Miriplatin | A lipophilic derivative of cisplatin | CAS#250159-48-9

MedKoo Cat#: 120200 | Name: Miriplatin hydrate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Miriplatin (MPT) is a novel platinum complex used in TACE that shows promise for the treatment of hepatocellular carcinoma (HCC). Miriplatin is a lipophilic platinum complex that can be easily suspended in Lipiodol and gradually releases active platinum compounds in tumor tissue. Miriplatin is less severe toxicity profile compared to other platinum anticancer agents.

Chemical Structure

Miriplatin hydrate

CAS#250159-48-9 (hydrate)

Theoretical Analysis

MedKoo Cat#: 120200

Name: Miriplatin hydrate

CAS#: 250159-48-9 (hydrate)

Chemical Formula: C34H68N2O4Pt

Exact Mass: 0.0000

Molecular Weight: 764.00

Elemental Analysis: C, 52.22; H, 9.02; N, 3.58; O, 10.23; Pt, 24.95

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,250.00	Ready to ship
500mg	USD 2,450.00	Ready to ship
1g	USD 3,850.00	Ready to ship
2g	USD 5,850.00	Ready to ship

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Related CAS #

250159-48-9 (hydrate) 141977-79-9 (free base)

Synonym

SM 11355; SM-11355; SM11355; Miripla; Miriplatin; Miriplatin hydrate; MTP.

IUPAC/Chemical Name

(1R,2R)-cyclohexane-1,2-diamine;platinum(2+);tetradecanoate;hydrate

InChi Key

LWDBMUAJGMXQAY-GSEQGPDBSA-L

InChi Code

InChI=1S/2C14H28O2.C6H14N2.H2O.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);5-6H,1-4,7-8H2;1H2;/q;;;;+2/p-2/t;;5-,6-;;/m..1../s1

SMILES Code

O=C(O[Pt-2]1(OC(CCCCCCCCCCCCC)=O)[NH2+][C@H]2[C@@H](CCCC2)[NH2+]1)CCCCCCCCCCCCC.[H]O[H]

Appearance

White solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#TZC31105

QC Data

View QC data: current batch, Lot#TZC31105

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Miriplatin hydrate (SM-11355 hydrate) is a chemotherapy agent which belongs to the class of alkylating agents.

In vitro activity:

In vitro antitumor effects of miriplatin/LPD (Lipiodol Ultra-Fluide®, LPD) and cisplatin/LPD were examined using cell culture inserts. In this system, the LPD suspension does not make contact with the cells directly, but via membranes with tiny pores. IC50 values for rat ascite hepatoma AH109A cells after 7 days of exposure to miriplatin/LPD was 0.89 ± 015. Increasing the concentrations of miriplatin in LPD increased the platinum concentrations in medium at day 7 (Fig. 2b). In addition, miriplatin inhibited cell growth depending on their concentrations in the medium. Next, in vitro antitumor effects of miriplatin, cisplatin, and zinostatin stimalamer were examined in addition to those of DPC or DPI, both of which were detected as compounds released from miriplatin/LPD. IC50 values for AH109A cells after 3 days of exposure to DPC, DPI, cisplatin, and zinostatin stimalamer were 0.14 ± 0.07, 0.83 ± 0.32, 0.30 ± 0.07, and 0.13 ± 0.00 μg/mL, respectively. Miriplatin did not inhibit cell growth at the highest concentrations tested (20 μg/mL) probably due to its low water solubility. From these results, it was shown that platinum compounds released from miriplatin/LPD inhibited the growth of AH109A cells. Reference: Cancer Chemother Pharmacol. 2009 Jul; 64(3): 473–483. https://pubmed.ncbi.nlm.nih.gov/19104812/

In vivo activity:

Miriplatin/LPD and cisplatin/LPD (400 µg/head) were injected into the hepatic artery of tumor-bearing rats at the volume of 0.02 mL/head. When miriplatin/LPD was administered into the hepatic artery, LPD detected as white dots in the soft X-ray photograph was selectively retained in tumors, while it disappeared from non-tumor regions within 7 days (Fig. 5b). The platinum concentrations in AH109A tumors were higher than those in non-tumor regions on both days, irrespective of the agents. On the other hand, the platinum concentrations in tumors were higher after the administration of miriplatin/LPD than cisplatin/LPD on both days. In addition, in the case of miriplatin/LPD, 18 ± 15 and 17 ± 13 μg of platinum were disposed of in tumors at day 0 and day 7, respectively. These results indicate that platinum compounds were selectively disposed of in tumors after the intra-hepatic arterial administration of miriplatin/LPD. Reference: Cancer Chemother Pharmacol. 2009 Jul; 64(3): 473–483. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2691803/

