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Basic Information

Molecular Structure:
CAS No.:	41575-94-4
Name:	Carboplatin
Article Data:	15

Formula:	C₆H₁₂N₂O₄Pt
Molecular Weight:	371.252
Synonyms:	Platinum, diammine[1, 1-cyclobutanedicarboxylato (2-)-O,O]-, (SP-4-2)-;Paraplatin (TN);Platinum(II), (1, 1-cyclobutanedicarboxylato)diammine-, cis-;(SP-4-2)-diammine[cyclobutane-1,1-dicarboxylato(2-)-kappa(2)O,O]platinum;Cis-Diammine(1,1-cyclobutanedicarboxylato)platinum(II);Platinum, diamine(1, 1-cyclobutanedicarboxylato(2-)-O,O)-, (SP-4-2)-;Cis-(1,1-Cyclobutanedicarboxylato)diammineplatinum(II);azanide; cyclobutane-1,1-dicarboxylic acid; platinum;Paraplatin;cis- (1,1-Cyclobutanedicarboxylato)diammineplatinum(II);Platinum,diammine[1,1-cyclobutanedi(carboxylato- kO)(2-)]-,(SP-4-2)-;Carboplatin (USAN);cis-Diammine (1,1-cyclobutanedicarboxylato)platinum(II);Carboplatin (JAN/USP);1, 1-Cyclobutanedicarboxylate diammine platinum (II);diammine[cyclobutane-1,1-dicarboxylato(2-)-O,O']platinum;
EINECS:	255-446-0
Melting Point:	228-230 °C
Boiling Point:	366.4oCat 760 mmHg
Flash Point:	189.6oC
Solubility:	Soluble in water.
Appearance:	White Crystals
Hazard Symbols:	T
Risk Codes:	46-61-20/21/22-42/43-20/21
Safety:	53-22-26-36/37/39-45
Transport Information:	UN 2811
PSA:	59.08000
LogP:	0.81700

Synthetic route

: cis-diaminediiodoplatinum(II)

: 5445-51-2
cyclobutane-1,1'-dicarboxylic acid

: 41575-94-4
carboplatinum

Conditions

Conditions	Yield
With barium dihydroxide; silver sulfate In water byproducts: AgI, BaSO4; addn. of Ag2SO4 to slight excess of Pt-complex, stirring (4 h), filtration off of AgI, concn., addn. of soln. of ligand (neutralized with Ba(OH)2); filtration off of BaSO4, concn. (crystn.), washing (EtOH, Et2O), drying(vac.); elem. anal.;	88%
Stage #1: cis-diaminediiodoplatinum(II) With silver sulfate In water for 4h; Stage #2: cyclobutane-1,1'-dicarboxylic acid With barium hydroxide octahydrate In water	85%
Stage #1: cis-diaminediiodoplatinum(II) With silver nitrate In water Darkness; Stage #2: cyclobutane-1,1'-dicarboxylic acid With potassium hydroxide for 3h; pH=5;	50.3%
With potassium hydroxide In water; N,N-dimethyl-formamide Pt-compd. dissolved in DMF with heating, addn. of the acid and aq. KOH, heated in an unstoppered flask at 60°C for 20 h; cooled, filtered, addn. of ether;	40%

: 13841-96-8, 15978-93-5, 15978-94-6
cis-diamminediiodoplatinum (II)

Ag salt of cyclobutanedicarboxylic acid: Ag salt of cyclobutanedicarboxylic acid

: 41575-94-4
carboplatinum

Conditions

Conditions	Yield
In water at 20℃; for 48h; Darkness;	80%

: 15663-27-1
cisplatin

: 5445-51-2
cyclobutane-1,1'-dicarboxylic acid

: 41575-94-4
carboplatinum

Conditions

Conditions	Yield
With potassium hydroxide In water; N,N-dimethyl-formamide Pt-compd. dissolved in DMF with heating, addn. of the acid and aq. KOH, heated in an unstoppered flask at 60°C for 20 h; cooled, filtered, addn. of ether;	70%
With potassium hydroxide In N,N-dimethyl acetamide; water Pt-compd. dissolved in DMA, addn. of the acid and aq. KOH, heated in an unstoppered flask at 60°C for 20 h; cooled, filtered, addn. of ether;	35%

