Puromycin
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Identification
- Generic Name
- Puromycin
- DrugBank Accession Number
- DB08437
- Background
Puromycin is an antibiotic that prevents bacterial protein translation. It is utilized as a selective agent in laboratory cell cultures. Puromycin is toxic to both prokaryotic and eukaryotic cells, resulting in significant cell death at appropriate doses.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 471.5096
Monoisotopic: 471.223017073 - Chemical Formula
- C22H29N7O5
- Synonyms
- puromicina
- Puromycin
- External IDs
- 3123-L
- 3123L
- CL-13900
- P-638
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U60S ribosomal protein L10-like Not Available Humans U60S ribosomal protein L13a Not Available Humans U60S ribosomal protein L23 Not Available Humans U60S ribosomal protein L15 Not Available Humans U60S ribosomal protein L19 Not Available Humans U60S ribosomal protein L23a Not Available Humans UProbable ribosome biogenesis protein RLP24 Not Available Humans U60S ribosomal protein L26-like 1 Not Available Humans U60S ribosomal protein L8 Not Available Humans U60S ribosomal protein L37 Not Available Humans U60S ribosomal protein L3 Not Available Humans U60S ribosomal protein L11 Not Available Humans ULeucyl/phenylalanyl-tRNA--protein transferase Not Available Escherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Puromycin may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac The risk or severity of nephrotoxicity can be increased when Aceclofenac is combined with Puromycin. Acemetacin The risk or severity of nephrotoxicity can be increased when Puromycin is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Puromycin is combined with Acenocoumarol. Acetaminophen Puromycin may decrease the excretion rate of Acetaminophen which could result in a higher serum level. - Food Interactions
- Not Available
Categories
- Drug Categories
- Acids, Carbocyclic
- Agents that produce neuromuscular block (indirect)
- Aminoglycoside Antibacterials
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antimetabolites
- Antineoplastic Agents
- Antiparasitic Agents
- Antiprotozoals
- Carbohydrates
- Cinnamates
- Enzyme Inhibitors
- Glycosides
- Heterocyclic Compounds, Fused-Ring
- Nephrotoxic agents
- Noxae
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleosides
- Protein Synthesis Inhibitors
- Purine Nucleosides
- Purines
- Toxic Actions
- Trypanocidal Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. These are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Purine nucleosides
- Sub Class
- Purine 3'-deoxyribonucleosides
- Direct Parent
- Purine 3'-deoxyribonucleosides
- Alternative Parents
- Phenylalanine and derivatives / Alpha amino acid amides / 6-alkylaminopurines / Glycosylamines / Pentoses / Amphetamines and derivatives / Phenoxy compounds / Anisoles / Dialkylarylamines / Methoxybenzenes show 18 more
- Substituents
- 6-alkylaminopurine / 6-aminopurine / Alcohol / Alkyl aryl ether / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aminopyrimidine / Amphetamine or derivatives show 45 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- puromycins (CHEBI:17939)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 4A6ZS6Q2CL
- CAS number
- 53-79-2
- InChI Key
- RXWNCPJZOCPEPQ-NVWDDTSBSA-N
- InChI
- 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
- IUPAC Name
- (2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
- SMILES
- COC1=CC=C(C[C@H](N)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1
References
- General References
- Not Available
- External Links
- KEGG Compound
- C01610
- PubChem Compound
- 439530
- PubChem Substance
- 99444908
- ChemSpider
- 388623
- BindingDB
- 50277158
- ChEBI
- 17939
- ChEMBL
- CHEMBL469912
- ZINC
- ZINC000053147179
- PDBe Ligand
- PUY
- Wikipedia
- Puromycin
- PDB Entries
- 1q7y / 2dpt / 3q3d / 4tva / 5nc5 / 5yo1
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 168°C-182°C http://www.fermentek.co.il/puromycin.htm water solubility 50mg/ml http://www.fermentek.co.il/puromycin.htm - Predicted Properties
Property Value Source Water Solubility 1.01 mg/mL ALOGPS logP -0.1 ALOGPS logP -0.3 Chemaxon logS -2.7 ALOGPS pKa (Strongest Acidic) 12.35 Chemaxon pKa (Strongest Basic) 8.03 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 160.88 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 122.96 m3·mol-1 Chemaxon Polarizability 49.25 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9747 Blood Brain Barrier - 0.8691 Caco-2 permeable - 0.7728 P-glycoprotein substrate Substrate 0.737 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Non-inhibitor 0.9243 CYP450 2C9 substrate Non-substrate 0.8029 CYP450 2D6 substrate Non-substrate 0.8107 CYP450 3A4 substrate Substrate 0.7097 CYP450 1A2 substrate Non-inhibitor 0.9058 CYP450 2C9 inhibitor Non-inhibitor 0.9133 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9393 CYP450 3A4 inhibitor Non-inhibitor 0.724 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8922 Ames test Non AMES toxic 0.8607 Carcinogenicity Non-carcinogens 0.8681 Biodegradation Not ready biodegradable 0.9882 Rat acute toxicity 2.2651 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9903 hERG inhibition (predictor II) Non-inhibitor 0.5719
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 245.7454284 predictedDarkChem Lite v0.1.0 [M-H]- 202.08487 predictedDeepCCS 1.0 (2019) [M+H]+ 246.2764284 predictedDarkChem Lite v0.1.0 [M+H]+ 203.90974 predictedDeepCCS 1.0 (2019) [M+Na]+ 247.0384284 predictedDarkChem Lite v0.1.0 [M+Na]+ 209.51558 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
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1. Details60S ribosomal protein L10-like
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- May play a role in compensating for the inactivated X-linked gene during spermatogenesis.
