Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C6H14N2.C2O4.Pt |
Molecular Weight | 397.292 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Pt++].[O-]C(=O)C([O-])=O.N[C@@H]1CCCC[C@H]1N
InChI
InChIKey=ZROHGHOFXNOHSO-BNTLRKBRSA-L
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
Oxaliplatin (brand name Eloxatin), a new generation of platinum derivatives discovered by Prof Kidani in 1976 at Nagoya University in Japan, was licensed-in and developed by Debiopharm. Eloxatin is typically administered in combination with fluorouracil and leucovorin for the adjuvant treatment of stage III colon cancer and for the treatment of advanced carcinoma of the colon or rectum. 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 1,2-diaminocyclohexane (DACH) platinum, which covalently bind with macromolecules. Both inter- and intrastrand Pt-DNA crosslinks are formed. Crosslinks are formed between the N7 positions of two adjacent guanines (GG), adjacent adenine-guanines (AG), and guanines separated by an intervening nucleotide (GNG). These crosslinks inhibit DNA replication and transcription. Cytotoxicity is cell-cycle nonspecific.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15746072
Curator's Comment: Known to be CNS non-penetrant in nonhuman primates. Human data not available
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19255091 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ELOXATIN Approved UseOxaliplatin, used in combination with infusional 5-fluorouracil/leucovorin, is indicated for: •adjuvant treatment of stage III colon cancer in patients who have undergone complete resection of the primary tumor. •treatment of advanced colorectal cancer. Oxaliplatin injection is a platinum-based drug used in combination with infusional 5-fluorouracil/leucovorin, which is indicated for: •adjuvant treatment of stage III colon cancer in patients who have undergone complete resection of the primary tumor. (1) •treatment of advanced colorectal cancer. (1) Launch Date2002 |
|||
Primary | ELOXATIN Approved UseOxaliplatin, used in combination with infusional 5-fluorouracil/leucovorin, is indicated for: •adjuvant treatment of stage III colon cancer in patients who have undergone complete resection of the primary tumor. •treatment of advanced colorectal cancer. Oxaliplatin injection is a platinum-based drug used in combination with infusional 5-fluorouracil/leucovorin, which is indicated for: •adjuvant treatment of stage III colon cancer in patients who have undergone complete resection of the primary tumor. (1) •treatment of advanced colorectal cancer. (1) Launch Date2002 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.66 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16395593 |
130 mg/m² 1 times / 3 weeks steady-state, intravenous dose: 130 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OXALIPLATIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
205.75 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16395593 |
130 mg/m² 1 times / 3 weeks steady-state, intravenous dose: 130 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OXALIPLATIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42.84 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16395593 |
130 mg/m² 1 times / 3 weeks steady-state, intravenous dose: 130 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OXALIPLATIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10% |
PLATINUM plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
130 mg/m2 single, intravenous Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy, 56 years n = 1 Health Status: unhealthy Condition: colorectal cancer Age Group: 56 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hypersensitivity reaction... AEs leading to discontinuation/dose reduction: Hypersensitivity reaction (1 patient) Sources: |
135 mg/m2 1 times / 4 weeks multiple, intravenous Dose: 135 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 135 mg/m2, 1 times / 4 weeks Sources: |
unhealthy, 57 years (range: 26-81 years) n = 14 Health Status: unhealthy Condition: advanced cancer Age Group: 57 years (range: 26-81 years) Sex: M+F Population Size: 14 Sources: |
DLT: Neurotoxicity... |
150 mg/m2 1 times / 4 weeks multiple, intravenous Dose: 150 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 150 mg/m2, 1 times / 4 weeks Sources: |
