CISPLATIN

PRODUCT IDENTIFICATION
CAS NO. 15663-27-1

CISPLATIN

EINECS NO. 239-733-8
FORMULA Pt(NH3)2Cl2
MOL WT. 300.05

H.S. CODE

 2843.90.0000

TOXICITY

 Oral Rat LD50: 25800ug/kg
SYNONYMS CDDP; cis-DDP; DDP; cis-Diammine Dichloroplatinum(II);
Diaminedichloroplatinum; cis-Platinous diamine dichloride; cis Pt II; Neoplatin; Peyrone's chloride; Platiblastin; (SP-4-2)-Diaminedichloroplatinum; cis-Platinum(II) diammine Dichloride; cis-Diammineplatinum(II) Dichloride; (SP-4-2)-Diamminedichloroplatinum; Briplatin; Cismaplat; Cisplatyl; Citoplatino; Lederplatin; Neoplatin; Platamine; Platinex; Platiblastin; Platinol; Platinoxan; Platistin; Platosin; Randa;
SMILES

[Pt+2]([NH3])([Cl-])([Cl-])[NH3]

CLASSIFICATION

Antineoplastic agent, Cross-linking reagent, Indicator, Radiation-sensitizing agent, Platinum Complexes

EXTRA NOTES

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.
Overall Carcinogenic Evaluation: Group 2A
Other RN: 96081-74-2, 936542-99-3

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE yellow crystalline powder
MELTING POINT >270 C (Decomposes)
BOILING POINT  
SPECIFIC GRAVITY  
SOLUBILITY IN WATER Soluble (0.25g/100ml).  Slowly changes from the cis to the trans form in aqueous solution.

SOLVENT SOLUBILITY

Insoluble in most organic solvents. Soluble in DMF.

pH  
VAPOR DENSITY

 

AUTOIGNITION

 

NFPA RATINGS

 Health: 1; Flammability: 1; Instability: 0

REFRACTIVE INDEX

 

FLASH POINT  
STABILITY

Stable under ordinary conditions

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking: http://en.wikipedia.org/

Google Scholar Search: http://scholar.google.co.kr/

http://www.iupac.org/
The mechanism of action of platinum anti-tumor drugs. Abstract. A discussion is presented on the mechanism of action of platinum amine compounds, used as antitumor drugs. The relationship between biological acitivity and structure of the compounds is discussed, with special attention to the nature of the ligands coordinated to platinum. The primary biological target appears to be the interaction with nucleic acids, and therefore studies of the interaction of platinum amine compounds (both active and inactive ones) with nucleic acids and nucleic acid fragments are of great interest. Studies on mononucleotides have made clear that a strong preference exists for platinum binding at guanine—N7 sites. Investigations on oligonucleotides have shown that, when two neighboring guanines are present, chelation of the cis—Pt(NH3)2 unit (abbreviated cisplatin) is strongly preferred above all other possibilities. Studies on DNA ( in vivo and in vitro) have made clear that similar binding modes occur in DNA and oligonucleotides, and that - after cisplatin binding — the DNA structure is distorted in the same way as double-stranded oligonucleotides.

http://www.medclip.com/
Medical Videos - CisPlatin: Mechanism of Action

Local
Carboplatin, a platinum coordination compound which contains a platinum atom surrounded with two ammonia groups and two other ligands in a ring structure. Cisplatin is an analogue which has two chloride atoms instead of ring structure. Oxaliplatin contains a platinum atom complexed with 1,2-diaminocyclohexane and with an oxalate ligand as a leaving group. It is known that diaminocyclohexane group contributes greater cytotoxicity than cisplatin and carboplatin. Oxaliplatin is not generally cross-resistant to cisplatin or carboplatin. They are capable of forming platinum complexes producing inter- and intrastrand DNA crosslinks with neighboring guanine residues, resulting in DNA-mismatch repair (MMR) activity in the cancer cells. Carboplatin has less nephrotoxicity, neurotoxicity, ototoxicity and emetogenesis and more stability than cisplatin. They, platinum-based antineoplastics, have a broad spectrum of antitumor activity in the treatments of carcinomas of ovarian, testicular, bladder, small and non–small cell lung, head and neck carcinoma, and seminoma. They are synergistic with fluorouracil. They are radiation sensitive. The chemical designation of cisplatin is (SP-4-2)-diaminedichloroplatinum (II). It is a yellow crystalline powder; soluble in water and saline; administered intravenously. The chemical designation of carboplatin is (SP-4-2)-diammine [1,1-cyclobutanedicarboxylato (2-)-0, 0']- platinum (II). It is a white crystalline powder; soluble in water; insoluble in ethanol, acetone, and dimethylacetamide; administered intravenously. The chemical designation of oxaliplatin is SP-4-2-(1R-trans))- (1,2-cyclohexanediamine-N,N')- (ethanedioato(2-)-O,O') platinum (II). It is a white crystalline powder; soluble in water; very slightly soluble in methanol; insoluble in ethanol, hexane, benzene and acetone.

