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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

Molecular Formula C22H29N7O5
Molecular Weight 471.5096
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

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.
Substance Class Chemical
Record UNII
4A6ZS6Q2CL
Record Status Validated (UNII)
Record Version