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15663-27-1

Basic Information
CAS No.: 15663-27-1
Name: Cisplatin
Article Data: 205
Cas Database
Molecular Structure:
Molecular Structure of 15663-27-1 (Cisplatin)
Formula: Cl2H6N2Pt
Molecular Weight: 300.047
Synonyms: Neoplatin;Platosin;cis-dichlorodi-ammine platinum(ii);cis-Diammineplatinum(II) dichloride;cis-Dichlorodiamminoplatinum(II);CPDD;cisPt(II);cis-Platinum(II) diaminodichloride;Platinum(II), diamminedichloro-, cis-;Biocisplatinum;Cisplatyl;DDP (antitumor agent);Cisplatinum;azane; platinum(+2) cation; dichloride;
EINECS: 239-733-8
Density: 3.7 g/cm3
Melting Point: 340 °C (dec.)(lit.)
Boiling Point: N/A
Flash Point: N/A
Solubility: <0.1 g/100 mL at 19 °C in water
Appearance: Orange-yellow to deep yellow solid or powder
Hazard Symbols: ToxicT
Risk Codes: 45-25-41-60-46-42/43-36/37/38
Safety: 53-26-39-45-99-36/37/39-22
Transport Information: UN 3288 6.1/PG 2
PSA: 24.72000
LogP: 2.02430
Synthetic route

ammonium acetate

10025-99-7

potassium tetrachloroplatinate(II)

potassium chloride

15663-27-1

cisplatin

Conditions
ConditionsYield
In water at 100℃; for 0.233333h; Temperature; Time; Concentration; Microwave irradiation;90%
7647-01-0

hydrogenchloride

pyrophosphatotetraamminediplatinum(II)

15663-27-1

cisplatin

Conditions
ConditionsYield
In hydrogenchloride Pt complex transformed in HCl soln. at 25°C with no oxidants;85%

cis-diaminediiodoplatinum(II)

potassium chloride

15663-27-1

cisplatin

Conditions
ConditionsYield
Stage #1: cis-diaminediiodoplatinum(II) With silver nitrate In water at 80℃; for 2h;
Stage #2: potassium chloride at 80℃; for 0.166667h;
73%
Stage #1: cis-diaminediiodoplatinum(II) With silver nitrate In water at 80℃; for 0.333333h; Darkness;
Stage #2: potassium chloride at 0℃; for 0.25h;
60%
Stage #1: cis-diaminediiodoplatinum(II) With silver nitrate In water at 50℃; for 24h;
Stage #2: potassium chloride
Stage #1: cis-diaminediiodoplatinum(II) With silver nitrate In water at 70℃; for 1.5h; Darkness;
Stage #2: potassium chloride In water at 70℃; for 1h; Darkness;

ammonium platinum(II) chloride

7664-41-7

ammonia

15663-27-1

cisplatin

Conditions
ConditionsYield
In water byproducts: {Pt(NH3)4}{PtCl4}; mixing of a soln. of (NH4)2(PtCl4) in cold H2O with 5 n NH3 soln. and storing for 12-18 h at 0°C;; washing with ice water and treatment on a filter with boiling H2O; addn. of half concd. HCl soln. to the soln. and filtration after 24 h; washing with ice water, then with alcohol; drying in air;;66.7%
In water byproducts: {Pt(NH3)4}{PtCl4}; mixing of a soln. of (NH4)2(PtCl4) in cold H2O with 5 n NH3 soln. and storing for 12-18 h at 0°C;; washing with ice water and treatment on a filter with boiling H2O; addn. of half concd. HCl soln. to the soln. and filtration after 24 h; washing with ice water, then with alcohol; drying in air;;66.7%
With NH4-oxalate In water formation from (NH4)2(PtCl4), aq. NH4 oxalate and NH3 soln.;;
With NH4-oxalate In water formation from (NH4)2(PtCl4), aq. NH4 oxalate and NH3 soln.;;

cis-diaminediiodoplatinum(II)

