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Identification
NameOxaliplatin
Accession NumberDB00526  (APRD00186)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionOxaliplatin is a platinum-based chemotherapy drug in the same family as cisplatin and carboplatin. It is typically administered in combination with fluorouracil and leucovorin in a combination known as Folfox for the treatment of colorectal cancer. Compared to cisplatin the two amine groups are replaced by cyclohexyldiamine for improved antitumour activity. The chlorine ligands are replaced by the oxalato bidentate derived from oxalic acid in order to improve water solubility. Oxaliplatin is marketed by Sanofi-Aventis under the trademark Eloxatin®.
Structure
Thumb
Synonyms
Diaminocyclohexane Oxalatoplatinum
L-OHP
Oxalatoplatin
Oxalatoplatinum
oxaliplatine
oxaliplatino
oxaliplatinum
External Identifiers
  • JM-83
  • NSC-266046
  • RP-54780
  • SR-96669
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Oxaliplatinsolution5 mgintravenousActavis Pharma Company2015-12-16Not applicableCanada
Act Oxaliplatinpowder for solution100 mgintravenousActavis Pharma CompanyNot applicableNot applicableCanada
Act Oxaliplatinpowder for solution50 mgintravenousActavis Pharma CompanyNot applicableNot applicableCanada
Eloxatininjection, solution, concentrate5 mg/mLintravenousSanofi Aventis U.S. Llc2006-06-02Not applicableUs
Eloxatinsolution5 mgintravenousSanofi Aventis Canada Inc2007-07-17Not applicableCanada
Eloxatininjection, solution, concentrate5 mg/mLintravenousAventis Pharma Ltd.2009-07-22Not applicableUs
Eloxatininjection, solution, concentrate5 mg/mLintravenousSanofi Aventis U.S. Llc2006-06-02Not applicableUs
Eloxatinpowder for solution50 mgintravenousSanofi Aventis Canada Inc2008-06-272016-08-03Canada
Eloxatinpowder for solution100 mgintravenousSanofi Aventis Canada Inc2008-06-272016-08-04Canada
Oxaliplatininjection, solution, concentrate5 mg/mLintravenousWinthrop U.S.2015-09-01Not applicableUs
Oxaliplatininjection, solution, concentrate5 mg/mLintravenousWinthrop U.S.2014-07-07Not applicableUs
Oxaliplatinsolution5 mgintravenousHospira Healthcare Corporation2015-12-17Not applicableCanada
Oxaliplatininjection, solution, concentrate5 mg/mLintravenousWinthrop U.S.2014-07-07Not applicableUs
Oxaliplatininjection, solution, concentrate50 mg/10mLintravenousAPP Pharmaceuticals, LLC2014-09-082016-03-31Us
Oxaliplatininjection, solution, concentrate50 mg/10mLintravenousTeva Parenteral Medicines, Inc.2009-08-11Not applicableUs
Oxaliplatininjection, solution, concentrate5 mg/mLintravenousWinthrop U.S.2015-09-01Not applicableUs
Oxaliplatininjection, solution, concentrate100 mg/20mLintravenousAPP Pharmaceuticals, LLC2014-09-08Not applicableUs
Oxaliplatininjection, solution, concentrate100 mg/20mLintravenousTeva Parenteral Medicines, Inc.2009-08-11Not applicableUs
Oxaliplatin for Injectionpowder for solution50 mgintravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Oxaliplatin for Injectionpowder for solution100 mgintravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Oxaliplatin Injectionsolution5 mgintravenousGeneric Medical Partners IncNot applicableNot applicableCanada
Oxaliplatin Injectionsolution5 mgintravenousTeva Canada Limited2015-12-16Not applicableCanada
Oxaliplatin Injectionsolution5 mgintravenousAccord Healthcare Inc2016-01-02Not applicableCanada
Oxaliplatin Injectionsolution5 mgintravenousSandoz Canada Incorporated2015-12-17Not applicableCanada
Oxaliplatin Injectionsolution5.0 mgintravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Oxaliplatin Injection USPsolution5 mgintravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
PMS-oxaliplatinsolution5 mgintravenousPharmascience Inc2015-12-16Not applicableCanada
Taro-oxaliplatinsolution5 mgintravenousTaro Pharmaceuticals IncNot applicableNot applicableCanada
