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61825-94-3

Basic Information
CAS No.: 61825-94-3
Name: Oxaliplatin
Molecular Structure:
Molecular Structure of 61825-94-3 (Oxaliplatin)
Formula: C8H14N2O4Pt
Molecular Weight: 371.25
Synonyms: Eloxatin;1-OHP;(1R,2R)-cyclohexane-1,2-diamine; oxalic acid; platinum(+2) cation;Eloxatin (TN);Trans-l-diaminocyclohexane oxalatoplatinum;Platinum, (1,2-cyclohexanediamine-N,N)(ethanedioato(2-)-O,O-, (SP-4-2-(1R-trans))-;Platinum, [ (1R,2R)-1,2-cyclohexanediamine-.kappa.N, .kappa.N][ethanedioato(2-)-.kappa.O1,.kappa.O2]-,(SP-4-2)-;(SP-4-2-(1R-trans))-(1,2-Cyclohexanediamine-N,N)(ethanedioato(2-)-O,O)platinum;RP 54780;Oxalatoplatinum;Oxaliplatin EP5;
EINECS: 274-613-9
Density:
Melting Point:
Boiling Point: 193.6oC at 760 mmHg
Flash Point: 75oC
Solubility: Soluble in water with heating and/or sonication
Appearance: White crystalline solid
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 36/37/38-40-42/43
Safety: 26-36
Transport Information: UN 2811
PSA: 104.64000
LogP: 0.61450
Synthetic route

cis-diacetato-trans-l-diaminocyclohexane platinum(II)

583-52-8

potassium oxalate

61825-94-3

oxaliplatin

Conditions
ConditionsYield
In water at 60 - 70℃; for 5 - 6h; Product distribution / selectivity; Heating / reflux;67%

cis-diacetato-trans-l-1,2-diaminocyclohexane platinum(II)

583-52-8

potassium oxalate

61825-94-3

oxaliplatin

Conditions
ConditionsYield
In water for 5 - 6h; Product distribution / selectivity; Heating / reflux;67%
144-62-7

oxalic acid

61825-94-3

oxaliplatin

Conditions
ConditionsYield
Stage #1: (1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II) With water; silver nitrate at 20 - 45℃; for 2.08333h;
Stage #2: oxalic acid With potassium hydroxide In water at 20℃; for 4h; pH=2.9; Product distribution / selectivity;
62.9%
Stage #1: (1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II) With silver nitrate In water at 20℃; for 70h;
Stage #2: With tetraethylammonium iodide In water for 16h;
Stage #3: oxalic acid In water for 4h;
54%
Stage #1: (1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II) With water; silver nitrate at 20℃; for 70h;
Stage #2: oxalic acid In water at 20℃; for 4h; Product distribution / selectivity;
40.3%

(trans-(R,R)-1,2-diaminocyclohexane)diiodoplatinum(II)

583-52-8

potassium oxalate

61825-94-3

oxaliplatin

Conditions
ConditionsYield
Stage #1: trans-(R,R)-(1,2-diaminocyclohexane)diiodoplatinum(II) With acetic acid; silver(l) oxide In water at 80 - 90℃; for 4h;
Stage #2: potassium oxalate In water at 60℃; for 5h; Product distribution / selectivity;
60%
61848-66-6

(1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II)

33081-83-3

bis(tetrabutylammonium)oxalate

61825-94-3

oxaliplatin

Conditions
ConditionsYield
In i-Amyl alcohol; water at 85 - 88℃; for 8 - 10h; Product distribution / selectivity;50%
61848-66-6

(1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II)

144-62-7

oxalic acid

61825-94-3

oxaliplatin

C12H28N4O2Pt2

Conditions
ConditionsYield
Stage #1: (1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II); water With silver nitrate at 20℃; for 48h;
Stage #2: oxalic acid In water at 20℃; for 4h; Product distribution / selectivity;
A 44.1%
B n/a
61848-66-6

(1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II)

61825-94-3

oxaliplatin

Conditions
ConditionsYield
In water41%

cis-dichloro-trans-l-1,2-diaminocyclohexane platinum(II)

144-62-7

oxalic acid

61825-94-3

oxaliplatin

Conditions
ConditionsYield
With silver(l) oxide In water at 60 - 100℃; for 13 - 14h; Product distribution / selectivity;38%
61848-66-6

(1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II)

