CYCLOHEXIMIDE

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 Search

SMILES

C[C@H]1C[C@H](C)C(=O)[C@@H](C1)[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

Molecular Formula	C15H23NO4
Molecular Weight	281.3474
Charge	0
Count

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

Description
Sources: https://www.google.com/patents/US3915803 | https://www.ncbi.nlm.nih.gov/pubmed/932247 | https://www.ncbi.nlm.nih.gov/pubmed/6746349

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 Target	Pharmacology	Condition	Potency
translation 13 Target ID: GO:0006412 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28971619 \| https://www.ncbi.nlm.nih.gov/pubmed/9434890	Inhibitor 8504		6.6 µM [IC50]
FK506-binding protein 1A 9 Target ID: CHEMBL1902 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10479292	Inhibitor 8504		3.4 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Plasmodium falciparum malaria 63 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3515175	Primary	Basic research	Unknown Approved Use Unknown
Psoriasis 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/932247	Primary	Preclinical	Unknown Approved Use Unknown
Pancreatitis 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/73498	Primary	Preclinical	Unknown Approved Use Unknown
Basal cell carcinoma 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/486324	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Eukaryotic translation initiation factor-6 enhances histamine and IL-2 production in mast cells.	2001-03-01	11207322
Gene expression of osteoclast differentiation factor is induced by lipopolysaccharide in mouse osteoblasts via Toll-like receptors.	2001-03-01	11207318
Interleukin-1beta enhances bradykinin-induced phosphoinositide hydrolysis and Ca2+ mobilization in canine tracheal smooth-muscle cells: involvement of the Ras/Raf/mitogen-activated protein kinase (MAPK) kinase (MEK)/MAPK pathway.	2001-03-01	11171124
Dmrt1 expression is regulated by follicle-stimulating hormone and phorbol esters in postnatal Sertoli cells.	2001-03	11181532
Differential induction of rat hepatic cytochromes P450 3A1, 3A2, 2B1, 2B2, and 2E1 in response to pyridine treatment.	2001-03	11181506
Regulation of the leptin content of obese human adipose tissue.	2001-03	11171593
A novel retinoid-response gene set in vascular smooth muscle cells.	2001-02-23	11181072
LDL downregulates CYP51 in porcine vascular endothelial cells and in the arterial wall through a sterol regulatory element binding protein-2-dependent mechanism.	2001-02-16	11179193
Natural protection from apoptosis by surfactant protein A in type II pneumocytes.	2001-02-15	11161717
Acquisition of CD80 (B7-1) by T cells.	2001-02-15	11160311
Estradiol down regulates expression of vasoactive intestinal polypeptide receptor type-1 in breast cancer cell lines.	2001-02-14	11165054
Chemioxyexcitation (delta pO2/ROS)-dependent release of IL-1 beta, IL-6 and TNF-alpha: evidence of cytokines as oxygen-sensitive mediators in the alveolar epithelium.	2001-02-07	11161456
Anticancer drugs induce increased mitochondrial cytochrome c expression that precedes cell death.	2001-02-01	11221830
Differential induction of stearoyl-CoA desaturase and acyl-CoA oxidase genes by fibrates in HepG2 cells.	2001-02-01	11172741
Differential regulation of the expression of CD95 ligand, receptor activator of nuclear factor-kappa B ligand (RANKL), TNF-related apoptosis-inducing ligand (TRAIL), and TNF-alpha during T cell activation.	2001-02-01	11160247
The effects of particulate wear debris, cytokines, and growth factors on the functions of MG-63 osteoblasts.	2001-02	11216681
Vasopressin pressor receptor-mediated activation of HPA axis by acute ethanol stress in rats.	2001-02	11208575
Transcriptional induction of matrix metalloproteinase-13 (collagenase-3) by 1alpha,25-dihydroxyvitamin D3 in mouse osteoblastic MC3T3-E1 cells.	2001-02	11204422
Periovulatory changes in catfish ovarian oestradiol-17beta, oestrogen-2-hydroxylase and catechol-O-methyltransferase during GnRH analogue-induced ovulation and in vitro induction of oocyte maturation by catecholoestrogens.	2001-02	11182761
Constitutive intracellular expression and activation-induced cell surface up-regulation of CD44v3 in human T lymphocytes.	2001-02	11180125
Cloned neuropeptide Y (NPY) Y1 and pancreatic polypeptide Y4 receptors expressed in Chinese hamster ovary cells show considerable agonist-driven internalization, in contrast to the NPY Y2 receptor.	2001-02	11179953
Differential in vitro suppressive effects of steroids on leukocyte phagocytosis in two teleosts, tilapia and common carp.	2001-02	11178882
Serum amyloid P-component-induced colony-stimulating factors production by macrophages.	2001-02	11169219
cAMP stimulation of vasopressin and oxytocin release and regulation of vasopressin mRNA stability: role of auto-facilitation.	2001-02	11168841
A comparative molecular-physiological study of submergence response in lowland and deepwater rice.	2001-02	11161052
Apoptotic events in a human ovarian cancer cell line exposed to anthracyclines.	2001-02	11160608
Relative enzymatic activity, protein stability, and tissue distribution of human steroid-metabolizing UGT2B subfamily members.	2001-02	11159850
Regulation of phosphate uptake in primary cultured rabbit renal proximal tubule cells by glucocorticoids: evidence for nongenomic as well as genomic mechanisms.	2001-02	11159843
Regulation of metallothionein II messenger ribonucleic acid measures exogenous estrogen receptor-beta activity in SAOS-2 and LNCaPLN3 cells.	2001-02	11159835
Nuclear factor-kappaB-mediated X-linked inhibitor of apoptosis protein expression prevents rat granulosa cells from tumor necrosis factor alpha-induced apoptosis.	2001-02	11159825
Regulation of monocyte chemoattractant protein (MCP)-1 transcription by interferon-gamma (IFN-gamma) in human astrocytoma cells: postinduction refractory state of the gene, governed by its upstream elements.	2001-02	11156954
Reactive oxygen species mediate tumor necrosis factor alpha-converting, enzyme-dependent ectodomain shedding induced by phorbol myristate acetate.	2001-02	11156944
Differential sensitivity of breast cancer cells to tumor necrosis factor-alpha: involvement of protein kinase C.	2001-01-26	11162606
Hemoglobin increases endothelin-1 in endothelial cells by decreasing nitric oxide.	2001-01-26	11162595
Pretreatment with paclitaxel enhances apo-2 ligand/tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis of prostate cancer cells by inducing death receptors 4 and 5 protein levels.	2001-01-15	11212279
Role of caspases and mitochondria in the steroid-induced programmed cell death of a motoneuron during metamorphosis.	2001-01-15	11203705
Regulation of GP63 mRNA stability in promastigotes of virulent and attenuated Leishmania chagasi.	2001-01-15	11166386
Murine and human SDF2L1 is an endoplasmic reticulum stress-inducible gene and encodes a new member of the Pmt/rt protein family.	2001-01-12	11162531
Heregulin regulation of urokinase plasminogen activator and its receptor: human breast epithelial cell invasion.	2001-01-01	11196194
Induction of P-glycoprotein mRNA transcripts by cycloheximide in animal tissues: evidence that class I Pgp is transcriptionally regulated whereas class II Pgp is post-transcriptionally regulated.	2001-01	11216854
Evidence that phosphorylation of human Upfl protein varies with intracellular location and is mediated by a wortmannin-sensitive and rapamycin-sensitive PI 3-kinase-related kinase signaling pathway.	2001-01	11214180
Neuronal death is an active, caspase-dependent process after moderate but not severe DNA damage.	2001-01	11208915
Group II metabotropic glutamate receptor activation protects striatal dopaminergic nerve terminals against MPP+-induced neurotoxicity along with brain-derived neurotrophic factor induction.	2001-01	11208898
The ameliorating effect of the water layer of Fructus Schisandrae on cycloheximide-induced amnesia in rats: interaction with drugs acting at neurotransmitter receptors.	2001-01	11207061
Expression of vascular endothelial growth factor in human monocyte/macrophages stimulated with lipopolysaccharide.	2001-01	11204570
The jasmonate-inducible AP2/ERF-domain transcription factor ORCA3 activates gene expression via interaction with a jasmonate-responsive promoter element.	2001-01	11169181
Stimulation of tetrahydrobiopterin synthesis induced by insulin: possible involvement of phosphatidylinositol 3-kinase.	2001-01	11167133
Mechanism of colchicine-induced steroidogenesis in rat adrenocortical cells.	2001	11180406
Role of endogenous zinc in the enhancement of bone protein synthesis associated with bone growth of newborn rats.	2001	11156471
Polysaccharide Krestin enhances manganese superoxide dismutase activity and mRNA expression in mouse peritoneal macrophages.	2000	11154046

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:46:39 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:39 GMT 2025`
Record UNII	98600C0908
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CICLOHEXIMIDE

Preferred Name

English

CYCLOHEXIMIDE

Official Name

English

3-[(R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]glutarimide

Systematic Name

English

cicloheximide [INN]

Common Name

English

NSC-185

Code

English

2,6-PIPERIDINEDIONE, 4-(2-(3,5-DIMETHYL-2-OXOCYCLOHEXYL)-2-HYDROXYETHYL)-, (1S-(1.ALPHA.(S*),3.ALPHA.,5.BETA.))-

Common Name

English

CYCLOHEXIMIDE [USAN]

Common Name

English

U-4527

Code

English

CICLOHEXIMIDE [MART.]

Common Name

English

CYCLOHEXIMIDE [HSDB]

Common Name

English

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

Systematic Name

English

4-((2R)-2-((1S,3S,5S)-3,5-DIMETHYL-2-OXOCYCLOHEXYL)-2-HYDROXYETHYL)PIPERIDINE-2,6-DIONE

Systematic Name

English

CYCLOHEXIMIDE [ISO]

Common Name

English

CYCLOHEXIMIDE [MI]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

43401