DEVIMISTAT

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 Search

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	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25405166 | https://www.ncbi.nlm.nih.gov/pubmed/24612826

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
alpha-Ketoglutarate dehydrogenase complex 1 Target ID: alpha-Ketoglutarate dehydrogenase complex Sources: https://www.ncbi.nlm.nih.gov/pubmed/25405166	Inhibitor 8297
Pyruvate dehydrogenase kinase 4 Target ID: CHEMBL2096665 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25405166	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Small-cell lung cancer 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27732654	Primary	Phase II 1132	Unknown Approved Use Unknown
Acute myeloid leukemia 136 Sources: https://www.clinicaltrials.gov/ct2/show/NCT01520805	Primary	Phase II 1132	Unknown Approved Use Unknown
Myelodysplastic syndromes 58 Sources: https://www.clinicaltrials.gov/ct2/show/NCT01520805	Primary	Phase II 1132	Unknown Approved Use Unknown
Pancreatic cancer 97 Sources: https://www.clinicaltrials.gov/ct2/show/NCT01830322	Primary	Phase II 1132	Unknown Approved Use Unknown
Granulocytic sarcoma 1 Sources: https://www.clinicaltrials.gov/ct2/show/NCT02484391	Primary	Phase II 1132	Unknown Approved Use Unknown
Bile duct cancer 1 Sources: https://www.clinicaltrials.gov/ct2/show/NCT01766219	Primary	Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 1537 CYP2C8 693 CYP2C19 991

Drug as victim

Target	Modality	Activity
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/21722089/	major
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/21722089/	major
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/21722089/	minor
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/21722089/	minor
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=174007465	no

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY582805	https://www.001chemical.com/chem/95809-78-2
AA Blocks	AA00IJDP	https://www.aablocks.com/goods/Goods/detail?id=AA00IJDP
AK Scientific, Inc. (AKSCI)	Y0307	http://www.aksci.com/item_detail.php?cat=Y0307
Aaron Chemicals	AR00IK5H	http://www.aaronchem.com/95809-78-2
AbMole Bioscience	M2297	http://www.abmole.com/products/cpi-613.html
Accela ChemBio Inc	SY234319	http://www.accelachem.com/cn/search.html?keyword=SY234319&attname=GoodsCode
Achemtek	0102-013964	http://www.achemtek.com/95809-78-2
Alfa Chemistry	AP95809782	https://reagents.alfa-chemistry.com/product/6-8-bis-benzylthio-octanoic-acid-cas-95809-78-2-18960.html
Ambeed	A158224	https://www.ambeed.com/products/95809-78-2.html
Ambinter	Amb22170017	http://www.ambinter.com/reference/22170017
Angel Pharmatech	AG154278	http://www.angelpharmatech.com/95809-78-2.html
Angene	AGN-PC-0WAEQH	http://www.angenechemical.com/productshow/AGN-PC-0WAEQH.html
Ark Pharm	AK174899	http://www.arkpharminc.com/products/95809-78-2.html
Aurora Fine Chemicals LLC	A17.913.361	http://online.aurorafinechemicals.com/info?ID=A17.913.361
Aurum Pharmatech LLC	S-7818	http://www.Aurumpharmatech.com/Product/ProductDetails/S_7818
AvaChem Scientific	6231	https://www.avachem.com/productSearch.asp?6231
Axon MedChem	2125	https://www.axonmedchem.com/product/2125
BLD Pharm	BD304646	http://www.bldpharm.com/products/95809-78-2.html
BOC Sciences	95809-78-2	https://www.bocsci.com/cpi-613-cas-95809-78-2-item-84-460986.html
BioChemPartner	BCP04663	http://www.biochempartner.com/95809-78-2-BCP04663
BioCrick	BCC2287	http://www.biocrick.com/CPI-613-BCC2287.html
BioSynth	J-518174	https://www.biosynth.com/en/products/all-products/products/J-518174.html
Boerchem	BC261916	http://www.boerchem.com/?product_43049.html
CSNpharm	CSN15809	https://www.csnpharm.com/products/cpi-613.html
Chem Scene	CS-0961	http://www.chemscene.com/95809-78-2.html
ChemShuttle	109753	http://www.chemshuttle.com/catalogsearch/result/?q=95809-78-2&cat=
Chemspace	CSSB00015190091	https://chem-space.com/CSSB00015190091
Combi-Blocks	QJ-1160	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-1160
DC Chemicals	DC10591	http://www.dcchemicals.com/product_show-CPI-613.html
Excenen	EX-A2043	https://www.excenen.com/searchresultlist.php?id=95809-78-2
Lab Network	LN01263216	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01263216
Matrix Scientific	146661	https://www.matrixscientific.com/146661.html
MedChem Express	HY-15453	https://www.medchemexpress.com/CPI-613.html
MolPort	MolPort-023-219-128	https://www.molport.com/shop/molecule-link/MolPort-023-219-128
Molcore	MC582805	https://www.molcore.com/product/95809-78-2
MuseChem	I005683	https://www.musechem.com/product/I005683.html
Parchem	110983	https://www.parchem.com/chemical-supplier-distributor/-Octanoic-acid--6-8-bis[(phenylMethyl)thio]--110983.aspx
Renno Tech	RL06062	http://www.rennotech.com/product_show.asp?id=6310
Selleck Chemicals	S2776	http://www.selleckchem.com/products/cpi-613.html
Sigma-Aldrich	SML0404_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/sml0404?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S525750	http://www.smolecule.com/products/s525750
Sun-shine Chemical	CPI-613	http://www.sun-shinechem.com/95809-78-2.html
TCI (Tokyo Chemical Industry)	B5368	http://www.tcichemicals.com/eshop/en/us/commodity/B5368/index.html
THE BioTek	bt-267086	https://www.thebiotek.com/product/inhibitors/bt-267086
Tocris	5348	https://www.tocris.com/products/6-8-bis-benzylthio-octanoic-acid_5348
Yuhao Chemical	RT13191	http://www.chemyuhao.com/95809-78-2.html
abcr GmbH	AB453185	http://www.abcr.com/shop/en/AB453185
eNovation Chemicals	D501926	https://www.enovationchem.com/ProductDetails.asp?ProductID=D501926

PubMed

Title	Date	PubMed
		252160752
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	21722089

Patents

Sample Use Guides

In Vivo Use Guide

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 Vitro Use Guide

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 UTC 2023` Edited by `admin` on `Fri Dec 15 16:23:41 UTC 2023`
Record UNII	E76113IR49
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEVIMISTAT

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