Teva-oxaliplatin Injectionsolution5 mgintravenousTeva Canada LimitedNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxaliplatininjection, powder, lyophilized, for solution5 mg/mLintravenousSagent Pharmaceuticals2012-08-09Not applicableUs
Oxaliplatinpowder, for solution50 mg/10mLintravenousPfizer Laboratories Div Pfizer Inc.2012-08-09Not applicableUs
Oxaliplatininjection, powder, lyophilized, for solution5 mg/mLintravenousHospira Worldwide, Inc.2009-09-30Not applicableUs
Oxaliplatininjection, solution, concentrate100 mg/20mLintravenousSun Pharma Global FZE2014-04-09Not applicableUs
Oxaliplatininjection, solution5 mg/mLintravenousSandoz Inc2015-03-01Not applicableUs
Oxaliplatinpowder, for solution50 mg/10mLintravenousMylan Institutional LLC2012-08-09Not applicableUs
Oxaliplatininjection, solution5 mg/mLintravenousSagent Pharmaceuticals2014-09-15Not applicableUs
Oxaliplatininjection, solution5 mg/mLintravenousPfizer Laboratories Div Pfizer Inc.2012-08-09Not applicableUs
Oxaliplatininjection, solution, concentrate5 mg/mLintravenousHospira Worldwide, Inc.2009-08-07Not applicableUs
Oxaliplatininjection, powder, lyophilized, for solution50 mg/10mLintravenousSun Pharma Global FZE2009-08-19Not applicableUs
Oxaliplatininjection, solution5 mg/mLintravenousSandoz Inc2015-03-01Not applicableUs
Oxaliplatininjection, solution5 mg/mLintravenousMylan Institutional LLC2012-08-09Not applicableUs
Oxaliplatininjection, powder, lyophilized, for solution5 mg/mLintravenousActavis Pharma, Inc.2015-01-05Not applicableUs
Oxaliplatininjection, solution5 mg/mLintravenousPfizer Laboratories Div Pfizer Inc.2012-08-09Not applicableUs
Oxaliplatininjection, solution, concentrate5 mg/mLintravenousFresenius Kabi USA, LLC2010-06-11Not applicableUs
Oxaliplatininjection, powder, lyophilized, for solution100 mg/20mLintravenousSun Pharma Global FZE2009-08-19Not applicableUs
Oxaliplatininjection, powder, lyophilized, for solution5 mg/mLintravenousSagent Pharmaceuticals2012-08-09Not applicableUs
Oxaliplatinpowder, for solution100 mg/20mLintravenousMylan Institutional LLC2012-08-09Not applicableUs
Oxaliplatininjection, solution, concentrate50 mg/10mLintravenousSun Pharma Global FZE2014-04-09Not applicableUs
Oxaliplatinpowder, for solution100 mg/20mLintravenousPfizer Laboratories Div Pfizer Inc.2012-08-09Not applicableUs
Oxaliplatininjection, solution5 mg/mLintravenousMylan Institutional LLC2012-08-09Not applicableUs
Oxaliplatininjection, powder, lyophilized, for solution5 mg/mLintravenousHospira Worldwide, Inc.2009-09-30Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII04ZR38536J
CAS number61825-94-3
WeightAverage: 397.294
Monoisotopic: 397.060149
Chemical FormulaC8H14N2O4Pt
InChI KeyZROHGHOFXNOHSO-BNTLRKBRSA-L
InChI
InChI=1S/C6H14N2.C2H2O4.Pt/c7-5-3-1-2-4-6(5)8;3-1(4)2(5)6;/h5-6H,1-4,7-8H2;(H,3,4)(H,5,6);/q;;+2/p-2/t5-,6-;;/m1../s1
IUPAC Name
(3aR,7aR)-octahydro-2',5'-dioxaspiro[cyclohexa[d]1,3-diaza-2-platinacyclopentane-2,1'-cyclopentane]-3',4'-dione
SMILES
[H][N]1([H])[C@@H]2CCCC[[email protected]]2[N]([H])([H])[Pt]11OC(=O)C(=O)O1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclohexylamines. These are organic compounds containing a cyclohexylamine moiety, which consist of a cyclohexane ring attached to an amine group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassCyclohexylamines
Direct ParentCyclohexylamines
Alternative Parents
Substituents
  • Cyclohexylamine
  • Dicarboxylic acid or derivatives
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic transition metal salt
  • Amine
  • Carbonyl group
  • Primary amine
  • Organooxygen compound
  • Primary aliphatic amine
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic cation
  • Aliphatic homomonocyclic compound
Molecular FrameworkNot Available
External Descriptors
Pharmacology
IndicationUsed in combination with infusional 5-FU/LV, is indicated for the treatment of advanced carcinoma of the colon or rectum and for adjuvant treatment of stage III colon cancer patients who have undergone complete resection of the primary tumor.
