Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C18H37NO2 |
| Molecular Weight | 299.4919 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO
InChI
InChIKey=WWUZIQQURGPMPG-KRWOKUGFSA-N
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1
Sphingosine harbors two chiral centers and therefore exhibits four stereoisomers, only one of which, the D-erythro (2S,3R) is known to exist naturally. ERYTHRO-SPHINGOSINE, (±)- is a mixture of two isomers: inactive ERYTHRO-SPHINGOSINE, (+)- and the active ERYTHRO-SPHINGOSINE, (-), also known as D-erythro (2S,3R)-SPHINGOSINE or D-erythro –SPHINGOSINE. It was found, that D-erythro –SPHINGOSINE acts as a potent inhibitor of protein kinase C and of transient receptor potential melastatin 7 (TRPM7). Besides, was shown, that sphingosine may be efficacious against alveolar rhabdomyosarcoma, irrespective of TP53 mutation status. It also could evolve as alternative treatment options for aggressive lymphomas via PKC inhibition, apoptosis, and autophagy.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2093867 |
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Target ID: http://www.uniprot.org/uniprot/W0FXB0 |
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Target ID: Q96QT4 Gene ID: 54822.0 Gene Symbol: TRPM7 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Use of D-erythro-sphingosine as a pharmacological inhibitor of protein kinase C in human platelets. | 1991 Sep 1 |
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| Ursodeoxycholic acid enhances glucocorticoid-induced tyrosine aminotransferase-gene expression in cultured rat hepatocytes. | 1997 Nov 26 |
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| Inhibition of arachidonic acid release and cytosolic phospholipase A2 alpha activity by D-erythro-sphingosine. | 2004 Jan 19 |
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| ACTH regulates steroidogenic gene expression and cortisol biosynthesis in the human adrenal cortex via sphingolipid metabolism. | 2004 Nov |
Patents
Sample Use Guides
Exogenous addition of D-erythro-sphingosine inhibited the responses in a concentration-dependent manner in the two cell lines: PC12 and L929. D-erythro-sphingosine significantly inhibited mastoparan-, but not Na3VO4-, stimulated arachidonic acid release in PC12 cells. D-erythro-S1P showed no effect on the responses. Production of prostaglandin F2alpha was suppressed by D-erythro-sphingosine (10 microM) in PC12 cells.
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2733-29-1
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m10144
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SUBSTANCE RECORD
