Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Geneticin
- DrugBank Accession Number
- DB04263
- Background
Geneticin (also known as G418) is an aminoglycoside antibiotic similar in structure to gentamicin B1, produced by Micromonospora rhodorangea. Geneticin blocks polypeptide synthesis by inhibiting the elongation step in both prokaryotic and eukaryotic cells and is commonly used in laboratory research to select genetically engineered cells. Resistance to Geneticin is conferred by the neo gene from Tn5 encoding an aminoglycoside 3‘-phosphotransferase, APH 3‘ II.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Geneticin (DB04263)
- Weight
- Average: 496.5524
Monoisotopic: 496.27444352 - Chemical Formula
- C20H40N4O10
- Synonyms
- Not Available
- External IDs
- Antibiotic G 418
- Antibiotic G-418
- G-418
- G418
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AOrnithine decarboxylase inhibitorHumans - 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
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Geneticin 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 Geneticin is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Geneticin is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Geneticin is combined with Acenocoumarol. Acetaminophen Geneticin 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 aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Aminocyclitol glycosides
- Alternative Parents
- 2-deoxystreptamine aminoglycosides / O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Monosaccharides / Tertiary alcohols / 1,2-aminoalcohols / Oxacyclic compounds show 5 more
- Substituents
- 1,2-aminoalcohol / 2-deoxystreptamine aminoglycoside / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino cyclitol glycoside / Aminocyclitol or derivatives / Cyclic alcohol / Cyclitol or derivatives show 18 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- A08F5XTI6G
- CAS number
- 49863-47-0
- InChI Key
- BRZYSWJRSDMWLG-DJWUNRQOSA-N
- InChI
- InChI=1S/C20H40N4O10/c1-6(25)14-11(27)10(26)9(23)18(32-14)33-15-7(21)4-8(22)16(12(15)28)34-19-13(29)17(24-3)20(2,30)5-31-19/h6-19,24-30H,4-5,21-23H2,1-3H3/t6-,7+,8-,9-,10-,11+,12+,13-,14-,15-,16+,17-,18-,19-,20+/m1/s1
- IUPAC Name
- (2R,3S,4R,5R,6S)-5-amino-6-{[(1R,2S,3S,4R,6S)-4,6-diamino-3-{[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-2-[(1R)-1-hydroxyethyl]oxane-3,4-diol
- SMILES
- [H][C@]1(O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O[C@]([H])([C@@H](C)O)[C@@H](O)[C@H](O)[C@H]1N
References
- General References
- Not Available
- External Links
- KEGG Compound
- C17703
- PubChem Compound
- 123865
- PubChem Substance
- 46505367
- ChemSpider
- 110402
- ChEMBL
- CHEMBL215226
- ZINC
- ZINC000043543817
- PDBe Ligand
- GET
- Wikipedia
- G418
- PDB Entries
- 1mwl / 1njj / 3td1 / 4k32 / 4p3s / 4u4o / 5c4k / 5ndg / 5u18 / 5xz1 … show 4 more
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 58.3 mg/mL ALOGPS logP -2.4 ALOGPS logP -5.3 Chemaxon logS -0.93 ALOGPS pKa (Strongest Acidic) 12.42 Chemaxon pKa (Strongest Basic) 9.6 Chemaxon Physiological Charge 4 Chemaxon Hydrogen Acceptor Count 14 Chemaxon Hydrogen Donor Count 10 Chemaxon Polar Surface Area 248.39 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 114 m3·mol-1 Chemaxon Polarizability 50.29 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9308 Blood Brain Barrier - 0.9911 Caco-2 permeable - 0.7061 P-glycoprotein substrate Substrate 0.6041 P-glycoprotein inhibitor I Non-inhibitor 0.6588 P-glycoprotein inhibitor II Non-inhibitor 0.9628 Renal organic cation transporter Non-inhibitor 0.9159 CYP450 2C9 substrate Non-substrate 0.8212 CYP450 2D6 substrate Non-substrate 0.8552 CYP450 3A4 substrate Substrate 0.5694 CYP450 1A2 substrate Non-inhibitor 0.9021 CYP450 2C9 inhibitor Non-inhibitor 0.9028 CYP450 2D6 inhibitor Non-inhibitor 0.929 CYP450 2C19 inhibitor Non-inhibitor 0.9209 CYP450 3A4 inhibitor Non-inhibitor 0.9578 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9114 Ames test Non AMES toxic 0.6652 Carcinogenicity Non-carcinogens 0.9575 Biodegradation Not ready biodegradable 0.9789 Rat acute toxicity 1.9026 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9973 hERG inhibition (predictor II) Non-inhibitor 0.9179
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0103900000-5e197a80c5b930893366 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-054k-0502900000-9938bb967d379202a651 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0905100000-1ba19bfbbfa490435945 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0904500000-5674394a1c62fc133d16 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0092-4897600000-8b7973aa2743fc5d1668 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0aed-1977700000-34d12bec8fc5ddbf74c4 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 226.464623 predictedDarkChem Lite v0.1.0 [M-H]- 189.42293 predictedDeepCCS 1.0 (2019) [M+H]+ 226.561323 predictedDarkChem Lite v0.1.0 [M+H]+ 191.26607 predictedDeepCCS 1.0 (2019) [M+Na]+ 226.149523 predictedDarkChem Lite v0.1.0 [M+Na]+ 197.47475 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the first and rate-limiting step of polyamine biosynthesis that converts ornithine into putrescine, which is the precursor for the polyamines, spermidine and spermine. Polyamines are essential for cell proliferation and are implicated in cellular processes, ranging from DNA replication to apoptosis
- Specific Function
- ornithine decarboxylase activity
- Gene Name
- ODC1
- Uniprot ID
- P11926
- Uniprot Name
- Ornithine decarboxylase
- Molecular Weight
- 51147.73 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22