- Gene Name
- RPL10L
- Uniprot ID
- Q96L21
- Uniprot Name
- 60S ribosomal protein L10-like
- Molecular Weight
- 24518.595 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
2. Details60S ribosomal protein L13a
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- Associated with ribosomes but is not required for canonical ribosome function and has extra-ribosomal functions. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex ...
- Gene Name
- RPL13A
- Uniprot ID
- P40429
- Uniprot Name
- 60S ribosomal protein L13a
- Molecular Weight
- 23577.11 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
3. Details60S ribosomal protein L23
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- Not Available
- Gene Name
- RPL23
- Uniprot ID
- P62829
- Uniprot Name
- 60S ribosomal protein L23
- Molecular Weight
- 14865.335 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
4. Details60S ribosomal protein L15
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- Not Available
- Gene Name
- RPL15
- Uniprot ID
- P61313
- Uniprot Name
- 60S ribosomal protein L15
- Molecular Weight
- 24145.945 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
5. Details60S ribosomal protein L19
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- Not Available
- Gene Name
- RPL19
- Uniprot ID
- P84098
- Uniprot Name
- 60S ribosomal protein L19
- Molecular Weight
- 23465.775 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
6. Details60S ribosomal protein L23a
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- This protein binds to a specific region on the 26S rRNA.
- Gene Name
- RPL23A
- Uniprot ID
- P62750
- Uniprot Name
- 60S ribosomal protein L23a
- Molecular Weight
- 17694.885 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- Involved in the biogenesis of the 60S ribosomal subunit. Ensures the docking of GTPBP4/NOG1 to pre-60S particles (By similarity).
- Gene Name
- RSL24D1
- Uniprot ID
- Q9UHA3
- Uniprot Name
- Probable ribosome biogenesis protein RLP24
- Molecular Weight
- 19621.02 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
8. Details60S ribosomal protein L26-like 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- Not Available
- Gene Name
- RPL26L1
- Uniprot ID
- Q9UNX3
- Uniprot Name
- 60S ribosomal protein L26-like 1
- Molecular Weight
- 17256.2 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
9. Details60S ribosomal protein L8
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- Not Available
- Gene Name
- RPL8
- Uniprot ID
- P62917
- Uniprot Name
- 60S ribosomal protein L8
- Molecular Weight
- 28024.52 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
10. Details60S ribosomal protein L37
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- Binds to the 23S rRNA.
- Gene Name
- RPL37
- Uniprot ID
- P61927
- Uniprot Name
- 60S ribosomal protein L37
- Molecular Weight
- 11077.81 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
11. Details60S ribosomal protein L3
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- The L3 protein is a component of the large subunit of cytoplasmic ribosomes.
- Gene Name
- RPL3
- Uniprot ID
- P39023
- Uniprot Name
- 60S ribosomal protein L3
- Molecular Weight
- 46108.72 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
12. Details60S ribosomal protein L11
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Structural constituent of ribosome
- Specific Function
- Binds to 5S ribosomal RNA (By similarity). Required for rRNA maturation and formation of the 60S ribosomal subunits. Promotes nucleolar location of PML (By similarity).
- Gene Name
- RPL11
- Uniprot ID
- P62913
- Uniprot Name
- 60S ribosomal protein L11
- Molecular Weight
- 20252.235 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Transferase activity, transferring amino-acyl groups
- Specific Function
- Functions in the N-end rule pathway of protein degradation where it conjugates Leu, Phe and, less efficiently, Met from aminoacyl-tRNAs to the N-termini of proteins containing an N-terminal arginin...
- Gene Name
- aat
- Uniprot ID
- P0A8P1
- Uniprot Name
- Leucyl/phenylalanyl-tRNA--protein transferase
- Molecular Weight
- 26618.275 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:31 / Updated at February 21, 2021 18:52