Ixabepilone

Ixabepilone
Clinical data
Pronunciation	/ˌɪksəˈbɛpɪloʊn/; IKS-ə-BE-pi-lohn
Trade names	Ixempra
Other names	Azaepothilone B
AHFS/Drugs.com	Monograph
MedlinePlus	a608042
License data	US DailyMed: Ixabepilone; US FDA: Ixabepilone;
Routes of; administration	Intravenous infusion
ATC code	L01DC04 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	N/A
Protein binding	67 to 77%
Metabolism	Extensive, hepatic, CYP3A4-mediated
Elimination half-life	52 hours
Excretion	Fecal (mostly) and renal
Identifiers
	IUPAC name (1R,5S,6S,7R,10S,14S,16S)-6,10-dihydroxy-1,5,7,; 9,9-pentamethyl-14-[(E)-1-(2-methyl-1,3-thiazol-; 4-yl)prop-1-en-2-yl]-17-oxa-13-azabicyclo[14.1.0]; heptadecane-8,12-dione;
CAS Number	219989-84-1 ;
PubChem CID	6445540;
IUPHAR/BPS	6824;
DrugBank	DB04845 ;
ChemSpider	20145579 ;
UNII	K27005NP0A;
KEGG	D04645 ;
ChEMBL	ChEMBL1201752 ;
CompTox Dashboard (EPA)	DTXSID70870252 ;
ECHA InfoCard	100.158.736
Chemical and physical data
Formula	C27H42N2O5S
Molar mass	506.70 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Cc3nc(/C=C(\C)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1)cs3;
	InChI 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 ; Key:FABUFPQFXZVHFB-PVYNADRNSA-N ;
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Ixabepilone (INN; also known as azaepothilone B, codenamed BMS-247550) is a pharmaceutical drug developed by Bristol-Myers Squibb as a chemotherapeutic medication for cancer.

Clinical data

Pronunciation	/ˌɪksəˈbɛpɪloʊn/ IKS-ə-BE-pi-lohn
Trade names	Ixempra
Other names	Azaepothilone B
AHFS/Drugs.com	Monograph
MedlinePlus	a608042
License data	US DailyMed: Ixabepilone US FDA: Ixabepilone
Routes of administration	Intravenous infusion
ATC code	L01DC04 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	N/A
Protein binding	67 to 77%
Metabolism	Extensive, hepatic, CYP3A4-mediated
Elimination half-life	52 hours
Excretion	Fecal (mostly) and renal
Identifiers
IUPAC name (1R,5S,6S,7R,10S,14S,16S)-6,10-dihydroxy-1,5,7, 9,9-pentamethyl-14-[(E)-1-(2-methyl-1,3-thiazol- 4-yl)prop-1-en-2-yl]-17-oxa-13-azabicyclo[14.1.0] heptadecane-8,12-dione
CAS Number	219989-84-1^N
PubChem CID	6445540
IUPHAR/BPS	6824
DrugBank	DB04845^Y
ChemSpider	20145579^Y
UNII	K27005NP0A
KEGG	D04645^Y
ChEMBL	ChEMBL1201752^N
CompTox Dashboard (EPA)	DTXSID70870252
ECHA InfoCard	100.158.736
Chemical and physical data
Formula	C₂₇H₄₂N₂O₅S
Molar mass	506.70 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Cc3nc(/C=C(\C)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1)cs3
InChI 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^Y Key:FABUFPQFXZVHFB-PVYNADRNSA-N^Y
^NY (what is this?) (verify)