Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H29N7O5.ClH |
| Molecular Weight | 507.971 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
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=MXJUOYXSYWPMAR-IHFNEQFUSA-N
InChI=1S/C22H29N7O5.ClH/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);1H/t14-,15+,16+,18+,22+;/m0./s1
| 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 |
| 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 |
DescriptionSources: 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/18313307Curator'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
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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| TCDD and omeprazole prime platelets through the aryl hydrocarbon receptor (AhR) non-genomic pathway. | 2015-05-19 |
|
| Identification and evaluation of novel acetolactate synthase inhibitors as antifungal agents. | 2013-05 |
|
| 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. | 2012-09-07 |
|
| Cellular growth kinetics distinguish a cyclophilin inhibitor from an HSP90 inhibitor as a selective inhibitor of hepatitis C virus. | 2012 |
|
| Macromolecular synthesis inhibitors perturb glucocorticoid receptor trafficking. | 2011-09 |
|
| Melatonin promotes puromycin-induced apoptosis with activation of caspase-3 and 5'-adenosine monophosphate-activated kinase-alpha in human leukemia HL-60 cells. | 2011-05 |
|
| Dentin sialophosphoprotein (DSPP) gene-silencing inhibits key tumorigenic activities in human oral cancer cell line, OSC2. | 2010-11-12 |
|
| A novel envelope mediated post entry restriction of murine leukaemia virus in human cells is Ref1/TRIM5α independent. | 2010-10-07 |
|
| Rhabdastrellic acid-A induced autophagy-associated cell death through blocking Akt pathway in human cancer cells. | 2010-08-17 |
|
| Mechanisms of IL-12 synthesis by human dendritic cells treated with the chemical sensitizer NiSO4. | 2010-07-01 |
|
| Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. | 2010-07 |
|
| Radiotherapy suppresses angiogenesis in mice through TGF-betaRI/ALK5-dependent inhibition of endothelial cell sprouting. | 2010-06-11 |
|
| miR-22 forms a regulatory loop in PTEN/AKT pathway and modulates signaling kinetics. | 2010-05-27 |
|
| ATP-binding cassette transporters as pitfalls in selection of transgenic cells. | 2010-04-15 |
|
| A predictive computational model of the kinetic mechanism of stimulus-induced transducer methylation and feedback regulation through CheY in archaeal phototaxis and chemotaxis. | 2010-03-18 |
|
| Multi-gene targeted antiangiogenic therapies for experimental corneal neovascularization. | 2010-02-27 |
|
| The zinc-fingers of KREPA3 are essential for the complete editing of mitochondrial mRNAs in Trypanosoma brucei. | 2010-01-27 |
|
| Transplantation of human neural stem cells transduced with Olig2 transcription factor improves locomotor recovery and enhances myelination in the white matter of rat spinal cord following contusive injury. | 2009-09-22 |
|
| Caveolae contribute to the apoptosis resistance induced by the alpha(1A)-adrenoceptor in androgen-independent prostate cancer cells. | 2009-09-18 |
|
| Oxygen consumption can regulate the growth of tumors, a new perspective on the Warburg effect. | 2009-09-15 |
|
| Distinct roles for basal and induced COX-2 in podocyte injury. | 2009-09 |
|
| Functional analysis of a dominant negative mutation of interferon regulatory factor 5. | 2009 |
|
| Influence of cellular ERalpha/ERbeta ratio on the ERalpha-agonist induced proliferation of human T47D breast cancer cells. | 2008-10 |
|
| [Establishment of BHK-21 cell lines stably expressing FMDV 3Dpol gene by retroviral-mediated gene transfer technique]. | 2008-08 |
|
| Melatonin antagonizes the intrinsic pathway of apoptosis via mitochondrial targeting of Bcl-2. | 2008-04 |
|
| The changing management of acute bronchitis in Britain, 1940-1970: the impact of antibiotics. | 2008-01 |
|
| Thyroid cancer imaging in vivo by targeting the anti-apoptotic molecule galectin-3. | 2008 |
|
| HPV16 E7-dependent transformation activates NHE1 through a PKA-RhoA-induced inhibition of p38alpha. | 2008 |
|
| A new generation of pPRIG-based retroviral vectors. | 2007-11-30 |
|
| A function for a specific zinc metalloprotease of African trypanosomes. | 2007-10-19 |
|
| Biological characteristics of Chinese hamster ovary cells transfected with bovine Prnp. | 2007-06 |
|
| Increased cyclosporine bioavailability induced by experimental nephrotic syndrome in rats. | 2007-05 |
|
| RNA-editing-mediated exon evolution. | 2007 |
|
| Oligonucleotide-based microarray analysis of retinoic acid target genes in the protochordate, Ciona intestinalis. | 2005-08 |
|
| Functional consequences of integrin-linked kinase activation in podocyte damage. | 2005-02 |
|
| 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. | 2004-10 |
|
| No evidence for involvement of SDHD in neuroblastoma pathogenesis. | 2004-08-24 |
|
| M-CSF, TNFalpha and RANK ligand promote osteoclast survival by signaling through mTOR/S6 kinase. | 2003-10 |
|
| Synergistic activation of human LDL receptor expression by SCAP ligand and cytokine oncostatin M. | 2003-01-01 |
|
| [Effects of antisense bcl-2 or survivin on the growth of human neuroblastoma cell line SK-N-MC]. | 2002-11-25 |
|
| Alterations in the distribution of plasma fibronectin and the ultrastructure of podocytes in the peripheral glomerular loops in nephrotic rats. | 1998-11 |
|
| Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996-12 |
|
| Superinduction of 2,3,7,8-tetrachlorodibenzo-p-dioxin-inducible expression of aldehyde dehydrogenase by the inhibition of protein synthesis. | 1991-10-31 |
|
| Effects of YM264, a novel PAF antagonist, on puromycin aminonucleoside-induced nephropathy in the rat. | 1991-04-30 |
|
| Analogs of 3'-amino-3'-deoxyadenosine inhibit HIV-1 replication. | 1989-12 |
|
| Drug-associated glomerulopathies. | 1986 |
|
| Superinduction of cytochrome P1-450 gene transcription by inhibition of protein synthesis in wild type and variant mouse hepatoma cells. | 1985-05-10 |
|
| Indication for central vagal endorphinergic control of heart rate in dogs. | 1981-05-22 |
|
| Ribosome structure: localization of N6,N6-dimethyladenosine by electron microscopy of a ribosome-antibody complex. | 1977-04 |
|
| Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains. | 1973-09 |
Patents
Sample Use Guides
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
Edited
Mon Mar 31 17:45:04 GMT 2025
by
admin
on
Mon Mar 31 17:45:04 GMT 2025
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| Record UNII |
6512V828QH
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| Record Status |
Validated (UNII)
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| Record Version |
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23618032
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PARENT -> SALT/SOLVATE |
