Satraplatin
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MedKoo CAT#: 202570

CAS#: 129580-63-8

Description: Satraplatin, also known as JM216 and BMS182751, is a platinum compound that is currently under investigation as one treatment of patients with advanced prostate cancer who have failed previous chemotherapy. It has not yet received approval from the U.S. Food and Drug Administration. Satraplatin is the first orally active platinum-based chemotherapeutic drug.

Chemical Structure

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Satraplatin
CAS# 129580-63-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 202570
Name: Satraplatin
CAS#: 129580-63-8
Chemical Formula: C10H22Cl2N2O4Pt
Exact Mass: 499.06
Molecular Weight: 500.280
Elemental Analysis: C, 24.01; H, 4.43; Cl, 14.17; N, 5.60; O, 12.79; Pt, 38.99

Price and Availability

Size Price Availability Quantity
5mg USD 375
10mg USD 700
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Synonym: BMS182751; BMS 182751; BMS-182751; JM 216; JM-216; JM216; Satraplatin

IUPAC/Chemical Name: (OC-6-43)-bis(acetato)amminedichloro(cyclohexylamine)platinum

InChi Key: CKNPWBAXEKSCRG-UHFFFAOYSA-J

InChi Code: InChI=1S/C6H13N.2C2H4O2.2ClH.H3N.Pt/c7-6-4-2-1-3-5-6;2*1-2(3)4;;;;/h6H,1-5,7H2;2*1H3,(H,3,4);2*1H;1H3;/q;;;;;;+4/p-4

SMILES Code: CC(O[Pt]([NH2]C1CCCCC1)(Cl)(Cl)([NH3])OC(C)=O)=O

Appearance: 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 soluble in water.

Shelf Life: >5 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:   According to news published in 8 Jul 2008, GPC Biotech AG  reported that the Company has been informed by its partner for satraplatin in Europe that they plan to withdraw the Marketing Authorization Application (MAA) for satraplatin plus prednisone for the treatment of hormone-refractory prostate cancer patients whose prior chemotherapy has failed. This decision was based on a list of outstanding issues received following review by the Committee for Medicinal Products for Human Use (CHMP) of the European Medicines Agency (EMEA) of the filing, which indicates that the opinion of the Committee is that the application is currently not approvable based on the information provided. see: http://www.medicalnewstoday.com/articles/116301.php .      

Product Data:
Product Data
Instruction:
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Biological target: Satraplatin is an alkylating agent.
In vitro activity: Satraplatin displays greater antiproliferative effects than cisplatin in lymphoma cell lines. Specific gene mutations, including MTAP deficiency, are key factors associated with heightened sensitivity to satraplatin. This distinct activity profile and the presence of MTAP deficiency make satraplatin a promising candidate for targeted therapies in certain lymphatic malignancies, like primary central nervous system lymphoma and cutaneous T-cell lymphoma. Reference: Nanotechnology. 2021 Sep 2;32(47). https://pubmed.ncbi.nlm.nih.gov/34388738/
In vivo activity: In a non-human primate study, satraplatin was well-tolerated and had presence in the central nervous system. Despite its greater lipophilicity, satraplatin's CSF penetration was similar to that of carboplatin and cisplatin. These findings support the development of phase I trials for satraplatin in treating childhood solid tumors. Reference: Cancer Chemother Pharmacol. 2012 Jan;69(1):247-52. https://pubmed.ncbi.nlm.nih.gov/21706317/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 10.0 19.99

Preparing Stock Solutions

The following data is based on the product molecular weight 500.28 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.

