Details of the Drug

General Information of Drug (ID: DM2OZ3G)

Drug Name

Ixabepilone

Synonyms

Azaepothilone B; BMS-247550; Ixempra (TN)

Indication

Disease Entry	ICD 11	Status	REF
Breast cancer	2C60-2C65	Approved	[1]
Breast carcinoma	N.A.	Approved	[2]
------------------------------------------------------------------------------------

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

506.7

Logarithm of the Partition Coefficient (xlogp)

3.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Clearance: The drug present in the plasma can be removed from the body at the rate of 10 mL/min/kg [4]
Elimination: 5.6% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 52 hours [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1.9735 micromolar/kg/day [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.2% [4]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 11 L/kg [4]

Chemical Identifiers

Formula: C27H42N2O5S
IUPAC Name: (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
Canonical SMILES: C[C@H]1CCC[C@@]2([C@@H](O2)C[C@H](NC(=O)C[C@@H](C(C(=O)[C@@H]([C@H]1O)C)(C)C)O)/C(=C/C3=CSC(=N3)C)/C)C
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
InChIKey: FABUFPQFXZVHFB-PVYNADRNSA-N

Cross-matching ID

PubChem CID: 6445540
ChEBI ID: CHEBI:63605
CAS Number: 219989-84-1
DrugBank ID: DB04845
TTD ID: D0W2EK
VARIDT ID: DR01285
INTEDE ID: DR0900
ACDINA ID: D01188

Combinatorial Drugs (CBD)

Click to Jump to the Detailed CBD Information of This Drug

Repurposed Drugs (RPD)

Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Tubulin (TUB)	TTML2WA	NOUNIPROTAC	Stablizer	[6]

------------------------------------------------------------------------------------

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[7]

------------------------------------------------------------------------------------

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[8]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Breast cancer

ICD Disease Classification

2C60-2C65

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Tubulin (TUB)	DTT	NO-GeName	7.94E-02	0.35	0.43
P-glycoprotein 1 (ABCB1)	DTP	P-GP	1.53E-04	-6.93E-01	-2.04E+00
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	2.96E-01	-3.35E-01	-1.10E+00

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Ixabepilone

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Ixabepilone caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[9]
-----------

Coadministration of a Drug Treating the Disease Different from Ixabepilone (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Ivosidenib	DM8S6T7	Moderate	Increased metabolism of Ixabepilone caused by Ivosidenib mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[9]
Arn-509	DMT81LZ	Moderate	Increased metabolism of Ixabepilone caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[9]
Dronedarone	DMA8FS5	Moderate	Decreased metabolism of Ixabepilone caused by Dronedarone mediated inhibition of CYP450 enzyme.	Angina pectoris [BA40]	[9]
Erdafitinib	DMI782S	Moderate	Decreased clearance of Ixabepilone due to the transporter inhibition by Erdafitinib.	Bladder cancer [2C94]	[10]
Pexidartinib	DMS2J0Z	Moderate	Increased metabolism of Ixabepilone caused by Pexidartinib mediated induction of CYP450 enzyme.	Bone/articular cartilage neoplasm [2F7B]	[9]
Ivacaftor	DMZC1HS	Moderate	Decreased metabolism of Ixabepilone caused by Ivacaftor mediated inhibition of CYP450 enzyme.	Cystic fibrosis [CA25]	[11]
MK-8228	DMOB58Q	Moderate	Decreased metabolism of Ixabepilone caused by MK-8228 mediated inhibition of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[9]
Cenobamate	DM8KLU9	Moderate	Increased metabolism of Ixabepilone caused by Cenobamate mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[9]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Ixabepilone caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[9]
Tazemetostat	DMWP1BH	Moderate	Increased metabolism of Ixabepilone caused by Tazemetostat mediated induction of CYP450 enzyme.	Follicular lymphoma [2A80]	[9]
Ripretinib	DM958QB	Moderate	Decreased clearance of Ixabepilone due to the transporter inhibition by Ripretinib.	Gastrointestinal stromal tumour [2B5B]	[12]
Boceprevir	DMBSHMF	Moderate	Decreased metabolism of Ixabepilone caused by Boceprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[9]
Telaprevir	DMMRV29	Moderate	Decreased metabolism of Ixabepilone caused by Telaprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[9]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of peripheral neuropathy by the combination of Ixabepilone and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[13]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Ixabepilone caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[9]
Teriflunomide	DMQ2FKJ	Major	Additive immunosuppressive effects by the combination of Ixabepilone and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[14]
Berotralstat	DMWA2DZ	Major	Decreased clearance of Ixabepilone due to the transporter inhibition by Berotralstat.	Innate/adaptive immunodeficiency [4A00]	[15]
Denosumab	DMNI0KO	Moderate	Additive immunosuppressive effects by the combination of Ixabepilone and Denosumab.	Low bone mass disorder [FB83]	[16]
Crizotinib	DM4F29C	Moderate	Decreased metabolism of Ixabepilone caused by Crizotinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[9]
Brigatinib	DM7W94S	Moderate	Increased metabolism of Ixabepilone caused by Brigatinib mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[17]
Ceritinib	DMB920Z	Moderate	Decreased metabolism of Ixabepilone caused by Ceritinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[9]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Ixabepilone caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[9]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Ixabepilone caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[18]
Idelalisib	DM602WT	Moderate	Decreased metabolism of Ixabepilone caused by Idelalisib mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[9]
IPI-145	DMWA24P	Moderate	Decreased metabolism of Ixabepilone caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[19]
Arry-162	DM1P6FR	Moderate	Decreased clearance of Ixabepilone due to the transporter inhibition by Arry-162.	Melanoma [2C30]	[12]
Vemurafenib	DM62UG5	Moderate	Increased metabolism of Ixabepilone caused by Vemurafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[9]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Ixabepilone caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[9]
Lasmiditan	DMXLVDT	Moderate	Decreased clearance of Ixabepilone due to the transporter inhibition by Lasmiditan.	Migraine [8A80]	[20]
Tecfidera	DM2OVDT	Moderate	Additive immunosuppressive effects by the combination of Ixabepilone and Tecfidera.	Multiple sclerosis [8A40]	[21]
Siponimod	DM2R86O	Major	Additive immunosuppressive effects by the combination of Ixabepilone and Siponimod.	Multiple sclerosis [8A40]	[12]
Fingolimod	DM5JVAN	Major	Additive immunosuppressive effects by the combination of Ixabepilone and Fingolimod.	Multiple sclerosis [8A40]	[22]
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Ixabepilone and Ocrelizumab.	Multiple sclerosis [8A40]	[23]
Ozanimod	DMT6AM2	Major	Additive immunosuppressive effects by the combination of Ixabepilone and Ozanimod.	Multiple sclerosis [8A40]	[24]
Fedratinib	DM4ZBK6	Moderate	Decreased metabolism of Ixabepilone caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[9]
Omacetaxine mepesuccinate	DMPU2WX	Moderate	Additive immunosuppressive effects by the combination of Ixabepilone and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[25]
Netupitant	DMEKAYI	Moderate	Decreased metabolism of Ixabepilone caused by Netupitant mediated inhibition of CYP450 enzyme.	Nausea/vomiting [MD90]	[9]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Ixabepilone caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[26]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Ixabepilone caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[27]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Ixabepilone caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[28]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Ixabepilone caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[9]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Ixabepilone caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[9]
Canakinumab	DM8HLO5	Moderate	Additive immunosuppressive effects by the combination of Ixabepilone and Canakinumab.	Rheumatoid arthritis [FA20]	[29]
Rilonacept	DMGLUQS	Moderate	Additive immunosuppressive effects by the combination of Ixabepilone and Rilonacept.	Rheumatoid arthritis [FA20]	[29]
Golimumab	DMHZV7X	Major	Additive immunosuppressive effects by the combination of Ixabepilone and Golimumab.	Rheumatoid arthritis [FA20]	[30]
Anthrax vaccine	DM9GSWY	Moderate	Antagonize the effect of Ixabepilone when combined with Anthrax vaccine.	Sepsis [1G40-1G41]	[31]
Voxelotor	DMCS6M5	Moderate	Decreased metabolism of Ixabepilone caused by Voxelotor mediated inhibition of CYP450 enzyme.	Sickle-cell disorder [3A51]	[9]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Ixabepilone caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[24]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Ixabepilone caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[12]
Armodafinil	DMGB035	Minor	Increased metabolism of Ixabepilone caused by Armodafinil mediated induction of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[32]
LEE011	DMMX75K	Moderate	Decreased metabolism of Ixabepilone caused by LEE011 mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[9]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Ixabepilone caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[33]
Elagolix	DMB2C0E	Moderate	Increased metabolism of Ixabepilone caused by Elagolix mediated induction of CYP450 enzyme.	Uterine fibroid [2E86]	[9]
-----------