7647-14-5

sodium chloride

15663-27-1

cisplatin

Conditions
ConditionsYield
With silver nitrate In N,N-dimethyl acetamide; water at 60℃; Darkness;61.7%

ammonium acetate

7647-01-0

hydrogenchloride

magnus green salt

15663-27-1

cisplatin

Conditions
ConditionsYield
With acetic acid In water Magnus salt suspended in water; ammmonium acetate added; pH adjusted to 5.4 (acetic acid); mixt. heated for 1 h; cooled; filtered; concd. HCl added; cis-Pt(NH3)2Cl2 sepd.; soln. heated at about 95°C for 1.5 h; cooled; trans-Pt(NH3)2Cl2 sepd.; elem. anal.;A 40%
B 39%

cis-{Pt(glycyl-α-alanine)2(NH3)2}*H2O

15663-27-1

cisplatin

Conditions
ConditionsYield
With HCl In not given Joergensen splitting in the presence of concd. HCl;10%

cis-diamminediaquaplatinum(II)

potassium chloride

15663-27-1

cisplatin

ammonium carbonate

hydrogen chloroplatinate(II)

15663-27-1

cisplatin

Conditions
ConditionsYield
In not given pptn. from H2(PtCl4) soln. with (NH4)2CO3;;
In not given pptn. from H2(PtCl4) soln. with (NH4)2CO3;;

hydrogen chloroplatinate(II)

7664-41-7

ammonia

15663-27-1

cisplatin

Conditions
ConditionsYield
In ammonia byproducts: {Pt(NH3)4}Cl2*H2O; formation by treating of H2(PtCl4) soln. with excess NH3;;
In ammonia byproducts: {Pt(NH3)4}{PtCl4}; formation by treating a cold H2(PtCl4) soln. with NH3 soln.;; recrystn. of the ppt. in boiling H2O;;
In not given addn. of NH3 to H2(PtCl4);;
In ammonia byproducts: {Pt(NH3)4}Cl2*H2O; aq. ammonia=NH3; formation by treating of H2(PtCl4) soln. with excess NH3;;
In ammonia byproducts: {Pt(NH3)4}{PtCl4}; aq. ammonia=NH3; formation by treating a cold H2(PtCl4) soln. with NH3 soln.;; recrystn. of the ppt. in boiling H2O;;
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History

 The compound cis-PtCl2(NH3)2 was first described by M. Peyrone in 1845. Approved for clinical use by the United States Food and Drug Administration (FDA) in 1978.

Specification

The Cisplatin, with the CAS registry number 15663-27-1,is also known as cis-Diaminedichloroplatinum(II). It belongs to the product categories of ammine metal halide;Anti Cancer Reagents;chemical reaction,pharm,electronic,materials. Its EINECS number is 239-733-8. This chemical's molecular formula is Cl2H6N2Pt and molecular weight is 300.05. What's more,Its systematic name is Cisplatin.It is a Crystalline which is an inorganic and water-soluble platinum complex. After undergoing hydrolysis, it reacts with DNA to produce both intra and interstrand crosslinks. These crosslinks appear to impair replication and transcription of DNA. The cytotoxicity of cisplatin correlates with cellular arrest in the G2 phase of the cell cycle.

You can still convert the following datas into molecular structure:
(1)SMILES:[NH3][Pt]([NH3])(Cl)Cl;
(2)Std. InChI:InChI=1S/2ClH.2H3N.Pt/h2*1H;2*1H3;/q;;;;+2/p-2;
(3)Std. InChIKey:LXZZYRPGZAFOLE-UHFFFAOYSA-L;

Safety Information of Cisplatin:
The Cisplatin is Irritating to eyes, respiratory system and skin and it may cause sensitization by inhalation and skin contact. so it should avoid exposure - obtain special instructions before use. It is risk of serious damage to the eyes.  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. When you use it ,wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

The toxicity data of Cisplatin are as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo unreported 19200ug/kg/12 (19.2mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR Journal of Pediatrics. Vol. 103, Pg. 1006, 1983.
dog LDLo intravenous 2500ug/kg (2.5mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN

GASTROINTESTINAL: OTHER CHANGES
Toxicology and Applied Pharmacology. Vol. 25, Pg. 230, 1973.
frog LD50 parenteral 17mg/kg (17mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Journal of Comparative Pathology. Vol. 103, Pg. 387, 1990.
guinea pig LD50 intraperitoneal 9700ug/kg (9.7mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR Toxicology and Applied Pharmacology. Vol. 33, Pg. 320, 1975.
human TDLo intradermal 40ng/kg (.00004mg/kg) SKIN AND APPENDAGES (SKIN): PRIMARY IRRITATION: AFTER TOPICAL EXPOSURE

SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE
Cancer Research. Vol. 35, Pg. 2766, 1975.
human TDLo intravenous 500ug/kg/13D- (.5mg/kg) BLOOD: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: RENAL FUNCTION TESTS DEPRESSED
Cancer Treatment Reports. Vol. 62, Pg. 693, 1978.
human TDLo intravenous 1500ug/kg/6D- (1.5mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

KIDNEY, URETER, AND BLADDER: RENAL FUNCTION TESTS DEPRESSED

SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR
Cancer Chemotherapy Reports, Part 1. Vol. 57, Pg. 191, 1973.
human TDLo intravenous 2500ug/kg (2.5mg/kg) KIDNEY, URETER, AND BLADDER: RENAL FUNCTION TESTS DEPRESSED

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

GASTROINTESTINAL: NAUSEA OR VOMITING
Cancer Chemotherapy Reports, Part 1. Vol. 59, Pg. 647, 1975.
human TDLo intravenous 72mg/kg/25D-I (72mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Cancer Treatment Reports. Vol. 62, Pg. 1591, 1978.
mammal (species unspecified) LDLo intravenous 8mg/kg (8mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 28(4), Pg. 285, 2000.
man TDLo intravenous 2140ug/kg/5D- (2.14mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Japanese Journal of Medicine. Vol. 23, Pg. 283, 1984.
man TDLo parenteral 2140ug/kg/5D- (2.14mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Nippon Naika Gakkai Zasshi. Journal of the Japanese Society of Internal Medicine. Vol. 72, Pg. 1426, 1983.
monkey LDLo intravenous 250ug/kg (.25mg/kg)   Cancer Vol. 33, Pg. 1219, 1974.
mouse LD50 intramuscular 17900ug/kg (17.9mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BLOOD: NORMOCYTIC ANEMIA
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 723, 1982.
mouse LD50 intraperitoneal 6600ug/kg (6.6mg/kg)   Journal of Medicinal Chemistry. Vol. 34, Pg. 414, 1991.
mouse LD50 intravenous 11mg/kg (11mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 90, 1984.
mouse LD50 oral 32700ug/kg (32.7mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Kiso to Rinsho. Clinical Report. Vol. 15, Pg. 5669, 1981.
mouse LD50 parenteral 22mg/kg (22mg/kg)   International Journal of Radiation Oncology, Biology, Physics. Vol. 5, Pg. 1417, 1979.
mouse LD50 subcutaneous 13mg/kg (13mg/kg)   Journal de Pharmacie de Belgique. Vol. 41, Pg. 286, 1986.
mouse LD50 unreported 10900ug/kg (10.9mg/kg)   Gan to Kagaku Ryoho. Cancer and Chemotherapy. Vol. 13, Pg. 280, 1986.
rat LD unreported > 5mg/kg (5mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Journal of Toxicological Sciences. Vol. 24, Pg. 337, 1999.
rat LD50 intramuscular 9200ug/kg (9.2mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BLOOD: NORMOCYTIC ANEMIA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 723, 1982.
rat LD50 intraperitoneal 6400ug/kg (6.4mg/kg)   Journal of Toxicological Sciences. Vol. 18, Pg. 31, 1993.
rat LD50 intravenous 8mg/kg (8mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES JNCI, Journal of the National Cancer Institute. Vol. 67, Pg. 201, 1981.
rat LD50 oral 25800ug/kg (25.8mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BLOOD: NORMOCYTIC ANEMIA
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 723, 1982.
rat LD50 subcutaneous 8100ug/kg (8.1mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Kiso to Rinsho. Clinical Report. Vol. 15, Pg. 5669, 1981.