PharmacodynamicsOxaliplatin selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of Oxaliplatin-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed.
Mechanism of actionOxaliplatin undergoes nonenzymatic conversion to active derivatives via displacement of the labile oxalate ligand. Several transient reactive species are formed, including monoaquo and diaquo DACH platinum, which covalently bind with macromolecules. After activation, oxaliplatin binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and transcription. Cytotoxicity is cell-cycle nonspecific.
Related Articles
AbsorptionBioavailability is complete following intravenous administration. When a single 2-hour intravenous infusion of oxaliplatin at a dose of 85 mg/m^2 is given, the peak serum concentration was 0.814 mcg/mL.
Volume of distribution
  • 440 L [single 2-hour IV infusion at dose of 85 mg/m^2]
    At the end of a 2-hour infusion of oxaliplatin, approximately 15% of the administered platinum is present in the systemic circulation. The remaining 85% is rapidly distributed into tissues or eliminated in the urine.
Protein bindingPlasma protein binding of platinum (active metabolite) is irreversible and is greater than 90%, primarily to albumin and gamma-globulins. It is also irreversibly binds to erythrocytes.
Metabolism

Oxaliplatin undergoes nonenzymatic conversion in physiologic solutions to active derivatives via displacement of the labile oxalate ligand. Several transient reactive species are formed, including monoaquo and diaquo DACH platinum, which covalently bind with macromolecules. There is no evidence of cytochrome P450-mediated metabolism in vitro.

Route of eliminationThe major route of platinum elimination is renal excretion. At five days after a single 2-hour infusion of oxaliplatin, urinary elimination accounted for about 54% of the platinum eliminated, with fecal excretion accounting for only about 2%.
Half lifeThe decline of ultrafilterable platinum levels following oxaliplatin administartion is triphasic, with two distribution phases: t1/2α; 0.43 hours and t1/2β; 16.8 hours. This is followed by a long terminal elimination phase that lasts 391 hours (t1/2γ).
Clearance
  • 10 – 17 L/h [renal clearance]
ToxicityThere have been five cases of oxaliplatin overdose reported. One patient received two 130 mg/m2 doses of oxaliplatin (cumulative dose of 260 mg/m2) within a 24-hour period. The patient experienced Grade 4 thrombocytopenia (<25,000/mm3) without any bleeding, which resolved. Two other patients were mistakenly administered oxaliplatin instead of carboplatin. One patient received a total oxaliplatin dose of 500 mg and the other received 650 mg. The first patient experienced dyspnea, wheezing, paresthesia, profuse vomiting and chest pain on the day of administration. She developed respiratory failure and severe bradycardia, and subsequently did not respond to resuscitation efforts. The other patient also experienced dyspnea, wheezing, paresthesia, and vomiting. Most common adverse reactions (incidence ≥ 40%) were peripheral sensory neuropathy, neutropenia, thrombocytopenia, anemia, nausea, increase in transaminases and alkaline phosphatase, diarrhea, emesis, fatigue and stomatitis.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8638
Blood Brain Barrier+0.7667
Caco-2 permeable-0.6453
P-glycoprotein substrateSubstrate0.5056
P-glycoprotein inhibitor INon-inhibitor0.9332
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9289
CYP450 2C9 substrateNon-substrate0.8846
CYP450 2D6 substrateNon-substrate0.8094
CYP450 3A4 substrateNon-substrate0.6064
CYP450 1A2 substrateNon-inhibitor0.8403
CYP450 2C9 inhibitorNon-inhibitor0.8686
CYP450 2D6 inhibitorNon-inhibitor0.8997
CYP450 2C19 inhibitorNon-inhibitor0.8189
CYP450 3A4 inhibitorNon-inhibitor0.8337
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9872
Ames testNon AMES toxic0.6034
CarcinogenicityNon-carcinogens0.938
BiodegradationNot ready biodegradable0.9796
Rat acute toxicity2.3765 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8879
hERG inhibition (predictor II)Non-inhibitor0.938
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • App pharmaceuticals llc
  • Ebewe pharma ges mbh nfg kg
  • Fresenius kabi oncology plc
  • Hospira inc
  • Hospira worldwide pty