144-62-7

oxalic acid

61825-94-3

oxaliplatin

Conditions
ConditionsYield
With silver(l) oxide In water at 60 - 100℃; for 13 - 14h; Product distribution / selectivity;38%

[Pt((1R,2R)-(-)-1,2-diaminocyclohexane)(H2O)2]SO4

144-62-7

oxalic acid

61825-94-3

oxaliplatin

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 20h; pH=6;35%
With sodium hydroxide at 20℃; for 20h; pH=6;33%

cis-diiodo-trans-l-1,2-diaminocyclohexane platinum(II)

144-62-7

oxalic acid

61825-94-3

oxaliplatin

Conditions
ConditionsYield
With silver(l) oxide In water at 90 - 100℃; for 10 - 12h; Product distribution / selectivity;30%

(trans-(R,R)-1,2-diaminocyclohexane)diiodoplatinum(II)

144-62-7

oxalic acid

61825-94-3

oxaliplatin

Conditions
ConditionsYield
With silver(l) oxide In water at 90 - 100℃; for 10 - 12h; Product distribution / selectivity;30%
10025-99-7

potassium tetrachloroplatinate(II)

144-62-7

oxalic acid

trans-1,2-cyclohexanediamine

61825-94-3

oxaliplatin

Conditions
ConditionsYield
With potassium iodide; silver(l) oxide In water at 90 - 100℃; for 10 - 12h; Product distribution / selectivity;20%
10025-99-7

potassium tetrachloroplatinate(II)

20439-47-8

(1R,2R)-1,2-diaminocyclohexane

144-62-7

oxalic acid

61825-94-3

oxaliplatin

Conditions
ConditionsYield
With silver(l) oxide In water at 90 - 100℃; for 10 - 12h;20%

potassium platinum(II) oxalate

trans-1,2-cyclohexanediamine

61825-94-3

oxaliplatin

Conditions
ConditionsYield
With acetic acid In water at 90℃; for 6h; pH=6.6 - 7.5; Product distribution / selectivity;15%
In water; acetone at 95℃; for 1.5h; Product distribution / selectivity;15%

cis-bis(methanesulphonato)-trans-l-1,2-diaminocyclohexane platinum(II)

583-52-8

potassium oxalate

61825-94-3

oxaliplatin

Conditions
ConditionsYield
In water for 6h; Product distribution / selectivity; Heating / reflux;

C6H18N2O2Pt(2+)*2NO3(1-)

1113-38-8

ammonium oxalate

61825-94-3

oxaliplatin

Conditions
ConditionsYield
In water at 45℃; for 8h;

2CH3O3S(1-)*C6H18N2O2Pt(2+)

61825-94-3

oxaliplatin

Conditions
ConditionsYield
Product distribution / selectivity;

[Pt(OH)2(trans-(1R,2R)-diaminocyclohexane)]

144-62-7

oxalic acid

61825-94-3

oxaliplatin

C12H28N4O2Pt2

Conditions
ConditionsYield
In water at 20℃; for 4h; Product distribution / selectivity;
61848-66-6

(1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II)

61825-94-3

oxaliplatin

Conditions
ConditionsYield
purifn. by HPLC; elem.anal.;;

platinum(IV)Cl2 oxalate (1R, 2R-cyclohexandiamine)

61825-94-3

oxaliplatin

Conditions
ConditionsYield
In water at room temp. in sunlight; chromy.; UV;
With ascorbic acid In water at room temp. in the dark; chromy.; UV;

[Pt(OH)2(trans-(1R,2R)-diaminocyclohexane)]

62-76-0

sodium oxalate

61825-94-3

oxaliplatin

C12H28N4O2Pt2

Conditions
ConditionsYield
at 20℃; for 2 - 4h; pH=12; Product distribution / selectivity; Absence of light;

[Pt(OH)2(trans-(1R,2R)-diaminocyclohexane)]

61825-94-3

oxaliplatin

C12H28N4O2Pt2

Conditions
ConditionsYield
With oxalic acid In water for 4h; Product distribution / selectivity;

cis-bismethanesulphonato-trans-l-1,2-diaminocyclohexane platinum(II)

583-52-8

potassium oxalate

61825-94-3

oxaliplatin

Conditions
ConditionsYield
In water for 6h; Product distribution / selectivity; Heating / reflux;

bis(3-carboxypropanoato)(trans-1R,2R-diaminocyclohexane)oxalatoplatinum(IV)