unhealthy, 57 years (range: 26-81 years) n = 14 Health Status: unhealthy Condition: advanced cancer Age Group: 57 years (range: 26-81 years) Sex: M+F Population Size: 14 Sources: |
DLT: Neurotoxicity... |
175 mg/m2 1 times / 4 weeks multiple, intravenous Dose: 175 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 175 mg/m2, 1 times / 4 weeks Sources: |
unhealthy, 57 years (range: 26-81 years) n = 7 Health Status: unhealthy Condition: advanced cancer Age Group: 57 years (range: 26-81 years) Sex: M+F Population Size: 7 Sources: |
DLT: Neurotoxicity... |
200 mg/m2 1 times / 4 weeks multiple, intravenous Dose: 200 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 200 mg/m2, 1 times / 4 weeks Co-administed with:: highest studied dose Sources: |
unhealthy, 57 years (range: 26-81 years) n = 5 Health Status: unhealthy Condition: advanced cancer Age Group: 57 years (range: 26-81 years) Sex: M+F Population Size: 5 Sources: |
DLT: Neurotoxicity... |
55 mg/m2 multiple, intravenous Dose: 55 mg/m2 Route: intravenous Route: multiple Dose: 55 mg/m2 Co-administed with:: 5-fluoruracil Sources: leucovorin |
unhealthy, 58 years n = 1 Health Status: unhealthy Condition: colon cancer Age Group: 58 years Sex: F Population Size: 1 Sources: |
Disc. AE: Thrombocytopenia... AEs leading to discontinuation/dose reduction: Thrombocytopenia (1 patient) Sources: |
150 mg/m2 1 times / 3 weeks single, intravenous (total) Dose: 150 mg/m2, 1 times / 3 weeks Route: intravenous Route: single Dose: 150 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 60 years (range: 33-75 years) n = 29 Health Status: unhealthy Age Group: 60 years (range: 33-75 years) Sex: M+F Population Size: 29 Sources: |
Disc. AE: Diarrhoea... AEs leading to discontinuation/dose reduction: Diarrhoea (grade 3, 1 patient) Sources: |
725 mg/m2 single, intravenous (total) Dose: 725 mg/m2 Route: intravenous Route: single Dose: 725 mg/m2 Sources: |
unhealthy, 60 years (range: 33-75 years) n = 29 Health Status: unhealthy Age Group: 60 years (range: 33-75 years) Sex: M+F Population Size: 29 Sources: |
Disc. AE: Peripheral sensory neuropathy... AEs leading to discontinuation/dose reduction: Peripheral sensory neuropathy (1 patient) Sources: |
900 mg/m2 single, intravenous (total) Dose: 900 mg/m2 Route: intravenous Route: single Dose: 900 mg/m2 Sources: |
unhealthy, 60 years (range: 33-75 years) n = 29 Health Status: unhealthy Age Group: 60 years (range: 33-75 years) Sex: M+F Population Size: 29 Sources: |
Disc. AE: Peripheral sensory neuropathy... AEs leading to discontinuation/dose reduction: Peripheral sensory neuropathy (1 patient) Sources: |
925 mg/m2 single, intravenous (total) Dose: 925 mg/m2 Route: intravenous Route: single Dose: 925 mg/m2 Sources: |
unhealthy, 60 years (range: 33-75 years) n = 29 Health Status: unhealthy Age Group: 60 years (range: 33-75 years) Sex: M+F Population Size: 29 Sources: |
Disc. AE: Peripheral sensory neuropathy... AEs leading to discontinuation/dose reduction: Peripheral sensory neuropathy (1 patient) Sources: |
130 mg/m2 1 times / 3 weeks multiple, intravenous Dose: 130 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 130 mg/m2, 1 times / 3 weeks Co-administed with:: capecitabine(2000 mg/m2 for 14 days followed by 7 days of rest) Sources: trastuzumab(initial dose of 8 mg/kg and 6 mg/kg every 21 days thereafter) |
unhealthy, 64 years n = 1 Health Status: unhealthy Condition: gastric cancer Age Group: 64 years Sex: M Population Size: 1 Sources: |
Disc. AE: Lhermitte's sign... AEs leading to discontinuation/dose reduction: Lhermitte's sign (1 patient) Sources: |
85 mg/m2 1 times / 2 weeks multiple, intravenous Recommended Dose: 85 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 85 mg/m2, 1 times / 2 weeks Co-administed with:: leucovorin(200 mg/m2 intravenous infusion in 5% Dextrose Injection given over 120 minutes) Sources: |
unhealthy, adult Health Status: unhealthy Condition: advanced colorectal cancer Age Group: adult Sex: M Sources: |
Other AEs: Anaphylactic reaction... Other AEs: Anaphylactic reaction Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypersensitivity reaction | 1 patient Disc. AE |
130 mg/m2 single, intravenous Dose: 130 mg/m2 Route: intravenous Route: single Dose: 130 mg/m2 Sources: |
