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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
Structure of PUROMYCIN MONOHYDROCHLORIDE

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

HIDE SMILES / InChI

Description
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

Curator's Comment: Known to be CNS active in mouse. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Indication for central vagal endorphinergic control of heart rate in dogs.
1981 May 22
Effects of YM264, a novel PAF antagonist, on puromycin aminonucleoside-induced nephropathy in the rat.
1991 Apr 30
Superinduction of 2,3,7,8-tetrachlorodibenzo-p-dioxin-inducible expression of aldehyde dehydrogenase by the inhibition of protein synthesis.
1991 Oct 31
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Alterations in the distribution of plasma fibronectin and the ultrastructure of podocytes in the peripheral glomerular loops in nephrotic rats.
1998 Nov
Functional consequences of integrin-linked kinase activation in podocyte damage.
2005 Feb
Increased cyclosporine bioavailability induced by experimental nephrotic syndrome in rats.
2007 May
A new generation of pPRIG-based retroviral vectors.
2007 Nov 30
Influence of cellular ERalpha/ERbeta ratio on the ERalpha-agonist induced proliferation of human T47D breast cancer cells.
2008 Oct
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
Macromolecular synthesis inhibitors perturb glucocorticoid receptor trafficking.
2011 Sep
Cellular growth kinetics distinguish a cyclophilin inhibitor from an HSP90 inhibitor as a selective inhibitor of hepatitis C virus.
2012
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 Vivo Use Guide
Unknown
Route of Administration: Unknown
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 MONOHYDROCHLORIDE
Common Name English
ADENOSINE, 3'-((2-AMINO-3-(4-METHOXYPHENYL)-1-OXOPROPYL)AMINO)-3'-DEOXY-N,N-DIMETHYL-, MONOHYDROCHLORIDE, (S)-
Systematic Name English
Code System Code Type Description
FDA UNII
6512V828QH
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
PUBCHEM
23618032
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
CAS
3506-23-8
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY