DOFEQUIDAR FUMARATE

Details

Stereochemistry	RACEMIC
Molecular Formula	2C30H31N3O3.3C4H4O4
Molecular Weight	1311.3874
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.OC(COC1=C2C=CC=NC2=CC=C1)CN3CCN(CC3)C(=O)C(C4=CC=CC=C4)C5=CC=CC=C5.OC(COC6=C7C=CC=NC7=CC=C6)CN8CCN(CC8)C(=O)C(C9=CC=CC=C9)C%10=CC=CC=C%10

InChI

InChIKey=ZGMJYTYLTJFNCS-VQYXCCSOSA-N

InChI=1S/2C30H31N3O3.3C4H4O4/c2*34-25(22-36-28-15-7-14-27-26(28)13-8-16-31-27)21-32-17-19-33(20-18-32)30(35)29(23-9-3-1-4-10-23)24-11-5-2-6-12-24;3*5-3(6)1-2-4(7)8/h2*1-16,25,29,34H,17-22H2;3*1-2H,(H,5,6)(H,7,8)/b;;3*2-1+

HIDE SMILES / InChI

Molecular Formula	C30H31N3O3
Molecular Weight	481.5854
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://newdrugapprovals.org/2016/01/08/16608/
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800003023 | http://en.pharmacodia.com/web/drug/1_4626.html | https://newdrugapprovals.org/tag/ms-209/ | https://www.ncbi.nlm.nih.gov/pubmed/15648956 | https://www.ncbi.nlm.nih.gov/pubmed/8002634

Dofequidar (MS-209), a quinolone-derived sphingomyelin synthase inhibitor that blocks P-glycoprotein and multidrug resistance-associated protein-1, is under development by Schering for the potential treatment of multidrug resistant tumors. MS-209 had been in phase III clinical trials for the treatment of breast cancer and non-small lung cancer. But this research was discontinued in 2004. Detected adverse events are: nausea, vomiting, leukopenia, neutropenia, anorexia, constipation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8002634 \| https://www.ncbi.nlm.nih.gov/pubmed/9272120 \| http://en.pharmacodia.com/web/drug/1_4626.html	Inhibitor 8297
Multidrug resistance-associated protein 1 15 Target ID: CHEMBL3004 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15648956 \| https://newdrugapprovals.org/2016/01/08/16608/	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17179098 http://adisinsight.springer.com/drugs/800003023	Primary	Phase II 1132	Unknown Approved Use Unknown
Non-small cell lung cancer 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15648956 http://adisinsight.springer.com/drugs/800003023	Primary	Phase III 656	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16144929 http://adisinsight.springer.com/drugs/800003023	Primary	Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A 214 P-gp 1461 MRP1 106 MRP 7 BCRP 699	UGT 192

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=363678095	inconclusive [IC50 26.837 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=363678095	yes [IC50 1.6933 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=363678095	yes [IC50 11.9877 uM]
CYP3A 298	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10463589/	yes [Ki 0.75 uM]
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19673889/	yes
MRP 7	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10049760/	yes
MRP1 172	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19673889/	yes
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/7828268/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT 192	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10201824/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY516611	https://www.001chemical.com/chem/129716-58-1
001 Chemical	DY526830	https://www.001chemical.com/chem/153653-31-7
001 Chemical	DY526831	https://www.001chemical.com/chem/153653-33-9
Achemtek	0102-014539	http://www.achemtek.com/129716-58-1
Aurora Fine Chemicals LLC	A14.516.538	http://online.aurorafinechemicals.com/info?ID=A14.516.538
BLD Pharm	BD630094	http://www.bldpharm.com/products/129716-58-1.html
BOC Sciences	129716-58-1	https://www.bocsci.com/dofequidar-cas-129716-58-1-item-84-244906.html
BioChemPartner	BCP24839	http://www.biochempartner.com/129716-58-1-BCP24839
BioCrick	BCC4176	http://www.biocrick.com/Dofequidar-BCC4176.html
CSNpharm	CSN17662	https://www.csnpharm.com/products/dofequidar.html
Chem Scene	CS-2042	http://www.chemscene.com/129716-58-1.html
DC Chemicals	DC24094	http://www.dcchemicals.com/product_show-DC24094.html
Lab Network	LN01341955	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01341955
MedChem Express	HY-17013	https://www.medchemexpress.com/Dofequidar.html
MolPort	MolPort-046-418-318	https://www.molport.com/shop/molecule-link/MolPort-046-418-318
Molcore	MC516611	https://www.molcore.com/product/129716-58-1
Molcore	MC526830	https://www.molcore.com/product/153653-31-7
Molcore	MC526831	https://www.molcore.com/product/153653-33-9
MuseChem	I001137	https://www.musechem.com/product/I001137.html
Smolecule	S548834	http://www.smolecule.com/products/s548834
THE BioTek	bt-288240	https://www.thebiotek.com/product/inhibitors/bt-288240
eNovation Chemicals	D672528	https://www.enovationchem.com/ProductDetails.asp?ProductID=D672528

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

900 mg 30 minutes before each dose of doxorubicin (on days 1 - 14).

Route of Administration: Oral

In Vitro Use Guide

Intracellular accumulation of [3H]-VCR in HL60R cells increased by approximately 2.5 times at 120 and 180 min in the presence of 10 uM Dofequidar (P < 0.05). Similarly, 10 uM Dofequidar increased by approximately twofold the intracellular accumulation of [3H]-VCR in H460 cells.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:29:22 GMT 2023` Edited by `admin` on `Sat Dec 16 08:29:22 GMT 2023`
Record UNII	3DM793MFSE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DOFEQUIDAR FUMARATE

Common Name

English

4-(DIPHENYLACETYL)-ALPHA-((5-QUINOLINYLOXY)METHYL)-1-PIPERAZINEETHANOL (E)-2-BUTENEDIOATE (2:3) (SALT)

Systematic Name

English

MS-209

Code

English

1-PIPERAZINEETHANOL, 4-(DIPHENYLACETYL)-ALPHA-((5-QUINOLINYLOXY)METHYL)-, (E)-2-BUTENEDIOATE (2:3) (SALT)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1744