GZX

(1~{S},3~{S},7~{S},10~{R},11~{S},12~{S},16~{R})-8,8,10,12,16-pentamethyl-3-[(~{E})-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-7,11-bis(oxidanyl)-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione

Created: 2020-10-19
Last modified:  2021-11-09

Help

Find related ligands:

Chemical Details

Formal Charge0
Atom Count77
Chiral Atom Count7
Bond Count79
Aromatic Bond Count5
2D diagram of GZX
Toggle HydrogenToggle Labels

Chemical Component Summary

Name(1~{S},3~{S},7~{S},10~{R},11~{S},12~{S},16~{R})-8,8,10,12,16-pentamethyl-3-[(~{E})-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-7,11-bis(oxidanyl)-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
SynonymsIxabepilone
Systematic Name (OpenEye OEToolkits)(1~{S},3~{S},7~{S},10~{R},11~{S},12~{S},16~{R})-8,8,10,12,16-pentamethyl-3-[(~{E})-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-7,11-bis(oxidanyl)-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
FormulaC27 H42 N2 O5 S
Molecular Weight506.698
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.385C[CH]1CCC[C]2(C)O[CH]2C[CH](NC(=O)C[CH](O)C(C)(C)C(=O)[CH](C)[CH]1O)C(C)=Cc3csc(C)n3
SMILESOpenEye OEToolkits2.0.7Cc1nc(cs1)C=C(C)C2CC3C(O3)(CCCC(C(C(C(=O)C(C(CC(=O)N2)O)(C)C)C)O)C)C
Canonical SMILESCACTVS3.385 C[C@H]1CCC[C@@]2(C)O[C@H]2C[C@H](NC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]1O)C(/C)=C/c3csc(C)n3
Canonical SMILESOpenEye OEToolkits2.0.7 Cc1nc(cs1)/C=C(\C)/[C@@H]2C[C@H]3[C@](O3)(CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](CC(=O)N2)O)(C)C)C)O)C)C
InChIInChI1.03 InChI=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
InChIKeyInChI1.03 FABUFPQFXZVHFB-PVYNADRNSA-N

Drug Info: DrugBank

DrugBank IDDB04845 
NameIxabepilone
Groups
  • approved
  • investigational
DescriptionIxabepilone is an epothilone B analog developed by Bristol-Myers Squibb as a cancer drug. It was FDA approved on October 16, 2007, for the treatment of unresponsive aggressive metastatic or locally advanced breast cancer. Ixabepilone is administered through injection, and will be marketed under the trade name Ixempra. Ixabepilone is a semisynthetic analogue of epothilone B. It has a lactone–lactam modification that minimizes susceptibility to esterase degradation.
Synonyms
  • Aza-epothilone B
  • Ixabepilone
  • Azaepothilone B
Brand NamesIxempra
IndicationInvestigated for use/treatment in breast cancer, head and neck cancer, melanoma, lung cancer, lymphoma (non-hodgkin's), prostate cancer, renal cell carcinoma, and cancer/tumors (unspecified).
Categories
  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • Cytochrome P-450 CYP3A Substrates
  • Cytochrome P-450 CYP3A4 Substrates
ATC-CodeL01DC04
CAS number219989-84-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Tubulin beta-3 chainMREIVHIQAGQCGNQIGAKFWEVISDEHGIDPSGNYVGDSDLQLERISVY...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
P-glycoprotein 1MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...unknownsubstrate,inhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1201752
PubChem 6445540
ChEMBL CHEMBL1201752
ChEBI CHEBI:95095, CHEBI:63605