DEFOSLIMOD

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C53H102N2O20P2
Molecular Weight	1149.3259
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCC[C@@H](O)CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](O)[C@H]2NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)O[C@H]1COP(O)(O)=O

InChI

InChIKey=UUVVKHSZRKZOGM-CUECXTGJSA-N

InChI=1S/C53H102N2O20P2/c1-4-7-10-13-16-19-22-25-28-31-39(57)34-44(58)54-47-42(38-71-76(64,65)66)73-43(49(61)50(47)62)37-70-53-48(51(63)52(41(36-56)74-53)75-77(67,68)69)55-45(59)35-40(32-29-26-23-20-17-14-11-8-5-2)72-46(60)33-30-27-24-21-18-15-12-9-6-3/h39-43,47-53,56-57,61-63H,4-38H2,1-3H3,(H,54,58)(H,55,59)(H2,64,65,66)(H2,67,68,69)/t39-,40-,41-,42+,43-,47+,48-,49-,50-,51-,52-,53-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C53H102N2O20P2
Molecular Weight	1149.3259
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12744882 | https://www.ncbi.nlm.nih.gov/pubmed/23547558

Defoslimod is an analog of lipopolysaccharide endotoxin-derived lipid A obtained from E. coli, developed as an immunomodulatory adjuvant and an immunotherapeutic agent for the treatment of cancer. Defoslimod acts as an agonist of Toll-like receptor (TLR) 2/4. In a phase 1 clinical study in patients with solid tumors, conducted in 2007, defoslimod was administered as an intravenous infusion. The therapy was well tolerated at biologically active concentrations, with 3 patients of 17 exhibited disease stabilization with a mean duration of 4 months. No further development of the drug was reported.

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:37:50 UTC 2023` Edited by `admin` on `Fri Dec 15 19:37:50 UTC 2023`
Record UNII	HC3530GGGG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEFOSLIMOD

Official Name

English

2-DEOXY-6-O-(2-DEOXY-2-((R)-3-HYDROXYTETRADECANAMIDO)-.BETA.-D-GLUCOPYRANOSYL)-2-((R)-3-HYDROXYTETRADECANAMIDO)-.ALPHA.-D-GLUCOPYRANOSE 1,6'-BIS(DIHYDROGEN PHOSPHATE) 2'(3)-LAURATE

Common Name

English

OM-174

Code

English

OM174

Code

English

.ALPHA.-D-GLUCOPYRANOSE, 2-DEOXY-6-O-(2-DEOXY-2-((1-OXO-3-((1-OXODODECYL)OXY)TETRADECYL)AMINO)-4-O-PHOSPHONO-.BETA.-D-GLUCOPYRANOSYL)-2-((3-HYDROXY-1-OXOTETRADECYL)AMINO)-, 1-(DIHYDROGEN PHOSPHATE), (2(R),6(R))-

Common Name

English

defoslimod [INN]

Common Name

English

.ALPHA.-D-GLUCOPYRANOSE, 2-DEOXY-6-O-(2-DEOXY-2-(((3R)-1-OXO-3-((1-OXODODECYL)OXY)TETRADECYL)AMINO)-4-O-PHOSPHONO-.BETA.-D-GLUCOPYRANOSYL)-2-(((3R)-3-HYDROXY-1-OXOTETRADECYL)AMINO)-, 1-(DIHYDROGEN PHOSPHATE)

Common Name

English

Code System Code Type Description

NCI_THESAURUS

C169880