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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H41NO6S
Molecular Weight 507.683
Optical Activity ( - )
Defined Stereocenters 7 / 7
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PATUPILONE

SMILES

C[C@H]1CCC[C@@]2(C)O[C@H]2C[C@H](OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]1O)C(\C)=C\C3=CSC(C)=N3

InChI

InChIKey=QXRSDHAAWVKZLJ-PVYNADRNSA-N
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

HIDE SMILES / InChI

Molecular Formula C27H41NO6S
Molecular Weight 507.683
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT00262990 | https://clinicaltrials.gov/ct2/show/NCT00273312 | https://www.ncbi.nlm.nih.gov/pubmed/27872763 | https://www.ncbi.nlm.nih.gov/pubmed/15860865

Patupilone is a compound isolated from the myxobacterium Sorangium cellulosum. Similar to paclitaxel, Patupilone induces microtubule polymerization and stabilizes microtubules against depolymerization conditions. In addition to promoting tubulin polymerization and stabilization of microtubules, this agent is cytotoxic for cells overexpressing P-glycoprotein, a characteristic that distinguishes it from the taxanes. Epothilone B may cause complete cell-cycle arrest. Patupilone failed a phase III trial for ovarian cancer in 2010.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.7 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
139 ng/mL
11 mg/m² single, intravenous
dose: 11 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PATUPILONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1386 ng × h/mL
11 mg/m² single, intravenous
dose: 11 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PATUPILONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
100 h
11 mg/m² single, intravenous
dose: 11 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PATUPILONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
moderate [IC50 ~5 uM]
no (co-administration study)
Comment: Omeprazole Cmax and AUC(0-12h) were decreased by 21% and 19%.
moderate [IC50 ~5 uM]
no (co-administration study)
Comment: Midazolam Cmax was reduces by 33% and AUC(0-12h) was increased by 1%.
no
no
weak [IC50 25 uM]
no (co-administration study)
Comment: S-warfarin Cmax and AUC(0-168h) were increased by 2% and 8%.
yes [EC50 12.6 uM]
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL

Sample Use Guides

Patupilone (Novartis, Basel, Switzerland) was administered every 3 weeks either as a bolus (20 min), 1-day continuous infusion (24 h) or 5-day continuous infusion (16-h per day over 5 days) at dose levels of 6.5, 7.0, 7.5, 8.0, 9.0 and 10.0 mg/m2 until disease progression, unacceptable toxicity or withdrawal of consent.
Route of Administration: Intravenous
Cortices were dissected from embryonic 15.5mice and incubated in papain (20U/mL, Worthington) containing DNase (10 U/𝜇L, Sigma) for 40min at 37∘C. Enzyme-digested cortices were washed three times with MEM (Cellgro) containing 10% heat inactivated fetal bovine serum (Hyclone) and dissociated in culture medium. Dissociated neurons were then centrifuged to remove the supernatant and counted cells were plated on glass coverslips coated with 100 𝜇g/mL poly-D-lysine (Sigma) and grown in Neurobasal A (Gibco) medium containing Glutamax (1%, Thermo Fisher Scientific) and B27 (2%, Thermo Fisher Scientific) supplements. 5 hr after plating, neurons were treated with epothilone B (from 1 pM to 1 𝜇M and 10pM or 1 nM) for 3 days in low-density cultures (5 x 104 cells in 1.9 cm2) or overnight (17–19hr) in high-density cultures (2 x 105 cells in 1.9 cm2). Neurons were then fixed and analyzed for viability, axon growth, and microtubule structure.
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:01:06 UTC 2023
Edited
by admin
on Thu Jul 06 02:01:06 UTC 2023
Record UNII
UEC0H0URSE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PATUPILONE
INN   MART.   WHO-DD  
INN  
Official Name English
Patupilone [WHO-DD]
Common Name English
EPO906
Code English
4,17-DIOXABICYCLO(14.1.0)HEPTADECANE-5,9-DIONE, 7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-((1E)-1-METHYL-2-(2-METHYL-4-THIAZOLYL)ETHENYL)-, (1S,3S,7S,10R,11S,12S,16R)-
Systematic Name English
GNF-PF-193
Code English
patupilone [INN]
Common Name English
PATUPILONE [MART.]
Common Name English
(1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-((E)-1-METHYL-2-(2-METHYL-1,3-THIAZOL-4-YL)VINYL)-4,17-DIOXABICYCLO(14.1.0)HEPTADECANE-5,9-DIONE
Systematic Name English
EPO-906A
Code English
EPO B
Common Name English
EPO906A
Code English
(-)-Epothilone B
Common Name English
EPITHILONE B
Common Name English
EPO-906
Code English
EPOTHILONE B [MI]
Common Name English
EPOTHILONE B
MI  
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 298809
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
FDA ORPHAN DRUG 210205
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
NCI_THESAURUS C1922
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
NCI_THESAURUS C67437
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
FDA ORPHAN DRUG 298909
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
EU-Orphan Drug EU/3/09/687
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
Code System Code Type Description
MESH
C093788
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
PRIMARY
ChEMBL
CHEMBL94657
Created by admin on Thu Jul 06 02:01:06 UTC 2023 , Edited by admin on Thu Jul 06 02:01:06 UTC 2023
PRIMARY
PUBCHEM
448013
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
PRIMARY
NCI_THESAURUS
C1623
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
PRIMARY
INN
8320
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
PRIMARY
CAS
152044-54-7
Created by admin on Thu Jul 06 02:01:06 UTC 2023 , Edited by admin on Thu Jul 06 02:01:06 UTC 2023
PRIMARY
FDA UNII
UEC0H0URSE
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
PRIMARY
MERCK INDEX
M4954
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB03010
Created by admin on Thu Jul 06 02:01:06 UTC 2023 , Edited by admin on Thu Jul 06 02:01:06 UTC 2023
PRIMARY
SMS_ID
100000126141
Created by admin on Thu Jul 06 02:01:07 UTC 2023 , Edited by admin on Thu Jul 06 02:01:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID4046862
Created by admin on Thu Jul 06 02:01:06 UTC 2023 , Edited by admin on Thu Jul 06 02:01:06 UTC 2023
PRIMARY
CHEBI
31550
Created by admin on Thu Jul 06 02:01:06 UTC 2023 , Edited by admin on Thu Jul 06 02:01:06 UTC 2023
PRIMARY
EVMPD
SUB33376
Created by admin on Thu Jul 06 02:01:06 UTC 2023 , Edited by admin on Thu Jul 06 02:01:06 UTC 2023
PRIMARY
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DERIVATIVE -> PARENT
TARGET->LIGAND
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ACTIVE MOIETY