  • Sun pharma global inc
  • Teva parenteral medicines inc
Packagers
Dosage forms
FormRouteStrength
Injection, solution, concentrateintravenous5 mg/mL
Solutionintravenous5 mg
Injection, powder, lyophilized, for solutionintravenous100 mg/20mL
Injection, powder, lyophilized, for solutionintravenous5 mg/mL
Injection, powder, lyophilized, for solutionintravenous50 mg/10mL
Injection, solutionintravenous5 mg/mL
Injection, solution, concentrateintravenous100 mg/20mL
Injection, solution, concentrateintravenous50 mg/10mL
Powder, for solutionintravenous100 mg/20mL
Powder, for solutionintravenous50 mg/10mL
Powder for solutionintravenous100 mg
Powder for solutionintravenous50 mg
Solutionintravenous5.0 mg
Prices
Unit descriptionCostUnit
Oxaliplatin 100 mg vial1650.0USD vial
Oxaliplatin 50 mg vial825.0USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2196922 No2004-06-012015-08-07Canada
US5290961 No1993-01-122013-01-12Us
US5420319 Yes1997-02-092017-02-09Us
US5716988 Yes1996-02-072016-02-07Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility27.5 mg/mLALOGPS
logP-0.47ALOGPS
logS-1.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area85.82 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity67.52 m3·mol-1ChemAxon
Polarizability21.9 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Masazumi Eriguchi, “Liposome preparations containing oxaliplatin.” U.S. Patent US20040022842, issued February 05, 2004.

US20040022842
General References
  1. Pasetto LM, D'Andrea MR, Rossi E, Monfardini S: Oxaliplatin-related neurotoxicity: how and why? Crit Rev Oncol Hematol. 2006 Aug;59(2):159-68. Epub 2006 Jun 27. [PubMed:16806962 ]
  2. Graham J, Mushin M, Kirkpatrick P: Oxaliplatin. Nat Rev Drug Discov. 2004 Jan;3(1):11-2. [PubMed:14756144 ]
External Links
ATC CodesL01XA03
AHFS Codes
  • 10:00
PDB EntriesNot Available
FDA labelDownload (2.35 MB)
MSDSDownload (38.4 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Oxaliplatin can be increased when it is combined with Abiraterone.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Oxaliplatin.
AzithromycinThe metabolism of Oxaliplatin can be decreased when combined with Azithromycin.
BevacizumabBevacizumab may increase the cardiotoxic activities of Oxaliplatin.
BortezomibThe metabolism of Oxaliplatin can be decreased when combined with Bortezomib.
BupropionThe serum concentration of Oxaliplatin can be increased when it is combined with Bupropion.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Oxaliplatin.
CaffeineThe metabolism of Oxaliplatin can be decreased when combined with Caffeine.
CarbamazepineThe metabolism of Oxaliplatin can be increased when combined with Carbamazepine.
CitalopramThe metabolism of Oxaliplatin can be decreased when combined with Citalopram.
ClotrimazoleThe metabolism of Oxaliplatin can be decreased when combined with Clotrimazole.
ClozapineThe risk or severity of adverse effects can be increased when Oxaliplatin is combined with Clozapine.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Oxaliplatin.
Cyproterone acetateThe serum concentration of Oxaliplatin can be decreased when it is combined with Cyproterone acetate.
DeferasiroxThe serum concentration of Oxaliplatin can be increased when it is combined with Deferasirox.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Oxaliplatin.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Oxaliplatin.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Oxaliplatin.
DigoxinDigoxin may decrease the cardiotoxic activities of Oxaliplatin.
DisulfiramThe metabolism of Oxaliplatin can be decreased when combined with Disulfiram.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Oxaliplatin.
EltrombopagThe serum concentration of Oxaliplatin can be increased when it is combined with Eltrombopag.
FingolimodOxaliplatin may increase the immunosuppressive activities of Fingolimod.
FluvoxamineThe metabolism of Oxaliplatin can be decreased when combined with Fluvoxamine.
IsoniazidThe metabolism of Oxaliplatin can be decreased when combined with Isoniazid.
LeflunomideThe risk or severity of adverse effects can be increased when Oxaliplatin is combined with Leflunomide.
LidocaineThe metabolism of Oxaliplatin can be decreased when combined with Lidocaine.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Oxaliplatin.
