ANISOMYCIN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H19NO4.ClH
Molecular Weight	301.766
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.COC1=CC=C(C[C@H]2NC[C@H](O)[C@H]2OC(C)=O)C=C1

InChI

InChIKey=GLVJGDLQHBCCEP-UDYGKFQRSA-N

InChI=1S/C14H19NO4.ClH/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;1H/t12-,13+,14+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C14H19NO4
Molecular Weight	265.305
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Quinone reductase inhibitors block SAPK/JNK and NFkappaB pathways and potentiate apoptosis.	1999 Oct 29	10531305
Vitamin D3 up-regulated protein 1 mediates oxidative stress via suppressing the thioredoxin function.	2000 Jun 15	10843682
Deficiency of the stress kinase p38alpha results in embryonic lethality: characterization of the kinase dependence of stress responses of enzyme-deficient embryonic stem cells.	2000 Mar 6	10704466
Transient activation of Jun N-terminal kinases and protection from apoptosis by the insulin-like growth factor I receptor can be suppressed by dicumarol.	2001 Jun 1	11278392
Selective activation of Src family kinases and JNK by low levels of chromium(VI).	2003 Aug 1	12902192
Cocaine treatment increases expression of a 40 kDa catecholamine-regulated protein in discrete brain regions.	2003 Jan	12422371
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
Hypoxia-responsive growth factors upregulate periostin and osteopontin expression via distinct signaling pathways in rat pulmonary arterial smooth muscle cells.	2004 Oct	15121739
Ribotoxic stress response to the trichothecene deoxynivalenol in the macrophage involves the SRC family kinase Hck.	2005 Jun	15772366
Complete inhibition of anisomycin and UV radiation but not cytokine induced JNK and p38 activation by an aryl-substituted dihydropyrrolopyrazole quinoline and mixed lineage kinase 7 small interfering RNA.	2005 May 13	15737997
Inhibition of ERK pathway or protein synthesis during reexposure to drugs of abuse erases previously learned place preference.	2006 Feb 21	16473939
Basolateral amygdala involvement in memory reconsolidation processes that facilitate drug context-induced cocaine seeking.	2009 Sep	19712099
Design and characterization of a potent and selective dual ATP- and substrate-competitive subnanomolar bidentate c-Jun N-terminal kinase (JNK) inhibitor.	2011 Sep 22	21815634
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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:39:25 GMT 2023` Edited by `admin` on `Fri Dec 15 18:39:25 GMT 2023`
Record UNII	X7UY1KIB0A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANISOMYCIN HYDROCHLORIDE

Common Name

English

ANISOMYCIN HCL

Common Name

English

3,4-PYRROLIDINEDIOL, 2-(P-METHOXYBENZYL)-, 3-ACETATE, HYDROCHLORIDE

Common Name

English

3,4-PYRROLIDINEDIOL, 2-((4-METHOXYPHENYL)METHYL)-, 3-ACETATE, HYDROCHLORIDE, (2R-(2.ALPHA.,3.ALPHA.,4.BETA.))-

Common Name

English

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

Common Name

English

ANISOMYCIN HYDROCHLORIDE [MI]

Common Name

English

ANISOMYCIN, HYDROCHLORIDE

Common Name

English

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

Common Name

English

3,4-PYRROLIDINEDIOL, 2-((4-METHOXYPHENYL)METHYL)-, 3-ACETATE, HYDROCHLORIDE (1:1), (2R,3S,4S)-

Common Name

English

Code System Code Type Description

FDA UNII

X7UY1KIB0A