Oxytetracycline

Identification

Summary

Oxytetracycline is a tetracycline antibiotic used to treat a wide variety of susceptible bacterial infections.

Brand Names
Terramycin, Urobiotic
Generic Name
Oxytetracycline
DrugBank Accession Number
DB00595
Background

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

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Weight
Average: 460.434
Monoisotopic: 460.148180376
Chemical Formula
C22H24N2O9
Synonyms
  • 5-Hydroxytetracycline
  • Embryostat
  • Hydroxytetracyclinum
  • Mepatar
  • Ossitetraciclina
  • Oxitetraciclina
  • Oxyterracin
  • Oxyterracine
  • Oxytetracyclin
  • Oxytétracycline
  • Oxytetracycline
  • Oxytetracycline (anhydrous)
  • Oxytetracycline amphoteric
  • Oxytetracyclinum

Pharmacology

Indication

Oxytetracycline 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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatLocalized infectionCombination Product in combination with: Polymyxin B (DB00781)••••••••••••••••••••
Used in combination for prophylaxis ofSkin infectionsCombination Product in combination with: Polymyxin B (DB00781)••••••••••••••••••••
Used in combination for prophylaxis ofSkin infectionsCombination Product in combination with: Polymyxin B (DB00781)••••••••••••••••••••
Used in combination to treatSuperficial ocular infectionsCombination Product in combination with: Polymyxin B (DB00781)••••••••••••••••••••
Treatment ofSusceptible bacteria••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Oxytetracycline 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 action

Oxytetracycline 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.

TargetActionsOrganism
A30S ribosomal protein S9
inhibitor
Escherichia coli (strain K12)
A30S ribosomal protein S4
inhibitor
Escherichia coli (strain K12)
U16S ribosomal RNA
inhibitor
Enteric bacteria and other eubacteria
Absorption

Readily absorbed following oral administration.

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
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Toxicity

Adverse 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.

Pathways
PathwayCategory
Oxytetracycline Action PathwayDrug action
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.
DrugInteraction
AcamprosateThe excretion of Acamprosate can be decreased when combined with Oxytetracycline.
AcenocoumarolOxytetracycline may increase the anticoagulant activities of Acenocoumarol.
AcetylcysteineThe therapeutic efficacy of Acetylcysteine can be decreased when used in combination with Oxytetracycline.
Acetylsalicylic acidThe excretion of Oxytetracycline can be decreased when combined with Acetylsalicylic acid.
AcitretinThe risk or severity of pseudotumor cerebri can be increased when Acitretin is combined with Oxytetracycline.
Food Interactions
  • Avoid milk and dairy products. Take at least 1 hour before or two hours after consuming dairy products.
  • Take separate from meals. Take at least one hour before or two hours after a meal.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Oxytetracycline calciumC8MRZ07FDV13303-91-8KIPLYOUQVMMOHB-MXWBXKMOSA-L
Oxytetracycline dihydrateX20I9EN9556153-64-6SRRPEXWCHWWJOC-JEKSYDDFSA-N
Oxytetracycline hydrochloride4U7K4N52ZM2058-46-0UBDNTYUBJLXUNN-IFLJXUKPSA-N
Oxytetracycline monocalciumM90SJ24J2X7179-50-2QJHKFWPAQRFQBG-IFLJXUKPSA-L
International/Other Brands
Adamycin (Teva) / Anglocycline (Anglopak) / Corsamycin (Corsa Industries) / Oxacin (Doctor's Chemical Works) / Oxypan (Adcock Ingram Pharmaceuticals) / Oxyterracyna (Chema) / Terrados (Pfizer) / Tetran (Wagner Pharmafax) / Tetrasona (Medifarma)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TerramycinCapsule250 mg/1OralPfizer Labs2005-12-07Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
GEOTRIL POMADOxytetracycline hydrochloride (30 mg/g) + Polymyxin B sulfate (1.25 mg/g)OintmentTopicalİ.E. ULAGAY İLAÇ SAN. TÜRK A.Ş.2020-08-142021-03-18Turkey flag
HEKSA 30 MG/G + 10000 I.U./G MERHEMOxytetracycline (30 mg/g) + Polymyxin B (10000 IU/g)OintmentTopicalPOLİFARMA İLAÇ SAN. VE TİC. A.Ş.1986-07-09Not applicableTurkey flag
HEKSA DERI MERHEMIOxytetracycline (30 mg/g) + Polymyxin B (10000 IU/g)OintmentTopicalPOLİFARMA İLAÇ SAN. VE TİC. A.Ş.1986-07-092024-01-23Turkey flag
OXYLIMOxytetracycline dihydrate (100 MG/2ML) + Lidocaine (40 MG/2ML)Solutionบริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด1985-04-242020-09-29Thailand flag
POLIMISIN DERI MERHEMI, 14.2 GOxytetracycline hydrochloride (30 mg/g) + Polymyxin B sulfate (10000 U)OintmentTopicalKOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş.2009-07-30Not applicableTurkey flag

