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
Superinduction of cytochrome P1-450 gene transcription by inhibition of protein synthesis in wild type and variant mouse hepatoma cells.	1985 May 10	2985607
Drug-associated glomerulopathies.	1986	2940667
Analogs of 3'-amino-3'-deoxyadenosine inhibit HIV-1 replication.	1989 Dec	2611044
Superinduction of 2,3,7,8-tetrachlorodibenzo-p-dioxin-inducible expression of aldehyde dehydrogenase by the inhibition of protein synthesis.	1991 Oct 31	1953764
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996 Dec	9039272
Induction of heme oxygenase-1 by phenylarsine oxide. Studies in cultured primary liver cells.	2001 Oct	11768235
Induction and superinduction of 2,3,7,8-tetrachlorodibenzo-rho-dioxin-inducible poly(ADP-ribose) polymerase: role of the aryl hydrocarbon receptor/aryl hydrocarbon receptor nuclear translocator transcription activation domains and a labile transcription repressor.	2002 Aug 15	12147270
[Effects of antisense bcl-2 or survivin on the growth of human neuroblastoma cell line SK-N-MC].	2002 Nov 25	12609062
Synergistic activation of human LDL receptor expression by SCAP ligand and cytokine oncostatin M.	2003 Jan 1	12524230
M-CSF, TNFalpha and RANK ligand promote osteoclast survival by signaling through mTOR/S6 kinase.	2003 Oct	14502240
No evidence for involvement of SDHD in neuroblastoma pathogenesis.	2004 Aug 24	15331017
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
Oligonucleotide-based microarray analysis of retinoic acid target genes in the protochordate, Ciona intestinalis.	2005 Aug	15977162
Functional consequences of integrin-linked kinase activation in podocyte damage.	2005 Feb	15673299
RNA-editing-mediated exon evolution.	2007	17326827
Biological characteristics of Chinese hamster ovary cells transfected with bovine Prnp.	2007 Jun	17519565
Increased cyclosporine bioavailability induced by experimental nephrotic syndrome in rats.	2007 May	17632584
A new generation of pPRIG-based retroviral vectors.	2007 Nov 30	18053131
A function for a specific zinc metalloprotease of African trypanosomes.	2007 Oct 19	17953481
Thyroid cancer imaging in vivo by targeting the anti-apoptotic molecule galectin-3.	2008	19020658
HPV16 E7-dependent transformation activates NHE1 through a PKA-RhoA-induced inhibition of p38alpha.	2008	18953413
Melatonin antagonizes the intrinsic pathway of apoptosis via mitochondrial targeting of Bcl-2.	2008 Apr	18339127
[Establishment of BHK-21 cell lines stably expressing FMDV 3Dpol gene by retroviral-mediated gene transfer technique].	2008 Aug	18972644
The changing management of acute bronchitis in Britain, 1940-1970: the impact of antibiotics.	2008 Jan	18180811
Influence of cellular ERalpha/ERbeta ratio on the ERalpha-agonist induced proliferation of human T47D breast cancer cells.	2008 Oct	18644836
Functional analysis of a dominant negative mutation of interferon regulatory factor 5.	2009	19430534
Mechanisms of IL-12 synthesis by human dendritic cells treated with the chemical sensitizer NiSO4.	2010 Jul 1	20525893
Dentin sialophosphoprotein (DSPP) gene-silencing inhibits key tumorigenic activities in human oral cancer cell line, OSC2.	2010 Nov 12	21103065
A novel envelope mediated post entry restriction of murine leukaemia virus in human cells is Ref1/TRIM5α independent.	2010 Oct 7	20929586
Macromolecular synthesis inhibitors perturb glucocorticoid receptor trafficking.	2011 Sep	21569845
Identification and evaluation of novel acetolactate synthase inhibitors as antifungal agents.	2013 May	23478965
TCDD and omeprazole prime platelets through the aryl hydrocarbon receptor (AhR) non-genomic pathway.	2015 May 19	25797602

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 GMT 2023` Edited by `admin` on `Fri Dec 15 15:07:33 GMT 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