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.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
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
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
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
27701
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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
4Not Yet RecruitingTreatment0.5-14 Year Old Children With Nephroblastoma1somestatusstop reasonjust information to hide
3Unknown StatusTreatmentAcne Vulgaris II or III Degree / Furuncle1somestatusstop reasonjust information to hide
0TerminatedTreatmentOsteomyelitis1somestatusstop reasonjust information to hide

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
OintmentOphthalmic
OintmentOphthalmic3 %
OintmentOphthalmic30 MG/G
CapsuleOral250 mg
Ointment10 mg/g
Ointment
SuspensionOphthalmic
InjectionTopical100 mg/2mL
InjectionTopical250 mg/2mL
InjectionTopical50 mg/mL
TabletBuccal135.870 mg
CapsuleOral250 mg/1
Injection50 MG/ML
OintmentOphthalmic
OintmentOphthalmic1 %
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

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General 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.
Specific Function
RNA binding
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
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.
Specific Function
mRNA 5'-UTR binding
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
Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
Specific Function
antioxidant activity
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
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
Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651)
Specific Function
alpha-ketoglutarate transmembrane transporter activity
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
Functions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity)
Specific Function
organic anion transmembrane transporter activity
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Organic anion transporter 3
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
Antiporter that mediates the transport of conjugated steroids and other specific organic anions at the basal membrane of syncytiotrophoblast and at the apical membrane of proximal tubule epithelial cells, in exchange for anionic compounds (PubMed:10660625, PubMed:11907186, PubMed:15037815, PubMed:15102942, PubMed:15291761, PubMed:15576633, PubMed:17229912, PubMed:18501590, PubMed:26277985, PubMed:28027879). May be responsible for placental absorption of fetal-derived steroid sulfates such as estrone sulfate (E1S) and the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S), as well as clearing waste products and xenobiotics from the fetus (PubMed:12409283). Maybe also be involved in placental urate homeostasis (PubMed:17229912). Facilitates the renal reabsorption of organic anions such as urate and derived steroid sulfates (PubMed:15037815, PubMed:17229912). Organic anion glutarate acts as conteranion for E1S renal uptake (PubMed:15037815, PubMed:17229912). Possible transport mode may also include DHEA-S/E1S exchange (PubMed:28027879). Also interacts with inorganic anions such as chloride and hydroxyl ions, therefore possible transport modes may include E1S/Cl(-), E1S/OH(-), urate/Cl(-) and urate/OH(-) (PubMed:17229912). Also mediates the transport of prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may be involved in their renal excretion (PubMed:11907186). Also able to uptake anionic drugs, diuretics, bile salts and ochratoxin A (PubMed:10660625, PubMed:26277985). Mediates the unidirectional efflux of glutamate and aspartate (PubMed:28027879). Glutamate efflux down its transmembrane gradient may drive SLC22A11/OAT4-mediated placental uptake of E1S (PubMed:26277985)
Specific Function
organic anion transmembrane transporter activity
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
Functions as a Na(+)-independent bidirectional multispecific transporter (PubMed:11327718, PubMed:18216183, PubMed:21446918, PubMed:28945155). Contributes to the renal and hepatic elimination of endogenous organic compounds from the systemic circulation into the urine and bile, respectively (PubMed:11327718, PubMed:25904762). Capable of transporting a wide range of purine and pyrimidine nucleobases, nucleosides and nucleotides, with cGMP, 2'deoxyguanosine and GMP being the preferred substrates (PubMed:11327718, PubMed:18216183, PubMed:26377792, PubMed:28945155). Functions as a pH- and chloride-independent cGMP bidirectional facilitative transporter that can regulate both intracellular and extracellular levels of cGMP and may be involved in cGMP signaling pathways (PubMed:18216183, PubMed:26377792). Mediates orotate/glutamate bidirectional exchange and most likely display a physiological role in hepatic release of glutamate into the blood (PubMed:21446918). Involved in renal secretion and possible reabsorption of creatinine (PubMed:25904762, PubMed:28945155). Able to uptake prostaglandin E2 (PGE2) and may contribute to PGE2 renal excretion (Probable). Also transports alpha-ketoglutarate and urate (PubMed:11327718, PubMed:26377792). Apart from the orotate/glutamate exchange, the counterions for the uptake of other SLC22A7/OAT2 substrates remain to be identified (PubMed:26377792)
Specific Function
alpha-ketoglutarate transmembrane transporter activity
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 October 21, 2024 12:53