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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:04 UTC
HMDB IDHMDB0015152
Secondary Accession Numbers
  • HMDB15152
Metabolite Identification
Common NameMinocycline
DescriptionMinocycline, also known as minociclina or minomycin, 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. Thus, minocycline is considered to be a linear tetracycline lipid molecule. Minocycline's effects are related to the inhibition of protein synthesis. However, the agent is no longer recommended to be employed as prophylaxis as it is capable of eliciting problematic adverse effects like dizziness and vertigo. Tetracyclines like minocycline bind to the 30S ribosomal subunit, preventing the binding of tRNA to the mRNA-ribosome complex and interfering with protein synthesis. Minocycline has also been found to produce thyroid hyperplasia in rats and dogs. Minocycline passes directly through the lipid bilayer or passively diffuses through porin channels in the bacterial membrane. Minocycline is a drug which is used for the treatment of infections caused by susceptible strains of microorganisms, such as rocky mountain spotted fever, typhus fever and the typhus group, q fever, rickettsial pox and tick fevers caused by rickettsiae, upper respiratory tract infections caused by streptococcus pneumoniae and for the treatment of asymptomatic carriers of neisseria meningitidis. A tetracycline analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant staphylococcus infections. Minocycline is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In humans, minocycline is involved in minocycline action pathway. Current research is examining the possible neuroprotective effects of minocycline against progression of Huntington's Disease, an inherited neurodegenerative disorder. Minocycline has been observed to cause a dark discoloration of the thyroid in experimental animals (rats, minipigs, dogs and monkeys).
Structure
Data?1582753264
Synonyms
ValueSource
(4S,4AS,5ar,12as)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamideChEBI
7-Dimethylamino-6-demethyl-6-deoxytetracyclineChEBI
MinociclinaChEBI
MinociclinumChEBI
MinomycinChEBI
MINOKegg
Chemical FormulaC23H27N3O7
Average Molecular Weight457.4764
Monoisotopic Molecular Weight457.184900233
IUPAC Name(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Traditional Nameminocycline
CAS Registry Number10118-90-8
SMILES
[H][C@@]12CC3=C(C(O)=CC=C3N(C)C)C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2
InChI Identifier
InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27,29-30,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1
InChI KeyDYKFCLLONBREIL-KVUCHLLUSA-N
Chemical Taxonomy
Description 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
  • Naphthacene
  • Tetracene
  • Anthracene carboxylic acid or derivatives
  • Tetralin
  • Tertiary aliphatic/aromatic amine
  • Aryl ketone
  • Dialkylarylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexenone
  • Aralkylamine
  • Benzenoid
  • Vinylogous acid
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Tertiary amine
  • Carboxamide group
  • Primary carboxylic acid amide
  • Ketone
  • Polyol
  • Carboxylic acid derivative
  • Enol
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.07 g/LNot Available
LogP0.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.07 g/LALOGPS
logP-0.03ALOGPS
logP-3.3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)-2.3ChemAxon
pKa (Strongest Basic)8.25ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area164.63 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity122.54 m³·mol⁻¹ChemAxon
