U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H23NO4
Molecular Weight 281.3474
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLOHEXIMIDE

SMILES

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

InChI

InChIKey=YPHMISFOHDHNIV-FSZOTQKASA-N
InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1

HIDE SMILES / InChI

Description

Cycloheximide is an antibiotic produced by fermentation culture of Streptomyces griseus, Streptomyces noursei, Streptomyces albulus, Streptomyces naraensis, or other cycloheximide-producing microorganism. It was first discovered by A. Whiffen et al. in 1946. She observed the activity of the compound against the yeasts and it became known as the first antifungal antibiotic. Cycloheximide has been marketed as a plant fungicide for many years and this use continues mainly against fungal diseases of turf and for powdery mildew on roses. More recently, cycloheximide has been recognized and is being developed as an abscission agent for citrus fruits and olives. Due to significant toxic side effects, including DNA damage, teratogenesis, and other reproductive effects, cycloheximide is generally used only in in vitro research applications, and is not suitable for human use as a therapeutic compound. Cycloheximide is an antimitotic and an inhibitor of the synthesis of both DNA and protein.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
6.6 µM [IC50]
3.4 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Mice were injected ip with 4.8 mg cycloheximide in 150 ul isotonic saline
Route of Administration: Intraperitoneal
In Vitro Use Guide
After administration of the protein synthesis inhibitor cycloheximide (4 ug/mL) to fully spread hepatoma Hep G2 cells, cell growth was arrested and change of the OWLS signal became noticeable within 6 h after drug administration.