You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameOxytetracycline
Accession NumberDB00595  (APRD00019)
TypeSmall Molecule
GroupsApproved
Description

A tetracycline analog isolated from the actinomycete streptomyces rimosus and used in a wide variety of clinical conditions. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
5-HydroxytetracyclineNot AvailableNot Available
EmbryostatNot AvailableIS
HydroxytetracyclinumNot AvailableIS
MepatarNot AvailableIS
OxitetraciclinaSpanishINN
OxyterracinNot AvailableNot Available
OxyterracineNot AvailableNot Available
OxytetracyclinGermanINN
OxytétracyclineFrenchINN
Oxytetracycline (anhydrous)Not AvailableNot Available
Oxytetracycline amphotericNot AvailableNot Available
OxytetracyclinumLatinINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AdamycinTeva
AnglocyclineAnglopak
CorsamycinCorsa Industries
OxacinDoctor's Chemical Works
OxypanAdcock Ingram Pharmaceuticals
OxyterracynaChema
TerradosPfizer
TerramycinPfizer
TetranWagner Pharmafax
TetrasonaMedifarma
Brand mixtures
Brand NameIngredients
GeokortonOxytetracycline and Hydrocortisone
GeonistinOxytetracycline and Nystatin
HeksaOxytetracycline and Polymyxin B
Hydrocortison med TerramycinOxytetracycline and Hydrocortisone
HydrocyclinOxytetracycline and Hydrocortisone
OximedOxytetracycline and Hydrocortisone
OxycortOxytetracycline and Hydrocortisone
OxylimAtlantic
OxyoftalOxytetracycline and Polymycin B
UnguentumOxytetracycline and Hydrocortisone
Salts
Name/CASStructureProperties
Oxytetracycline Hydrochloride
2058-46-0
Thumb
  • InChI Key: SVDOODSCHVSYEK-IFLJXUKPSA-N
  • Monoisotopic Mass: 496.124858115
  • Average Mass: 496.895
DBSALT000645
Categories
CAS number79-57-2
WeightAverage: 460.434
Monoisotopic: 460.148180376
Chemical FormulaC22H24N2O9
InChI KeyIWVCMVBTMGNXQD-PXOLEDIWSA-N
InChI
InChI=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
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
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
Taxonomy
DescriptionThis compound 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
  • Tetracene
  • Naphthacene
  • Anthracene carboxylic acid or derivatives
  • Tetralin
  • Aryl ketone
  • Aralkylamine
  • Benzenoid
  • Vinylogous acid
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Polyol
  • Ketone
  • Carboxamide group
  • Enol
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationOxytetracycline 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.
PharmacodynamicsOxytetracycline is known as a broad-spectrum antibiotic due to its activity against such a wide range of infections. It was the second of the tetracyclines to be discovered. Oxytetracycline, like other tetracyclines, is used to treat many infections common and rare. Its better absorption profile makes it preferable to tetracycline for moderately severe acne, but alternatives sould be sought if no improvement occurs by 3 months.
Mechanism of actionOxytetracycline inhibits cell growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Oxytetracycline is lipophilic and can easily pass through the cell membrane or passively diffuses through porin channels in the bacterial membrane.
AbsorptionReadily absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityAdverse effects may include stomach or bowel upsets and rarely allergic reactions. Very rarely severe headache and vision problems may be signs of dangerous intracranial hypertenion.
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.85
Blood Brain Barrier-0.9881
Caco-2 permeable-0.8706
P-glycoprotein substrateSubstrate0.699
P-glycoprotein inhibitor INon-inhibitor0.8038
P-glycoprotein inhibitor IINon-inhibitor0.8628
Renal organic cation transporterNon-inhibitor0.9562
CYP450 2C9 substrateNon-substrate0.8008
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6551
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9144
CYP450 2D6 substrateNon-inhibitor0.9293
CYP450 2C19 substrateNon-inhibitor0.9099
CYP450 3A4 substrateNon-inhibitor0.8567
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8086
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8632
BiodegradationNot ready biodegradable0.9941
Rat acute toxicity2.3159 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9946
hERG inhibition (predictor II)Non-inhibitor0.7466
Pharmacoeconomics
Manufacturers
  • Pfizer laboratories div pfizer inc
  • John j ferrante
  • Impax laboratories inc
  • Proter laboratory spa
  • Purepac pharmaceutical co
  • West ward pharmaceutical corp
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Terramycin-polymyx eye ointm3.85USD g
Oxytetracycline hcl powder3.59USD g
Terramycin 250 mg/2 ml ampul2.22USD ml
Terramycin im 100 mg/2 ml amp1.24USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point184.5 °CPhysProp
water solubility313 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.90SANGSTER (1994)
logS-3.14ADME Research, USCD
pKa3.27 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility1.4 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity115.4 m3·mol-1ChemAxon
Polarizability43.4 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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.

US4584135
General ReferenceNot Available
External Links
ATC CodesD06AA03G01AA07J01AA06S01AA04
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (73.1 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 30S ribosomal protein S9

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
30S ribosomal protein S9 P0A7X3 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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. Pubmed
  3. Aminov RI, Chee-Sanford JC, Garrigues N, Mehboob A, Mackie RI: Detection of tetracycline resistance genes by PCR methods. Methods Mol Biol. 2004;268:3-13. Pubmed
  4. Skold SE: RNA-protein complexes identified by crosslinking of polysomes. Biochimie. 1981 Jan;63(1):53-60. Pubmed

2. 30S ribosomal protein S4

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
30S ribosomal protein S4 P0A7V8 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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. Pubmed
  3. Aminov RI, Chee-Sanford JC, Garrigues N, Mehboob A, Mackie RI: Detection of tetracycline resistance genes by PCR methods. Methods Mol Biol. 2004;268:3-13. Pubmed
  4. Skold SE: RNA-protein complexes identified by crosslinking of polysomes. Biochimie. 1981 Jan;63(1):53-60. Pubmed

3. 16S rRNA

Kind: nucleotide

Organism: Enteric bacteria and other eubacteria

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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. Pubmed
  3. Engemann CA, Adams L, Knapp CW, Graham DW: Disappearance of oxytetracycline resistance genes in aquatic systems. FEMS Microbiol Lett. 2006 Oct;263(2):176-82. Pubmed
  4. Tsai HJ, Huang CW: Phenotypic and molecular characterization of isolates of Ornithobacterium rhinotracheale from chickens and pigeons in Taiwan. Avian Dis. 2006 Dec;50(4):502-7. Pubmed

Transporters

1. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. Pubmed

2. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. Pubmed

3. Solute carrier family 22 member 11

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 11 Q9NSA0 Details

References:

  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. Pubmed

4. Solute carrier family 22 member 7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 7 Q9Y694 Details

References:

  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11