MexiletineThe metabolism of Oxaliplatin can be decreased when combined with Mexiletine.
NatalizumabThe risk or severity of adverse effects can be increased when Oxaliplatin is combined with Natalizumab.
NevirapineThe metabolism of Oxaliplatin can be decreased when combined with Nevirapine.
NicotineThe metabolism of Oxaliplatin can be decreased when combined with Nicotine.
OsimertinibThe serum concentration of Oxaliplatin can be decreased when it is combined with Osimertinib.
OuabainOuabain may decrease the cardiotoxic activities of Oxaliplatin.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Oxaliplatin.
Peginterferon alfa-2bThe serum concentration of Oxaliplatin can be increased when it is combined with Peginterferon alfa-2b.
PhenobarbitalThe metabolism of Oxaliplatin can be increased when combined with Phenobarbital.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Oxaliplatin.
PrimidoneThe metabolism of Oxaliplatin can be increased when combined with Primidone.
Rabies vaccineThe risk or severity of adverse effects can be increased when Oxaliplatin is combined with Rabies vaccine.
RifampicinThe metabolism of Oxaliplatin can be increased when combined with Rifampicin.
RoflumilastRoflumilast may increase the immunosuppressive activities of Oxaliplatin.
RolapitantThe serum concentration of Oxaliplatin can be increased when it is combined with Rolapitant.
RopiniroleThe metabolism of Oxaliplatin can be decreased when combined with Ropinirole.
SimeprevirThe metabolism of Oxaliplatin can be decreased when combined with Simeprevir.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Oxaliplatin.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Oxaliplatin.
TenofovirThe metabolism of Oxaliplatin can be decreased when combined with Tenofovir.
TeriflunomideThe serum concentration of Oxaliplatin can be decreased when it is combined with Teriflunomide.
TheophyllineThe metabolism of Oxaliplatin can be decreased when combined with Theophylline.
TiclopidineThe metabolism of Oxaliplatin can be decreased when combined with Ticlopidine.
TofacitinibOxaliplatin may increase the immunosuppressive activities of Tofacitinib.
TrastuzumabTrastuzumab may increase the neutropenic activities of Oxaliplatin.
VemurafenibThe serum concentration of Oxaliplatin can be increased when it is combined with Vemurafenib.
Food InteractionsNot Available

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
cross-linking/alkylation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Sharma S, Gong P, Temple B, Bhattacharyya D, Dokholyan NV, Chaney SG: Molecular dynamic simulations of cisplatin- and oxaliplatin-d(GG) intrastand cross-links reveal differences in their conformational dynamics. J Mol Biol. 2007 Nov 9;373(5):1123-40. Epub 2007 Aug 23. [PubMed:17900616 ]
  4. Zhu G, Chang P, Lippard SJ: Recognition of platinum-DNA damage by poly(ADP-ribose) polymerase-1. Biochemistry. 2010 Jul 27;49(29):6177-83. doi: 10.1021/bi100775t. [PubMed:20550106 ]
  5. Ramachandran S, Temple BR, Chaney SG, Dokholyan NV: Structural basis for the sequence-dependent effects of platinum-DNA adducts. Nucleic Acids Res. 2009 May;37(8):2434-48. doi: 10.1093/nar/gkp029. Epub 2009 Mar 2. [PubMed:19255091 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d 24-hydroxylase 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:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
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, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compou...
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular Weight:
60845.33 Da
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 ]
  2. Song IS, Savaraj N, Siddik ZH, Liu P, Wei Y, Wu CJ, Kuo MT: Role of human copper transporter Ctr1 in the transport of platinum-based antitumor agents in cisplatin-sensitive and cisplatin-resistant cells. Mol Cancer Ther. 2004 Dec;3(12):1543-9. [PubMed:15634647 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glutathione transferase activity
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Acts on 1,2-epoxy-3-(4-nitrophenoxy)propane, phenethylisothiocyanate 4-nitrobenzyl chloride and 4-nitrophenethyl bromide. Displays glutathione peroxidase activity with cumene hydroperoxide.
Gene Name:
GSTT1
Uniprot ID:
P30711
Molecular Weight:
27334.755 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Zinc ion binding
Specific Function:
Metallothioneins have a high content of cysteine residues that bind various heavy metals; these proteins are transcriptionally regulated by both heavy metals and glucocorticoids.