unhealthy, 56 years n = 1 Health Status: unhealthy Condition: colorectal cancer Age Group: 56 years Sex: F Population Size: 1 Sources: |
Neurotoxicity | 50% DLT |
135 mg/m2 1 times / 4 weeks multiple, intravenous Dose: 135 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 135 mg/m2, 1 times / 4 weeks Sources: |
unhealthy, 57 years (range: 26-81 years) n = 14 Health Status: unhealthy Condition: advanced cancer Age Group: 57 years (range: 26-81 years) Sex: M+F Population Size: 14 Sources: |
Neurotoxicity | 64% DLT |
150 mg/m2 1 times / 4 weeks multiple, intravenous Dose: 150 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 150 mg/m2, 1 times / 4 weeks Sources: |
unhealthy, 57 years (range: 26-81 years) n = 14 Health Status: unhealthy Condition: advanced cancer Age Group: 57 years (range: 26-81 years) Sex: M+F Population Size: 14 Sources: |
Neurotoxicity | 71% DLT |
175 mg/m2 1 times / 4 weeks multiple, intravenous Dose: 175 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 175 mg/m2, 1 times / 4 weeks Sources: |
unhealthy, 57 years (range: 26-81 years) n = 7 Health Status: unhealthy Condition: advanced cancer Age Group: 57 years (range: 26-81 years) Sex: M+F Population Size: 7 Sources: |
Neurotoxicity | 100% DLT |
200 mg/m2 1 times / 4 weeks multiple, intravenous Dose: 200 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 200 mg/m2, 1 times / 4 weeks Co-administed with:: highest studied dose Sources: |
unhealthy, 57 years (range: 26-81 years) n = 5 Health Status: unhealthy Condition: advanced cancer Age Group: 57 years (range: 26-81 years) Sex: M+F Population Size: 5 Sources: |
Thrombocytopenia | 1 patient Disc. AE |
55 mg/m2 multiple, intravenous Dose: 55 mg/m2 Route: intravenous Route: multiple Dose: 55 mg/m2 Co-administed with:: 5-fluoruracil Sources: leucovorin |
unhealthy, 58 years n = 1 Health Status: unhealthy Condition: colon cancer Age Group: 58 years Sex: F Population Size: 1 Sources: |
Diarrhoea | grade 3, 1 patient Disc. AE |
150 mg/m2 1 times / 3 weeks single, intravenous (total) Dose: 150 mg/m2, 1 times / 3 weeks Route: intravenous Route: single Dose: 150 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 60 years (range: 33-75 years) n = 29 Health Status: unhealthy Age Group: 60 years (range: 33-75 years) Sex: M+F Population Size: 29 Sources: |
Peripheral sensory neuropathy | 1 patient Disc. AE |
725 mg/m2 single, intravenous (total) Dose: 725 mg/m2 Route: intravenous Route: single Dose: 725 mg/m2 Sources: |
unhealthy, 60 years (range: 33-75 years) n = 29 Health Status: unhealthy Age Group: 60 years (range: 33-75 years) Sex: M+F Population Size: 29 Sources: |
Peripheral sensory neuropathy | 1 patient Disc. AE |
900 mg/m2 single, intravenous (total) Dose: 900 mg/m2 Route: intravenous Route: single Dose: 900 mg/m2 Sources: |
unhealthy, 60 years (range: 33-75 years) n = 29 Health Status: unhealthy Age Group: 60 years (range: 33-75 years) Sex: M+F Population Size: 29 Sources: |
Peripheral sensory neuropathy | 1 patient Disc. AE |
925 mg/m2 single, intravenous (total) Dose: 925 mg/m2 Route: intravenous Route: single Dose: 925 mg/m2 Sources: |
unhealthy, 60 years (range: 33-75 years) n = 29 Health Status: unhealthy Age Group: 60 years (range: 33-75 years) Sex: M+F Population Size: 29 Sources: |
Lhermitte's sign | 1 patient Disc. AE |
130 mg/m2 1 times / 3 weeks multiple, intravenous Dose: 130 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 130 mg/m2, 1 times / 3 weeks Co-administed with:: capecitabine(2000 mg/m2 for 14 days followed by 7 days of rest) Sources: trastuzumab(initial dose of 8 mg/kg and 6 mg/kg every 21 days thereafter) |
unhealthy, 64 years n = 1 Health Status: unhealthy Condition: gastric cancer Age Group: 64 years Sex: M Population Size: 1 Sources: |
Anaphylactic reaction | 85 mg/m2 1 times / 2 weeks multiple, intravenous Recommended Dose: 85 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 85 mg/m2, 1 times / 2 weeks Co-administed with:: leucovorin(200 mg/m2 intravenous infusion in 5% Dextrose Injection given over 120 minutes) Sources: |
unhealthy, adult Health Status: unhealthy Condition: advanced colorectal cancer Age Group: adult Sex: M Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 29.0 |
no | |||
not significant | ||||
not significant | ||||
not significant | ||||
