NAV

Patupilone

Identification

Generic Name
Patupilone
DrugBank Accession Number
DB03010
Background

Epothilone B is a 16-membered macrolide that mimics the biological effects of taxol.

Type
Small Molecule
Groups
Experimental, Investigational
Structure
3D
Similar Structures
Weight
Average: 507.683
Monoisotopic: 507.265458739
Chemical Formula
C27H41NO6S
Synonyms
  • (−)-epothilone B
  • Epo B
  • Epothilone B
  • patupilona
  • Patupilone
External IDs
  • EPO 906
  • EPO 906A
  • EPO-906
  • EPO-906A
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Pharmacology

Indication

Investigated for use/treatment in ovarian cancer, lung cancer, brain cancer, breast cancer, and gastric cancer.

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Contraindications & Blackbox Warnings
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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. Epothilone B possess the same biological effects as taxol both in vitro and in cultured cells. This is because they share the same binding site, as well as binding affinity to the microtubule. Like taxol, epothilone B binds to the αβ-tubulin heterodimer subunit. Once bound, the rate of αβ-tubulin dissociation decreases, thus stabilizing the microtubules. Furthermore, epothilone B has also been shown to induce tubulin polymerization into microtubules without the presence of GTP. This is caused by formation of microtubule bundles throughout the cytoplasm. Finally, epothilone B also causes cell cycle arrest at the G2-M transition phase, thus leading to cytotoxicity and eventually cell apoptosis.

TargetActionsOrganism
UTubulin alpha 3C/D chainNot AvailableHumans
UTubulin beta chainNot AvailableHumans
UTubulin beta-1 chainNot AvailableHumans
UTubulin beta-4B chainNot AvailableHumans
UTubulin beta-4A chainNot AvailableHumans
UTubulin alpha-4A chainNot AvailableHumans
UTubulin beta-3 chainNot AvailableHumans
UTubulin alpha-1C chainNot AvailableHumans
UTubulin alpha-8 chainNot AvailableHumans
UTubulin alpha-1B chainNot AvailableHumans
UTubulin alpha-1A chainNot AvailableHumans
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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 Patupilone.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with Patupilone.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Patupilone.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Patupilone.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Patupilone.
Food Interactions
Not Available

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 / Epoxides / Dialkyl ethers
show 5 more
Substituents
2,4-disubstituted 1,3-thiazole / Alcohol / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Dialkyl ether
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
1,3-thiazole, oxabicycloalkane (CHEBI:42432) / Macrolides and lactone polyketides (C12154) / Macrolides and lactone polyketides (LMPK04000041)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
UEC0H0URSE
CAS number
152044-54-7
InChI Key
QXRSDHAAWVKZLJ-PVYNADRNSA-N
InChI
InChI=1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
IUPAC Name
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
SMILES
[H]\C(=C(\C)[C@]1([H])C[C@]2([H])O[C@]2(C)CCC[C@]([H])(C)[C@]([H])(O)[C@@]([H])(C)C(=O)C(C)(C)[C@@]([H])(O)CC(=O)O1)C1=CSC(C)=N1

References

Synthesis Reference

Richard Taylor, "Derivatives of epothilone B and D and synthesis thereof." U.S. Patent US20030176473, issued September 18, 2003.

US20030176473
General References
Not Available
KEGG Compound
C12154
PubChem Compound
448013
PubChem Substance
46505629
ChemSpider
10213816
BindingDB
50103627
ChEBI
31550
ChEMBL
CHEMBL94657
ZINC
ZINC000003951737
Therapeutic Targets Database
DNC000616
PDBe Ligand
EPB
PDB Entries
1q5d / 6s8m / 7dae

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAbdominal wall neoplasm / Fallopian Tube Cancer / Ovarian Cancer1
3CompletedTreatmentEstrogen Receptor Negative / Estrogen Receptor Positive / HER2 negative / HER2-positive / Progesterone Receptor Negative / Progesterone Receptor Positive / Recurrent Breast Carcinoma / Stage IIIC Breast Cancer AJCC v6 / Stage IV Breast Cancer AJCC v6 and v71
2Active Not RecruitingTreatmentAdenosquamous Cell Carcinoma of the Endometrium / Endometrial Adenocarcinomas / Endometrial Clear Cell Adenocarcinoma / Endometrial Papillary Serous Carcinoma / Recurrent Uterine Corpus Cancer / Stage IIIA Uterine Corpus Cancer AJCC v7 / Stage IIIB Uterine Corpus Cancer AJCC v7 / Stage IIIC Uterine Corpus Cancer AJCC v7 / Stage IVA Uterine Corpus Cancer AJCC v7 / Stage IVB Uterine Corpus Cancer AJCC v71
2Active Not RecruitingTreatmentBilateral Breast Carcinoma / HER2 negative / Invasive Breast Carcinoma1
2CompletedTreatmentAbdominal wall neoplasm / Fallopian Tube Neoplasms / Ovarian Neoplasms1

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 Solubility0.00342 mg/mLALOGPS
logP3.7ALOGPS
logP4.12Chemaxon
logS-5.2ALOGPS
pKa (Strongest Acidic)14.09Chemaxon
pKa (Strongest Basic)2.73Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area109.25 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity134.76 m3·mol-1Chemaxon
Polarizability56.11 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8471
Blood Brain Barrier+0.6791
Caco-2 permeable-0.5935
P-glycoprotein substrateSubstrate0.7384
P-glycoprotein inhibitor INon-inhibitor0.8232
P-glycoprotein inhibitor IINon-inhibitor0.9779
Renal organic cation transporterNon-inhibitor0.9193
CYP450 2C9 substrateNon-substrate0.84
CYP450 2D6 substrateNon-substrate0.8309
CYP450 3A4 substrateSubstrate0.622
CYP450 1A2 substrateInhibitor0.5065
CYP450 2C9 inhibitorNon-inhibitor0.7468
CYP450 2D6 inhibitorNon-inhibitor0.9114
CYP450 2C19 inhibitorNon-inhibitor0.6114
CYP450 3A4 inhibitorNon-inhibitor0.7163
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8841
Ames testNon AMES toxic0.5816
CarcinogenicityNon-carcinogens0.933
BiodegradationReady biodegradable0.5
Rat acute toxicity2.7983 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9924
hERG inhibition (predictor II)Non-inhibitor0.935
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-0000900000-b7ccf84aa609b1edbd83
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000090000-0893b4115586dba8be22
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0000900000-f088a9e203a27ad14a6d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052r-0100950000-88ff1829cfe97a4b7adf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9600000000-28628148316841cf2238
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-9300000000-7a731868c56442370488
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-232.3404614
predicted
DarkChem Lite v0.1.0
[M-H]-218.2938614
predicted
DarkChem Lite v0.1.0
[M-H]-217.65941
predicted
DeepCCS 1.0 (2019)
[M+H]+232.1324614
predicted
DarkChem Lite v0.1.0
[M+H]+218.9551614
predicted
DarkChem Lite v0.1.0
[M+H]+219.72212
predicted
DeepCCS 1.0 (2019)
[M+Na]+232.5744614
predicted
DarkChem Lite v0.1.0
[M+Na]+218.4275614
predicted
DarkChem Lite v0.1.0
[M+Na]+225.9652
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
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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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  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 June 13, 2005 13:24 / Updated at January 14, 2023 19:03