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{{Drugbox
| verifiedrevid = 447808729
| IUPAC_name = (''OC''-6-43)-bis(acetato)amminedichloro(cyclohexylamine)platinum
| image = Satraplatin.svg
| image2 = Satraplatin-from-xtal-1995-Mercury-3D-balls.png
<!--Clinical data-->
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| routes_of_administration = Oral


==Introduction==
<!--Pharmacokinetic data-->
<p>&nbsp;</p>
| bioavailability =
<p> <span style="font-size: 13px; line-height: 1.5em;">Satraplatin is a </span>] that has demonstrated antitumor activity. Satraplatin has displayed activity against multiple platinum-sensitive and platinum resistant human tumor cell lines.<span style="font-size: 13px; line-height: 1.5em;"> </span>Satraplatin is currently being investigated as a possible treatment for patients with advanced prostate cancer who have previously endured unsuccessful chemotherapy. Satraplatin has not received approval from the ] yet<span style="font-size: 13px; line-height: 1.5em;">.</span> Recently satraplatin has become a novel oral platinum analogue with a better toxicity profile than ]. When compared to cisplatin, satraplatin is more hydrophobic and demonstrates efficacy in cisplatin-resistant cell lines.<strong style="font-family: inherit; font-style: inherit; line-height: 1.5em;">&nbsp;</strong><strong>&nbsp;</strong>
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =


<strong>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; </strong><table style="margin-left: 0px; margin-right: 0px; float: right; background-color: #ffffff;" class="wikitable sortable pbSortable" align="right" border="0" width="300"><caption>SATRAPLATIN</caption><tr>
<!--Identifiers-->
<td style="border-color: #000000; text-align: center;">]<blockquote></blockquote></td>
| CAS_number_Ref = {{cascite|correct|??}}
</tr>
| CAS_number = 129580-63-8
<tr>
| ATC_prefix = L01
<td style="border-color: #000000; background-color: #b4b4b4; text-align: center;">
| ATC_suffix = XA04
<p><span style="color: #3366ff;"><strong>Systematic </strong></span><strong>IUPAC Name</strong>&nbsp;<strong> </strong></p>
| PubChem = 123974
</td>
| ChEBI_Ref = {{ebicite|correct|EBI}}
</tr>
| ChEBI = 85609
<tr>
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
<td style="border-color: #000000; background-color: #ffffff; text-align: center;"><span style="font-size: 75%;">platinum<sup>4+</sup>cyclohexanamine diacetate amine dichloride</span></td>
| DrugBank =
</tr>
| UNII_Ref = {{fdacite|correct|FDA}}
<tr>
| UNII = 8D7B37T28G
<td style="border-color: #000000; background-color: #b4b4b4; text-align: center;"><strong>Chemical Data</strong></td>
</tr>
<tr>
<td style="border-color: #000000;"><span style="color: #3366ff;"><strong>Formula </strong></span><strong>&nbsp;</strong>C<sub>10</sub>H<sub>22</sub>Cl<sub>2</sub>N<sub>2</sub>O<sub>4</sub>Pt</td>
</tr>
<tr>
<td style="border-color: #000000;"><span style="color: #3366ff;"><strong>Molecular Weight</strong></span> 500.283 g/mol</td>
</tr>
<tr>
<td style="border-color: #000000; text-align: center; background-color: #b4b4b4;"><strong>Properties</strong></td>
</tr>
<tr>
<td style="border-color: #000000; text-align: left;"><strong><span style="color: #3366ff;">State </span></strong>Solid</td>
</tr>
<tr>
<td style="border-color: #000000; text-align: left;"><strong><span style="color: #3366ff;">pKa </span></strong>10.45</td>
</tr>
<tr>
<td style="border-color: #000000; text-align: left;"><span style="color: #3366ff;"><strong>logP</strong></span> 1.17</td>
</tr>
<tr>
<td style="border-color: #000000; text-align: center; background-color: #b4b4b4;"><strong>&nbsp;Identifiers</strong></td>
</tr>
<tr>
<td style="border-color: #000000;"><span style="color: #3366ff;"><strong>CAS Number</strong></span> 129580-63-8</td>
</tr>
<tr>
<td style="border-color: #000000;"><strong><span style="color: #3366ff;">Alternative Names</span></strong> JM216 </td>
</tr>
<tr>
<td style="border-color: #000000;"><strong><span style="color: #3366ff;">PubChem</span></strong> CID 123974</td>
</tr>
<tr>
<td style="border-color: #000000;"><span style="color: #3366ff;"><strong>Trade Name</strong></span>&nbsp;Orplatna</td>
</tr>
<tr>
<td style="border-color: #000000; text-align: center; background-color: #b4b4b4;"><strong>Drug Summary</strong><span style="color: #3366ff;"><strong>&nbsp;</strong></span></td>
</tr>
<tr>
<td style="border-color: #000000; text-align: left;">
<p><span style="color: #3366ff;"><strong>Indication </strong></span>Cancer</p>
</td>
</tr>
<tr>
<td style="border-color: #000000; text-align: left;">
<p><span style="color: #3366ff;"><strong>Route of Administration </strong></span>Oral</p>
</td>
</tr>


</table>
<!--Chemical data-->
| C=10 | H=22 | Cl=2 | N=2 | O=4 | Pt=1
| molecular_weight = 500.277 g/mol
| synonyms = BMY 45594<br>BMS 182751<br>(''OC''-6-43)-bis(acetato)amminedichlorocyclohexylamine platinum(IV)
}}
'''Satraplatin''' (], codenamed '''JM216''') is a ] agent that is under investigation as one treatment of patients with advanced ] who have failed previous ]. It has not yet received approval from the U.S. ].<ref>{{cite journal |title=The status of platinum anticancer drugs in the clinic and in clinical trials |journal=Dalton Transactions |volume=39 |pages=8113–27 |year=2010 |doi=10.1039/C0DT00292E |last1=Wheate |first1=Nial J. |authorlink1=Nial J. Wheate |last2=Walker |first2=Shonagh |last3=Craig |first3=Gemma E. |last4=Oun |first4=Rabbab |issue=35 |pmid=20593091 }}</ref> First mentioned in the medical literature in 1993,<ref>{{cite journal |vauthors=Kelland LR, Abel G, McKeage MJ, etal |title=Preclinical antitumor evaluation of bis-acetato-ammine-dichloro-cyclohexylamine platinum(IV): an orally active platinum drug |journal=Cancer Res |volume=53 |issue=11 |pages=2581–6 |year=1993 |pmid=8388318 |url=http://cancerres.aacrjournals.org/cgi/reprint/53/11/2581.pdf |format=PDF}}</ref> satraplatin is the first orally active platinum-based chemotherapeutic drug;<ref>{{cite journal |author=Choy H, Park C, Yao M |title=Current status and future prospects for satraplatin, an oral platinum analogue |journal=Clin Cancer Res |volume=14 |issue=6 |pages=1633–8 |year=2008 |pmid=18347164 |doi=10.1158/1078-0432.CCR-07-2176}}</ref> other available platinum analogues—], ], and ]—must be given ].


== Medical Use ==
It is made available in the United States jointly by ] and GPC Biotech under the name SPERA (SatraPlatin Expanded Rapid Access).
<p>&nbsp;</p>

<p> <span style="color: #000000;">Satraplatin is an orally bioavailable platinum chemotherapeutic agent under development for several cancer types, including ] (HRPC). Satraplatin is being developed for the treatment of men with chemorefractory HRPC for several reasons. It's relative ease of administration, potential lack of cross-resistance with other platinum agents, clinical benefits seen in early studies of HRPC, and an unmet need in this patient population after ] failure. As men who have progressed after docetaxel and ] have an expected median survival of approximately 12 months, there is great opportunity for improved palliation in this disease. Satraplatin may provide a palliative benefit for these men in terms of progression-free survival according to the most recent analyses of the phase III SPARC trial comparing satraplatin and prednisone to prednisone alone in the second-line setting for HRPC, and is currently under ] review for this indication. Whether satraplatin and prednisone offer an advantage over docetaxel retreatment or other cytotoxic agents in this setting is an unanswered question and worthy of study.</span></p>
The drug has also been used in the treatment of lung and ovarian cancers. The proposed mode of action is that the compound binds to the ] of cancer cells rendering them incapable of ].<ref></ref>
<p> <span style="color: #000000;">Satraplatin has a favorable toxicity profile, and appears to have clinical activity against a variety of malignancies such as ], ] and ].&nbsp;<span style="color: #000000;">&nbsp;</span></span><span style="color: #000000;"><span style="color: #000000;"><span style="color: #000000;">The oral route of administration and the intermittent schedule makes it very convenient for clinical use. Despite this, a FDA-approved indication has not yet been achieved. The only Phase III trial with satraplatin was conducted in pre-treated metastatic prostate cancer(CRPC), revealing an improvement in progression-free survival but no overall survival benefit.&nbsp;<span style="color: #000000;">&nbsp;</span></span></span></span></p>
<p>&nbsp;&nbsp;</p>


