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Revision as of 07:09, 18 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 469154998 of page Ixabepilone for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').  Latest revision as of 21:07, 5 November 2024 edit Photocyte (talk | contribs)Extended confirmed users1,787 editsm →History: Highlight just how similar the structures are 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
⚫ | verifiedrevid = 477495917
| Watchedfields = changed
⚫ | verifiedrevid = 400125244
| IUPAC_name = (1''R'',5''S'',6''S'',7''R'',10''S'',14''S'',16''S'')-6,10-dihydroxy-1,5,7,<br>9,9-pentamethyl-14--17-oxa-13-azabicyclo<br>heptadecane-8,12-dione | IUPAC_name = (1''R'',5''S'',6''S'',7''R'',10''S'',14''S'',16''S'')-6,10-dihydroxy-1,5,7,<br>9,9-pentamethyl-14--17-oxa-13-azabicyclo<br>heptadecane-8,12-dione
| image = Ixabepilone.svg | image = Ixabepilone.svg
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| DailyMedID = Ixabepilone
| legal_US = Rx-only | legal_US = Rx-only
| legal_status = | legal_status =
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<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 6824
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 219989-84-1 --> | CAS_number = 219989-84-1
| ATC_prefix = L01 | ATC_prefix = L01
| ATC_suffix = DC04<!--will come into effect January 2008--> | ATC_suffix = DC04<!--will come into effect January 2008-->
| PubChem = 6445540 | PubChem = 6445540
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04845 | DrugBank = DB04845
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 20145579 | ChemSpiderID = 20145579
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = K27005NP0A | UNII = K27005NP0A
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04645 | KEGG = D04645
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1201752 --> | ChEMBL = 1201752

<!--Chemical data-->
| C=27 | H=42 | N=2 | O=5 | S=1 | C=27 | H=42 | N=2 | O=5 | S=1
| molecular_weight = 506.698 g/mol
| smiles = Cc3nc(/C=C(\C)1C2O2(C)CCC(C)(O)(C)C(=O)C(C)(C)(O)CC(=O)N1)cs3 | smiles = Cc3nc(/C=C(\C)1C2O2(C)CCC(C)(O)(C)C(=O)C(C)(C)(O)CC(=O)N1)cs3
| InChI = 1/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
| InChIKey = FABUFPQFXZVHFB-PVYNADRNBP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1 | StdInChI = 1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
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| synonyms = Azaepothilone B | synonyms = Azaepothilone B
}} }}
'''Ixabepilone''' (]; also known as '''azaepothilone B''', codenamed '''BMS-247550''') is a pharmaceutical drug developed by ] as a ] medication for cancer.<ref>{{cite web|url=https://www.cancer.org/treatment/treatments-and-side-effects/cancer-drugs.html|title=More information on cancer drugs|website=www.cancer.org}}</ref>

==History==
Ixabepilone is a ] ] of ] B, a natural chemical compound produced by '']''.<ref name="pmid18463327">{{cite journal | vauthors = Goodin S | title = Novel cytotoxic agents: epothilones | journal = American Journal of Health-System Pharmacy | volume = 65 | issue = 10 Suppl 3 | pages = S10–S15 | date = May 2008 | pmid = 18463327 | doi = 10.2146/ajhp080089 }}</ref> The structural difference between Epothilone B and Ixabepilone consists of only a single atom oxygen-to-nitrogen subsitution that converts the ester into an amide. Epothilone B itself could not be developed as a pharmaceutical drug because of poor ] and ].<ref name="pmid18347795">{{cite journal | vauthors = Lee FY, Borzilleri R, Fairchild CR, Kamath A, Smykla R, Kramer R, Vite G | title = Preclinical discovery of ixabepilone, a highly active antineoplastic agent | journal = Cancer Chemotherapy and Pharmacology | volume = 63 | issue = 1 | pages = 157–166 | date = December 2008 | pmid = 18347795 | doi = 10.1007/s00280-008-0724-8 | doi-access = free }}</ref> Ixabepilone was designed through ] to improve upon these properties.<ref name="pmid18347795"/>

