ANISOMYCIN

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6027796 | https://www.ncbi.nlm.nih.gov/pubmed/16452648

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
translation 13 Target ID: GO:0006412 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6027796 \| https://www.ncbi.nlm.nih.gov/pubmed/4601392	Inhibitor 8297
apoptotic process 48 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12402161	Activator 1430
MAPK cascade 4 Target ID: GO:0000165 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19286921 \| https://www.ncbi.nlm.nih.gov/pubmed/17202844 \| https://www.ncbi.nlm.nih.gov/pubmed/16581040	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27404124 https://www.ncbi.nlm.nih.gov/pubmed/27879498 https://www.ncbi.nlm.nih.gov/pubmed/26783004	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Protein synthesis inhibitors attenuate seizures induced in rats by lithium plus pilocarpine.	1994 Sep	7925839
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	9545260
Stress-induced immediate-early gene, egr-1, involves activation of p38/JNK1.	1998 Jun 4	9671412
Activation of JNK pathway and induction of apoptosis by manganese in PC12 cells.	1998 Oct	9751194
Rapid nucleolytic degradation of the small cytoplasmic Y RNAs during apoptosis.	1999 Aug 27	10455152
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	12663670
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	12660819
Hypoxia-responsive growth factors upregulate periostin and osteopontin expression via distinct signaling pathways in rat pulmonary arterial smooth muscle cells.	2004 Oct	15121739
Novel signaling stimulated by arsenite increases cholesterol metabolism through increases in unphosphorylated steroidogenic acute regulatory (StAR) protein.	2005 Feb 28	15713539
Arsenic trioxide inhibits nuclear receptor function via SEK1/JNK-mediated RXRalpha phosphorylation.	2005 Oct	16184197
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	16038797
A pharmacologically-based array to identify targets of cyclosporine A-induced toxicity in cultured renal proximal tubule cells.	2012 Jan 15	22155090
Targets and intracellular signaling mechanisms for deoxynivalenol-induced ribosomal RNA cleavage.	2012 Jun	22491426
BET inhibition as a single or combined therapeutic approach in primary paediatric B-precursor acute lymphoblastic leukaemia.	2013 Jul 19	23872705

Patents

Sample Use Guides

In Vivo Use Guide

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

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.

Name

Type

Language

ANISOMYCIN

Common Name

English

FLAGECIDIN

Common Name

English

3,4-PYRROLIDINEDIOL, 2-((4-METHOXYPHENYL)METHYL)-, 3-ACETATE, (2R,3S,4S)-

Common Name

English

NSC-76712

Code

English

ANISOMYCIN, (-)-

Common Name

English

(2R,3S,4S)-2-(P-METHOXYPHENYLMETHYL)-3-ACETOXY-4-HYDROXYPYRROLIDINE

Common Name

English

(2R,3S,4S)-2-((4-METHOXYPHENYL)METHYL)-3,4-PYRROLIDINEDIOL 3-ACETATE

Common Name

English

ANISOMYCIN [MI]

Common Name

English

(2R,3S,4S)-2-(P-METHOXYBENZYL)-3,4-PYRROLIDINEDIOL 3-ACETATE

Common Name

English

(-)-ANISOMYCIN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258