Polarizability45.9 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-5198300000-09d1a0f95ca289894a54Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ab9-4101926000-ecf9ee87bcf7587066caSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0001900000-6e678a7f126753a02d03Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00dr-0139100000-ff75a26ae387147257dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0293000000-c2ff616578522f961ba6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0390000000-d52131f98ad1d88e178cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0fki-1690000000-e5a98a7122d0379c17ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00dr-1980000000-8e1add1bcba675eab919Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-2940000000-5fb719a03faa19bc3eceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-6920000000-fb4c9cde9587edd4015eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-9300000000-6299955440e9be195128Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0000900000-6f7513e3aaa9e86725ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0011900000-ed3a433871dc9cea2d9fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dr-0559300000-4e1a4ba6692c21980caeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dr-0696000000-f57972687a1b0ffe9411Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1491000000-1847e0c78206ea2f84c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4l-0000900000-ae91ec031bca8b95216eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0001900000-0bc6e4a0b16f4acd3d1dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uei-1149100000-2ea03125f37fabe56999Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001r-1192000000-476045d8accb26d18bb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-015i-1390000000-f6a75360809f9018052aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0000900000-24f0aa03e70485995bfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-0011900000-d0312060b105b95120e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi1-1349400000-c2d44f2b203b8c8a0d99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-d44b457b4826431b60bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0006900000-d21619964135e5793a97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-8049000000-c546414319e04333465dSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01017 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01017 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01017
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00018686
Chemspider ID16735907
KEGG Compound IDC07225
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMinocycline
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDMIY
ChEBI ID50694
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gough A, Chapman S, Wagstaff K, Emery P, Elias E: Minocycline induced autoimmune hepatitis and systemic lupus erythematosus-like syndrome. BMJ. 1996 Jan 20;312(7024):169-72. [PubMed:8563540 ]
  2. Chen M, Ona VO, Li M, Ferrante RJ, Fink KB, Zhu S, Bian J, Guo L, Farrell LA, Hersch SM, Hobbs W, Vonsattel JP, Cha JH, Friedlander RM: Minocycline inhibits caspase-1 and caspase-3 expression and delays mortality in a transgenic mouse model of Huntington disease. Nat Med. 2000 Jul;6(7):797-801. [PubMed:10888929 ]
  3. Tikka TM, Koistinaho JE: Minocycline provides neuroprotection against N-methyl-D-aspartate neurotoxicity by inhibiting microglia. J Immunol. 2001 Jun 15;166(12):7527-33. [PubMed:11390507 ]
  4. Song Y, Wei EQ, Zhang WP, Zhang L, Liu JR, Chen Z: Minocycline protects PC12 cells from ischemic-like injury and inhibits 5-lipoxygenase activation. Neuroreport. 2004 Oct 5;15(14):2181-4. [PubMed:15371729 ]
  5. Nirmalananthan N, Greensmith L: Amyotrophic lateral sclerosis: recent advances and future therapies. Curr Opin Neurol. 2005 Dec;18(6):712-9. [PubMed:16280684 ]
  6. Wikipedia [Link]
  7. MEDSAFE [Link]

Enzymes

General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595
References
  1. Song Y, Wei EQ, Zhang WP, Zhang L, Liu JR, Chen Z: Minocycline protects PC12 cells from ischemic-like injury and inhibits 5-lipoxygenase activation. Neuroreport. 2004 Oct 5;15(14):2181-4. [PubMed:15371729 ]
  2. Song Y, Wei EQ, Zhang WP, Ge QF, Liu JR, Wang ML, Huang XJ, Hu X, Chen Z: Minocycline protects PC12 cells against NMDA-induced injury via inhibiting 5-lipoxygenase activation. Brain Res. 2006 Apr 26;1085(1):57-67. Epub 2006 Mar 30. [PubMed:16574083 ]
  3. Chu LS, Fang SH, Zhou Y, Yu GL, Wang ML, Zhang WP, Wei EQ: Minocycline inhibits 5-lipoxygenase activation and brain inflammation after focal cerebral ischemia in rats. Acta Pharmacol Sin. 2007 Jun;28(6):763-72. [PubMed:17506934 ]
General function:
Involved in iron ion binding
Specific function:
Plays a role in apoptosis. Suppression of the anti- apoptotic members or activation of the pro-apoptotic members of the Bcl-2 family leads to altered mitochondrial membrane permeability resulting in release of cytochrome c into the cytosol. Binding of cytochrome c to Apaf-1 triggers the activation of caspase-9, which then accelerates apoptosis by activating other caspases
Gene Name:
CYCS
Uniprot ID:
P99999
Molecular weight:
11748.7
References
  1. Zhu S, Stavrovskaya IG, Drozda M, Kim BY, Ona V, Li M, Sarang S, Liu AS, Hartley DM, Wu DC, Gullans S, Ferrante RJ, Przedborski S, Kristal BS, Friedlander RM: Minocycline inhibits cytochrome c release and delays progression of amyotrophic lateral sclerosis in mice. Nature. 2002 May 2;417(6884):74-8. [PubMed:11986668 ]
  2. Matsuki S, Iuchi Y, Ikeda Y, Sasagawa I, Tomita Y, Fujii J: Suppression of cytochrome c release and apoptosis in testes with heat stress by minocycline. Biochem Biophys Res Commun. 2003 Dec 19;312(3):843-9. [PubMed:14680842 ]
  3. Chu HC, Lin YL, Sytwu HK, Lin SH, Liao CL, Chao YC: Effects of minocycline on Fas-mediated fulminant hepatitis in mice. Br J Pharmacol. 2005 Jan;144(2):275-82. [PubMed:15665864 ]
  4. Heo K, Cho YJ, Cho KJ, Kim HW, Kim HJ, Shin HY, Lee BI, Kim GW: Minocycline inhibits caspase-dependent and -independent cell death pathways and is neuroprotective against hippocampal damage after treatment with kainic acid in mice. Neurosci Lett. 2006 May 8;398(3):195-200. Epub 2006 Feb 15. [PubMed:16469440 ]
  5. Mansson R, Hansson MJ, Morota S, Uchino H, Ekdahl CT, Elmer E: Re-evaluation of mitochondrial permeability transition as a primary neuroprotective target of minocycline. Neurobiol Dis. 2007 Jan;25(1):198-205. Epub 2006 Oct 24. [PubMed:17067803 ]
  6. Kim HS, Suh YH: Minocycline and neurodegenerative diseases. Behav Brain Res. 2009 Jan 23;196(2):168-79. doi: 10.1016/j.bbr.2008.09.040. Epub 2008 Oct 11. [PubMed:18977395 ]
General function:
Involved in growth factor activity
Specific function:
Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells
Gene Name:
IL1B
Uniprot ID:
P01584
Molecular weight:
30747.7
References
  1. Sadowski T, Steinmeyer J: Minocycline inhibits the production of inducible nitric oxide synthase in articular chondrocytes. J Rheumatol. 2001 Feb;28(2):336-40. [PubMed:11246672 ]
  2. Oringer RJ, Al-Shammari KF, Aldredge WA, Iacono VJ, Eber RM, Wang HL, Berwald B, Nejat R, Giannobile WV: Effect of locally delivered minocycline microspheres on markers of bone resorption. J Periodontol. 2002 Aug;73(8):835-42. [PubMed:12211491 ]
  3. Amin AR, Attur MG, Thakker GD, Patel PD, Vyas PR, Patel RN, Patel IR, Abramson SB: A novel mechanism of action of tetracyclines: effects on nitric oxide synthases. Proc Natl Acad Sci U S A. 1996 Nov 26;93(24):14014-9. [PubMed:8943052 ]
  4. Steinmeyer J, Daufeldt S, Taiwo YO: Pharmacological effect of tetracyclines on proteoglycanases from interleukin-1-treated articular cartilage. Biochem Pharmacol. 1998 Jan 1;55(1):93-100. [PubMed:9413935 ]
General function:
Involved in metalloendopeptidase activity
Specific function:
May play an essential role in local proteolysis of the extracellular matrix and in leukocyte migration. Could play a role in bone osteoclastic resorption. Cleaves KiSS1 at a Gly-|-Leu bond. Cleaves type IV and type V collagen into large C-terminal three quarter fragments and shorter N-terminal one quarter fragments. Degrades fibronectin but not laminin or Pz-peptide
Gene Name:
MMP9
Uniprot ID:
P14780
Molecular weight:
78457.5
References
  1. Brundula V, Rewcastle NB, Metz LM, Bernard CC, Yong VW: Targeting leukocyte MMPs and transmigration: minocycline as a potential therapy for multiple sclerosis. Brain. 2002 Jun;125(Pt 6):1297-308. [PubMed:12023318 ]
  2. Sutton TA, Kelly KJ, Mang HE, Plotkin Z, Sandoval RM, Dagher PC: Minocycline reduces renal microvascular leakage in a rat model of ischemic renal injury. Am J Physiol Renal Physiol. 2005 Jan;288(1):F91-7. Epub 2004 Sep 7. [PubMed:15353401 ]
  3. Koistinaho M, Malm TM, Kettunen MI, Goldsteins G, Starckx S, Kauppinen RA, Opdenakker G, Koistinaho J: Minocycline protects against permanent cerebral ischemia in wild type but not in matrix metalloprotease-9-deficient mice. J Cereb Blood Flow Metab. 2005 Apr;25(4):460-7. [PubMed:15674236 ]
  4. Lee CZ, Yao JS, Huang Y, Zhai W, Liu W, Guglielmo BJ, Lin E, Yang GY, Young WL: Dose-response effect of tetracyclines on cerebral matrix metalloproteinase-9 after vascular endothelial growth factor hyperstimulation. J Cereb Blood Flow Metab. 2006 Sep;26(9):1157-64. Epub 2006 Jan 4. [PubMed:16395286 ]
  5. Machado LS, Kozak A, Ergul A, Hess DC, Borlongan CV, Fagan SC: Delayed minocycline inhibits ischemia-activated matrix metalloproteinases 2 and 9 after experimental stroke. BMC Neurosci. 2006 Jul 17;7:56. [PubMed:16846501 ]
General function:
Involved in growth factor activity
Specific function:
Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of blood vessels. Binds to the FLT1/VEGFR1 and KDR/VEGFR2 receptors, heparan sulfate and heparin. NRP1/Neuropilin-1 binds isoforms VEGF-165 and VEGF-145. Isoform VEGF165B binds to KDR but does not activate downstream signaling pathways, does not activate angiogenesis and inhibits tumor growth
Gene Name:
VEGFA
Uniprot ID:
P15692
Molecular weight:
27042.2
References
  1. Sasamura H, Takahashi A, Miyao N, Yanase M, Masumori N, Kitamura H, Itoh N, Tsukamoto T: Inhibitory effect on expression of angiogenic factors by antiangiogenic agents in renal cell carcinoma. Br J Cancer. 2002 Mar 4;86(5):768-73. [PubMed:11875741 ]
  2. Yao JS, Chen Y, Zhai W, Xu K, Young WL, Yang GY: Minocycline exerts multiple inhibitory effects on vascular endothelial growth factor-induced smooth muscle cell migration: the role of ERK1/2, PI3K, and matrix metalloproteinases. Circ Res. 2004 Aug 20;95(4):364-71. Epub 2004 Jul 15. [PubMed:15256478 ]
  3. Rocchetti R, Talevi S, Margiotta C, Calza R, Corallini A, Possati L: Antiangiogenic drugs for chemotherapy of bladder tumours. Chemotherapy. 2005 Oct;51(6):291-9. Epub 2005 Oct 13. [PubMed:16224178 ]
General function:
Involved in protein binding
Specific function:
Thiol protease that cleaves IL-1 beta between an Asp and an Ala, releasing the mature cytokine which is involved in a variety of inflammatory processes. Important for defense against pathogens. Cleaves and activates sterol regulatory element binding proteins (SREBPs). Can also promote apoptosis
Gene Name:
CASP1
Uniprot ID:
P29466
Molecular weight:
45158.2
References
  1. Chen M, Ona VO, Li M, Ferrante RJ, Fink KB, Zhu S, Bian J, Guo L, Farrell LA, Hersch SM, Hobbs W, Vonsattel JP, Cha JH, Friedlander RM: Minocycline inhibits caspase-1 and caspase-3 expression and delays mortality in a transgenic mouse model of Huntington disease. Nat Med. 2000 Jul;6(7):797-801. [PubMed:10888929 ]
  2. Sanchez Mejia RO, Ona VO, Li M, Friedlander RM: Minocycline reduces traumatic brain injury-mediated caspase-1 activation, tissue damage, and neurological dysfunction. Neurosurgery. 2001 Jun;48(6):1393-9; discussion 1399-401. [PubMed:11383749 ]
  3. Vincent JA, Mohr S: Inhibition of caspase-1/interleukin-1beta signaling prevents degeneration of retinal capillaries in diabetes and galactosemia. Diabetes. 2007 Jan;56(1):224-30. [PubMed:17192486 ]
  4. Kim HS, Suh YH: Minocycline and neurodegenerative diseases. Behav Brain Res. 2009 Jan 23;196(2):168-79. doi: 10.1016/j.bbr.2008.09.040. Epub 2008 Oct 11. [PubMed:18977395 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular weight:
59970.9
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 ]
General function:
Involved in ion 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). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
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 ]
General function:
Involved in transmembrane transport
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:
60025.0
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 ]