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| CAS No.: | 61825-94-3 |
|---|---|
| Name: | Oxaliplatin |
| Article Data: | 22 |
| Molecular Structure: | |
|
|
|
| Formula: | C8H14N2O4Pt |
| Molecular Weight: | 397.29 |
| 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 |
| 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: |
 Xn,  Xi
|
| Risk Codes: | 36/37/38-40-42/43 |
| Safety: | 26-36 |
| Transport Information: | UN 2811 |
| PSA: | 104.64000 |
| LogP: | 0.61450 |
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| Conditions | Yield |
|---|---|
| In water at 60 - 70℃; for 5 - 6h; Product distribution / selectivity; Heating / reflux; | 67% |
- 583-52-8
potassium oxalate
- 61825-94-3
oxaliplatin
| Conditions | Yield |
|---|---|
| In water for 5 - 6h; Product distribution / selectivity; Heating / reflux; | 67% |
- 144-62-7
oxalic acid
- 61825-94-3
oxaliplatin
| Conditions | Yield |
|---|---|
| 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% |
- 583-52-8
potassium oxalate
- 61825-94-3
oxaliplatin
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| In i-Amyl alcohol; water at 85 - 88℃; for 8 - 10h; Product distribution / selectivity; | 50% |
- 61848-66-6
(1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II)
- 7732-18-5
water
- 144-62-7
oxalic acid
- 61825-94-3
oxaliplatin
| Conditions | Yield |
|---|---|
| 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)
- 15843-43-3, 31038-77-4
silver oxalate
- 61825-94-3
oxaliplatin
| Conditions | Yield |
|---|---|
| In water | 41% |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With silver(l) oxide In water at 60 - 100℃; for 13 - 14h; Product distribution / selectivity; | 38% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide at 20℃; for 20h; pH=6; | 35% |
| With sodium hydroxide at 20℃; for 20h; pH=6; | 33% |
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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: Xn
,Xi
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))- .