==References== ==References==
<p>&nbsp;</p>
{{reflist}}
<ol>

<li>''Walker, Shonagh; Craig, Gemma E (2010) "The status of platinum anticancer drugs in the clinic and in clinical trials." Dalton Transactions (39) (35): 8133-27 Digital object Identifier doi:10.1039/C0DT00292E''</li>
{{Chemotherapeutic agents}}
<li>''&nbsp;Paola, Eugenio Donato Di et al (2012) &ldquo;An Open-Label, Dose-Finding Study of the Combination of Satraplatin and Gemcitabine in Patients with Advanced Solid Tumors.&rdquo; Frontiers in Oncology 2: 175. PMC. Web. 19 Apr. 2016.''</li>
{{Platinum compounds}}
<li><em>Vaishampayan UN. (2009) "Satraplatin: </em><em>Leading the new generation of oral platinum agents." Expert opinion on investigational drugs. ;18(11):10.1517/13543780903362437. doi:10.1517/13543780903362437.</em></li>

<li>''&nbsp;<span style="font-size: 13px; line-height: 1.5em;">Andrew J Armstrong; Daniel J George (2007) "Satraplatin in the treatment of hormone-refractory metastatic prostate cancer", &nbsp;</span><span style="font-size: 13px; line-height: 1.5em;">Ther Clin Risk Manag.&nbsp;2007 October;&nbsp;3(5): 877&ndash;883.&nbsp;Published online 2007 October.</span>''</li>
]
<li><em>Macmillan Cancer Support. ENgland: Registered Office 89 Albert Embankment, London, 2012.&nbsp;&nbsp;<a href="<nowiki>http://www.nhs.uk/ipgmedia/national/Macmillan%20Cancer%20Support/Assets/SatraplatinMCS5pages.pdf</nowiki>"</em></li>
]
<li>''Choy, Hak; Park, Clinton; Yao, Min (2008). "Current Status and Future Prospects for Satraplatin, an Oral Platinum Analogue". Clin Cancer Res.&nbsp;14; 1633&nbsp;doi: 10.1158/1078-0432.CCR-07-2176''</li>
]
<li>''Johnstone, Timothy; Lippard, Stephen (2014). "Improvements in the synthesis and understanding of the iodo-bridged intermediate en route to the Pt(IV) prodrug Satraplatin". Inorganica Chimica Acta. 22-1693.&nbsp;doi:10.1016/j.ica.2014.08.047''</li>
]
<li>''Walker, Shonagh; Craig, Gemma E (2010) "The status of platinum anticancer drugs in the clinic and in clinical trials." Dalton Transactions (39) (35): 8133-27 Digital object Identifier doi:10.1039/C0DT00292E''

</li>

</ol>
{{antineoplastic-drug-stub}}
<p>&nbsp;</p>
<p>&nbsp;</p>
== External Links ==
* <p>&nbsp;https://pubchem.ncbi.nlm.nih.go</p><ul>
<li>http://www.drugbank.ca/drugs/DB04996</li>
<li>http://dspace.mit.edu/openaccess-disseminate/1721.1/96862</li>
<li>http://www.sciencedirect.com/science/article/pii/S0020169314005477</li>
<li>http://clincancerres.aacrjournals.org/content/14/6/1633.full</li>
<li>https://en.wikipedia.org/Prostate_cancer</li>
</ul>
<p>&nbsp;</p>
<p>&nbsp;</p>
<div style="width: 1px; height: 1px; overflow: hidden;"><span style="color: #333333; font-family: 'Open Sans', sans-serif; font-size: 16px; font-style: normal; font-weight: 600; line-height: 22.8571px; background-color: #ffe7af;">Macmillian Cancer Support.&nbsp;</span><em style="color: #333333; font-family: 'Open Sans', sans-serif; font-size: 16px; font-weight: 600; line-height: 22.8571px; background-color: #ffe7af;">Macmillian Cancer Support</em><span style="color: #333333; font-family: 'Open Sans', sans-serif; font-size: 16px; font-style: normal; font-weight: 600; line-height: 22.8571px; background-color: #ffe7af;">. Macmillian Cancer Support, 2012. Print.&nbsp;</span><span style="color: #333333; font-family: 'Open Sans', sans-serif; font-size: 16px; font-style: normal; font-weight: 600; line-height: 22.8571px; background-color: #ffe7af;"><a href="http://www.nhs.uk/ipgmedia/national/Macmillan">http://www.nhs.uk/ipgmedia/national/Macmillan</a> Cancer Support/Assets/SatraplatinMCS5pages.pdf</span></div>

Revision as of 12:10, 26 April 2016

Introduction

 

Satraplatin is a Platimun-based antineoplastic that has demonstrated antitumor activity. Satraplatin has displayed activity against multiple platinum-sensitive and platinum resistant human tumor cell lines. Satraplatin is currently being investigated as a possible treatment for patients with advanced prostate cancer who have previously endured unsuccessful chemotherapy. Satraplatin has not received approval from the Food and Drug Administration yet. Recently satraplatin has become a novel oral platinum analogue with a better toxicity profile than cisplatin. When compared to cisplatin, satraplatin is more hydrophobic and demonstrates efficacy in cisplatin-resistant cell lines.                        