not significant | ||||
not significant | ||||
not significant | ||||
not significant |
PubMed
Title | Date | PubMed |
---|---|---|
Oxaliplatin exerts potent in vitro cytotoxicity in colorectal and pancreatic cancer cell lines and liver metastases. | 2000 Sep-Oct |
|
Plasma and cerebrospinal fluid pharmacokinetics of intravenous oxaliplatin, cisplatin, and carboplatin in nonhuman primates. | 2005 Feb 15 |
|
Structural basis for the sequence-dependent effects of platinum-DNA adducts. | 2009 May |
Patents
Sample Use Guides
Adjuvant treatment in patients with stage III colon cancer is recommended for a total of 6 months, i.e., 12 cycles, every 2 weeks, according to the dose schedule described below for previously treated patients with advanced colorectal cancer.
The recommended dose schedule given every two weeks is as follows:
Day 1: ELOXATIN 85 mg/m2 IV infusion in 250-500 mL D5W and leucovorin 200 mg/m2 IV infusion in D5W both given over 120 minutes at the same time in separate bags using a Y-line, followed by 5-FU 400 mg/m2 IV bolus given over 2-4 minutes, followed by 5-FU 600 mg/m2 IV infusion in 500 mL D5W (recommended) as a 22-hour continuous infusion. Day 2: Leucovorin 200 mg/m2 IV infusion over 120 minutes, followed by 5-FU 400 mg/m2 IV bolus given over 2-4 minutes, followed by 5-FU 600 mg/m2 IV infusion in 500 mL D5W (recommended) as a 22-hour continuous infusion.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11062751
The anti-proliferative effects of oxaliplatin in human HT29 and NMG64/84 colon and COLO-357 MIA PaCa-2 and PMH2/89 pancreatic cancer cell lines and in fresh liver metastases from patients with colorectal and pancreatic cancer were investigated using the human tumor colony forming assay. Oxaliplatin significantly inhibited the colony formation in all cell lines in a concentration- and time-dependent manner. All liver tumors displayed a significant concentration-dependent inhibition of colony formation after exposure to oxaliplatin for 2 hours. The IC50 of oxaliplatin of 9 of the 10 tumors was < 10 micrograms/ml.
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
561716
Created by
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WHO-VATC |
QL01XA03
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WHO-ATC |
L01XA03
Created by
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FDA ORPHAN DRUG |
560816
Created by
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FDA ORPHAN DRUG |
605617
Created by
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LIVERTOX |
NBK548456
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NCI_THESAURUS |
C1450
Created by
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NDF-RT |
N0000175073
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NDF-RT |
N0000175413
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FDA ORPHAN DRUG |
69492
Created by
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6012
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C030110
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DB00526
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31941
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04ZR38536J
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7433
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4210
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1481204
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61825-94-3
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m8281
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DTXSID0036760
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04ZR38536J
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100000085171
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SUB09490MIG
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266046
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32592
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Oxaliplatin
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CHEMBL414804
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OXALIPLATIN
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C1181
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KK-45
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9887054
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ACTIVE MOIETY