Gene Name:
MT1A
Uniprot ID:
P04731
Molecular Weight:
6120.19 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Zinc ion binding
Specific Function:
Metallothioneins have a high content of cysteine residues that bind various heavy metals; these proteins are transcriptionally regulated by both heavy metals and glucocorticoids.
Gene Name:
MT2A
Uniprot ID:
P02795
Molecular Weight:
6042.05 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Peroxidase activity
Specific Function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular Weight:
83867.71 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Zinc ion binding
Specific Function:
Destroys radicals which are normally produced within the cells and which are toxic to biological systems.
Gene Name:
SOD1
Uniprot ID:
P00441
Molecular Weight:
15935.685 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
S-nitrosoglutathione binding
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name:
GSTP1
Uniprot ID:
P09211
Molecular Weight:
23355.625 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Protein homodimerization activity
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM1
Uniprot ID:
P09488
Molecular Weight:
25711.555 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Superoxide dismutase activity
Specific Function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO1
Uniprot ID:
P15559
Molecular Weight:
30867.405 Da
References
  1. Link [Link]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Quaternary ammonium group 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-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Burger H, Zoumaro-Djayoon A, Boersma AW, Helleman J, Berns EM, Mathijssen RH, Loos WJ, Wiemer EA: Differential transport of platinum compounds by the human organic cation transporter hOCT2 (hSLC22A2). Br J Pharmacol. 2010 Feb;159(4):898-908. doi: 10.1111/j.1476-5381.2009.00569.x. Epub 2010 Jan 8. [PubMed:20067471 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Ahlin G, Karlsson J, Pedersen JM, Gustavsson L, Larsson R, Matsson P, Norinder U, Bergstrom CA, Artursson P: Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1. J Med Chem. 2008 Oct 9;51(19):5932-42. doi: 10.1021/jm8003152. Epub 2008 Sep 13. [PubMed:18788725 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Copper uptake transmembrane transporter activity
Specific Function:
High-affinity, saturable copper transporter involved in dietary copper uptake.
Gene Name:
SLC31A1
Uniprot ID:
O15431
Molecular Weight:
21090.545 Da
References
  1. Howell SB, Safaei R, Larson CA, Sailor MJ: Copper transporters and the cellular pharmacology of the platinum-containing cancer drugs. Mol Pharmacol. 2010 Jun;77(6):887-94. doi: 10.1124/mol.109.063172. Epub 2010 Feb 16. [PubMed:20159940 ]
  2. Song IS, Savaraj N, Siddik ZH, Liu P, Wei Y, Wu CJ, Kuo MT: Role of human copper transporter Ctr1 in the transport of platinum-based antitumor agents in cisplatin-sensitive and cisplatin-resistant cells. Mol Cancer Ther. 2004 Dec;3(12):1543-9. [PubMed:15634647 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Toxin transporter activity
Specific Function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular Weight:
61279.485 Da
References
  1. Yokoo S, Masuda S, Yonezawa A, Terada T, Katsura T, Inui K: Significance of organic cation transporter 3 (SLC22A3) expression for the cytotoxic effect of oxaliplatin in colorectal cancer. Drug Metab Dispos. 2008 Nov;36(11):2299-306. doi: 10.1124/dmd.108.023168. Epub 2008 Aug 18. [PubMed:18710896 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular Weight:
72313.47 Da
References
  1. Ceckova M, Vackova Z, Radilova H, Libra A, Buncek M, Staud F: Effect of ABCG2 on cytotoxicity of platinum drugs: interference of EGFP. Toxicol In Vitro. 2008 Dec;22(8):1846-52. doi: 10.1016/j.tiv.2008.09.001. Epub 2008 Sep 9. [PubMed:18801423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Organic anion transmembrane transporter activity
Specific Function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular Weight:
174205.64 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Copper-exporting atpase activity
Specific Function:
Involved in the export of copper out of the cells, such as the efflux of hepatic copper into the bile.
Gene Name:
ATP7B
Uniprot ID:
P35670
Molecular Weight:
157261.34 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Superoxide dismutase copper chaperone activity
Specific Function:
May supply copper to copper-requiring proteins within the secretory pathway, when localized in the trans-Golgi network. Under conditions of elevated extracellular copper, it relocalized to the plasma membrane where it functions in the efflux of copper from cells.
Gene Name:
ATP7A
Uniprot ID:
Q04656
Molecular Weight:
163372.275 Da
References
  1. Link [Link]
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Drug created on June 13, 2005 07:24 / Updated on September 29, 2016 03:39