SATRAPLATIN
Molecular Structure
Molecular Structure

Systematic IUPAC Name 

platinumcyclohexanamine diacetate amine dichloride
Chemical Data
Formula  C10H22Cl2N2O4Pt
Molecular Weight 500.283 g/mol
Properties
State Solid
pKa 10.45
logP 1.17
 Identifiers
CAS Number 129580-63-8
Alternative Names JM216
PubChem CID 123974
Trade Name Orplatna
Drug Summary 

Indication Cancer

Route of Administration Oral

Medical Use

 

Satraplatin is an orally bioavailable platinum chemotherapeutic agent under development for several cancer types, including hormone-refractory prostate cancer (HRPC). Satraplatin is being developed for the treatment of men with chemorefractory HRPC for several reasons. It's relative ease of administration, potential lack of cross-resistance with other platinum agents, clinical benefits seen in early studies of HRPC, and an unmet need in this patient population after Docetaxel failure. As men who have progressed after docetaxel and Prednisone have an expected median survival of approximately 12 months, there is great opportunity for improved palliation in this disease. Satraplatin may provide a palliative benefit for these men in terms of progression-free survival according to the most recent analyses of the phase III SPARC trial comparing satraplatin and prednisone to prednisone alone in the second-line setting for HRPC, and is currently under Food and Drug Administration review for this indication. Whether satraplatin and prednisone offer an advantage over docetaxel retreatment or other cytotoxic agents in this setting is an unanswered question and worthy of study.

Satraplatin has a favorable toxicity profile, and appears to have clinical activity against a variety of malignancies such as Breast Cancer, Prostate cancer and Lung cancer.  The oral route of administration and the intermittent schedule makes it very convenient for clinical use. Despite this, a FDA-approved indication has not yet been achieved. The only Phase III trial with satraplatin was conducted in pre-treated metastatic prostate cancer(CRPC), revealing an improvement in progression-free survival but no overall survival benefit.  

  

References

 

  1. Walker, Shonagh; Craig, Gemma E (2010) "The status of platinum anticancer drugs in the clinic and in clinical trials." Dalton Transactions (39) (35): 8133-27 Digital object Identifier doi:10.1039/C0DT00292E
  2.  Paola, Eugenio Donato Di et al (2012) “An Open-Label, Dose-Finding Study of the Combination of Satraplatin and Gemcitabine in Patients with Advanced Solid Tumors.” Frontiers in Oncology 2: 175. PMC. Web. 19 Apr. 2016.
  3. Vaishampayan UN. (2009) "Satraplatin: Leading the new generation of oral platinum agents." Expert opinion on investigational drugs. ;18(11):10.1517/13543780903362437. doi:10.1517/13543780903362437.
  4.  Andrew J Armstrong; Daniel J George (2007) "Satraplatin in the treatment of hormone-refractory metastatic prostate cancer",  Ther Clin Risk Manag. 2007 October; 3(5): 877–883. Published online 2007 October.
  5. Macmillan Cancer Support. ENgland: Registered Office 89 Albert Embankment, London, 2012.  <a href="http://www.nhs.uk/ipgmedia/national/Macmillan%20Cancer%20Support/Assets/SatraplatinMCS5pages.pdf"
  6. Choy, Hak; Park, Clinton; Yao, Min (2008). "Current Status and Future Prospects for Satraplatin, an Oral Platinum Analogue". Clin Cancer Res. 14; 1633 doi: 10.1158/1078-0432.CCR-07-2176
  7. Johnstone, Timothy; Lippard, Stephen (2014). "Improvements in the synthesis and understanding of the iodo-bridged intermediate en route to the Pt(IV) prodrug Satraplatin". Inorganica Chimica Acta. 22-1693. doi:10.1016/j.ica.2014.08.047
  8. Walker, Shonagh; Craig, Gemma E (2010) "The status of platinum anticancer drugs in the clinic and in clinical trials." Dalton Transactions (39) (35): 8133-27 Digital object Identifier doi:10.1039/C0DT00292E

 

 

External Links

 

 

Macmillian Cancer Support. Macmillian Cancer Support. Macmillian Cancer Support, 2012. Print. <a href="http://www.nhs.uk/ipgmedia/national/Macmillan">http://www.nhs.uk/ipgmedia/national/Macmillan</a> Cancer Support/Assets/SatraplatinMCS5pages.pdf