PUROMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H29N7O5
Molecular Weight	471.5096
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C[C@H](N)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N3C=NC4=C3N=CN=C4N(C)C)C=C1

InChI

InChIKey=RXWNCPJZOCPEPQ-NVWDDTSBSA-N

InChI=1S/C22H29N7O5/c1-28(2)19-17-20(25-10-24-19)29(11-26-17)22-18(31)16(15(9-30)34-22)27-21(32)14(23)8-12-4-6-13(33-3)7-5-12/h4-7,10-11,14-16,18,22,30-31H,8-9,23H2,1-3H3,(H,27,32)/t14-,15+,16+,18+,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H29N7O5
Molecular Weight	471.5096
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB08437https://www.drugbank.ca/drugs/DB08437 | https://www.ncbi.nlm.nih.gov/pubmed/4949424 | https://www.ncbi.nlm.nih.gov/pubmed/18313307
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68011691 | https://www.ncbi.nlm.nih.gov/pubmed/4590173

Puromycin dihydrochloride belongs to the aminonucleoside family of antibiotics and is isolated from Streptomyces alboniger. Since the partial structure of this antibiotic showed it to be a purine derivative, puromycin was assigned as its generic name. Puromycin is a broad spectrum antibiotic and antibacterial agent. It is active against Gram-positive microorganisms, less active against acid-fast bacilli, and weakly active against Gram-negative microorganisms. It acts very quickly and can kill 99% of the cells within 2 days. It also exhibits antitumor activity in studies on brain tumor cells. Puromycin is a protein synthesis inhibitor that causes premature chain termination by acting as an analog of the 3’-terminal end of aminoacyl-tRNA. It has been used to study transcriptional regulatory mechanisms that control the sequential and coordinate expression of genes during cell differentiation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4949424	Inhibitor 8297
translation 13 Target ID: GO:0006412 Sources: https://www.drugbank.ca/drugs/DB08437	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578
Unknown 2578

PubMed

Title	Date	PubMed
Ribosome structure: localization of N6,N6-dimethyladenosine by electron microscopy of a ribosome-antibody complex.	1977 Apr	323854
Analogs of 3'-amino-3'-deoxyadenosine inhibit HIV-1 replication.	1989 Dec	2611044
Synergistic activation of human LDL receptor expression by SCAP ligand and cytokine oncostatin M.	2003 Jan 1	12524230
Superinduction of CYP1A1 in MCF10A cultures by cycloheximide, anisomycin, and puromycin: a process independent of effects on protein translation and unrelated to suppression of aryl hydrocarbon receptor proteolysis by the proteasome.	2004 Oct	15385644
A function for a specific zinc metalloprotease of African trypanosomes.	2007 Oct 19	17953481
Distinct roles for basal and induced COX-2 in podocyte injury.	2009 Sep	19643929
Oxygen consumption can regulate the growth of tumors, a new perspective on the Warburg effect.	2009 Sep 15	19753307
ATP-binding cassette transporters as pitfalls in selection of transgenic cells.	2010 Apr 15	20018165
Radiotherapy suppresses angiogenesis in mice through TGF-betaRI/ALK5-dependent inhibition of endothelial cell sprouting.	2010 Jun 11	20552031
A predictive computational model of the kinetic mechanism of stimulus-induced transducer methylation and feedback regulation through CheY in archaeal phototaxis and chemotaxis.	2010 Mar 18	20298562
A novel envelope mediated post entry restriction of murine leukaemia virus in human cells is Ref1/TRIM5α independent.	2010 Oct 7	20929586
DEF6, a novel substrate for the Tec kinase ITK, contains a glutamine-rich aggregation-prone region and forms cytoplasmic granules that co-localize with P-bodies.	2012 Sep 7	22829599

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Mouse J774A.1 macrophages, vascular smooth muscle cells (SMCs) isolated from rabbit aorta, and murine C2C12 myoblasts were treated in vitro with the protein synthesis inhibitor puromycin (24 h with different concentrations of puromycin (0–20 uM) or 35 uM puromycin for 0–48 h). Cell death was initiated in all cell types in a concentration- and time-dependent manner. Macrophage and SMCs death induced by puromycin was characterized by cleavage of procaspase-3 and internucleosomal DNA fragmentation, typical of apoptosis.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:07:33 UTC 2023` Edited by `admin` on `Fri Dec 15 15:07:33 UTC 2023`
Record UNII	4A6ZS6Q2CL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PUROMYCIN

Official Name

English

puromycin [INN]

Common Name

English

Puromycin [WHO-DD]

Common Name

English

PUROMYCIN [USAN]

Common Name

English

GNF-PF-2016

Code

English

3123L

Code

English

PUROMYCIN [MI]

Common Name

English

ADENOSINE, 3'-((2-AMINO-3-(4-METHOXYPHENYL)-1-OXOPROPYL)AMINO)-3'-DEOXY-N,N-DIMETHYL-, (S)-

Systematic Name

English

3'-(L-.ALPHA.-AMINO-P-METHOXYHYDROCINNAMAMIDO)-3'-DEOXY-N,N-DIMETHYLADENOSINE

Common Name

English

CL-13900

Code

English

CL 13,900

Code

English

3123-L

Code

English

P-638

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C259