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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H45ClN4O6.2CH4O3S
Molecular Weight 941.505
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIMCODAR DIMESYLATE

SMILES

CS(O)(=O)=O.CS(O)(=O)=O.COC1=CC(=CC(OC)=C1OC)C(=O)C(=O)N(C)[C@@H](CC2=CC=C(Cl)C=C2)C(=O)N(CC3=CC=CC=C3)C(CCC4=CC=NC=C4)CCC5=CC=NC=C5

InChI

InChIKey=LXIAWDJOQUWVQS-SHRURHRBSA-N
InChI=1S/C43H45ClN4O6.2CH4O3S/c1-47(43(51)40(49)34-27-38(52-2)41(54-4)39(28-34)53-3)37(26-32-10-14-35(44)15-11-32)42(50)48(29-33-8-6-5-7-9-33)36(16-12-30-18-22-45-23-19-30)17-13-31-20-24-46-25-21-31;2*1-5(2,3)4/h5-11,14-15,18-25,27-28,36-37H,12-13,16-17,26,29H2,1-4H3;2*1H3,(H,2,3,4)/t37-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C43H45ClN4O6
Molecular Weight 749.294
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Timcodar (also known as VX-853) is a benzenepropanamide derivative patented by Vertex Pharmaceuticals Incorporated as an efflux pump inhibitor for the treatment of multi-drug resistant bacterial infection. Timcodar potentiates the activity of ethidium bromide (EtBr), a model efflux substrate, against three clinically significant gram-positive pathogens: Staphylococcus aureus, Enterococcus faecalis, and Streptococcus pneumoniae. Timcodar weakly inhibits M. tuberculosis growth in broth culture but shows a 10-fold increase in the growth inhibition of M. Tuberculosis cultured in host macrophage cells and demonstrated synergy with rifampin, moxifloxacin, and bedaquiline. In a mouse model of tuberculosis lung infection, timcodar reduces the likelihood of a relapse infection and potentiates the efficacies of rifampin and isoniazid. Timcodar in combination with Doxorubicin was studied in phase 1/2 clinical trials in patients with solid tumors, but no results have been published.

Approval Year

PubMed

PubMed

TitleDatePubMed
Timcodar (VX-853) Is a Non-FKBP12 Binding Macrolide Derivative That Inhibits PPARγ and Suppresses Adipogenesis.
2016
Patents

Patents

Sample Use Guides

orally every 8 hours on days 1-3, treatment repeats every 3 weeks
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:35:49 UTC 2023
Edited
by admin
on Fri Dec 15 16:35:49 UTC 2023
Record UNII
44277I316G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIMCODAR DIMESYLATE
USAN  
USAN  
Official Name English
Timcodar dimesilate [WHO-DD]
Common Name English
TIMCODAR DIMESYLATE [USAN]
Common Name English
TIMCODAR DIMESILATE
WHO-DD  
Common Name English
VX-853-2
Code English
Classification Tree Code System Code
NCI_THESAURUS C1744
Created by admin on Fri Dec 15 16:35:49 UTC 2023 , Edited by admin on Fri Dec 15 16:35:49 UTC 2023
Code System Code Type Description
USAN
JJ-28
Created by admin on Fri Dec 15 16:35:49 UTC 2023 , Edited by admin on Fri Dec 15 16:35:49 UTC 2023
PRIMARY
PUBCHEM
9811663
Created by admin on Fri Dec 15 16:35:49 UTC 2023 , Edited by admin on Fri Dec 15 16:35:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID50171411
Created by admin on Fri Dec 15 16:35:49 UTC 2023 , Edited by admin on Fri Dec 15 16:35:49 UTC 2023
PRIMARY
CAS
183313-30-6
Created by admin on Fri Dec 15 16:35:49 UTC 2023 , Edited by admin on Fri Dec 15 16:35:49 UTC 2023
PRIMARY
ChEMBL
CHEMBL2059028
Created by admin on Fri Dec 15 16:35:49 UTC 2023 , Edited by admin on Fri Dec 15 16:35:49 UTC 2023
PRIMARY
FDA UNII
44277I316G
Created by admin on Fri Dec 15 16:35:49 UTC 2023 , Edited by admin on Fri Dec 15 16:35:49 UTC 2023
PRIMARY
NCI_THESAURUS
C2443
Created by admin on Fri Dec 15 16:35:49 UTC 2023 , Edited by admin on Fri Dec 15 16:35:49 UTC 2023
PRIMARY
MESH
C494139
Created by admin on Fri Dec 15 16:35:49 UTC 2023 , Edited by admin on Fri Dec 15 16:35:49 UTC 2023
PRIMARY
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