Recalculate based on batch purity %
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. Chen D, Zhang X, Yang J, Liao X, Yang B, Gao C. Codelivery of satraplatin and aminopyrrolic receptor with Pluronic F127-based polyaniline nanoparticles with NIR induced release for combined chemotherapy. Nanotechnology. 2021 Sep 2;32(47). doi: 10.1088/1361-6528/ac1d78. PMID: 34388738. 2. Yamano Y, Shiiba M, Negoro K, Nakatani K, Kasamatsu A, Yamatoji M, Sakuma K, Ogoshi K, Iyoda M, Shinozuka K, Yokoe H, Wada T, Fujita S, Iwasawa S, Takiguchi Y, Tanzawa H, Uzawa K. Antitumor activity of satraplatin in cisplatin-resistant oral squamous cell carcinoma cells. Head Neck. 2011 Mar;33(3):309-17. doi: 10.1002/hed.21445. PMID: 20848452. 3. Marcus L, Murphy R, Fox E, McCully C, Cruz R, Warren KE, Meyer T, McNiff E, Balis FM, Widemann BC. The plasma and cerebrospinal fluid pharmacokinetics of the platinum analog satraplatin after intravenous administration in non-human primates. Cancer Chemother Pharmacol. 2012 Jan;69(1):247-52. doi: 10.1007/s00280-011-1659-z. Epub 2011 Jun 26. PMID: 21706317; PMCID: PMC6300136. 4. Selting KA, Wang X, Gustafson DL, Henry CJ, Villamil JA, McCaw DL, Tate D, Beittenmiller M, Garnett C, Robertson JD. Evaluation of satraplatin in dogs with spontaneously occurring malignant tumors. J Vet Intern Med. 2011 Jul-Aug;25(4):909-15. doi: 10.1111/j.1939-1676.2011.0727.x. Epub 2011 May 12. PMID: 21564292.
In vitro protocol: 1. Chen D, Zhang X, Yang J, Liao X, Yang B, Gao C. Codelivery of satraplatin and aminopyrrolic receptor with Pluronic F127-based polyaniline nanoparticles with NIR induced release for combined chemotherapy. Nanotechnology. 2021 Sep 2;32(47). doi: 10.1088/1361-6528/ac1d78. PMID: 34388738. 2. Yamano Y, Shiiba M, Negoro K, Nakatani K, Kasamatsu A, Yamatoji M, Sakuma K, Ogoshi K, Iyoda M, Shinozuka K, Yokoe H, Wada T, Fujita S, Iwasawa S, Takiguchi Y, Tanzawa H, Uzawa K. Antitumor activity of satraplatin in cisplatin-resistant oral squamous cell carcinoma cells. Head Neck. 2011 Mar;33(3):309-17. doi: 10.1002/hed.21445. PMID: 20848452.
In vivo protocol: 1. Marcus L, Murphy R, Fox E, McCully C, Cruz R, Warren KE, Meyer T, McNiff E, Balis FM, Widemann BC. The plasma and cerebrospinal fluid pharmacokinetics of the platinum analog satraplatin after intravenous administration in non-human primates. Cancer Chemother Pharmacol. 2012 Jan;69(1):247-52. doi: 10.1007/s00280-011-1659-z. Epub 2011 Jun 26. PMID: 21706317; PMCID: PMC6300136. 2. Selting KA, Wang X, Gustafson DL, Henry CJ, Villamil JA, McCaw DL, Tate D, Beittenmiller M, Garnett C, Robertson JD. Evaluation of satraplatin in dogs with spontaneously occurring malignant tumors. J Vet Intern Med. 2011 Jul-Aug;25(4):909-15. doi: 10.1111/j.1939-1676.2011.0727.x. Epub 2011 May 12. PMID: 21564292.

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1: Doshi G, Sonpavde G, Sternberg CN. Clinical and pharmacokinetic evaluation of satraplatin. Expert Opin Drug Metab Toxicol. 2012 Jan;8(1):103-11. doi: 10.1517/17425255.2012.636352. Epub 2011 Nov 19. Review. PubMed PMID: 22098065.

2: Bhargava A, Vaishampayan UN. Satraplatin: leading the new generation of oral platinum agents. Expert Opin Investig Drugs. 2009 Nov;18(11):1787-97. doi: 10.1517/13543780903362437. Review. PubMed PMID: 19888874.

3: Sonpavde G, Sternberg CN. Satraplatin for the therapy of castration-resistant prostate cancer. Future Oncol. 2009 Sep;5(7):931-40. doi: 10.2217/fon.09.84. Review. PubMed PMID: 19792961.

4: Choy H, Park C, Yao M. Current status and future prospects for satraplatin, an oral platinum analogue. Clin Cancer Res. 2008 Mar 15;14(6):1633-8. doi: 10.1158/1078-0432.CCR-07-2176. Review. PubMed PMID: 18347164.

5: Kelland L. Broadening the clinical use of platinum drug-based chemotherapy with new analogues. Satraplatin and picoplatin. Expert Opin Investig Drugs. 2007 Jul;16(7):1009-21. Review. PubMed PMID: 17594186.

6: McKeage MJ. Satraplatin in hormone-refractory prostate cancer and other tumour types: pharmacological properties and clinical evaluation. Drugs. 2007;67(6):859-69. Review. PubMed PMID: 17428104.

7: Satraplatin: BMS 182751, BMY 45594, JM 216. Drugs R D. 2007;8(2):125-32. Review. PubMed PMID: 17324011.

8: Choy H. Satraplatin: an orally available platinum analog for the treatment of cancer. Expert Rev Anticancer Ther. 2006 Jul;6(7):973-82. Review. PubMed PMID: 16831070.

9: Satraplatin. BMS 182751, BMY 45594, JM 216. Drugs R D. 2002;3(1):67-71. Review. PubMed PMID: 11881537.

10: Kelland LR. An update on satraplatin: the first orally available platinum anticancer drug. Expert Opin Investig Drugs. 2000 Jun;9(6):1373-82. Review. PubMed PMID: 11060749.