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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H27O9P
Molecular Weight 430.386
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of FOSTRIECIN

SMILES

C[C@@](O)(\C=C\[C@H]1CC=CC(=O)O1)[C@@H](C[C@@H](O)\C=C/C=C\C=C\CO)OP(O)(O)=O

InChI

InChIKey=ZMQRJWIYMXZORG-DSWNLJKISA-N
InChI=1S/C19H27O9P/c1-19(23,12-11-16-9-7-10-18(22)27-16)17(28-29(24,25)26)14-15(21)8-5-3-2-4-6-13-20/h2-8,10-12,15-17,20-21,23H,9,13-14H2,1H3,(H2,24,25,26)/b3-2-,6-4+,8-5-,12-11+/t15-,16+,17+,19+/m0/s1

HIDE SMILES / InChI
Molecular Formula C19H27O9P
Molecular Weight 430.386
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 4
Optical Activity UNSPECIFIED

Description

Fostriecin, an antitumor antibiotic produced by Streptomyces pulveraceus, is a strong inhibitor of serine/threonine protein phosphatases type 2A and type 4, and inhibits the catalytic activity of partially purified Topo II (type II topoisomerase) in a non-competitive manner.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Serine/threonine-protein phosphatase 2A catalytic subunit alpha isoform
7
Target ID: P67775
Gene ID: 5515.0
Gene Symbol: PPP2CA
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 3.2 nM [IC50]
Serine/threonine-protein phosphatase 4 catalytic subunit
2
Target ID: P60510
Gene ID: 5531.0
Gene Symbol: PPP4C
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 3.0 nM [IC50]
DNA topoisomerase 2-alpha
2
Target ID: P11388|||Q9UQP9
Gene ID: 7153.0
Gene Symbol: TOP2A
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 110.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
428
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6.354 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10070885
20 mg/m² 1 times / day single, intravenous
dose: 20 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FOSTRIECIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
9.965 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10070885
20 mg/m² 1 times / day single, intravenous
dose: 20 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FOSTRIECIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.76 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10070885
20 mg/m² 1 times / day single, intravenous
dose: 20 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FOSTRIECIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
47 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 47 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 47 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/14739664
Page: p.163
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/14739664
Page: p.163
DLT: Fainting, Hypotension...
Dose limiting toxicities:
Fainting (grade 3, 25%)
Hypotension (grade 1, 25%)
Blood creatinine increased (grade 2, 25%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/14739664
Page: p.163
20 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10070885
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/10070885
DLT: ALT increased...
Disc. AE: Oedema, Hypoalbuminaemia...
Dose limiting toxicities:
ALT increased (25%)
AEs leading to
discontinuation/dose reduction:
Oedema (grade 2, 25%)
Hypoalbuminaemia (grade 2, 25%)
Proteinuria (25%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/10070885
AEs

AEs

AESignificanceDosePopulation
Hypotension grade 1, 25%
DLT
47 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 47 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 47 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/14739664
Page: p.163
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/14739664
Page: p.163
Blood creatinine increased grade 2, 25%
DLT
47 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 47 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 47 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/14739664
Page: p.163
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/14739664
Page: p.163
Fainting grade 3, 25%
DLT
47 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 47 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 47 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/14739664
Page: p.163
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/14739664
Page: p.163
ALT increased 25%
DLT
20 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10070885
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/10070885
Proteinuria 25%
Disc. AE
20 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10070885
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/10070885
Hypoalbuminaemia grade 2, 25%
Disc. AE
20 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10070885
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/10070885
Oedema grade 2, 25%
Disc. AE
20 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10070885
unhealthy, ADULT
n = 4
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 4
Sources:
https://pubmed.ncbi.nlm.nih.gov/10070885
Sourcing

Sourcing

Vendor/AggregatorIDURL
Cayman Chemical
14749
http://www.caymanchem.com/app/template/Product.vm/catalog/14749
Compound Cloud
16759606
Compound Cloud
6913994
Tocris
1840
https://www.tocris.com/search.php?Type=QuickSearch&Value=1840
eMolecules
36550750
https://orderbb.emolecules.com/search/#?query=36550750
eMolecules
76745947
https://orderbb.emolecules.com/search/#?query=76745947
eMolecules
76745948
https://orderbb.emolecules.com/search/#?query=76745948
PubMed

PubMed

TitleDatePubMed
Patents

Patents

US20120065171
2

Sample Use Guides

In Vivo Use Guide
Fostriecin was administered intravenously over 60 min on days 1-5 at 4-week intervals. Dose was escalated from 2 mg m(-2) day(-1) to 20 mg m(-2) day(-1) in 20 patients.
Route of Administration: Intravenous
In Vitro Use Guide
Fostriecin pretreatment significantly attenuated the inhibitory effects of salbutamol. For that was investigated the effects of fostriecin on the inhibition of histamine release from HLMC, on β-adrenoceptor-driven responses in mast cells and on desensitization. Long-term incubation (24 h) of mast cells with fostriecin (10-6 M) resulted in a significant (p < 0.001) reduction in the maximal response (from 41.2 [± 3.0] to 29.9 [± 4.2] %) to salbutamol following fostriecin treatment.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:27:12 GMT 2023
Edited
by admin
on Fri Dec 15 17:27:12 GMT 2023
Record UNII
ZO1648L551
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FOSTRIECIN
INN   WHO-DD  
INN  
Official Name English
2H-PYRAN-2-ONE, 5,6-DIHYDRO-6-((1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-TRIHYDROXY-3-METHYL-4-(PHOSPHONOOXY)-1,7,9,11-TRIDECATETRAEN-1-YL)-, (6R)-
Systematic Name English
PHOSPHOTRIENIN
Common Name English
fostriecin [INN]
Common Name English
(6R)-5,6-DIHYDRO-6-((1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-TRIHYDROXY-3-METHYL-4-(PHOSPHONOOXY)-1,7,9,11-TRIDECATETRAENYL)-2H-PYRAN-2-ONE
Systematic Name English
(+)-FOSTRIECIN
Common Name English
CL 1565A
Code English
Fostriecin [WHO-DD]
Common Name English
NSC-339638
Code English
CL-1565A
Code English
2H-PYRAN-2-ONE, 5,6-DIHYDRO-6-((1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-TRIHYDROXY-3-METHYL-4-(PHOSPHONOOXY)-1,7,9,11-TRIDECATETRAENYL)-, (6R)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1968
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
NCI_THESAURUS C2159
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID00868985
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
FDA UNII
ZO1648L551
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
NSC
339638
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL172545
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
CHEBI
167004
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
CAS
87810-56-8
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
SMS_ID
100000080444
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
MESH
C040313
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
PUBCHEM
6913994
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
WIKIPEDIA
Fostriecin
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
EVMPD
SUB07808MIG
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
INN
5904
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
NCI_THESAURUS
C1372
Created by admin on Fri Dec 15 17:27:12 GMT 2023 , Edited by admin on Fri Dec 15 17:27:12 GMT 2023
PRIMARY
Related Record Type Details
Structure of FOSTRIECIN SODIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of FOSTRIECIN
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NIH
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