==Pharmacology==
Much like ], Ixabepilone acts to stabilize ]s.<ref>{{cite journal | vauthors = Lopus M, Smiyun G, Miller H, Oroudjev E, Wilson L, Jordan MA | title = Mechanism of action of ixabepilone and its interactions with the βIII-tubulin isotype | journal = Cancer Chemotherapy and Pharmacology | volume = 76 | issue = 5 | pages = 1013–1024 | date = November 2015 | pmid = 26416565 | doi = 10.1007/s00280-015-2863-z | s2cid = 1842156 }}</ref><ref name="pmid18321240">{{cite journal | vauthors = Denduluri N, Swain SM | title = Ixabepilone for the treatment of solid tumors: a review of clinical data | journal = Expert Opinion on Investigational Drugs | volume = 17 | issue = 3 | pages = 423–435 | date = March 2008 | pmid = 18321240 | doi = 10.1517/13543784.17.3.423 | s2cid = 71169099 }}</ref><ref name="pmid18945860">{{cite journal | vauthors = Goodin S | title = Ixabepilone: a novel microtubule-stabilizing agent for the treatment of metastatic breast cancer | journal = American Journal of Health-System Pharmacy | volume = 65 | issue = 21 | pages = 2017–2026 | date = November 2008 | pmid = 18945860 | doi = 10.2146/ajhp070628 }}</ref>
It is highly potent, capable of damaging cancer cells in very low concentrations, and retains activity in cases where tumor cells are insensitive to taxane type drugs.<ref name="pancreas">{{cite journal | vauthors = Vulfovich M, Rocha-Lima C | title = Novel advances in pancreatic cancer treatment | journal = Expert Review of Anticancer Therapy | volume = 8 | issue = 6 | pages = 993–1002 | date = June 2008 | pmid = 18533808 | doi = 10.1586/14737140.8.6.993 | s2cid = 20049942 }}</ref>

==Approval==
On October 16, 2007, the U.S. ] approved ixabepilone for the treatment of aggressive ] or locally advanced ] no longer responding to currently available chemotherapies.<ref>{{cite web |url= https://www.medicalnewstoday.com/releases/85726.php |title=FDA Approves IXEMPRA(TM) (ixabepilone), A Semi-Synthetic Analog Of Epothilone B, For The Treatment Of Advanced Breast Cancer|website=Medical News Today}}</ref> In November 2008, the ] has refused a marketing authorisation for Ixabepilone.<ref>{{cite web | work = European Medicines Agency | title = Questions and answers on recommendation for the refusal of the marketing authorisation for Ixempra | id = Doc. Ref. EMEA/602569/2008 | url = http://www.ema.europa.eu/docs/en_GB/document_library/Summary_of_opinion_Initial_authorisation/human/000930/WC500014746.pdf | location = London | date = 20 November 2008 }} </ref>

Ixabepilone is administered through injection, and is marketed under the trade name '''Ixempra'''.

==Clinical uses==
Ixabepilone, in combination with ], has demonstrated effectiveness in the treatment of metastatic or locally advanced breast cancer in patients after failure of an ] and a ].<ref name="pmid17968020">{{cite journal | vauthors = Thomas ES, Gomez HL, Li RK, Chung HC, Fein LE, Chan VF, Jassem J, Pivot XB, Klimovsky JV, de Mendoza FH, Xu B, Campone M, Lerzo GL, Peck RA, Mukhopadhyay P, Vahdat LT, Roché HH | display-authors = 6 | title = Ixabepilone plus capecitabine for metastatic breast cancer progressing after anthracycline and taxane treatment | journal = Journal of Clinical Oncology | volume = 25 | issue = 33 | pages = 5210–5217 | date = November 2007 | pmid = 17968020 | doi = 10.1200/JCO.2007.12.6557 | doi-access = free }}</ref>

It has been investigated for use in treatment of ].<ref name="pmid17261851">{{cite journal | vauthors = Aghajanian C, Burris HA, Jones S, Spriggs DR, Cohen MB, Peck R, Sabbatini P, Hensley ML, Greco FA, Dupont J, O'Connor OA | display-authors = 6 | title = Phase I study of the novel epothilone analog ixabepilone (BMS-247550) in patients with advanced solid tumors and lymphomas | journal = Journal of Clinical Oncology | volume = 25 | issue = 9 | pages = 1082–1088 | date = March 2007 | pmid = 17261851 | doi = 10.1200/JCO.2006.08.7304 | doi-access = free }}</ref>
In pancreatic cancer phase two trial it showed some promising results (used alone). Combination therapy trials are ongoing.<ref name="pancreas"/>

== References ==
{{reflist|2}}

== External links ==
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{{Chemotherapeutic agents}}

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