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

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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.

Drug	Interaction
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Abemaciclib	The metabolism of Abemaciclib 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 serum concentration of Alprazolam can be increased when it is combined with Epothilone D.

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Food Interactions

Not Available

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][C@]1(C\C=C(C)/CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@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 / 7dad

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
2	Completed	Treatment	Breast Cancer	1
2	Completed	Treatment	Colorectal Cancer	1
2	Completed	Treatment	Lung Cancers	1
2	Terminated	Treatment	Lung Cancers	1
2	Terminated	Treatment	Prostate Cancer	1
1	Completed	Treatment	Neoplastic Disease	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

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Details1. Tubulin alpha-3C/D chain

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. [Article]
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. [Article]

Details2. Tubulin beta chain

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. [Article]
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. [Article]

Details3. Tubulin beta-1 chain

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. [Article]
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. [Article]

Details4. Tubulin beta-4B chain

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. [Article]
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. [Article]

Details5. Tubulin beta-4A chain

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. [Article]
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. [Article]

Details6. Tubulin alpha-4A chain

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. [Article]
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. [Article]

Details7. Tubulin beta-3 chain

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. [Article]
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. [Article]

Details8. Tubulin alpha-1C chain

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. [Article]
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. [Article]

Details9. Tubulin alpha-8 chain

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. [Article]
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. [Article]

Details10. Tubulin alpha-1B chain

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. [Article]
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. [Article]

Details11. Tubulin alpha-1A chain

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. [Article]
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. [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

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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52

Epothilone D

Identification

Structure for Epothilone D (DB01873)

Pharmacology

Interactions

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References

References

References

References

References

References

References

References

References

Enzymes

References