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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H18ClF5N6O.C4H6O4.2H2O
Molecular Weight 618.939
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEVIPABULIN SUCCINATE

SMILES

O.O.OC(=O)CCC(O)=O.CNCCCOC1=CC(F)=C(C(F)=C1)C2=C(N[C@@H](C)C(F)(F)F)N3N=CN=C3N=C2Cl

InChI

InChIKey=FWNIBMRSBSSPNP-DXYFNVQQSA-N
InChI=1S/C18H18ClF5N6O.C4H6O4.2H2O/c1-9(18(22,23)24)28-16-14(15(19)29-17-26-8-27-30(16)17)13-11(20)6-10(7-12(13)21)31-5-3-4-25-2;5-3(6)1-2-4(7)8;;/h6-9,25,28H,3-5H2,1-2H3;1-2H2,(H,5,6)(H,7,8);2*1H2/t9-;;;/m0.../s1

HIDE SMILES / InChI

Molecular Formula C18H18ClF5N6O
Molecular Weight 464.82
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H6O4
Molecular Weight 118.088
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Cevipabulin is a synthetic, water-soluble tubulin-binding agent with potential antineoplastic activity. Cevipabulin appears to bind at the vinca-binding site on tubulin but seems to act more similar to taxane-site binding agents in that it enhances tubulin polymerization and does not induce tubulin depolymerization. The disruption in microtubule dynamics may eventually inhibit cell division and reduce cellular growth.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary

Sample Use Guides

In Vivo Use Guide
Patients were treated with TTI-237 (Cevipabulin) intravenously on days 1, 8 and 15 of a 28-day cycle at dose of 4.5, 9, 15, 22.5 and 31.5 mg/m2 .
Route of Administration: Intravenous
In Vitro Use Guide
HeLa cells were harvested by trypsinization, washed, counted, and distributed to wells of 96-well flat-bottomed microtiter plates at 1,000 cells per well in 200 AL of medium. All plates were incubated at 37C in humidified 5% CO2 in air for ~24 h. On day 2, compounds for test were diluted and added to wells. Compounds were dissolved in DMSO at 10 to 20 mkmol/L. For each compound, nine serial 2-fold dilutions were prepared in DMSO. Ten microliters of each dilution was transferred to 100 mkL of medium and mixed well, and then 5 AL of this dilution were transferred in triplicate or quadruplicate to wells containing cells. The final high concentration of each compound was typically 5 mkmol/L. All cultures, including controls with no compound, contained a final concentration of 0.27% DMSO. After 3 d of culture with test compounds (day 5 overall), the MTS assay (Promega; CellTiter 96 aqueous nonradioactive cell proliferation assay) was done on all wells.
Substance Class Chemical
Created
by admin
on Mon Oct 21 23:44:13 UTC 2019
Edited
by admin
on Mon Oct 21 23:44:13 UTC 2019
Record UNII
8XI0CX98LY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEVIPABULIN SUCCINATE
USAN   WHO-DD  
USAN  
Official Name English
CEVIPABULIN SUCCINATE [USAN]
Common Name English
TTI-237 SUCCINATE DIHYDRATE
Code English
BUTANEDIOIC ACID, COMPD. WITH 5-CHLORO-6-(2,6-DIFLUORO-4-(3-(METHYLAMINO)PROPOXY)PHENYL)-N-((1S)-2,2,2-TRIFLUORO-1-METHYLETHYL)(1,2,4)TRIAZOLO(1,5-A)PYRIMIDIN-7-AMINE (1:1), DIHYDRATE
Common Name English
CEVIPABULIN SUCCINATE [WHO-DD]
Common Name English
5-CHLORO-6-(2,6-DIFLUORO-4-(3-(METHYLAMINO)PROPOXY)PHENYL)-N-((1S)-2,2,2-TRIFLUORO-1-METHYLETHYL)(1,2,4)TRIAZOLO(1,5-A)PYRIMIDIN-7-AMINE SUCCINATE DIHYDRATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C25974
Created by admin on Mon Oct 21 23:44:13 UTC 2019 , Edited by admin on Mon Oct 21 23:44:13 UTC 2019
Code System Code Type Description
CAS
852954-81-5
Created by admin on Mon Oct 21 23:44:13 UTC 2019 , Edited by admin on Mon Oct 21 23:44:13 UTC 2019
PRIMARY
NCI_THESAURUS
C96746
Created by admin on Mon Oct 21 23:44:13 UTC 2019 , Edited by admin on Mon Oct 21 23:44:13 UTC 2019
PRIMARY
ChEMBL
CHEMBL1182714
Created by admin on Mon Oct 21 23:44:13 UTC 2019 , Edited by admin on Mon Oct 21 23:44:13 UTC 2019
PRIMARY
PUBCHEM
17755247
Created by admin on Mon Oct 21 23:44:13 UTC 2019 , Edited by admin on Mon Oct 21 23:44:13 UTC 2019
PRIMARY
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ACTIVE MOIETY