⏷ Show the Full List of 53 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Ethanol	E00023	702	Antimicrobial preservative; Penetration agent; Solvent
Polyoxyl 35 castor oil	E00660	Not Available	Emulsifying agent; Solubilizing agent; Surfactant
--------------------

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Ixabepilone 15mg/vial injectable	15mg/vial	Injectable	Intravenous
Ixabepilone 45mg/vial injectable	45mg/vial	Injectable	Intravenous

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6824).
2	Ixabepilone FDA Label
3	BDDCS applied to over 900 drugs
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	Mullard A: 2010 FDA drug approvals. Nat Rev Drug Discov. 2011 Feb;10(2):82-5.
7	Ixabepilone, a novel microtubule-targeting agent for breast cancer, is a substrate for P-glycoprotein (P-gp/MDR1/ABCB1) but not breast cancer resistance protein (BCRP/ABCG2). J Pharmacol Exp Ther. 2011 May;337(2):423-32.
8	The effect of ketoconazole on the pharmacokinetics and pharmacodynamics of ixabepilone: a first in class epothilone B analogue in late-phase clinical development. Clin Cancer Res. 2008 May 1;14(9):2701-9.
9	Product Information. Ixempra (ixabepilone). Bristol-Myers Squibb, Princeton, NJ.
10	Product Information. Balversa (erdafitinib). Janssen Products, LP, Horsham, PA.
11	Product Information. Kalydeco (ivacaftor). Vertex Pharmaceuticals, Cambridge, MA.
12	Cerner Multum, Inc. "Australian Product Information.".
13	Carrion C, Espinosa E, Herrero A, Garcia B "Possible vincristine-isoniazid interaction." Ann Pharmacother 29 (1995): 201. [PMID: 7756727]
14	Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.
15	Product Information. Intelence (etravirine). Ortho Biotech Inc, Bridgewater, NJ.
16	Product Information. Prolia (denosumab). Amgen USA, Thousand Oaks, CA.
17	Product Information. Alunbrig (brigatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
18	Product Information. Retevmo (selpercatinib). Lilly, Eli and Company, Indianapolis, IN.
19	Product Information. Copiktra (duvelisib). Verastem, Inc., Needham, MA.
20	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
21	Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA.
22	Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
23	Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
24	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
25	Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
26	EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
27	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
28	Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
29	Product Information. Arcalyst (rilonacept). Regeneron Pharmaceuticals Inc, Tarrytown, NY.
30	Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA.
31	CDC. Centers for Disease Control and Prevention/ "Recommendations of the advisory committtee on immunization practices (ACIP): use of vaccines and immune globulins in persons with altered immunocompetence." MMWR Morb Mortal Wkly Rep 42(RR-04) (1993): 1-18. [PMID: 20300058]
32	Doherty MM, Charman WN "The mucosa of the small intestine: how clinically relevant as an organ of drug metabolism?" Clin Pharmacokinet 41 (2002): 235-53. [PMID: 11978143]
33	Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.