Satraplatin | CAS#129580-63-8 | MedKoo Biosciences

MedKoo Cat#: 202570 | Name: Satraplatin

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Description:

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

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

Satraplatin

CAS#129580-63-8

Theoretical Analysis

MedKoo Cat#: 202570

Name: Satraplatin

CAS#: 129580-63-8

Chemical Formula: C10H22Cl2N2O4Pt

Exact Mass: 499.0604

Molecular Weight: 500.28

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 500.00
10mg	USD 850.00

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Related CAS #

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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

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	10.0	19.99

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 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.

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:

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.

1: Jiang X, Yang Q, Qi R, Yan L. Nanoparticle-Mediated Delivery of Satraplatin to Overcome Cisplatin Drug Resistance. J Funct Biomater. 2023 Jul 22;14(7):387. doi: 10.3390/jfb14070387. PMID: 37504882; PMCID: PMC10381687. 2: Liaw BC, Tsao CK, Seng S, Jun T, Gong Y, Galsky MD, Oh WK. Biomarker Development Trial of Satraplatin in Patients with Metastatic Castration- Resistant Prostate Cancer. Oncologist. 2023 Apr 6;28(4):366-e224. doi: 10.1093/oncolo/oyac224. PMID: 36519763; PMCID: PMC10078918. 3: Tsvetkova D, Ivanova S. Application of Approved Cisplatin Derivatives in Combination Therapy against Different Cancer Diseases. Molecules. 2022 Apr 11;27(8):2466. doi: 10.3390/molecules27082466. PMID: 35458666; PMCID: PMC9031877. 4: Zander T, Xue J, Markson G, Dahm F, Renner C. Satraplatin Demonstrates High Cytotoxic Activity Against Genetically Defined Lymphoid Malignancies. Anticancer Res. 2022 Apr;42(4):1821-1832. doi: 10.21873/anticanres.15658. PMID: 35347000. 5: Fahmy SA, Ponte F, Grande G, Fawzy IM, Mandour AA, Sicilia E, Azzazy HME. Synthesis, Characterization and Host-Guest Complexation of Asplatin: Improved In Vitro Cytotoxicity and Biocompatibility as Compared to Cisplatin. Pharmaceuticals (Basel). 2022 Feb 21;15(2):259. doi: 10.3390/ph15020259. PMID: 35215372; PMCID: PMC8875750. 6: 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. 7: He G, Xie X, Siddik ZH. Protein expression profiling identifies differential modulation of homologous recombination by platinum-based antitumor agents. Cancer Chemother Pharmacol. 2020 Jun;85(6):1129-1140. doi: 10.1007/s00280-020-04085-1. Epub 2020 May 28. PMID: 32468080; PMCID: PMC7402587. 8: Trigub ММ, Filatova NV, Areshidze DА, Sen' VD, Terentiev АА. Comparison of the Effect of Platinum (IV) Complexes on Spheroids and Monolayer Culture of HeLa Cells. Bull Exp Biol Med. 2020 Feb;168(4):583-588. doi: 10.1007/s10517-020-04757-1. Epub 2020 Mar 9. PMID: 32152850. 9: Karmakar S, Poetsch I, Kowol CR, Heffeter P, Gibson D. Synthesis and Cytotoxicity of Water-Soluble Dual- and Triple-Action Satraplatin Derivatives: Replacement of Equatorial Chlorides of Satraplatin by Acetates. Inorg Chem. 2019 Dec 16;58(24):16676-16688. doi: 10.1021/acs.inorgchem.9b02796. Epub 2019 Dec 2. PMID: 31790216. 