Details of the Drug

General Information of Drug (ID: DM89JLN)

Drug Name

Apixaban

Synonyms

GG2; BMS 562247-01; BMS-562247; Eliquis (TN); BMS-562247-01; Apixaban (JAN/USAN/INN); BMS-562247-01, Apixaban; Ro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid amide; 1-(4-Methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahyd

Indication

Disease Entry	ICD 11	Status	REF
Thrombosis	DB61-GB90	Approved	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

459.5

Logarithm of the Partition Coefficient (xlogp)

2.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Bioavailability: The bioavailability of drug is 50% [2]
Clearance: The clearance of drug is 3.3 L/h [2]
Elimination: 56% of an orally administered dose is recovered in the feces and 24.5-28.8% of the dose is recovered in the urine [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 12.7 +/- 8.55 hours [2]
Metabolism: The drug is metabolized via the CYP3A4 [2]
Unbound Fraction: The unbound fraction of drug in plasma is 0.13% [3]
Vd: The volume of distribution (Vd) of drug is approximately 21 L []

Chemical Identifiers

Formula: C25H25N5O4
IUPAC Name: 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydropyrazolo[3,4-c]pyridine-3-carboxamide
Canonical SMILES: COC1=CC=C(C=C1)N2C3=C(CCN(C3=O)C4=CC=C(C=C4)N5CCCCC5=O)C(=N2)C(=O)N
InChI: InChI=1S/C25H25N5O4/c1-34-19-11-9-18(10-12-19)30-23-20(22(27-30)24(26)32)13-15-29(25(23)33)17-7-5-16(6-8-17)28-14-3-2-4-21(28)31/h5-12H,2-4,13-15H2,1H3,(H2,26,32)
InChIKey: QNZCBYKSOIHPEH-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 10182969
ChEBI ID: CHEBI:72296
CAS Number: 503612-47-3
DrugBank ID: DB06605
TTD ID: D0I5HF
VARIDT ID: DR00211
INTEDE ID: DR0122
ACDINA ID: D00040

Combinatorial Drugs (CBD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Coagulation factor Xa (F10)	TTCIHJA	FA10_HUMAN	Inhibitor	[4]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[5]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[6]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[7]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[8]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[8]
Cytochrome P450 1A2 (CYP1A2)	DEJGDUW	CP1A2_HUMAN	Substrate	[8]
Cytochrome P450 3A5 (CYP3A5)	DEIBDNY	CP3A5_HUMAN	Substrate	[9]
Cytochrome P450 2C8 (CYP2C8)	DES5XRU	CP2C8_HUMAN	Substrate	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Thrombosis

ICD Disease Classification

DB61-GB90

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Coagulation factor Xa (F10)	DTT	F10	4.84E-02	-0.28	-0.9
P-glycoprotein 1 (ABCB1)	DTP	P-GP	2.04E-02	-1.13E+00	-1.00E+00
Breast cancer resistance protein (ABCG2)	DTP	BCRP	2.10E-01	3.71E-01	7.59E-01
Cytochrome P450 2C8 (CYP2C8)	DME	CYP2C8	1.73E-04	1.53E-01	7.44E-01
Cytochrome P450 1A2 (CYP1A2)	DME	CYP1A2	1.44E-01	-3.59E-01	-1.14E+00
Cytochrome P450 3A5 (CYP3A5)	DME	CYP3A5	3.51E-02	1.53E+00	1.16E+00
Mephenytoin 4-hydroxylase (CYP2C19)	DME	CYP2C19	1.02E-01	-2.84E-01	-7.34E-01
Cytochrome P450 2C9 (CYP2C9)	DME	CYP2C9	1.62E-02	-4.23E-01	-1.25E+00
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	5.84E-01	-1.61E-01	-3.61E-01