61825-94-3

oxaliplatin

Conditions
ConditionsYield
In aq. phosphate buffer pH=7; Electrochemical reaction;

C76H124N6O14Pt

61825-94-3

oxaliplatin

B

1239481-01-6

C34H56N2O5

Conditions
ConditionsYield
With sodium L-ascorbate In water

C15H26N2O8Pt

61825-94-3

oxaliplatin

Conditions
ConditionsYield
With C49H42N7Ru(3+)*3F6P(1-); water-d2 for 1h; Irradiation;

phorbiplatin

61825-94-3

oxaliplatin

Conditions
ConditionsYield
With sodium L-ascorbate In N,N-dimethyl-formamide; acetonitrile for 0.166667h; pH=7.4; Mechanism; Irradiation;

C43H50N6O9Pt

61825-94-3

oxaliplatin

B

pyropheophorbide a acid

Conditions
ConditionsYield
With sodium L-ascorbate In N,N-dimethyl-formamide for 0.166667h; pH=7.4; Mechanism; Irradiation;

t-[Pt(DACH)(ox)(OOCCH2CH2CH2CH2CH2CH2CH3)(OOCCH3)]

61825-94-3

oxaliplatin

Conditions
ConditionsYield
With sodium L-ascorbate In aq. phosphate buffer at 37℃; under 760.051 Torr; pH=7.4; Kinetics; Darkness;
61825-94-3

oxaliplatin

7722-84-1

dihydrogen peroxide

[Pt(1,2-diaminocyclohexane)(OH)2(ox)]

Conditions
ConditionsYield
for 12h;94%
61825-94-3

oxaliplatin

64-17-5

ethanol

7722-84-1

dihydrogen peroxide

c,c,t-(1R,2R-diaminocyclohexane)oxalatoethoxidohydroxoplatinum(IV)

Conditions
ConditionsYield
In water at 70℃; for 5h;92%
61825-94-3

oxaliplatin

7722-84-1

dihydrogen peroxide

[(1R,2R)-cyclohexane-1,2-diamine-N,N']dihydroxidooxalato-platinum(IV),trans-[Pt(OH)2(ox)(R,R-chxn)]

Conditions
ConditionsYield
In water at 50℃; for 1h;90%
In water at 20℃; for 24h; Darkness;89%
In water at 70℃; for 5h;80.6%
61825-94-3

oxaliplatin

7722-84-1

dihydrogen peroxide

(SP-4-2)-(trans-R,R-cyclohexane-1,2-diamine)dihydroxo(oxalato) platinum(IV)

Conditions
ConditionsYield
In water at 50℃; for 5h; Darkness;90%
In water at 60 - 65℃; Darkness;74%
In water at 60℃; for 4h;71%
61825-94-3

oxaliplatin

7722-84-1

dihydrogen peroxide

[(1R,2R)-cyclohexane-1,2-diamine-N,N']dihydroxidooxalato-platinum(IV),trans-[Pt(OH)2(ox)(R,R-chxn)]

Conditions
ConditionsYield
at 50℃; for 1h;90%
61825-94-3

oxaliplatin

128-09-6

N-chloro-succinimide

hydroxychlorooxaliplatin(IV)

Conditions
ConditionsYield
at 20℃; for 3h; Darkness;89.3%
at 20℃; Inert atmosphere;89.2%
at 60℃; Darkness;89%
61825-94-3

oxaliplatin

128-09-6

N-chloro-succinimide

trans-Pt(IV)Cl2(oxalato)(l-1,2-cyclohexanediamine)

Conditions
ConditionsYield
In ethanol for 8h; Darkness; Reflux;89%
61825-94-3

oxaliplatin

516-12-1

N-iodo-succinimide

trans-[Pt(trans-(1R, 2R)-1,2-cyclohexanediammine)(oxalate)(C4H4NO2)l]

Conditions
ConditionsYield
In ethanol at 20℃; for 8h; Darkness;84%
61825-94-3

oxaliplatin

7722-84-1

dihydrogen peroxide

79-08-3

bromoacetic acid

2-bromoaceto-[(1R,2R)-cyclohexane-1,2-diamine-N,N']hydroxidooxalatoplatinum(IV)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h;83%
61825-94-3

oxaliplatin

128-08-5

N-Bromosuccinimide

trans-[Pt(trans-(1R,2R)-1,2-cyclohexanediammine)(oxalate)(OH)Br]