10: Cho H, Shin I, Cho K, Yoon H, Yoo EK, Kim MJ, Park S, Lee IK, Kim ND, Sim T. Identification of Novel Resorcinol Amide Derivatives as Potent and Specific Pyruvate Dehydrogenase Kinase (PDHK) Inhibitors. J Med Chem. 2019 Sep 26;62(18):8461-8479. doi: 10.1021/acs.jmedchem.9b00565. Epub 2019 Sep 13. PMID: 31469962. 11: Kastner A, Poetsch I, Mayr J, Burda JV, Roller A, Heffeter P, Keppler BK, Kowol CR. A Dogma in Doubt: Hydrolysis of Equatorial Ligands of PtIV Complexes under Physiological Conditions. Angew Chem Int Ed Engl. 2019 May 27;58(22):7464-7469. doi: 10.1002/anie.201900682. Epub 2019 Apr 25. PMID: 30870571; PMCID: PMC6766845. 12: Ma J, Liu H, Xi Z, Hou J, Li Y, Niu J, Liu T, Bi S, Wang X, Wang C, Wang J, Xie S, Wang PG. Protected and De-protected Platinum(IV) Glycoconjugates With GLUT1 and OCT2-Mediated Selective Cancer Targeting: Demonstrated Enhanced Transporter-Mediated Cytotoxic Properties in vitro and in vivo. Front Chem. 2018 Sep 21;6:386. doi: 10.3389/fchem.2018.00386. PMID: 30298127; PMCID: PMC6160541. 13: Šebesta F, Baxová K, Burda JV. Redox Potentials for Tetraplatin, Satraplatin, Its Derivatives, and Ascorbic Acid: A Computational Study. Inorg Chem. 2018 Feb 5;57(3):951-962. doi: 10.1021/acs.inorgchem.7b01894. Epub 2018 Jan 24. PMID: 29363964. 14: Goldberg VE, Polyakova TY, Popova NO, Vysotskaya VV, Simolina EI, Belevich YV, Tuzikova TP, Goldberg AV, Zhdanov VV, Miroshnichenko LA, Udut EV, Simanina EV, Dygai AM, Zyuz'kov GN. Assessment of Erythroid and Granulocytic Hematopoietic Lineages in Patients with Non-Small-Cell Lung Carcinoma. Bull Exp Biol Med. 2017 Aug;163(4):469-474. doi: 10.1007/s10517-017-3830-y. Epub 2017 Aug 29. PMID: 28853075. 15: Wu Y, Lai RY. Tunable Signal-Off and Signal-On Electrochemical Cisplatin Sensor. Anal Chem. 2017 Sep 19;89(18):9984-9989. doi: 10.1021/acs.analchem.7b02353. Epub 2017 Aug 25. PMID: 28799328. 16: Ma J, Wang Q, Huang Z, Yang X, Nie Q, Hao W, Wang PG, Wang X. Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery. J Med Chem. 2017 Jul 13;60(13):5736-5748. doi: 10.1021/acs.jmedchem.7b00433. Epub 2017 Jun 27. PMID: 28603992. 17: Ritacco I, Al Assy M, Abd El-Rahman MK, Fahmy SA, Russo N, Shoeib T, Sicilia E. Hydrolysis in Acidic Environment and Degradation of Satraplatin: A Joint Experimental and Theoretical Investigation. Inorg Chem. 2017 May 15;56(10):6013-6026. doi: 10.1021/acs.inorgchem.7b00945. Epub 2017 Apr 28. PMID: 28452475. 18: Yap SQ, Chin CF, Hong Thng AH, Pang YY, Ho HK, Ang WH. Finely Tuned Asymmetric Platinum(IV) Anticancer Complexes: Structure-Activity Relationship and Application as Orally Available Prodrugs. ChemMedChem. 2017 Feb 20;12(4):300-311. doi: 10.1002/cmdc.201600577. Epub 2017 Jan 11. PMID: 28028938. 19: Doucette KA, Hassell KN, Crans DC. Selective speciation improves efficacy and lowers toxicity of platinum anticancer and vanadium antidiabetic drugs. J Inorg Biochem. 2016 Dec;165:56-70. doi: 10.1016/j.jinorgbio.2016.09.013. Epub 2016 Oct 3. PMID: 27751591. 20: Mumyatova VA, Balakina AA, Filatova NV, Sen' VD, Korepin AG, Terentev AA. Effect of Cytotoxic Compounds on Activity of Antioxidant Enzyme System in MCF-7 and H1299 Cells. Bull Exp Biol Med. 2016 May;161(1):179-83. doi: 10.1007/s10517-016-3371-9. Epub 2016 Jun 6. PMID: 27265137.