	Solvent	mg/mL	mM
Solubility
	DMSO	0.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 764.00 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Hanada M, Baba A, Tsutsumishita Y, Noguchi T, Yamaoka T, Chiba N, Nishikaku F. Intra-hepatic arterial administration with miriplatin suspended in an oily lymphographic agent inhibits the growth of tumors implanted in rat livers by inducing platinum-DNA adducts to form and massive apoptosis. Cancer Chemother Pharmacol. 2009 Aug;64(3):473-83. doi: 10.1007/s00280-008-0895-3. Epub 2008 Dec 24. PMID: 19104812; PMCID: PMC2691803. 2. Hanada M, Baba A, Tsutsumishita Y, Noguchi T, Yamaoka T. Intra-hepatic arterial administration with miriplatin suspended in an oily lymphographic agent inhibits the growth of human hepatoma cells orthotopically implanted in nude rats. Cancer Sci. 2009 Jan;100(1):189-94. doi: 10.1111/j.1349-7006.2008.01010.x. Epub 2008 Nov 24. PMID: 19037997. 3. Hanada M, Baba A, Tsutsumishita Y, Noguchi T, Yamaoka T, Chiba N, Nishikaku F. Intra-hepatic arterial administration with miriplatin suspended in an oily lymphographic agent inhibits the growth of tumors implanted in rat livers by inducing platinum-DNA adducts to form and massive apoptosis. Cancer Chemother Pharmacol. 2009 Aug;64(3):473-83. doi: 10.1007/s00280-008-0895-3. Epub 2008 Dec 24. PMID: 19104812; PMCID: PMC2691803

In vitro protocol:

In vivo protocol:

1: Yasui D, Murata S, Onozawa S, Mine T, Ueda T, Sugihara F, Kawamoto C, Uchida E, Kumita S. Improved efficacy of transcatheter arterial chemoembolization using warmed miriplatin for hepatocellular carcinoma. Biomed Res Int. 2014;2014:359296. doi: 10.1155/2014/359296. Epub 2014 Sep 8. PubMed PMID: 25276780; PubMed Central PMCID: PMC4172877. 2: Arai H, Abe T, Takayama H, Toyoda M, Ueno T, Kakizaki S, Sato K. Safety and efficacy of balloon-occluded transcatheter arterial chemoembolization using miriplatin for hepatocellular carcinoma. Hepatol Res. 2014 Aug 8. doi: 10.1111/hepr.12403. [Epub ahead of print] PubMed PMID: 25132539. 3: Ishikawa T, Abe S, Inoue R, Sugano T, Watanabe Y, Iwanaga A, Seki K, Honma T, Nemoto T, Takeda K, Yoshida T. Predictive factor of local recurrence after balloon-occluded TACE with miriplatin (MPT) in hepatocellular carcinoma. PLoS One. 2014 Jul 21;9(7):e103009. doi: 10.1371/journal.pone.0103009. eCollection 2014. PubMed PMID: 25047920; PubMed Central PMCID: PMC4105420. 4: Ito T, Okubo H, Kokubu S, Miyazaki A, Ando H, Fujimura A, Watanabe S. Radiofrequency ablation combined with chemolipiodolization in a porcine liver: Comparison of the pharmacokinetic analysis with cisplatin powder and miriplatin. Hepatol Res. 2014 Jul 7. doi: 10.1111/hepr.12387. [Epub ahead of print] PubMed PMID: 25040841. 5: Otsuji K, Takai K, Nishigaki Y, Shimizu S, Hayashi H, Imai K, Suzuki Y, Hanai T, Ideta T, Miyazaki T, Tomita E, Shimizu M, Moriwaki H. Efficacy and safety of cisplatin versus miriplatin in transcatheter arterial chemoembolization and transarterial infusion chemotherapy for hepatocellular carcinoma: A randomized controlled trial. Hepatol Res. 2014 Jun 24. doi: 10.1111/hepr.12376. [Epub ahead of print] PubMed PMID: 24961745. 6: Okimoto K, Ogasawara S, Chiba T, Ooka Y, Oobu M, Azemoto R, Kanogawa N, Motoyama T, Suzuki E, Tawada A, Yoshikawa M, Yokosuka O. Efficacy of transcatheter arterial chemoembolization with miriplatin-lipiodol water-soluble contrast agent emulsion in patients with hepatocellular carcinoma. Anticancer Res. 2013 Dec;33(12):5603-9. PubMed PMID: 24324105. 7: Yamanaka T, Takaki H, Nakatsuka A, Uchida K, Junji U, Fujimori M, Hasegawa T, Yoneda M, Shiraishi T, Sakuma H, Yamakado K. Radiofrequency ablation after arterial injection of miriplatin-iodized oil suspension into swine liver: ablative zone size and tissue platinum concentration. Cardiovasc Intervent Radiol. 2014 Aug;37(4):1047-52. doi: 10.1007/s00270-013-0779-8. PubMed PMID: 24232037. 8: Hashimoto N, Iwazawa J, Ohue S, Mitani T. Effect of transarterial chemoembolization with miriplatin plus epirubicin on local control of hepatocellular carcinoma: a retrospective comparison with miriplatin monotherapy. Onco Targets Ther. 2013 Aug 1;6:1025-30. doi: 10.2147/OTT.S49443. eCollection 2013. PubMed PMID: 23986641; PubMed Central PMCID: PMC3753878. 9: Handa T, Imai Y, Sugawara K, Chikayama T, Nakazawa M, Ando S, Hamaoka K, Inao M, Nakayama N, Mochida S. Transcatheter arterial chemoembolization for hepatocellular carcinoma: Comparison of the therapeutic efficacies between miriplatin and epirubicin. Hepatol Res. 2013 Aug 19. doi: 10.1111/hepr.12225. [Epub ahead of print] PubMed PMID: 23957866. 10: Ueda T, Murata S, Yasui D, Mine T, Kumita S. Comparison of the antitumor efficacy of transcatheter arterial chemoembolization with a miriplatin-iodized oil suspension and a cisplatin-iodized oil suspension for hepatocellular carcinoma. Hepatol Res. 2013 Oct;43(10):1071-7. doi: 10.1111/hepr.12212. Epub 2013 Aug 19. PubMed PMID: 23905645.