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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
EmbryostatNot AvailableIS
HydroxytetracyclinumNot AvailableIS
MepatarNot AvailableIS
OxitetraciclinaSpanishINN
OxytetracyclinGermanINN
OxytétracyclineFrenchINN
OxytetracyclinumLatinINN
Salts
Name/CAS Structure Properties
Oxytetracycline Hydrochloride
2058-46-0
Thumb
  • InChI Key: SVDOODSCHVSYEK-IFLJXUKPSA-N
  • Monoisotopic Mass: 496.124858115
  • Average Mass: 496.895
DBSALT000645
Brand names
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
CategoriesNot Available
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)[C@H]2N(C)C
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassAcenes and Derivatives
SubclassNaphthacenes
Direct parentNaphthacenes
Alternative parentsAnthracenecarboxylic Acids and Derivatives; Anthraquinones; Tetralins; Phenols and Derivatives; Tertiary Alcohols; Polyols; Primary Carboxylic Acid Amides; Secondary Alcohols; Tertiary Amines; Ketones; Enolates; Carboxylic Acids; Enols; Polyamines
Substituentsanthraquinone; tetralin; phenol derivative; benzene; tertiary alcohol; polyol; tertiary amine; carboxamide group; ketone; primary carboxylic acid amide; secondary alcohol; polyamine; enol; carboxylic acid derivative; enolate; carboxylic acid; amine; alcohol; carbonyl group; organonitrogen compound
Classification descriptionThis compound belongs to the naphthacenes. These are compounds containing a naphthacene moiety, which is a polyaromatic hydrocarbon made of four linearly fused benzene rings.
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
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.85
Blood Brain Barrier - 0.9881
Caco-2 permeable - 0.8706
P-glycoprotein substrate Substrate 0.699
P-glycoprotein inhibitor I Non-inhibitor 0.8038
P-glycoprotein inhibitor II Non-inhibitor 0.8628
Renal organic cation transporter Non-inhibitor 0.9562
CYP450 2C9 substrate Non-substrate 0.8008
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Substrate 0.6551
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9144
CYP450 2D6 substrate Non-inhibitor 0.9293
CYP450 2C19 substrate Non-inhibitor 0.9099
CYP450 3A4 substrate Non-inhibitor 0.8567
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8086
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.8632
Biodegradation Not ready biodegradable 0.9941
Rat acute toxicity 2.3159 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9946
hERG inhibition (predictor II) Non-inhibitor 0.7466
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 ointm3.85USDg
Oxytetracycline hcl powder3.59USDg
Terramycin 250 mg/2 ml ampul2.22USDml
Terramycin im 100 mg/2 ml amp1.24USDml
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 solubility1.40e+00 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 area201.85ChemAxon
rotatable bond count2ChemAxon
refractivity115.4ChemAxon
polarizability43.4ChemAxon
number of rings4ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
KEGG CompoundC06624
PubChem Compound5280972
PubChem Substance46507025
ChemSpider4444458
ChEBI27701
ChEMBLCHEMBL1517
Therapeutic Targets DatabaseDAP000401
PharmGKBPA450757
Drug Product Database719315
RxListhttp://www.rxlist.com/cgi/generic2/oxytetracycline.htm
WikipediaOxytetracycline
ATC CodesD06AA03G01AA07J01AA06S01AA04
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(73.1 KB)
Interactions
Drug Interactions
Drug
AcitretinIncreased risk of intracranial hypertension
AmoxicillinPossible antagonism of action
AmpicillinPossible antagonism of action
BenzylpenicillinPossible antagonism of action
CalciumFormation of non-absorbable complexes
CarbenicillinPossible antagonism of action
ClavulanatePossible antagonism of action
CloxacillinPossible antagonism of action
DicloxacillinPossible antagonism of action
Ethinyl EstradiolThis anti-infectious agent could decrease the effect of the oral contraceptive
EtretinateIncreased risk of intracranial hypertension
FlucloxacillinPossible antagonism of action
Iron DextranFormation of non-absorbable complexes
IsotretinoinIncreased risk of intracranial hypertension
MagnesiumFormation of non-absorbable complexes
Penicillin VPossible antagonism of action
PiperacillinPossible antagonism of action
PivampicillinPossible antagonism of action
PivmecillinamPossible antagonism of action
TicarcillinOxytetracycline may reduce the effect of Ticarcillin by inhibiting bacterial growth. Ticarcillin exerts its effects on actively growing bacteria. To achieve synergism, Ticarcillin should be administered at least 2 hours prior to using Oxytetracycline.
TretinoinOxytetracycline may increase the adverse effects of oral Tretinoin. Increase risk of pseudotumour cerebri. Concurrent therapy should be avoided.
Food InteractionsNot Available

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

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
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11