PUROMYCIN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H29N7O5.2ClH
Molecular Weight	544.431
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.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=MKSVFGKWZLUTTO-FZFAUISWSA-N

InChI=1S/C22H29N7O5.2ClH/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);2*1H/t14-,15+,16+,18+,22+;;/m0../s1

HIDE SMILES / InChI

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
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.	1973 Sep	4202339
Indication for central vagal endorphinergic control of heart rate in dogs.	1981 May 22	7018912
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
Alterations in the distribution of plasma fibronectin and the ultrastructure of podocytes in the peripheral glomerular loops in nephrotic rats.	1998 Nov	9849860
Nephrin redistribution on podocytes is a potential mechanism for proteinuria in patients with primary acquired nephrotic syndrome.	2001 May	11337370
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
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
Increased cyclosporine bioavailability induced by experimental nephrotic syndrome in rats.	2007 May	17632584
A function for a specific zinc metalloprotease of African trypanosomes.	2007 Oct 19	17953481
HPV16 E7-dependent transformation activates NHE1 through a PKA-RhoA-induced inhibition of p38alpha.	2008	18953413
ATP-binding cassette transporters as pitfalls in selection of transgenic cells.	2010 Apr 15	20018165
The zinc-fingers of KREPA3 are essential for the complete editing of mitochondrial mRNAs in Trypanosoma brucei.	2010 Jan 27	20111718
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents.	2010 Jul	20116850
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
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
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.

Name

Type

Language

PUROMYCIN HYDROCHLORIDE

Official Name

English

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

Common Name

English

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

Systematic Name

English

CL-16536

Code

English

CL-13900 DIHYDROCHLORIDE

Code

English

PUROMYCIN DIHYDROCHLORIDE [MI]

Common Name

English

PUROMYCIN HYDROCHLORIDE [USAN]

Common Name

English

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

Systematic Name

English

PUROMYCIN DIHYDROCHLORIDE

Common Name

English

6-DIMETHYLAMINO-9-(3'-(P-METHOXY-L-PHENYLALANYLAMINO)-3'-DEOXY-.BETA.-D-RIBOFURANOSYL)PURINE DIHYDROCHLORIDE

Systematic Name

English

CL 16,536

Code

English

NSC-3055

Code

English

P-638 DIHYDROCHLORIDE

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C259