(SP-4-2)-((1R,2R)-1,2-Cyclohexanediamine-kappaN1,kappaN2)bis(tetradecanoato-kappaO)platinum
Basic information
- CAS
141977-79-9- Standard SMILES
CCCCCCCCCCCCCC(=O)[O-].CCCCCCCCCCCCCC(=O)[O-].N[C@@H]1CCCC[C@H]1N.[Pt+2]- InChIKey
BGIHRZPJIYJKAZ-BLUNCNMSSA-L- Molecular formula
- C34H68N2O4Pt
- Average molar mass
- 764 g/mol
- Monoisotopic mass
- 763.482703
Overview
Miriplatin is a lipophilic platinum complex and oxaliplatin analog that contains two myristate chains, with potential antineoplastic activity. Upon administration of miraplatin, the platinum moiety forms complexes with nucleophilic groups such as GC-rich sites in DNA, inducing intrastrand and interstrand DNA cross-links, as well as DNA-protein cross-links, resulting in apoptosis and cell growth inhibition. Compared to platinum alone, the lipophilic formulation allows increased delivery of platinum to the tumor site, thereby increasing efficacy while reducing systemic toxicity.
Names & identifiers
- Preferred name
- (SP-4-2)-((1R,2R)-1,2-Cyclohexanediamine-kappaN1,kappaN2)bis(tetradecanoato-kappaO)platinum
- IUPAC
- platinum(2+);bis(tetradecanoate);trans-(1R,2R)-cyclohexane-1,2-diamine
- English name
- Miriplatin
- Molecular formula
- C34H66N2O4Pt
- Molecular weight
- 762
Names & synonyms
MIRIPLAmiriplatinemiriplatinomiriplatinumRefChem:159050DTXCID401568073(SP-4-2)-((1R,2R)-1,2-Cyclohexanediamine-kappaN1,kappaN2)bis(tetradecanoato-kappaO)platinum141977-79-9780F0P8N4Icis-(((1R,2R)-1,2-cyclohexanediamine-N,N')bis(myristato))platinum (II)cyclohexane-1,2-diamine platinum(II) dimyristateDTXSID101136455
Show more names
MiboMiplatinSM 11355Mmiriplatin[(1R,2R)-1,2-Cyclohexanediamine]bis(myristato)platinum(SP-4-2)-[(1R,2R)-1,2-Cyclohexanediamine-kappaN,kappaN'])bis...Miriplatin,SM11355,inhibit,Inhibitor,SM 11355,DNA Alkylator/Crosslinker(SP-4-2)-[(1R,2R)-1,2-Cyclohexanediamine-κN1,κN2]bis(tetradecanoato-κO)platinumPlatinum,[(1R,2R)-1,2-cyclohexanediamine-kN1,kN2]bis(tetradecanoato-kO)-, (SP-4-2)-
MiriplatinSM-11355SM11355MFCD04113190(1R,2R)-cyclohexane-1,2-diamine;platinum(2+);tetradecanoateC34H68N2O4PtMIRIPLATIN [MI]MIRIPLATIN [WHO-DD]
Properties
Computed structural properties
- Topological polar surface area
- 132 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 22
- Heavy atoms
- 41
- Formal charge
- 0
- Complexity
- 212
Physicochemical properties
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- solubility
- 1 mg/mL · DMF : < 1 mg/mL (insoluble)
- form
- Solid
- color
- White to off-white
- InChI
- 1S/2C14H28O2.C6H12N2.Pt/c2*1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16;7-5-3-1-2-4-6(5)8;/h2*2-13H2,1H3,(H,15,16);5-8H,1-4H2;/q;;-2;+4/p-2/t;;5-,6-;/m..1./s1
- InChIKey
- DTRJSYSQELJDAW-BLUNCNMSSA-L
- SMILES
- CCCCCCCCCCCCCC(O[Pt]1(N[C@@H]2CCCC[C@H]2N1)OC(CCCCCCCCCCCCC)=O)=O
- FDA UNII
- 780 F0P8N4I · 780F0P8N4I
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 280 · P280-P305+P351+P338
- WGK Germany
- 3 · WGK 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Applications
UsesMiplatin is a platinum-based anticancer drug developed by Japan's Sumitomo Pharmaceutical Co., Ltd. It is used in the treatment of liver cancer, malignant lymphoma, non-small cell lung cancer, small cell lung cancer and superficial bladder cancer.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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