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Identification
NameOxytetracycline
Accession NumberDB00595  (APRD00019)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionA tetracycline analog isolated from the actinomycete streptomyces rimosus and used in a wide variety of clinical conditions. [PubChem]
Structure
Thumb
Synonyms
5-Hydroxytetracycline
Embryostat
Hydroxytetracyclinum
Mepatar
Oxitetraciclina
Oxyterracin
Oxyterracine
Oxytetracyclin
Oxytétracycline
Oxytetracycline (anhydrous)
Oxytetracycline amphoteric
Oxytetracyclinum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AdamycinTeva
AnglocyclineAnglopak
CorsamycinCorsa Industries
OxacinDoctor's Chemical Works
OxypanAdcock Ingram Pharmaceuticals
OxyterracynaChema
TerradosPfizer
TerramycinPfizer
TetranWagner Pharmafax
TetrasonaMedifarma
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Oxytetracycline calcium
13303-91-8
Thumb
  • InChI Key: KIPLYOUQVMMOHB-MXWBXKMOSA-L
  • Monoisotopic Mass: 958.2433016
  • Average Mass: 958.94
DBSALT001478
Oxytetracycline dihydrate
6153-64-6
Thumb
  • InChI Key: SRRPEXWCHWWJOC-JEKSYDDFSA-N
  • Monoisotopic Mass: 496.16930973
  • Average Mass: 496.469
DBSALT001618
Oxytetracycline hydrochloride
2058-46-0
Thumb
  • InChI Key: UBDNTYUBJLXUNN-IFLJXUKPSA-N
  • Monoisotopic Mass: 496.1248581
  • Average Mass: 496.9
DBSALT000645
Oxytetracycline mono-alkyl trimethyl ammonium
ThumbNot applicableDBSALT001638
Oxytetracycline monocalcium
7179-50-2
Thumb
  • InChI Key: QJHKFWPAQRFQBG-IFLJXUKPSA-L
  • Monoisotopic Mass: 498.0951212
  • Average Mass: 498.501
DBSALT001855
Categories
UNIISLF0D9077S
CAS number79-57-2
WeightAverage: 460.434
Monoisotopic: 460.148180376
Chemical FormulaC22H24N2O9
InChI KeyInChIKey=IWVCMVBTMGNXQD-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)[[email protected]]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.
Related Articles
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
Pathways
PathwayCategorySMPDB ID
Oxytetracycline Action PathwayDrug actionSMP00293
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 inhibitorNon-inhibitor0.9144
CYP450 2D6 inhibitorNon-inhibitor0.9293
CYP450 2C19 inhibitorNon-inhibitor0.9099
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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 ReferencesNot Available
External Links
ATC CodesS01AA04J01AA56D06AA03J01AA06G01AA07
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (73.1 KB)
Interactions
Drug Interactions
Drug
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Oxytetracycline.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Trna binding
Specific Function:
The C-terminal tail plays a role in the affinity of the 30S P site for different tRNAs. Mutations that decrease this affinity are suppressed in the 70S ribosome.
Gene Name:
rpsI
Uniprot ID:
P0A7X3
Molecular Weight:
14856.105 Da
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:17139284 ]
  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:17016423 ]
  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:15156014 ]
  4. Skold SE: RNA-protein complexes identified by crosslinking of polysomes. Biochimie. 1981 Jan;63(1):53-60. [PubMed:6163479 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Translation repressor activity, nucleic acid binding
Specific Function:
One of two assembly initiator proteins for the 30S subunit, it binds directly to 16S rRNA where it nucleates assembly of the body of the 30S subunit.With S5 and S12 plays an important role in translational accuracy; many suppressors of streptomycin-dependent mutants of protein S12 are found in this protein, some but not all of which decrease translational accuracy (ram, ribosomal ambiguity muta...
Gene Name:
rpsD
Uniprot ID:
P0A7V8
Molecular Weight:
23468.915 Da
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:17139284 ]
  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:17016423 ]
  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:15156014 ]
  4. Skold SE: RNA-protein complexes identified by crosslinking of polysomes. Biochimie. 1981 Jan;63(1):53-60. [PubMed:6163479 ]
3. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
unknown
Actions
inhibitor
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:17139284 ]
  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:17016423 ]
  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:16978353 ]
  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:17274285 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
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:11855680 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
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:11855680 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular Weight:
59970.945 Da
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:11855680 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha-ketoglutarate.
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular Weight:
60025.025 Da
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:11855680 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23