Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H41NO2 |
| Molecular Weight | 327.545 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCC\C=C\[C@H](O)[C@@H](CO)N(C)C
InChI
InChIKey=YRXOQXUDKDCXME-QWKHPXNBSA-N
InChI=1S/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m1/s1
| Molecular Formula | C20H41NO2 |
| Molecular Weight | 327.545 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
N,N-Dimethylsphingosine (also known as DMS) is an inhibitor of sphingosine kinase, which has been identified as an inducer of pain in a rat model of chronic pain. Recently was shown, that DMS through anti-parasitic and immunomodulatory actions, can be beneficial in the treatment of chronic phase of T. cruzi infection and was suggested that S1P-activated processes could be possible therapeutic targets for the treatment of Chagas disease cardiomyopathy.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| mitochondrial ceramidase overexpression up-regulates Bcl-2 protein level in K562 cells, probably through its metabolite sphingosine-1-phosphate. | 2004 Oct |
|
| Pharmacologic manipulation of sphingosine kinase in retinal endothelial cells: implications for angiogenic ocular diseases. | 2006 Nov |
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| MAO-A-induced mitogenic signaling is mediated by reactive oxygen species, MMP-2, and the sphingolipid pathway. | 2007 Jul 1 |
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| Small molecule activators of SIRT1 replicate signaling pathways triggered by calorie restriction in vivo. | 2009 Mar 10 |
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| Sphingosine kinase-1 pathway mediates high glucose-induced fibronectin expression in glomerular mesangial cells. | 2011 Dec |
|
| Bortezomib and sphingosine kinase inhibitor interact synergistically to induces apoptosis in BCR/ABl+ cells sensitive and resistant to STI571 through down-regulation Mcl-1. | 2011 Feb 4 |
Patents
Sample Use Guides
in mice: C57BL/6 mice infected with trypomastigotes (Colombian strain) were treated during the chronic phase of infection (6 months pos-infection) with N, N-Dimethylsphingosine (DMS) (200 µg/Kg/day; 3x week; i.p.).
Route of Administration:
Intraperitoneal
In vitro experiments indicated that N, N-Dimethylsphingosine (DMS) induced a dose-dependent reduction in [3H]-thymidine incorporation and ERK-1/2 activation via a protein kinase C (PKC) independent mechanism with an IC50 value of 12 ± 6 and 15 ± 10 µM respectively. DMS also reduced Akt signalling.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:17:48 GMT 2023
by
admin
on
Fri Dec 15 18:17:48 GMT 2023
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| Record UNII |
L9QRA71834
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| Record Status |
Validated (UNII)
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| Record Version |
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L9QRA71834
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N,N-DIMETHYLSPHINGOSINE
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122314-67-4
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6438166
Created by
admin on Fri Dec 15 18:17:48 GMT 2023 , Edited by admin on Fri Dec 15 18:17:48 GMT 2023
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