Oxytetracycline (CHEM002913)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2014-08-28 20:09:03 UTC
Update Date2026-05-14 16:43:23 UTC
Accession NumberCHEM002913
Identification
Common NameOxytetracycline
ClassSmall Molecule
DescriptionA tetracycline analog isolated from the actinomycete streptomyces rimosus and used in a wide variety of clinical conditions. [PubChem]
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Drug
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
  • Tetracycline
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-HydroxytetracyclineChEBI
OxitetraciclinaChEBI
OxyterracinChEBI
OxyterracineChEBI
OxytetracyclinChEBI
Oxytetracycline (anhydrous)ChEBI
Oxytetracycline amphotericChEBI
OxytetracyclinumChEBI
Oxytetracycline anhydrousKegg
Chemical FormulaC22H24N2O9
Average Molecular Mass460.434 g/mol
Monoisotopic Mass460.148 g/mol
CAS Registry Number79-57-2
IUPAC Name(4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Traditional Nameoxytetracycline
SMILES[H][C@@]12[C@@H](O)[C@@]3([H])C(C(=O)C4=C(O)C=CC=C4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C
InChI IdentifierInChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1
InChI KeyIWVCMVBTMGNXQD-PXOLEDIWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTetracyclines
Sub ClassNot Available
Direct ParentTetracyclines
Alternative Parents
Substituents
  • Tetracycline
  • Naphthacene
  • Tetracene
  • Anthracene carboxylic acid or derivatives
  • Tetralin
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexenone
  • Aralkylamine
  • Benzenoid
  • Tertiary alcohol
  • Vinylogous acid
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Tertiary amine
  • Carboxamide group
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Ketone
  • Polyol
  • Carboxylic acid derivative
  • Enol
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Bone Marrow
  • Heart
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Oxytetracycline Action PathwaySMP00293 Not Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point184.5°C
Boiling PointNot Available
Solubility313 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility1.4 g/LALOGPS
logP-0.99ALOGPS
logP-4.6ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)0.24ChemAxon
pKa (Strongest Basic)7.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area201.85 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity115.4 m³·mol⁻¹ChemAxon
Polarizability43.4 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0000900000-5672179671bb12c90e44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0000900000-50e9f5b99152f280cd90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1237900000-570a34d4c343b74d8b39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0011900000-b4730d1729a6ab3c3527Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ke-0357900000-f7d527caf2556638743bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9175000000-36d7da806594f0c25f3fSpectrum
Toxicity Profile
Route of ExposureReadily absorbed following oral administration.
Mechanism of ToxicityTetracyclines target the 28S small subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. As a result tetracyclines are cytotoxic to the most metabolically active cells or tissues including the heart, liver, thymus and bone-marrow. (5). The likely target of most tetracyclines is the 12S rRNA molecule in the mitochondrial ribosome, which is analogous to the 16S rRNA in bacterial ribosomes.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesOxytetracycline is indicated for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.
Minimum Risk LevelNot Available
Health EffectsSide effects from normal doses of tetracyclines are relatively minimal, but of particular note is phototoxicity. Tetracylclines increase the risk of sunburn under exposure to light from the sun or other sources. Tetracyclines may also cause stomach or bowel upsets, and, on rare occasions, allergic reactions. Very rarely, severe headache and vision problems may be signs of dangerous secondary intracranial hypertension, also known as pseudotumor cerebri. Tetracyclines are teratogens and cause tooth discolouration and poor tooth mineralization in the fetus as they develop in infancy. Symptoms of tetracycline overdose include anorexia, nausea, diarrhea, glossitis, dysphagia, enterocolitis and inflammatory lesions, skin reactions such as maculopapular and erythematous rashes, exfoliative dermatitis, photosensitivity, hypersensitivity reactions such as urticaria, angioneurotic oedema, anaphylaxis, anaphyl-actoid purpura, pericarditis, and exacerbation of systemic lupus erythematosus, benign intracranial hypertension in adults disappearing on discontinuation of the medicine, haematologic abnormalities such as haemolytic anaemia, thrombocytopenia, neutropenia, and eosinophilia.
SymptomsSymptoms may include stomach or bowel upsets and rarely allergic reactions. Very rarely severe headache and vision problems may be signs of dangerous intracranial hypertenion.
TreatmentDrug therapy is discontinued immediately; exchange transfusion may be required to remove the drug. Sometimes, phenobarbital (UGT induction) is used.
Concentrations
Not Available
DrugBank IDDB00595
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00017127
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOxytetracycline
Chemspider IDNot Available
ChEBI ID27701
PubChem Compound IDNot Available
Kegg Compound IDC06624
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Janos Balint, Laszlo Cseke, Ferenc Fabian, Lajos Kun, Miklos Szarvas, “Process for the preparation of an oxytetracycline-calcium silicate complex salt from fermentation broth.” U.S. Patent US4584135, issued April, 1951.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17386724
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17638695
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17870541
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=1833366
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21136283
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21488905
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22013404
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24247133
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24281679
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24290103
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24362004
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24510709
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24607684
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24853528
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24983832
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25019386
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=25035320
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=25081007