N-HEXANOYLSPHINGOSINE

First approved in 2014

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H47NO3
Molecular Weight	397.6349
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO)NC(=O)CCCCC

InChI

InChIKey=NPRJSFWNFTXXQC-QFWQFVLDSA-N

InChI=1S/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)/b19-18+/t22-,23+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C24H47NO3
Molecular Weight	397.6349
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10989654 | https://www.ncbi.nlm.nih.gov/pubmed/26116623 | https://www.ncbi.nlm.nih.gov/pubmed/27631768 | https://www.ncbi.nlm.nih.gov/pubmed/1312082

N-hexanoylsphingosine is biologically active, cell permeable but nonphysiologic ceramide analog. Liposomal N-hexanoylsphingosine activates protein phosphatase 1 to inhibit melanoma cells. N-hexanoylsphingosine activates a cytosolic serine/threonine protein phosphatase in a dose-dependent manner. It induces cytochrome c (Cyt c) release from isolated rat liver mitochondria. It sensitizes vincristine-induced anticancer activity in vivo and in vitro, involving activating AMPK-p53 signaling.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serine/threonine-protein phosphatase 2A catalytic subunit alpha isoform 7 Target ID: P63331 Gene ID: 103694903\|\|\|24672 Gene Symbol: Ppp2ca Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8393446	Activator 1430
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21935601	Activator 1430
Serine/threonine protein phosphatase PP1-alpha catalytic subunit 1 Target ID: CHEMBL2164 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27631768	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21935601	Primary	Basic research	Unknown Approved Use Unknown
Glioblastoma multiforme 30 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24065522 https://www.ncbi.nlm.nih.gov/pubmed/24319543	Primary	Basic research	Unknown Approved Use Unknown
Melanoma 88 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27631768	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Involvement of growth differentiation factor-15/macrophage inhibitory cytokine-1 (GDF-15/MIC-1) in oxLDL-induced apoptosis of human macrophages in vitro and in arteriosclerotic lesions.	2004 Nov	15459768
De novo ceramide biosynthesis is associated with resveratrol-induced inhibition of ornithine decarboxylase activity.	2007 Jul 15	17521618
A role for ceramide in driving cancer cell resistance to doxorubicin.	2008 Jul	18245173
ABCB1 protects kidney proximal tubule cells against cadmium-induced apoptosis: roles of cadmium and ceramide transport.	2011 Jun	21436125

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 15 mg C6 ceramide/5 ml saline/kg every two days for a total of 20 days

Route of Administration: Intravenous

In Vitro Use Guide

A short chain synthetic ceramide, N-hexanoylsphingosine, was employed to treat Molt-4 cells in the presence of serum. Addition of N-hexanoylsphingosine not only caused programmed cell death, it also induced significant cell cycle arrest. N-hexanoylsphingosine-induced cell cycle arrest occurred rapidly (within 4 h) and doses as low as 15 uM N-hexanoylsphingosine (approximately 4 nM/10(6) cells) were able to reproduce effects reminiscent of prolonged serum deprivation: almost complete G0/G1 arrest following 14 h of treatment.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:48:20 GMT 2023` Edited by `admin` on `Fri Dec 15 15:48:20 GMT 2023`
Record UNII	038753E78J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

N-HEXANOYLSPHINGOSINE

Systematic Name

English

CAPROOYL SPHINGOSINE [INCI]

Common Name

English

N-HEXANOYL-D-ERYTHRO-SPHINGOSINE

Common Name

English

CAPROOYL SPHINGOSINE

Official Name

English

C6-CERAMIDE

Brand Name

English

HEXANAMIDE, N-((1S,2R,3E)-2-HYDROXY-1-(HYDROXYMETHYL)-3-HEPTADECEN-1-YL)-

Systematic Name

English

N-CAPROYL-C18-SPHINGOSINE

Common Name

English

N-CAPROYLSPHINGOSINE

Systematic Name

English

HEXANAMIDE, N-((1S,2R,3E)-2-HYDROXY-1-(HYDROXYMETHYL)-3-HEPTADECENYL)-

Systematic Name

English

NSC-655091

Code

English

HEXANAMIDE, N-(2-HYDROXY-1-(HYDROXYMETHYL)-3-HEPTADECENYL)-, (R-(R*,S*-(E)))-

Common Name

English

Code System Code Type Description

DAILYMED

038753E78J