OXALIPLATIN

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

HIDE SMILES / InChI

Molecular Formula	C6H14N2
Molecular Weight	114.1888
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Pt
Molecular Weight	195.084
Charge	2
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C2O4
Molecular Weight	88.019
Charge	-2
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282	Crosslinking Agent 83

Conditions

Condition	Modality	Targets	Highest Phase	Product
Colon cancer 66	Primary		Approved 8,583	ELOXATIN
Carcinoma of the colon or rectum 2	Primary		Approved 8,583	ELOXATIN

C_max

Value	Dose	Co-administered	Analyte	Population
4.66 μg/mL	130 mg/m² 1 times / 3 weeks steady-state, intravenous		OXALIPLATIN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
205.75 μg × h/mL	130 mg/m² 1 times / 3 weeks steady-state, intravenous		OXALIPLATIN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
42.84 h	130 mg/m² 1 times / 3 weeks steady-state, intravenous		OXALIPLATIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
10%			PLATINUM plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
130 mg/m2 single, intravenous	unhealthy, 56 years	Disc. AE: Hypersensitivity reaction...
135 mg/m2 1 times / 4 weeks multiple, intravenous	unhealthy, 57 years (range: 26-81 years)	DLT: Neurotoxicity...
150 mg/m2 1 times / 4 weeks multiple, intravenous	unhealthy, 57 years (range: 26-81 years)	DLT: Neurotoxicity...
175 mg/m2 1 times / 4 weeks multiple, intravenous	unhealthy, 57 years (range: 26-81 years)	DLT: Neurotoxicity...
200 mg/m2 1 times / 4 weeks multiple, intravenous	unhealthy, 57 years (range: 26-81 years)	DLT: Neurotoxicity...

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AEs

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AE	Significance	Dose	Population
Hypersensitivity reaction	1 patient Disc. AE	130 mg/m2 single, intravenous	unhealthy, 56 years
Neurotoxicity	50% DLT	135 mg/m2 1 times / 4 weeks multiple, intravenous	unhealthy, 57 years (range: 26-81 years)
Neurotoxicity	64% DLT	150 mg/m2 1 times / 4 weeks multiple, intravenous	unhealthy, 57 years (range: 26-81 years)
Neurotoxicity	71% DLT	175 mg/m2 1 times / 4 weeks multiple, intravenous	unhealthy, 57 years (range: 26-81 years)
Neurotoxicity	100% DLT	200 mg/m2 1 times / 4 weeks multiple, intravenous	unhealthy, 57 years (range: 26-81 years)

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252	inhibitor 2,438	inhibitor 2,507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 110 CYP1A2 2,153 CYP2A6 879 CYP2C19 2,057 CYP2E1 1,060

Drug as perpetrator

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Target	Modality	Activity
CYP 150	inhibitor 4,027	no
CYP1A2 2,333	inhibitor 4,027	not significant
CYP2A6 911	inhibitor 4,027	not significant
CYP2C19 2,141	inhibitor 4,027	not significant
CYP2C9 2,497	inhibitor 4,027	not significant

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31941	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31941
ChemicalBook	CB1217931	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1217931
eMolecules	2733277	https://www.emolecules.com/cgi-bin/more?vid=2733277
eMolecules	36729906	https://www.emolecules.com/cgi-bin/more?vid=36729906
MolPort	MolPort-005-937-161	https://www.molport.com/shop/molecule-link/MolPort-005-937-161

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PubMed

Title	Date	PubMed
No data available in table

Patents

Sample Use Guides

In Vivo Use Guide

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

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.

Substance Class	Chemical
Record UNII	04ZR38536J
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

OXALIPLATIN

Official Name

English

PLATINUM, ((1R,2R)-1,2-CYCLOHEXANEDIAMINE-.KAPPA.N,.KAPPA.N')(ETHANEDIOATO(2-)-.KAPPA.O1,.KAPPA.O2)-, (SP-4-2)-

Preferred Name

English

OXALIPLATIN [JAN]

Common Name

English

Oxaliplatin [WHO-DD]

Common Name

English

OXALIPLATIN [MART.]

Common Name

English

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Classification Tree

Code System

Code

Designated

FDA ORPHAN DRUG

561716

Platinum compounds

WHO-VATC

QL01XA03

Platinum compounds

WHO-ATC

L01XA03

Designated

FDA ORPHAN DRUG

560816

Designated

FDA ORPHAN DRUG

605617

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Code System

Code

Type

Description

INN

6012

PRIMARY

MESH

C030110

PRIMARY

DRUG BANK

DB00526

PRIMARY

CHEBI

31941

PRIMARY

FDA UNII

04ZR38536J

PRIMARY

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Related Record

Type

Details


					X0LJ304HK9

OXALIPLATIN, C14-

LABELED -> NON-LABELED

Amount:


					04ZR38536J

OXALIPLATIN

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (HPLC)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [98 to 102] WEIGHT PERCENT (limits)


					482M00274D

OCT-2

TRANSPORTER -> SUBSTRATE

Comments:

MAY BE RESPONSIBLE FOR THE ACTIVITY OF OXALIPLATIN AGAINST against colorectal tumors

Interaction Type:

MAJOR


					04ZR38536J

OXALIPLATIN

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (HPLC)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [98 to 102] WEIGHT PERCENT (limits)


					ONY583280Z

OCT-1

TRANSPORTER -> SUBSTRATE

Comments:

MAY BE RESPONSIBLE FOR THE ACTIVITY OF OXALIPLATIN AGAINST against colorectal tumors

Interaction Type:

MAJOR

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Related Record

Type

Details


					9E7R5L6H31

Oxalic Acid

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [<0.1] WEIGHT PERCENT (limits)


					Z6N6X37D9R

DIAQUODIAMINOCYCLOHEXANEPLATINUM DINITRATE, (R,R)-

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [<0.1] WEIGHT PERCENT (limits)


					EDV9R3J9FW

OXALIPLATIN, (S,S)-

IMPURITY -> PARENT

Comments:

limites not given

Qualification:

EP


					A6IL7532PP

(1,2-CYCLOHEXANEDIAMINE-N,N') DIIODIDOPLATINUM(II), (SP-4-2-(1R-TRANS))-

IMPURITY -> PARENT

Amount:


					H1J83OU9AD

(R,R-1,2-DIAMINOCYCLOHEXANE)DINITRATOPLATINUM

IMPURITY -> PARENT

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Related Record

Type

Details


					04ZR38536J

OXALIPLATIN

ACTIVE MOIETY

Amount:

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator