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Details

Stereochemistry RACEMIC
Molecular Formula C22H28O2S2
Molecular Weight 388.587
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEVIMISTAT

SMILES

OC(=O)CCCCC(CCSCC1=CC=CC=C1)SCC2=CC=CC=C2

InChI

InChIKey=ZYRLHJIMTROTBO-UHFFFAOYSA-N
InChI=1S/C22H28O2S2/c23-22(24)14-8-7-13-21(26-18-20-11-5-2-6-12-20)15-16-25-17-19-9-3-1-4-10-19/h1-6,9-12,21H,7-8,13-18H2,(H,23,24)

HIDE SMILES / InChI

Molecular Formula C22H28O2S2
Molecular Weight 388.587
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

CPI-613 is a lipoate derivative synthesized to be catalytically inert but to potentially mimic lipoate catalytic intermediates. The drug is in phase II of clinical trials for the treatment of Myelodysplastic syndromes; Pancreatic cancer; Small cell lung cancer; Solid tumors; Bile duct cancer; Acute Myeloid leukemia. The mechanism of CPI-613 action can be explained by (I) inhibition of tumor cell pyruvate dehydrogenase complex (PDC) through activation of pyruvate dehydrogenase kinases leading to inactivating phosphorylation of the E1alpha-subunit of PDC; and (II) inhibition of alpha-ketoglutarate dehydrogenase.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: alpha-Ketoglutarate dehydrogenase complex
Conditions

Conditions

Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Formation and anti-tumor activity of uncommon in vitro and in vivo metabolites of CPI-613, a novel anti-tumor compound that selectively alters tumor energy metabolism.
2011 Aug
Patents

Sample Use Guides

Patients with bile duct cancer receive CPI-613 IV over 2 hours on days 1-5, 1 week prior to course. After that, they receive the drug IV over 2 hours on days 1 and 4 of weeks 1-3. Treatment repeats every 4 weeks for up to 2 courses. Patients with pancreatic cancer, small cell lung cancer, AML, and Myelodysplastic Syndrome receive 3,000 mg/m2 CPI-613 infused IV over 2 hours on Days 1 and 4 of each of the 3 treatment weeks.
Route of Administration: Intravenous
In the ATP production assay, H460 cells were seeded at 10,000 cells per well in RPMI (11 mM glucose, 2 mM glutamine) medium and grown overnight. The medium was then changed to RPMI without glucose and containing 10 mM pyruvate and 2 mM glutamine alone or together with 0.1 mM water soluble oleic acid. After 24 hours, the medium was replaced with fresh RPMI without glucose and containing either 10 mM pyruvate and 2 mM glutamine or 0.1 mM oleic acid and 0.5 mM aspartate (matched to overnight adaptation) and containing CPI-613 (240 uM) in the treated samples for 2 hours before ATP level measurements.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:23:41 GMT 2023
Edited
by admin
on Fri Dec 15 16:23:41 GMT 2023
Record UNII
E76113IR49
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEVIMISTAT
INN  
Official Name English
devimistat [INN]
Common Name English
OCTANOIC ACID, 6,8-BIS((PHENYLMETHYL)THIO)-
Common Name English
RAC-(6R)-6,8-BIS(BENZYLSULFANYL)OCTANOIC ACID
Systematic Name English
6,8-BIS-BENZYLSULFANYL-OCTANOIC ACID
Systematic Name English
Devimistat [WHO-DD]
Common Name English
CPI-613
Code English
(±)-6,8-BIS(BENZYLTHIO)OCTANOIC ACID
Systematic Name English
6,8-BIS(BENZYLTHIO)OCTANOIC ACID, (±)-
Common Name English
CPI613
Code English
6,8-BIS(BENZYLTHIO)OCTANOIC ACID
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 216505
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
FDA ORPHAN DRUG 621617
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
FDA ORPHAN DRUG 349911
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
FDA ORPHAN DRUG 406813
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
FDA ORPHAN DRUG 623117
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
NCI_THESAURUS C275
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
FDA ORPHAN DRUG 808021
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
FDA ORPHAN DRUG 777920
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
EU-Orphan Drug EU/3/18/2123
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
Code System Code Type Description
INN
10951
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
PRIMARY
DRUG BANK
DB12109
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
PRIMARY
WIKIPEDIA
Devimistat
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID70914807
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
PRIMARY
EVMPD
SUB187819
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
PRIMARY
CAS
95809-78-2
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
PRIMARY
SMS_ID
100000174193
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
PRIMARY
FDA UNII
E76113IR49
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
PRIMARY
NCI_THESAURUS
C80039
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
PRIMARY
PUBCHEM
24770514
Created by admin on Fri Dec 15 16:23:41 GMT 2023 , Edited by admin on Fri Dec 15 16:23:41 GMT 2023
PRIMARY
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