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
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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13945541 | https://www.ncbi.nlm.nih.gov/pubmed/5638887
Curator's Comment: Known to be CNS active in mouse. Human data not available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4949424 |
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Target ID: GO:0006412 Sources: https://www.drugbank.ca/drugs/DB08437 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Indication for central vagal endorphinergic control of heart rate in dogs. | 1981 May 22 |
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Effects of YM264, a novel PAF antagonist, on puromycin aminonucleoside-induced nephropathy in the rat. | 1991 Apr 30 |
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Superinduction of 2,3,7,8-tetrachlorodibenzo-p-dioxin-inducible expression of aldehyde dehydrogenase by the inhibition of protein synthesis. | 1991 Oct 31 |
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Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996 Dec |
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Alterations in the distribution of plasma fibronectin and the ultrastructure of podocytes in the peripheral glomerular loops in nephrotic rats. | 1998 Nov |
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Functional consequences of integrin-linked kinase activation in podocyte damage. | 2005 Feb |
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Increased cyclosporine bioavailability induced by experimental nephrotic syndrome in rats. | 2007 May |
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A new generation of pPRIG-based retroviral vectors. | 2007 Nov 30 |
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Influence of cellular ERalpha/ERbeta ratio on the ERalpha-agonist induced proliferation of human T47D breast cancer cells. | 2008 Oct |
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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 |
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Macromolecular synthesis inhibitors perturb glucocorticoid receptor trafficking. | 2011 Sep |
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Cellular growth kinetics distinguish a cyclophilin inhibitor from an HSP90 inhibitor as a selective inhibitor of hepatitis C virus. | 2012 |
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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 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18322149
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.
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23618032
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3506-23-8
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD