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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:54 UTC
HMDB IDHMDB0015235
Secondary Accession Numbers
  • HMDB15235
Metabolite Identification
Common NameQuinacrine
Descriptionquinacrine, also known as mepacrine, belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring. Based on a literature review a small amount of articles have been published on quinacrine.
Structure
Data?1582753273
Synonyms
ValueSource
2-Methoxy-6-chloro-9-diethylaminopentylaminoacridineChEBI
3-Chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridineChEBI
6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridineChEBI
MepacrineChEBI
N(4)-(6-Chloro-2-methoxy-9-acridinyl)-N(1),N(1)-diethyl-1,4-pentanediamineChEBI
QuinacrinKegg
Quinacrine dihydrochlorideHMDB, MeSH
Monomesylate, quinacrineMeSH, HMDB
Quinacrine dimesylateMeSH, HMDB
Quinacrine, (R)-isomerMeSH, HMDB
AcrichineMeSH, HMDB
Dihydrochloride, quinacrineMeSH, HMDB
Dimesylate, quinacrineMeSH, HMDB
Quinacrine hydrochlorideMeSH, HMDB
Quinacrine monoacetateMeSH, HMDB
Quinacrine monomesylateMeSH, HMDB
AtebrinMeSH, HMDB
Monohydrochloride, quinacrineMeSH, HMDB
Quinacrine dihyrochloride, (S)-isomerMeSH, HMDB
Quinacrine monohydrochlorideMeSH, HMDB
Quinacrine, (+-)-isomerMeSH, HMDB
Quinacrine, (S)-isomerMeSH, HMDB
AtabrineMeSH, HMDB
Hydrochloride, quinacrineMeSH, HMDB
Monoacetate, quinacrineMeSH, HMDB
Quinacrine dihydrochloride, dihydrateMeSH, HMDB
Quinacrine dihyrochloride, (R)-isomerMeSH, HMDB
Chemical FormulaC23H30ClN3O
Average Molecular Weight399.957
Monoisotopic Molecular Weight399.207740304
IUPAC Name6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine
Traditional Name6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine
CAS Registry Number83-89-6
SMILES
CCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C2
InChI Identifier
InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)
InChI KeyGPKJTRJOBQGKQK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridines
Alternative Parents
Substituents
  • Acridine
  • Haloquinoline
  • Chloroquinoline
  • Anisole
  • Alkyl aryl ether
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Benzenoid
  • Secondary ketimine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Azacycle
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point248 - 250 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0024 g/LNot Available
LogP5.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available195.668http://allccs.zhulab.cn/database/detail?ID=AllCCS00000989
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP6.13ALOGPS
logP5.15ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)10.33ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.39 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.96 m³·mol⁻¹ChemAxon
Polarizability46.32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+194.81330932474
DeepCCS[M-H]-192.37430932474
DeepCCS[M-2H]-226.89430932474
DeepCCS[M+Na]+203.18530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
QuinacrineCCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C24442.3Standard polar33892256
QuinacrineCCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C23275.3Standard non polar33892256
QuinacrineCCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C23326.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Quinacrine,1TMS,isomer #1CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C3163.2Semi standard non polar33892256
Quinacrine,1TMS,isomer #1CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C2820.3Standard non polar33892256
Quinacrine,1TMS,isomer #1CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C3866.6Standard polar33892256
Quinacrine,1TBDMS,isomer #1CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C(C)(C)C3336.3Semi standard non polar33892256
Quinacrine,1TBDMS,isomer #1CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C(C)(C)C3077.7Standard non polar33892256
Quinacrine,1TBDMS,isomer #1CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C(C)(C)C3927.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Quinacrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9025000000-fbef6d955948eb7f2a3f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinacrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinacrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinacrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , negative-QTOFsplash10-0002-0009200000-6e09844cb8551172f45c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , negative-QTOFsplash10-0002-0009200000-242960dc93e3658182f02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , negative-QTOFsplash10-0002-0019100000-85abeddd06ff2cce1fc92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0000900000-171d21b8fffe35f493d32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , positive-QTOFsplash10-0udl-0423900000-9f5ab94c444b1766bd012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , positive-QTOFsplash10-0006-0934000000-afa177ceaf2f17c891802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , positive-QTOFsplash10-0006-0964000000-cb8056f84bdb3a200fba2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , positive-QTOFsplash10-0006-0591000000-00e303f9525d62f012d42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine 10V, Positive-QTOFsplash10-0udi-0000900000-171d21b8fffe35f493d32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine 20V, Positive-QTOFsplash10-0udl-0423900000-9f5ab94c444b1766bd012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine 40V, Positive-QTOFsplash10-0006-0964000000-cb8056f84bdb3a200fba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine 30V, Positive-QTOFsplash10-0006-0934000000-afa177ceaf2f17c891802021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine 20V, Negative-QTOFsplash10-0002-0009200000-242960dc93e3658182f02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine 30V, Negative-QTOFsplash10-0002-0019100000-85abeddd06ff2cce1fc92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine 10V, Negative-QTOFsplash10-0002-0009200000-6e09844cb8551172f45c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine 50V, Positive-QTOFsplash10-0006-0591000000-00e303f9525d62f012d42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine 50V, Positive-QTOFsplash10-0006-0591000000-ec7a34b139a1f19af5f12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinacrine 20V, Positive-QTOFsplash10-0002-0009200000-d6edfe4dda8af03dcf552021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinacrine 10V, Positive-QTOFsplash10-0udi-0002900000-f41646003acc390ed8bb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinacrine 20V, Positive-QTOFsplash10-0zfu-4975600000-ad273f8cfc82a9f76e9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinacrine 40V, Positive-QTOFsplash10-009f-9251000000-556ea0aa9d5a370006a72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinacrine 10V, Negative-QTOFsplash10-0002-0009000000-b9379b7c57314e49af302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinacrine 20V, Negative-QTOFsplash10-0002-0019000000-79e7dea5a1914a86d0082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinacrine 40V, Negative-QTOFsplash10-00di-9065000000-35833408615f0d3aa74a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinacrine 10V, Positive-QTOFsplash10-0udi-0000900000-f4b3bd614216642b10252021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01103 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01103 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID232
KEGG Compound IDC07339
BioCyc IDATABRINE
BiGG IDNot Available
Wikipedia LinkQuinacrine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID8711
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bhatt RV: Camp laparoscopic sterilization deaths in Gujarat State, India, 1978-1980. Asia Oceania J Obstet Gynaecol. 1991 Dec;17(4):297-301. [PubMed:1839351 ]
  2. Zipper J, Cole LP, Goldsmith A, Wheeler R, Rivera M: Quinacrine hydrochloride pellets: preliminary data on a nonsurgical method of female sterilization. Int J Gynaecol Obstet. 1980;18(4):275-9. [PubMed:6109672 ]
  3. Peterson HB, Lubell I, DeStefano F, Ory HW: The safety and efficacy of tubal sterilization: an international overview. Int J Gynaecol Obstet. 1983 Apr;21(2):139-44. [PubMed:6136433 ]
  4. Toubi E, Kessel A, Rosner I, Rozenbaum M, Paran D, Shoenfeld Y: The reduction of serum B-lymphocyte activating factor levels following quinacrine add-on therapy in systemic lupus erythematosus. Scand J Immunol. 2006 Apr;63(4):299-303. [PubMed:16623930 ]
  5. Canete R, Escobedo AA, Gonzalez ME, Almirall P: Randomized clinical study of five days apostrophe therapy with mebendazole compared to quinacrine in the treatment of symptomatic giardiasis in children. World J Gastroenterol. 2006 Oct 21;12(39):6366-70. [PubMed:17072963 ]

Enzymes

General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
References
  1. Hellstrand M, Eriksson E, Nilsson CL: Dopamine D(2) receptor-induced COX-2-mediated production of prostaglandin E(2) in D(2)-transfected Chinese hamster ovary cells without simultaneous administration of a Ca(2+)-mobilizing agent. Biochem Pharmacol. 2002 Jun 15;63(12):2151-8. [PubMed:12110374 ]
  2. Ong WY, Lu XR, Ong BK, Horrocks LA, Farooqui AA, Lim SK: Quinacrine abolishes increases in cytoplasmic phospholipase A2 mRNA levels in the rat hippocampus after kainate-induced neuronal injury. Exp Brain Res. 2003 Feb;148(4):521-4. Epub 2002 Dec 11. [PubMed:12582837 ]
  3. Kim BC, Kim JH: Exogenous C2-ceramide activates c-fos serum response element via Rac-dependent signalling pathway. Biochem J. 1998 Mar 1;330 ( Pt 2):1009-14. [PubMed:9480923 ]
General function:
Involved in metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635
References
  1. Nuttle LC, Ligon AL, Farrell KR, Hester RL: Inhibition of phospholipase A2 attenuates functional hyperemia in the hamster cremaster muscle. Am J Physiol. 1999 Apr;276(4 Pt 2):H1289-94. [PubMed:10199854 ]
  2. Sastry BV, Hemontolor ME, Vidaver PS, Sastry WS, Janson VE: Influence of halothane on phospholipase A2 and enzymatic methylations in the rat retinal membranes. J Ocul Pharmacol Ther. 1999 Apr;15(2):165-78. [PubMed:10229494 ]
  3. Lohmann CH, Sagun R Jr, Sylvia VL, Cochran DL, Dean DD, Boyan BD, Schwartz Z: Surface roughness modulates the response of MG63 osteoblast-like cells to 1,25-(OH)(2)D(3) through regulation of phospholipase A(2) activity and activation of protein kinase A. J Biomed Mater Res. 1999 Nov;47(2):139-51. [PubMed:10449625 ]
  4. Schwartz Z, Sylvia VL, Del Toro F, Hardin RR, Dean DD, Boyan BD: 24R,25-(OH)(2)D(3) mediates its membrane receptor-dependent effects on protein kinase C and alkaline phosphatase via phospholipase A(2) and cyclooxygenase-1 but not cyclooxygenase-2 in growth plate chondrocytes. J Cell Physiol. 2000 Mar;182(3):390-401. [PubMed:10653606 ]
  5. Sylvia VL, Del Toro F, Dean DD, Hardin RR, Schwartz Z, Boyan BD: Effects of 1alpha,25-(OH)(2)D(3) on rat growth zone chondrocytes are mediated via cyclooxygenase-1 and phospholipase A(2). J Cell Biochem Suppl. 2001;Suppl 36:32-45. [PubMed:11455568 ]
General function:
Involved in histamine N-methyltransferase activity
Specific function:
Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name:
HNMT
Uniprot ID:
P50135
Molecular weight:
6045.9
References
  1. Grassmann S, Apelt J, Sippl W, Ligneau X, Pertz HH, Zhao YH, Arrang JM, Ganellin CR, Schwartz JC, Schunack W, Stark H: Imidazole derivatives as a novel class of hybrid compounds with inhibitory histamine N-methyltransferase potencies and histamine hH3 receptor affinities. Bioorg Med Chem. 2003 May 15;11(10):2163-74. [PubMed:12713826 ]
  2. Hui JY, Taylor SL: Inhibition of in vivo histamine metabolism in rats by foodborne and pharmacologic inhibitors of diamine oxidase, histamine N-methyltransferase, and monoamine oxidase. Toxicol Appl Pharmacol. 1985 Nov;81(2):241-9. [PubMed:3933141 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Tiberghien F, Loor F: Ranking of P-glycoprotein substrates and inhibitors by a calcein-AM fluorometry screening assay. Anticancer Drugs. 1996 Jul;7(5):568-78. [PubMed:8862725 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular weight:
62564.0
References
  1. Sweet DH, Pritchard JB: rOCT2 is a basolateral potential-driven carrier, not an organic cation/proton exchanger. Am J Physiol. 1999 Dec;277(6 Pt 2):F890-8. [PubMed:10600936 ]
  2. Dohgu S, Yamauchi A, Takata F, Sawada Y, Higuchi S, Naito M, Tsuruo T, Shirabe S, Niwa M, Katamine S, Kataoka Y: Uptake and efflux of quinacrine, a candidate for the treatment of prion diseases, at the blood-brain barrier. Cell Mol Neurobiol. 2004 Apr;24(2):205-17. [PubMed:15176436 ]
  3. Beck WT, Cirtain MC, Glover CJ, Felsted RL, Safa AR: Effects of indole alkaloids on multidrug resistance and labeling of P-glycoprotein by a photoaffinity analog of vinblastine. Biochem Biophys Res Commun. 1988 Jun 30;153(3):959-66. [PubMed:2898941 ]