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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H39NO
Molecular Weight 285.5084
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SPISULOSINE

SMILES

CCCCCCCCCCCCCCC[C@@H](O)[C@H](C)N

InChI

InChIKey=YRYJJIXWWQLGGV-ZWKOTPCHSA-N
InChI=1S/C18H39NO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18(20)17(2)19/h17-18,20H,3-16,19H2,1-2H3/t17-,18+/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H39NO
Molecular Weight 285.5084
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Deoxysphingoid bases as plasma markers in diabetes mellitus.
2010-08-16
Phase I safety, pharmacokinetic, and pharmacogenomic trial of ES-285, a novel marine cytotoxic agent, administered to adult patients with advanced solid tumors.
2009-06
Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols.
2008-08
Spisulosine (ES-285) induces prostate tumor PC-3 and LNCaP cell death by de novo synthesis of ceramide and PKCzeta activation.
2008-04-28
Compatibility and stability of the novel anticancer agent ES-285 x HCl formulated with 2-hydroxypropyl-beta-cyclodextrin in infusion devices.
2006-01
Kahalalide F and ES285: potent anticancer agents from marine molluscs.
2006
Pharmaceutical development of a parenteral lyophilised formulation of the investigational anticancer agent ES-285.HCl.
2005-10-13
Development and validation of a liquid chromatography-ultraviolet absorbance detection assay using derivatisation for the novel marine anticancer agent ES-285 x HCl [(2S,3R)-2-amino-3-octadecanol hydrochloride] and its pharmaceutical dosage form.
2003-12-12
Efficient synthesis of enantiomerically pure 2-acylaziridines: Facile syntheses of N-Boc-safingol, N-Boc-D-erythro-sphinganine, and N-Boc-spisulosine from a common intermediate.
2003-10-03
Phenylisothiocyanate and dansyl chloride precolumn derivatizations for the high-performance liquid chromatography analysis of the antitumoral agent ES-285 in dog plasma.
2003-07-05
Quantitative analysis of ES-285, an investigational marine anticancer drug, in human, mouse, rat, and dog plasma using coupled liquid chromatography and tandem mass spectrometry.
2003-05
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:52:04 GMT 2025
Edited
by admin
on Mon Mar 31 21:52:04 GMT 2025
Record UNII
ZX5D253CYY
Record Status Validated (UNII)
Record Version
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Name Type Language
ES-285
Preferred Name English
SPISULOSINE
WHO-DD  
Common Name English
3-OCTADECANOL, 2-AMINO-, (R-(R*,S*))-
Systematic Name English
(+)-SPISULOSINE
Common Name English
Spisulosine [WHO-DD]
Common Name English
SPISULOSINE 285
Common Name English
1-DEOXYSPHINGANINE
Systematic Name English
3-OCTADECANOL, 2-AMINO-, (2S,3R)-
Systematic Name English
Code System Code Type Description
SMS_ID
100000175281
Created by admin on Mon Mar 31 21:52:04 GMT 2025 , Edited by admin on Mon Mar 31 21:52:04 GMT 2025
PRIMARY
CHEBI
67109
Created by admin on Mon Mar 31 21:52:04 GMT 2025 , Edited by admin on Mon Mar 31 21:52:04 GMT 2025
PRIMARY
PUBCHEM
9925886
Created by admin on Mon Mar 31 21:52:04 GMT 2025 , Edited by admin on Mon Mar 31 21:52:04 GMT 2025
PRIMARY
EPA CompTox
DTXSID30432931
Created by admin on Mon Mar 31 21:52:04 GMT 2025 , Edited by admin on Mon Mar 31 21:52:04 GMT 2025
PRIMARY
FDA UNII
ZX5D253CYY
Created by admin on Mon Mar 31 21:52:04 GMT 2025 , Edited by admin on Mon Mar 31 21:52:04 GMT 2025
PRIMARY
CAS
196497-48-0
Created by admin on Mon Mar 31 21:52:04 GMT 2025 , Edited by admin on Mon Mar 31 21:52:04 GMT 2025
PRIMARY
CHEBI
67106
Created by admin on Mon Mar 31 21:52:04 GMT 2025 , Edited by admin on Mon Mar 31 21:52:04 GMT 2025
PRIMARY
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