Abiraterone can be decreased when combined with Epothilone D. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Epothilone D. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Epothilone D. Acetyldigitoxin The serum concentration of Acetyldigitoxin can be increased when it is combined with Epothilone D. Albendazole The metabolism of Albendazole can be decreased when combined with Epothilone D. Alectinib The metabolism of Alectinib can be decreased when combined with Epothilone D. Alfentanil The serum concentration of Alfentanil can be increased when it is combined with Epothilone D. Alfuzosin The metabolism of Alfuzosin can be decreased when combined with Epothilone D. Alpelisib The metabolism of Alpelisib can be decreased when combined with Epothilone D. Alprazolam The metabolism of Alprazolam can be decreased when combined with Epothilone D. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as epothilones and analogues. These are macrolides consisting of a 16-member lactone ring conjugated at the carbon 16 with a 1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group. Some epothilone analogues containing a lactam ring instead of the lactone ring.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Macrolides and analogues
- Sub Class
- Epothilones and analogues
- Direct Parent
- Epothilones and analogues
- Alternative Parents
- 2,4-disubstituted thiazoles / Heteroaromatic compounds / Secondary alcohols / Lactones / Cyclic ketones / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds show 3 more
- Substituents
- 2,4-disubstituted 1,3-thiazole / Alcohol / Aromatic heteromonocyclic compound / Azacycle / Azole / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Epothilone show 15 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Macrolides and lactone polyketides (C12039) / Macrolides and lactone polyketides (LMPK04000001)
Chemical Identifiers
- UNII
- T0358E0YUF
- CAS number
- 189453-10-9
- InChI Key
- XOZIUKBZLSUILX-GIQCAXHBSA-N
- InChI
- InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1
- IUPAC Name
- (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
- SMILES
- [H][[email protected]]1(C\C=C(C)/CCC[[email protected]](C)[[email protected]](O)[[email protected]@H](C)C(=O)C(C)(C)[[email protected]@H](O)CC(=O)O1)C(\C)=C\C1=CSC(C)=N1
References
- Synthesis Reference
Ludger Wessjohann, "Epothilone synthesis building blocks III and IV: asymmetrically substituted acyloins and acyloin derivatives, methods for their production and methods for the production of epothilones B, D and epothilone derivatives." U.S. Patent US20040082651, issued April 29, 2004.
US20040082651- General References
- Not Available
- External Links
- KEGG Compound
- C12039
- PubChem Compound
- 447865
- PubChem Substance
- 46508361
- ChemSpider
- 9400674
- ChEBI
- 29579
- ChEMBL
- CHEMBL96172
- ZINC
- ZINC000003951739
- PDBe Ligand
- EPD
- Wikipedia
- Epothilone
- PDB Entries
- 1pkf
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Breast Cancer 1 2 Completed Treatment Colorectal Cancers 1 2 Completed Treatment Lung Cancers 1 2 Terminated Treatment Lung Cancers 1 2 Terminated Treatment Prostate Cancer 1 1 Completed Treatment Neoplasms 1
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
Property Value Source Water Solubility 0.00246 mg/mL ALOGPS logP 4.54 ALOGPS logP 5.1 ChemAxon logS -5.3 ALOGPS pKa (Strongest Acidic) 14.09 ChemAxon pKa (Strongest Basic) 2.73 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 96.72 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 136.04 m3·mol-1 ChemAxon Polarizability 55.62 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8749 Blood Brain Barrier + 0.7345 Caco-2 permeable - 0.5948 P-glycoprotein substrate Substrate 0.689 P-glycoprotein inhibitor I Non-inhibitor 0.8151 P-glycoprotein inhibitor II Non-inhibitor 0.9518 Renal organic cation transporter Non-inhibitor 0.9136 CYP450 2C9 substrate Non-substrate 0.8473 CYP450 2D6 substrate Non-substrate 0.8372 CYP450 3A4 substrate Substrate 0.6028 CYP450 1A2 substrate Non-inhibitor 0.5443 CYP450 2C9 inhibitor Non-inhibitor 0.7697 CYP450 2D6 inhibitor Non-inhibitor 0.92 CYP450 2C19 inhibitor Non-inhibitor 0.612 CYP450 3A4 inhibitor Non-inhibitor 0.835 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8559 Ames test Non AMES toxic 0.6843 Carcinogenicity Non-carcinogens 0.9367 Biodegradation Not ready biodegradable 0.5931 Rat acute toxicity 2.8243 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9905 hERG inhibition (predictor II) Non-inhibitor 0.9322
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of cytoskeleton
- Specific Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Gene Name
- TUBA3C
- Uniprot ID
- Q13748
- Uniprot Name
- Tubulin alpha-3C/D chain
- Molecular Weight
- 49959.145 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Gene Name
- TUBB
- Uniprot ID
- P07437
- Uniprot Name
- Tubulin beta chain
- Molecular Weight
- 49670.515 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of cytoskeleton
- Specific Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain (By similarity).
- Gene Name
- TUBB1
- Uniprot ID
- Q9H4B7
- Uniprot Name
- Tubulin beta-1 chain
- Molecular Weight
- 50326.56 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Unfolded protein binding
- Specific Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Gene Name
- TUBB4B
- Uniprot ID
- P68371
- Uniprot Name
- Tubulin beta-4B chain
- Molecular Weight
- 49830.72 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of cytoskeleton
- Specific Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Gene Name
- TUBB4A
- Uniprot ID
- P04350
- Uniprot Name
- Tubulin beta-4A chain
- Molecular Weight
- 49585.475 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of cytoskeleton
- Specific Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Gene Name
- TUBA4A
- Uniprot ID
- P68366
- Uniprot Name
- Tubulin alpha-4A chain
- Molecular Weight
- 49923.995 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of cytoskeleton
- Specific Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain. TUBB3 plays a criti...
- Gene Name
- TUBB3
- Uniprot ID
- Q13509
- Uniprot Name
- Tubulin beta-3 chain
- Molecular Weight
- 50432.355 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural molecule activity
- Specific Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Gene Name
- TUBA1C
- Uniprot ID
- Q9BQE3
- Uniprot Name
- Tubulin alpha-1C chain
- Molecular Weight
- 49894.93 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Specific Function
- Gtp binding
- Gene Name
- TUBA8
- Uniprot ID
- Q9NY65
- Uniprot Name
- Tubulin alpha-8 chain
- Molecular Weight
- 50093.12 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Gene Name
- TUBA1B
- Uniprot ID
- P68363
- Uniprot Name
- Tubulin alpha-1B chain
- Molecular Weight
- 50151.24 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Specific Function
- Gtp binding
- Gene Name
- TUBA1A
- Uniprot ID
- Q71U36
- Uniprot Name
- Tubulin alpha-1A chain
- Molecular Weight
- 50135.25 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Enzymes
- 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
- 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. [PubMed:11020135]
Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:52
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