: 142159-62-4, 67063-11-0
diamine platinum sulfate

: barium cyclobutane-1,1-dicarboxylate monohydrate

: 41575-94-4
carboplatinum

Conditions

Conditions	Yield
In water heating Pt-complex and Ba-compd. in water at 60°C for 10 h; filtn., evapn. to dryness, dissolution of residue in DMF, hot filtn., concn., pptn. with ethanol, elem. anal.;	70%

: 15663-27-1
cisplatin

: 5445-51-2
cyclobutane-1,1'-dicarboxylic acid

: 1310-65-2
lithium hydroxide

: 41575-94-4
carboplatinum

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide Pt-compd. dissolved in DMF with heating, addn. of the acid and aq. LiOH, heated in an unstoppered flask at 60°C for 20 h; cooled, filtered, addn. of ether;	65%

...Expand

: cis-diaminediiodoplatinum(II)

: 1,1-cyclobutanedicarboxylic acid disilver salt

: 41575-94-4
carboplatinum

Conditions

Conditions	Yield
In ethanol; water at 20℃; for 48h; Darkness;	48%
In water byproducts: AgI; Pt- and Ag-complex mixed together in water, stirred in dark for 2-3 d; ppt. filtered, filtrate evapd. to dryness;
In water for 2 - 3h;

: cis-diaminediiodoplatinum(II)

: Ba(2+)*C6H6O4(2-)=Ba(C6H6O4)

: 7732-18-5
water

: silver sulfate

: 41575-94-4
carboplatinum

Conditions

Conditions	Yield
In water byproducts: AgI, BaSO4; addn. of cis-Pt(NH3)2I2 (1 mmol) to aq. soln. of Ag2SO4 (0.98 mmol), stirring for 4 h in dark, removal of ppt. (AgI), slowly addn. of BaC6H6O4 to filtrate (cis-(Pt(NH3)2(H2O)2)(SO4)), stirring for 20 min; filtration, evapn. of filtrate to dryness, addn. of MeOH, filtration, washing with Et2O, drying in vac.;

...Expand

: cis-diaminediiodoplatinum(II)

: 7732-18-5
water

: 100476-94-6
1,1-cyclobutanedicarboxylic acid disodium salt

: silver nitrate

: 41575-94-4
carboplatinum

Conditions

Conditions	Yield
In water; acetone byproducts: AgI, NaNO3; dissolving of cis-Pt(NH3)2I2 (1 mmol) in C3H6O, addn. of AgNO3 (2.2 mmol), stirring for 10-20 min, removal of ppt.(AgI), evapn. of filtrate, crystn. of Pt(NH3)2(ONO2)2 in Et2O, drying in vac., dissolving in H2O, addn. of Na2C6H6O4, stirring for 4-5 days; filtration, evapn. of filtrate to dryness, addn. of MeOH, filtration, washing with Et2O, drying in vac.;

Yield

In water; acetone byproducts: AgI, NaNO3; dissolving of cis-Pt(NH3)2I2 (1 mmol) in C3H6O, addn. of AgNO3 (2.2 mmol), stirring for 10-20 min, removal of ppt.(AgI), evapn. of filtrate, crystn. of Pt(NH3)2(ONO2)2 in Et2O, drying in vac., dissolving in H2O, addn. of Na2C6H6O4, stirring for 4-5 days; filtration, evapn. of filtrate to dryness, addn. of MeOH, filtration, washing with Et2O, drying in vac.;

...Expand

: 5445-51-2
cyclobutane-1,1'-dicarboxylic acid

: 41575-94-4
carboplatinum

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / water 2: water View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / water 2: water / 2 - 3 h View Scheme

: cis-diaminediiodoplatinum(II)

: Ba(2+)*C6H6O4(2-)=Ba(C6H6O4)

: 41575-94-4
carboplatinum

Conditions

Conditions	Yield
Stage #1: cis-diaminediiodoplatinum(II) With silver sulfate In water at 50℃; for 24h; Stage #2: Ba(2+)*C6H6O4(2-)=Ba(C6H6O4) In water at 40℃;

Raw Materials

Downstream Products

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Chemistry

Molecular Structure:

Molecular Formula: C₆H₁₂N₂O₄Pt
Molecular Weight: 371.2556
IUPAC Name: Azanide; cyclobutane-1,1-dicarboxylic acid; platinum
Synonyms of Carboplatin (CAS NO.41575-94-4): CCarboplatin [USAN:INN:BAN:JAN] ; 1,1-Cyclobutanedicarboxylate diammine platinum(II) ; CCRIS 3404 ; Carboplatine ; Carboplatine [French] ; Carboplatino ; Carboplatino [Spanish] ; Carboplatinum ; Carboplatinum [Latin] ; Cbdca ; Diammine(1,1-cyclobutanedicarboxylato)platinum (II) ; EINECS 255-446-0 ; HSDB 6957 ; JM 8 ; NSC 201345 ; NSC 241240 ; NSC-241240 ; Paraplatin ; Platinum(II), (1,1-cyclobutanedicarboxylato)diammine-, cis- ; UNII-BG3F62OND5 ; cis-(1,1-Cyclobutanedicarboxylato)diammineplatinum(II) ; Diammine(cyclobutane-1,1-dicarboxylato(2-)-O,O')platinum ; Platinum, diammine(1,1-cyclobutanedi(carboxylato-kappaO)(2-))-, (SP-4-2)- ; Platinum, diammine(1,1-cyclobutanedicarboxylato(2-))-, (SP-4-2)- ; Platinum, diammine(1,1-cyclobutanedicarboxylato(2-)-O,O')-, (SP-4-2)
CAS NO: 41575-94-4
Classification Code: Antineoplastic Antineoplastic Agents Cross-Linking Reagents Drug / Therapeutic Agent Indicators and Reagents Mutation data Reproductive Effect
Melting Point: 228-230 ° C
Flash Point: 189.6 °C
Enthalpy of Vaporization: 67.31 kJ/mol
Boiling Point: 366.4 °C at 760 mmHg
Vapour Pressure: 2.27E-06 mmHg at 25°C

History

Carboplatin (CAS NO.41575-94-4) was discovered and developed at the Institute of Cancer Research in London. Bristol-Myers Squibb gained Food and Drug Administration (FDA) approval for carboplatin, under the brand name Paraplatin, in March 1989. The drug went generic in October 2004. There are also generic versions of the drug available from APP Pharmaceuticals, Sicor (Teva), Bedford Laboratories, Pharmachemie, Sandoz, Hospira,Pliva, Spectrum.

Uses

Reduced nephrotoxicity and Antineoplastic
A study in mutant mice suggests that in the subset of women with breast cancer due to BRCA1 and BRCA2 genes (these cause a variety of familial breast cancer) carboplatin may be as much as 20 times more effective than the usual breast cancer treatments.However, similar data in humans has not yet been shown.
Carboplatin (CAS NO.41575-94-4) has also been used to treat testicular cancer patients with stage 1 seminoma. Recent research indicates that this treatment is more effective and has fewer side effects than adjuvant radiotherapy, It is as effective as radiotherapy at preventing development of seminoma in the remaining testicle.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	intravenous	> 31200ug/kg (31.2mg/kg)		Drugs in Japan Vol. -, Pg. 288, 1990.
mammal (species unspecified)	LD50	unreported	158mg/kg (158mg/kg)		Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. Vol. 22, Pg. 56, 1987. Link to PubMed
mouse	LD50	intraperitoneal	118mg/kg (118mg/kg)		European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 27, Pg. 611, 1992.
mouse	LD50	intravenous	89360ug/kg (89.36mg/kg)		National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse	LD50	unreported	180mg/kg (180mg/kg)		Recent Results in Cancer Research. Vol. 48, Pg. 12, 1974.
rat	LD50	intravenous	60900ug/kg (60.9mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	National Technical Information Service. Vol. PB288-374,
rat	LD50	oral	343mg/kg (343mg/kg)		Drugs in Japan Vol. -, Pg. 288, 1990.
rat	LD50	subcutaneous	72mg/kg (72mg/kg)		Drugs in Japan Vol. -, Pg. 288, 1990.

Safety Profile

Hazard Codes of Carboplatin (CAS NO.41575-94-4): Toxic T
Risk Statements: 46-61-20/21/22-42/43
R46: May cause heritable genetic damage.
R61: May cause harm to the unborn child.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements: 53-22-26-36/37/39-45
S53: Avoid exposure - obtain special instructions before use.
S22: Do not breathe dust.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: 2811
WGK Germany: 3