ACETOXYCYCLOHEXIMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H25NO6
Molecular Weight	339.3835
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1C[C@](C)(C[C@@H]([C@H](O)CC2CC(=O)NC(=O)C2)C1=O)OC(C)=O

InChI

InChIKey=UFDHNJJHPSGMFX-SQUSCZTCSA-N

InChI=1S/C17H25NO6/c1-9-7-17(3,24-10(2)19)8-12(16(9)23)13(20)4-11-5-14(21)18-15(22)6-11/h9,11-13,20H,4-8H2,1-3H3,(H,18,21,22)/t9-,12-,13+,17+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H25NO6
Molecular Weight	339.3835
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19112105 | https://www.ncbi.nlm.nih.gov/pubmed/18442799 | https://www.ncbi.nlm.nih.gov/pubmed/15670574

Acetoxycycloheximide is a protein synthesis inhibitor. Acetoxycycloheximide has been previously shown to induce rapid apoptosis mediated by the release of cytochrome c in human leukemia Jurkat cells. It has also been shown to block the TNF-alpha-induced activation of NF-kappaB via ectodomain shedding of TNF receptor 1 (TNF-R1) in human lung carcinoma A549 cells. Acetoxycycloheximide triggers the downregulation of cell surface TNF-R1 via the activation of ERK and p38 MAP kinase, thereby preventing activation of the NF-kappaB signaling pathway by TNF-alpha.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
translation 13 Target ID: GO:0006412 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5907359 \| https://www.ncbi.nlm.nih.gov/pubmed/5348288	Inhibitor 8504
Acetylcholinesterase 209 Target ID: CHEMBL3199 Sources: https://www.ncbi.nlm.nih.gov/pubmed/932721	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19112105	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Fat absorption during inhibition of protein synthesis: studies of lymph chylomicrons.	1972-02	5009119
Different lethal effects of mitomycin C and actinomycin D during the division cycle of HeLa cells.	1968-09	5664219
Memory impairment after subcutaneous injection of acetoxycycloheximide.	1968-05-03	5689416
Effect of acetoxycycloheximide on learning and memory of a light-dark discrimination.	1968-04-20	5648225

Patents

Sample Use Guides

In Vivo Use Guide

Mice: Subcutaneous injection of 240 ug of acetoxycycloheximide in mice rapidly produces marked inhibition of cerebral protein synthesis. Rats: Protein synthesis was inhibited by intraperitoneal acetoxycycloheximide (ACH), 0.25 mg/kg, 1 hr before lipid infusion.

Route of Administration: Other

In Vitro Use Guide

5 ug/ml oxycycloheximide has a restorative effect on survival of synchronous HeLa cells after pulse treatment with 0.1 ug/ml of mitomycin C.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:29:17 GMT 2025` Edited by `admin` on `Mon Mar 31 19:29:17 GMT 2025`
Record UNII	UX3Y1I395S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACETOXYCYCLOHEXIMIDE

Common Name

English

NSC-32743

Preferred Name

English

2,6-PIPERIDINEDIONE, 4-((2R)-2-((1S,3S,5R)-5-(ACETYLOXY)-3,5-DIMETHYL-2-OXOCYCLOHEXYL)-2-HYDROXYETHYL)-

Systematic Name

English

E-73

Code

English

ANTIBIOTIC SF 2441

Common Name

English

STREPTOVITACIN E-73

Common Name

English

STREPTOVITACIN E 73

Common Name

English

ANTIBIOTIC SF-2441

Common Name

English

Code System Code Type Description

CAS

2885-39-4