SALES SPECIFICATION

APPEARANCE

 yellow crystalline powder

IDENTIFICATION

Complies Test A,B

ASSAY

98.0 - 102.0% (HPLC)

PLATINUM CONTENT

64.4 - 65.2%

RELATED SUBSTANCE

1.0% max (Trichloroammineplatinate)

WATER

1.0% max

TRANSPORTATION
PACKING  
HAZARD CLASS 6.1 (Packing Group:II)
UN NO. 3288

GENERAL DESCRIPTION OF ALKYLATING AGENTS AS ANTITUMOR

Alkylating agents are used in cancer chemotherapy by the substitutiopn of alkyl groups for the hydrogen atoms in biological organic compounds present in cells to inhibit tumor growth with mutagenic activity. They cross-links DNA, makes the strands unable to seperate, and induces mutations. They are cell cycle non-specific drugs. Their effects primarily occurs in proliferating tissues which don't have time to mitose DNA repair systems. Classes of alkylating agents for antineoplastic include:
  • Nitrogen mustard
    • Chlorambucil (CAS RN: 305-03-3)
    • Mechlorethamine (CAS RN: 51-75-2)
    • Melphalan (CAS RN:148-82-3)
    • Uracil Mustard (CAS RN: 66-75-1)
    • Cyclophosphamide (CAS RN: 50-18-0)
    • Iphosphamide (CAS RN: 3778-73-2)
  • Nitrosoureas
    • Triethylenemelamine (CAS RN: 51-18-3)
    • Hexamethylmelamine (CAS RN: 645-05-6)
    • Bis-chloroethylnitrosourea (CAS RN: 154-93-8)
    • Chloroethylcyclohexylnitrosourea (CAS RN: 13010-47-4)
    • Streptozotocin (CAS RN: 18883-66-4)
  • Platinum compounds
    • Carboplatin (CAS RN: 41575-94-4)
    • Oxaliplatin (CAS RN: 61825-94-3)
    • Cisplatin (CAS CN: 15663-27-)
    • Tetraplatin (CAS RN: 62816-98-2)
    • (Carboxyphthalato)platinum (CAS RN: 65296-81-3)
  • Alkyl sulfonates
    • Busulfan (CAS RN: 55-98-1)
    • Mannosulfan  (CAS RN: 7518-35-6)
    • Treosulfan (CAS RN: 299-75-2)
  • Aziridines
    • Thiotepa (CAS RN: 52-24-4)
SAFETY INFORMATION

HAZARD OVERVIEW

Harmful if swallowed or in contact with skin. May cause an allergic skin reaction. Harmful if inhaled. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May damage fertility or the unborn child. OSHA Hazards:Target Organ Effect, Toxic by inhalation., Toxic by ingestion, Harmful by skin absorption., Skin and respiratory sensitizer, Teratogen. Target Organs: Bone marrow, ears, Kidney, Nerves., Liver injury may occur., Kidney injury may occur.

GHS

 

SIGNAL WORD

Danger

PICTOGRAMS

HAZARD STATEMENTS

H300-H318-H350

P STATEMENTS

P201-P264-P280-P301 + P310-P305 + P351 + P338-P308 + P313

EC DIRECTIVES

 

HAZARD CODES

T

RISK PHRASES

45-25-41

SAFETY PHRASES

53-26-39-45