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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 of PUROMYCIN

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

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
[Chemotherapy of experimental Chagas' disease. XII. Effects of puromycin alone and with primaquine].
1953 Oct-Dec
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.
1973 Sep
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
Oxygen consumption can regulate the growth of tumors, a new perspective on the Warburg effect.
2009 Sep 15
The zinc-fingers of KREPA3 are essential for the complete editing of mitochondrial mRNAs in Trypanosoma brucei.
2010 Jan 27
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents.
2010 Jul
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
Identification and evaluation of novel acetolactate synthase inhibitors as antifungal agents.
2013 May
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
INN   MI   USAN  
INN   USAN  
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
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
Code System Code Type Description
MESH
D011691
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY
CAS
53-79-2
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID8036788
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY
INN
1962
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY
DRUG BANK
DB08437
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY
SMS_ID
100000080845
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
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ChEMBL
CHEMBL469912
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY
CHEBI
60255
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY
NCI_THESAURUS
C787
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY
EVMPD
SUB10161MIG
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY
FDA UNII
4A6ZS6Q2CL
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
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PUBCHEM
439530
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY
MERCK INDEX
m9324
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
PUROMYCIN
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY
CHEBI
17939
Created by admin on Fri Dec 15 15:07:33 GMT 2023 , Edited by admin on Fri Dec 15 15:07:33 GMT 2023
PRIMARY