Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H19NO4 |
Molecular Weight | 265.305 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C[C@H]2NC[C@H](O)[C@H]2OC(C)=O)C=C1
InChI
InChIKey=YKJYKKNCCRKFSL-RDBSUJKOSA-N
InChI=1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m1/s1
Anisomycin (2-p-methoxyphenylmethyl-3-acetoxy-4-hydroxypyrrolidine) is an antibiotic isolated from cultures of various
Streptomyces. Anisomycin is a potent, structurally specific, and reversible inhibitor of protein biosynthesis in certain yeast and mammalian cells. The inhibition occurs subsequent to the formation of aminoacyl transfer ribonucleic acid but prior to the release of polypeptides from the polyribosome.
Anisomycin has unspecified effects that can produce temporary amnesia for a reactivated memory and they also could be responsible for any permanent effects that anisomycin produces. Anisomycin is known to cause apoptosis by activation of MAPK cascade.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16452648
Curator's Comment: Anisomycin is CNS active in animals. No human data available.
Originator
Sources: http://pubs.acs.org/doi/abs/10.1021/ja01644a076
Curator's Comment: # Pfizer
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0006412 |
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Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12402161 |
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Target ID: GO:0000165 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Screening for new compounds with antiherpes activity. | 1984 Oct |
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Protein synthesis inhibitors attenuate seizures induced in rats by lithium plus pilocarpine. | 1994 Sep |
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The phosphorylation of eukaryotic initiation factor eIF4E in response to phorbol esters, cell stresses, and cytokines is mediated by distinct MAP kinase pathways. | 1998 Apr 17 |
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Stress-induced immediate-early gene, egr-1, involves activation of p38/JNK1. | 1998 Jun 4 |
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Activation of JNK pathway and induction of apoptosis by manganese in PC12 cells. | 1998 Oct |
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Rapid nucleolytic degradation of the small cytoplasmic Y RNAs during apoptosis. | 1999 Aug 27 |
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The activation of c-Jun NH2-terminal kinase (JNK) by DNA-damaging agents serves to promote drug resistance via activating transcription factor 2 (ATF2)-dependent enhanced DNA repair. | 2003 Jun 6 |
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Immediate-early gene induction by the stresses anisomycin and arsenite in human osteosarcoma cells involves MAPK cascade signaling to Elk-1, CREB and SRF. | 2003 Mar 27 |
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Hypoxia-responsive growth factors upregulate periostin and osteopontin expression via distinct signaling pathways in rat pulmonary arterial smooth muscle cells. | 2004 Oct |
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Novel signaling stimulated by arsenite increases cholesterol metabolism through increases in unphosphorylated steroidogenic acute regulatory (StAR) protein. | 2005 Feb 28 |
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Arsenic trioxide inhibits nuclear receptor function via SEK1/JNK-mediated RXRalpha phosphorylation. | 2005 Oct |
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Phosphorylation of the retinoid x receptor at the omega loop, modulates the expression of retinoic-acid-target genes with a promoter context specificity. | 2005 Oct |
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A pharmacologically-based array to identify targets of cyclosporine A-induced toxicity in cultured renal proximal tubule cells. | 2012 Jan 15 |
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Targets and intracellular signaling mechanisms for deoxynivalenol-induced ribosomal RNA cleavage. | 2012 Jun |
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BET inhibition as a single or combined therapeutic approach in primary paediatric B-precursor acute lymphoblastic leukaemia. | 2013 Jul 19 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22004851
In order to make toxicological evaluation of Anisomycin, acute and four-week continuously intravenous toxicity studies were performed in mice. The calculated LD(50) for Anisomycin was 119.64 mg/kg. The mice were intravenously injected through mouse tail vein with a total dose of 5, 15, 30 and 60 mg/kg/mice of Anisomycin every other day for 4 weeks. Just in the high-dose mice, death of three mice happened and body weight of the mice was significantly decreased.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22684030
Treatment of U251 and U87 cells with anisomycin (0.01-8 μmol/L) inhibited the cell growth in time- and concentration-dependent manners (the IC(50) values at 48 h were 0.233±0.021 and 0.192±0.018 μmol/L, respectively). Anisomycin (4 μmol/L) caused 21.5%±2.2% and 25.3%±3.1% of apoptosis proportion, respectively, in U251 and U87 cells. In the two cell lines, anisomycin (4 μmol/L) activated p38 MAPK and JNK, and inactivated ERK1/2.
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C258
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ANISOMYCIN
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C95312
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SALT/SOLVATE (PARENT)
SUBSTANCE RECORD