Categories

ATC Codes
J01AA06 — OxytetracyclineG01AA07 — OxytetracyclineS01AA04 — OxytetracyclineA01AB25 — OxytetracyclineJ01AA56 — Oxytetracycline, combinationsD06AA03 — OxytetracyclineJ01AA20 — Combinations of tetracyclines
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Tetracyclines
Sub Class
Not Available
Direct Parent
Tetracyclines
Alternative Parents
Naphthacenes / Anthracenecarboxylic acids and derivatives / Tetralins / Aryl ketones / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Aralkylamines / Cyclohexenones / Tertiary alcohols / Vinylogous acids
show 9 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Amino acid or derivatives / Anthracene carboxylic acid or derivatives / Aralkylamine / Aromatic homopolycyclic compound / Aryl ketone / Benzenoid
show 24 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
tetracyclines (CHEBI:27701) / Linear tetracyclines, Antibiotic fungicides (C06624) / Linear tetracyclines (LMPK07000005)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
SLF0D9077S
CAS number
79-57-2
InChI Key
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(C=CC=C4O)[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C

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 References
  1. Agwuh KN, MacGowan A: Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines. J Antimicrob Chemother. 2006 Aug;58(2):256-65. Epub 2006 Jul 1. [Article]
KEGG Compound
C06624
PubChem Compound
54675779
PubChem Substance
46507025
ChemSpider
10482174
RxNav
7821
ChEBI
133011
ChEMBL
CHEMBL1517
ZINC
ZINC000095626782
Therapeutic Targets Database
DAP000401
PharmGKB
PA450757
PDBe Ligand
OTC
RxList
RxList Drug Page
Wikipedia
Oxytetracycline
PDB Entries
2xpw
MSDS
Download (73.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Not Yet RecruitingTreatment0.5-14 Year Old Children With Nephroblastoma1
3Unknown StatusTreatmentAcne Vulgaris II or III Degree / Furuncle1
0TerminatedTreatmentOsteomyelitis1

Pharmacoeconomics

Manufacturers
  • Pfizer laboratories div pfizer inc
  • John j ferrante
  • Impax laboratories inc
  • Proter laboratory spa
  • Purepac pharmaceutical co
  • West ward pharmaceutical corp
Packagers
  • Chifeng Pharmaceutical Co. Ltd.
  • Medisca Inc.
  • Norbrook Laboratories Ltd.
  • Pfizer Inc.
  • Proter SPA
  • Veterina Animal Health Ltd.
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
OintmentTopical
Injection
Solution
CapsuleOral250 mg
Ointment
SuspensionOphthalmic
InjectionTopical100 mg/2mL
InjectionTopical250 mg/2mL
InjectionTopical50 mg/mL
TabletBuccal135.870 mg
CapsuleOral250 mg/1
OintmentOphthalmic
OintmentOphthalmic
OintmentConjunctival; Ophthalmic
CapsuleOral500.000 mg
CapsuleOral
Solution50 mg/1ml
Injection, solution
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)184.5 °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-4.5Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.84Chemaxon
pKa (Strongest Basic)7.41Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area201.85 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity115.4 m3·mol-1Chemaxon
Polarizability43.22 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-0000900000-23a1c6d515e29eb3dfe8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0004900000-00d3ce620d8f5b16a54a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004l-0000900000-cdf8f82431134deda95e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0019400000-6697d3b1fd7b0cfe11e5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fdp-2897500000-209455e4c8a2f04229f8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ku-1191300000-3b66ecf3a012220a72fb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-211.3668821
predicted
DarkChem Lite v0.1.0
[M-H]-212.9238821
predicted
DarkChem Lite v0.1.0
[M-H]-211.8188821
predicted
DarkChem Lite v0.1.0
[M-H]-201.128
predicted
DeepCCS 1.0 (2019)
[M+H]+214.2909821
predicted
DarkChem Lite v0.1.0
[M+H]+213.6928821
predicted
DarkChem Lite v0.1.0
[M+H]+213.3443821
predicted
DarkChem Lite v0.1.0
[M+H]+203.14767
predicted
DeepCCS 1.0 (2019)
[M+Na]+214.2028821
predicted
DarkChem Lite v0.1.0
[M+Na]+213.6908821
predicted
DarkChem Lite v0.1.0
[M+Na]+213.1063821
predicted
DarkChem Lite v0.1.0
[M+Na]+209.0692
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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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
Uniprot Name
30S ribosomal protein S9
Molecular Weight
14856.105 Da
References
  1. 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. [Article]
  2. Skold SE: RNA-protein complexes identified by crosslinking of polysomes. Biochimie. 1981 Jan;63(1):53-60. [Article]
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 trans...
Gene Name
rpsD
Uniprot ID
P0A7V8
Uniprot Name
30S ribosomal protein S4
Molecular Weight
23468.915 Da
References
  1. 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. [Article]
  2. Skold SE: RNA-protein complexes identified by crosslinking of polysomes. Biochimie. 1981 Jan;63(1):53-60. [Article]
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Unknown
Actions
Inhibitor
In prokaryotes, the 16S rRNA is essential for recognizing the 5' end of mRNA and hence positioning it correctly on the ribosome. The 16S rRNA has a characteristic secondary structure in which half of the nucleotides are base-paired. The 16S rRNA sequence has been highly conserved and is often used for evolutionary and species comparative analysis.
References
  1. 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. [Article]
  2. 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. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Keswani N, Choudhary S, Kishore N: Quantitative aspects of recognition of the antibiotic drug oxytetracycline by bovine serum albumin: Calorimetric and spectroscopic studies The Journal of Chemical Thermodynamics. 2013 Mar;58:196-205. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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 ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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
Uniprot Name
Solute carrier family 22 member 11
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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 sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:33