Puromycin

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
TargetActionsOrganism
U60S ribosomal protein L10-likeNot AvailableHumans
U60S ribosomal protein L13aNot AvailableHumans
U60S ribosomal protein L23Not AvailableHumans
U60S ribosomal protein L15Not AvailableHumans
U60S ribosomal protein L19Not AvailableHumans
U60S ribosomal protein L23aNot AvailableHumans
UProbable ribosome biogenesis protein RLP24Not AvailableHumans
U60S ribosomal protein L26-like 1Not AvailableHumans
U60S ribosomal protein L8Not AvailableHumans
U60S ribosomal protein L37Not AvailableHumans
U60S ribosomal protein L3Not AvailableHumans
U60S ribosomal protein L11Not AvailableHumans
ULeucyl/phenylalanyl-tRNA--protein transferaseNot AvailableEscherichia 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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbacavirPuromycin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Aceclofenac is combined with Puromycin.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Puromycin is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Puromycin is combined with Acenocoumarol.
AcetaminophenPuromycin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Food Interactions
Not Available

Categories

Drug Categories
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
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
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)168°C-182°Chttp://www.fermentek.co.il/puromycin.htm
water solubility50mg/mlhttp://www.fermentek.co.il/puromycin.htm
Predicted Properties
PropertyValueSource
Water Solubility1.01 mg/mLALOGPS
logP-0.1ALOGPS
logP-0.3Chemaxon
logS-2.7ALOGPS
pKa (Strongest Acidic)12.35Chemaxon
pKa (Strongest Basic)8.03Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area160.88 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity122.96 m3·mol-1Chemaxon
Polarizability49.25 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9747
Blood Brain Barrier-0.8691
Caco-2 permeable-0.7728
P-glycoprotein substrateSubstrate0.737
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.9243
CYP450 2C9 substrateNon-substrate0.8029
CYP450 2D6 substrateNon-substrate0.8107
CYP450 3A4 substrateSubstrate0.7097
CYP450 1A2 substrateNon-inhibitor0.9058
CYP450 2C9 inhibitorNon-inhibitor0.9133
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9393
CYP450 3A4 inhibitorNon-inhibitor0.724
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8922
Ames testNon AMES toxic0.8607
CarcinogenicityNon-carcinogens0.8681
BiodegradationNot ready biodegradable0.9882
Rat acute toxicity2.2651 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9903
hERG inhibition (predictor II)Non-inhibitor0.5719
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0000900000-f82e7526c7ebd78049d9
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03k9-0900500000-0d48aed0c9497b5ab8f3
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-af8be24075f803a58153
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-571b6483dc540c02d098
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-08775f201fb11e558b53
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0000900000-6133e2c60106f3437756
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05fr-0005900000-a760a4943250cd5405b9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0809000000-eb619283ee6c689551e3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0w29-0900000000-ca39c6d95b7bd8fba81b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-253fadebaa39d03e1cd1
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0a4i-0219000000-6595a051c26ce2ee007b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0601900000-8553e218a811558e0d71
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0020900000-8a1688b2e6e07c2b0159
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0089-0921400000-93dc4e129d1191436eb7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ot-0932300000-c139db39285b050383bf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00fr-0910200000-8e3f5a753337c3d8a39d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900100000-10b3d0a67cbaba56dd10
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-245.7454284
predicted
DarkChem Lite v0.1.0
[M-H]-202.08487
predicted
DeepCCS 1.0 (2019)
[M+H]+246.2764284
predicted
DarkChem Lite v0.1.0
[M+H]+203.90974
predicted
DeepCCS 1.0 (2019)
[M+Na]+247.0384284
predicted
DarkChem Lite v0.1.0
[M+Na]+209.51558
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
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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
  1. 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
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
  1. 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
Not Available
Gene Name
RPL23
Uniprot ID
P62829
Uniprot Name
60S ribosomal protein L23
Molecular Weight
14865.335 Da
References
  1. 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
Not Available
Gene Name
RPL15
Uniprot ID
P61313
Uniprot Name
60S ribosomal protein L15
Molecular Weight
24145.945 Da
References
  1. 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
Not Available
Gene Name
RPL19
Uniprot ID
P84098
Uniprot Name
60S ribosomal protein L19
Molecular Weight
23465.775 Da
References
  1. 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
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
  1. 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
  1. 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
Not Available
Gene Name
RPL26L1
Uniprot ID
Q9UNX3
Uniprot Name
60S ribosomal protein L26-like 1
Molecular Weight
17256.2 Da
References
  1. 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
Not Available
Gene Name
RPL8
Uniprot ID
P62917
Uniprot Name
60S ribosomal protein L8
Molecular Weight
28024.52 Da
References
  1. 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
Binds to the 23S rRNA.
Gene Name
RPL37
Uniprot ID
P61927
Uniprot Name
60S ribosomal protein L37
Molecular Weight
11077.81 Da
References
  1. 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
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
  1. 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
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
  1. 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
  1. 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