Conditions
ConditionsYield
at 20℃; for 12h;81%
61825-94-3

oxaliplatin

7722-84-1

dihydrogen peroxide

111263-58-2, 111321-67-6, 111321-78-9, 198292-19-2

cis-oxalic acid (trans-1,2-cyclohexanediamine)dihydroxyplatinum(II)

Conditions
ConditionsYield
at 50℃;81%
108-30-5

succinic acid anhydride

61825-94-3

oxaliplatin

C16H24N2O12Pt

Conditions
ConditionsYield
Stage #1: oxaliplatin With dihydrogen peroxide In water at 20 - 50℃; for 27h; Darkness;
Stage #2: succinic acid anhydride In N,N-dimethyl-formamide at 50℃; for 24h; Darkness;
80%
61825-94-3

oxaliplatin

123-62-6

propionic acid anhydride

C15H26N2O8Pt

Conditions
ConditionsYield
Stage #1: oxaliplatin With dihydrogen peroxide In water at 20 - 50℃; for 27h;
Stage #2: propionic acid anhydride In N,N-dimethyl-formamide at 50℃; for 20h; Darkness;
80%
61825-94-3

oxaliplatin

7722-84-1

dihydrogen peroxide

(SP-4-2)-(trans-R,R-cyclohexane-1,2-diamine)dihydroxo(oxalato) platinum(IV)

Conditions
ConditionsYield
at 60℃; for 4h;78%
at 60℃; for 4h;76%
at 40℃; for 18h;
108-30-5

succinic acid anhydride

61825-94-3

oxaliplatin

C14H22N2O10Pt

Conditions
ConditionsYield
Stage #1: oxaliplatin With dihydrogen peroxide; acetic acid at 20℃; for 24h; Darkness;
Stage #2: succinic acid anhydride In N,N-dimethyl-formamide at 50℃; for 24h; Darkness;
76%
61825-94-3

oxaliplatin

10102-44-0

Nitrogen dioxide

7647-14-5

sodium chloride

(trans-l-1,2-diaminocyclohexane)oxalatochloronitroplatinum(IV)

Conditions
ConditionsYield
In water; acetone at 20℃; for 11.25h;75%
61825-94-3

oxaliplatin

7722-84-1

dihydrogen peroxide

64-19-7

acetic acid

(OC-6-44)-acetato[(1R,2R)-cyclohexane-1,2-diamine]hydroxidooxalatoplatinum(IV)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 48h; Darkness;75%
In water at 20℃; for 19h; Darkness;
61825-94-3

oxaliplatin

10102-44-0

Nitrogen dioxide

7647-15-6

sodium bromide

(trans-l-1,2-diaminocyclohexane)oxalatobromonitroplatinum(IV)

Conditions
ConditionsYield
In water; acetone at 20℃; for 18.7833h;74%
61825-94-3

oxaliplatin

128-08-5

N-Bromosuccinimide

trans-[Pt(trans-(1R,2R)-1,2-cyclohexanediammine)(oxalate)Br2]

Conditions
ConditionsYield
In ethanol at 20℃; for 12h;71%
79-21-0

peracetic acid

61825-94-3

oxaliplatin

(OC-6-44)-acetato[(1R,2R)-cyclohexane-1,2-diamine]hydroxidooxalatoplatinum(IV)

Conditions
ConditionsYield
With acetic acid for 24.5h;66%
61825-94-3

oxaliplatin

(SP-4-2)-(trans-R,R-cyclohexane-1,2-diamine)dihydroxo(oxalato) platinum(IV)

Conditions
ConditionsYield
With dihydrogen peroxide In water at 50℃; for 3h; Inert atmosphere;64.3%
With dihydrogen peroxide In water at 30℃; for 12h; Darkness;
With dihydrogen peroxide In water at 60 - 70℃; for 4h; Inert atmosphere;
61825-94-3

oxaliplatin

79-08-3

bromoacetic acid

di-2-bromoacetato[(1R,2R)-cyclohexane-1,2-diamine-N,N']oxalatoplatinum(IV)

Conditions
ConditionsYield
With dihydrogen peroxide In tetrahydrofuran at 20℃; for 24h;53%
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    61825-94-3

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    61825-94-3

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    Product name: Oxaliplatin Synonyms: trans-L-Diaminocyclohexane oxalatoplatinum Molecular formula: C8H12N2O4Pt Molecular weight: 395.27 Appearance: White loose block or amorphous solid CAS: 61825-94-3 Assay: 99% Appearance:white P

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  • Casno:

    61825-94-3

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Chemistry

Oxaliplatin is a platinum-based chemotherapy drug in the same family as cisplatin and carboplatin.  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.
Product Name: Oxaliplatin (CAS NO.61825-94-3)

Molecular Formula: C8H14N2O4Pt
Molecular Weight: 397.29g/mol
Mol File: 61825-94-3.mol
Appearance: White Crystalline Solid
Boiling point: 193.6 °C at 760 mmHg
Flash Point: 75 °C
Stability: Stable. Store cool. Incompatible with oxidizing agents.
Enthalpy of Vaporization: 42.98 kJ/mol
Vapour Pressure: 0.46 mmHg at 25°C
H-Bond Donor: 2
H-Bond Acceptor: 6
Structure Descriptors of Oxaliplatin (CAS NO.61825-94-3):
  IUPAC Name: (1R,2R)-cyclohexane-1,2-diamine; oxalate; platinum(4+)
  Canonical SMILES: C1CCC(C(C1)N)N.C(=O)(C(=O)[O-])[O-].[Pt+4]
  Isomeric SMILES: C1CC[C@H]([C@@H](C1)N)N.C(=O)(C(=O)[O-])[O-].[Pt+4]
  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;;+4/p-2/t5-,6-;;/m1../s1 
  InChIKey: PCRKGXHIGVOZKB-BNTLRKBRSA-L
Product Categories: Pharmaceutical material and intermeidates; Active Pharmaceutical Ingredients; Antineoplastic; Intermediates & Fine Chemicals; Pharmaceuticals

History

Oxaliplatin was discovered in 1976 at Nagoya City University in Japan by Professor Yoshinori Kidani, who was granted U.S. Patent 4,169,846 over the drug in 1979. Oxaliplatin was subsequently in-licensed by Debiopharm, a Swiss drug company headquartered in Lausanne and developed as an advanced colorectal cancer treatment. Debio licensed the drug to Sanofi-Aventis in 1994. Eloxatin gained European approval in 1996 (firstly in France) and approval by the U.S. Food and Drug Administration (FDA) in 2002.

Uses

It is typically administered in combination with fluorouracil and leucovorin in a combination known as FOLFOX for the treatment of colorectal cancer.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 19800ug/kg (19.8mg/kg)   Drugs of the Future. Vol. 14, Pg. 529, 1989.
rat LD50 intraperitoneal 14300ug/kg (14.3mg/kg)   Drugs of the Future. Vol. 14, Pg. 529, 1989.

Safety Profile

Safety Information of Oxaliplatin (CAS NO.61825-94-3):
Hazard Codes: XnHarmful,XiIrritant
Risk Statements: 36/37/38-40-42/43  
R36/37/38:Irritating to eyes, respiratory system and skin. 
R40:Limited evidence of a carcinogenic effect. 
R42/43:May cause sensitization by inhalation and skin contact.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
RIDADR: 2811
WGK Germany: 3
RTECS: TP2275850
HazardClass: 6.1(a)
PackingGroup: II

Specification

 Oxaliplatin , its CAS NO. is 61825-94-3, the synonyms are (SP-4-2-(1R-trans))-(1,2-Cyclohexanediamine-N,N')(ethanedioato(2-)-O,O')platinum ; Dacplat ; Eloxatin ; Elplat ; JM-83 ; Lipoxal ; Oxalato(1R,2R-cyclohexanediammine)platinum(II) ; Oxalato(trans-(-)-1,2-cyclohexanediamine)platinum(II) ; Oxalato(trans-1-1,2-cyclohexanediamine)platinum(II) ; Oxalatoplatinum ; UNII-04ZR38536J ; cis-((1R,2R)-1,2-Cyclohexanediamine-N,N')(oxalato(2-)-O,O')platinum ; trans-l-Diaminocyclohexane oxalatoplatinum ; Platinum, ((1R,2R)-1,2-cyclohexanediamine-.kappa.N,.kappa.N')(ethanedioato(2-)-kappaO1,kappaO2)-, (SP-4-2)- ; Platinum, (1,2-cyclohexanediamine-N,N')(ethanedioato(2-)-O,O')-, (SP-4-2-(1R-trans))- .

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