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 Apixaban

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Brilinta	DMBR01X	Major	Increased risk of bleeding by the combination of Apixaban and Brilinta.	Thrombosis [DB61-GB90]	[10]
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Coadministration of a Drug Treating the Disease Different from Apixaban (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Sarecycline	DMLZNIQ	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Sarecycline .	Acne vulgaris [ED80]	[10]
Ivosidenib	DM8S6T7	Moderate	Increased metabolism of Apixaban caused by Ivosidenib mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[11]
Arn-509	DMT81LZ	Major	Increased metabolism of Apixaban caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[10]
Gilteritinib	DMTI0ZO	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Gilteritinib.	Acute myeloid leukaemia [2A60]	[10]
Emapalumab	DMZG5WL	Moderate	Altered metabolism of Apixaban due to Emapalumab alters the formation of CYP450 enzymes.	Adaptive immunity immunodeficiency [4A01]	[10]
Siltuximab	DMGEATB	Moderate	Altered metabolism of Apixaban due to Siltuximab alters the formation of CYP450 enzymes.	Anemia [3A00-3A9Z]	[10]
Troleandomycin	DMUZNIG	Moderate	Decreased metabolism of Apixaban caused by Troleandomycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[10]
Erdafitinib	DMI782S	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Erdafitinib.	Bladder cancer [2C94]	[12]
Pexidartinib	DMS2J0Z	Moderate	Increased metabolism of Apixaban caused by Pexidartinib mediated induction of CYP450 enzyme.	Bone/articular cartilage neoplasm [2F7B]	[11]
HKI-272	DM6QOVN	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by HKI-272.	Breast cancer [2C60-2C6Y]	[10]
Tucatinib	DMBESUA	Major	Decreased metabolism of Apixaban caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[13]
PF-04449913	DMSB068	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by PF-04449913.	Chronic myelomonocytic leukaemia [2A40]	[10]
Levomilnacipran	DMV26S8	Moderate	Increased risk of bleeding by the combination of Apixaban and Levomilnacipran.	Chronic pain [MG30]	[14]
Regorafenib	DMHSY1I	Major	Increased risk of bleeding by the combination of Apixaban and Regorafenib.	Colorectal cancer [2B91]	[10]
Intedanib	DMSTA36	Moderate	Increased risk of bleeding by the combination of Apixaban and Intedanib.	Colorectal cancer [2B91]	[15]
Ulipristal	DMBNI20	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Ulipristal.	Contraceptive management [QA21]	[10]
Ardeparin	DMYRX8B	Major	Increased risk of bleeding by the combination of Apixaban and Ardeparin.	Coronary thrombosis [BA43]	[16]
Osilodrostat	DMIJC9X	Moderate	Decreased metabolism of Apixaban caused by Osilodrostat mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[10]
Lumacaftor	DMCLWDJ	Major	Increased metabolism of Apixaban caused by Lumacaftor mediated induction of CYP450 enzyme.	Cystic fibrosis [CA25]	[10]
Ivacaftor	DMZC1HS	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Ivacaftor.	Cystic fibrosis [CA25]	[10]
MK-8228	DMOB58Q	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by MK-8228.	Cytomegaloviral disease [1D82]	[10]
Danaparoid	DM6CLBN	Major	Increased risk of bleeding by the combination of Apixaban and Danaparoid.	Deep vein thrombosis [BD71]	[16]
Vilazodone	DM4LECQ	Moderate	Increased risk of bleeding by the combination of Apixaban and Vilazodone.	Depression [6A70-6A7Z]	[14]
Vortioxetine	DM6F1PU	Moderate	Increased risk of bleeding by the combination of Apixaban and Vortioxetine.	Depression [6A70-6A7Z]	[14]
Desvenlafaxine	DMHD4PE	Moderate	Increased risk of bleeding by the combination of Apixaban and Desvenlafaxine.	Depression [6A70-6A7Z]	[14]
Apigenin	DMI3491	Minor	Increased risk of bleeding by the combination of Apixaban and Apigenin.	Discovery agent [N.A.]	[17]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Apixaban caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[10]
Eslicarbazepine	DMZREFQ	Moderate	Increased metabolism of Apixaban caused by Eslicarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[11]
Tazemetostat	DMWP1BH	Major	Increased risk of bleeding by the combination of Apixaban and Tazemetostat.	Follicular lymphoma [2A80]	[10]
Avapritinib	DMK2GZX	Major	Increased risk of bleeding by the combination of Apixaban and Avapritinib.	Gastrointestinal stromal tumour [2B5B]	[10]
Boceprevir	DMBSHMF	Major	Decreased metabolism of Apixaban caused by Boceprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[13]
Daclatasvir	DMSFK9V	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Daclatasvir.	Hepatitis virus infection [1E50-1E51]	[10]
GS-5885	DMSL3DX	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by GS-5885.	Hepatitis virus infection [1E50-1E51]	[10]
GS-9857	DMYU6P5	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by GS-9857.	Hepatitis virus infection [1E50-1E51]	[10]
Cobicistat	DM6L4H2	Major	Decreased clearance of Apixaban due to the transporter inhibition by Cobicistat.	Human immunodeficiency virus disease [1C60-1C62]	[13]
BMS-201038	DMQTAGO	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by BMS-201038.	Hyper-lipoproteinaemia [5C80]	[10]
Levamlodipine	DM92S6N	Moderate	Decreased metabolism of Apixaban caused by Levamlodipine mediated inhibition of CYP450 enzyme.	Hypertension [BA00-BA04]	[10]
Lesinurad	DMUR64T	Moderate	Increased metabolism of Apixaban caused by Lesinurad mediated induction of CYP450 enzyme.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[11]
Suvorexant	DM0E6S3	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Suvorexant.	Insomnia [7A00-7A0Z]	[10]
Crizotinib	DM4F29C	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Crizotinib.	Lung cancer [2C25]	[10]
Ceritinib	DMB920Z	Moderate	Decreased metabolism of Apixaban caused by Ceritinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[10]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Apixaban caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[11]
Capmatinib	DMYCXKL	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Capmatinib.	Lung cancer [2C25]	[10]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Apixaban caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[10]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of bleeding by the combination of Apixaban and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[18]
Idelalisib	DM602WT	Moderate	Decreased metabolism of Apixaban caused by Idelalisib mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[10]
IPI-145	DMWA24P	Moderate	Decreased metabolism of Apixaban caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[10]
Acalabrutinib	DM7GCVW	Major	Increased risk of bleeding by the combination of Apixaban and Acalabrutinib.	Mature B-cell lymphoma [2A85]	[19]
Ibrutinib	DMHZCPO	Major	Increased risk of bleeding by the combination of Apixaban and Ibrutinib.	Mature B-cell lymphoma [2A85]	[20]
Ponatinib	DMYGJQO	Major	Increased risk of bleeding by the combination of Apixaban and Ponatinib.	Mature B-cell lymphoma [2A85]	[21]
Vemurafenib	DM62UG5	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Vemurafenib.	Melanoma [2C30]	[10]
LGX818	DMNQXV8	Moderate	Increased metabolism of Apixaban caused by LGX818 mediated induction of CYP450 enzyme.	Melanoma [2C30]	[22]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Apixaban caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[10]
Lasmiditan	DMXLVDT	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Lasmiditan.	Migraine [8A80]	[23]
Fedratinib	DM4ZBK6	Moderate	Decreased metabolism of Apixaban caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[10]
Ruxolitinib	DM7Q98D	Major	Increased risk of bleeding by the combination of Apixaban and Ruxolitinib.	Myeloproliferative neoplasm [2A20]	[10]
Vorapaxar	DMA16BR	Major	Increased risk of bleeding by the combination of Apixaban and Vorapaxar.	Myocardial infarction [BA41-BA43]	[24]
Rolapitant	DM8XP26	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Rolapitant.	Nausea/vomiting [MD90]	[25]
Netupitant	DMEKAYI	Moderate	Decreased metabolism of Apixaban caused by Netupitant mediated inhibition of CYP450 enzyme.	Nausea/vomiting [MD90]	[10]
Entrectinib	DMMPTLH	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Entrectinib.	Non-small cell lung cancer [2C25]	[10]
Nepafenac	DMYK490	Moderate	Increased risk of bleeding by the combination of Apixaban and Nepafenac.	Osteoarthritis [FA00-FA05]	[26]
Rucaparib	DM9PVX8	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Rucaparib.	Ovarian cancer [2C73]	[10]
MK-4827	DMLYGH4	Moderate	Increased risk of bleeding by the combination of Apixaban and MK-4827.	Ovarian cancer [2C73]	[10]
Istradefylline	DM20VSK	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Istradefylline.	Parkinsonism [8A00]	[10]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Apixaban caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[27]
Choline salicylate	DM8P137	Moderate	Increased risk of bleeding by the combination of Apixaban and Choline salicylate.	Postoperative inflammation [1A00-CA43]	[28]
Ixekizumab	DMXW92T	Moderate	Altered metabolism of Apixaban due to Ixekizumab alters the formation of CYP450 enzymes.	Psoriasis [EA90]	[10]
Golimumab	DMHZV7X	Moderate	Altered metabolism of Apixaban due to Golimumab alters the formation of CYP450 enzymes.	Rheumatoid arthritis [FA20]	[10]
Sarilumab	DMOGNXY	Moderate	Altered metabolism of Apixaban due to Sarilumab alters the formation of CYP450 enzymes.	Rheumatoid arthritis [FA20]	[10]
Voxelotor	DMCS6M5	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Voxelotor.	Sickle-cell disorder [3A51]	[10]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Apixaban caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[10]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Apixaban caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[10]
LEE011	DMMX75K	Moderate	Decreased metabolism of Apixaban caused by LEE011 mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[10]
Curcumin	DMQPH29	Minor	Increased risk of bleeding by the combination of Apixaban and Curcumin.	Solid tumour/cancer [2A00-2F9Z]	[29]
Plicamycin	DM7C8YV	Major	Increased risk of bleeding by the combination of Apixaban and Plicamycin.	Testicular cancer [2C80]	[10]
Fostamatinib	DM6AUHV	Moderate	Decreased clearance of Apixaban due to the transporter inhibition by Fostamatinib.	Thrombocytopenia [3B64]	[30]
Betrixaban	DM2C4RF	Major	Increased risk of bleeding by the combination of Apixaban and Betrixaban.	Venous thromboembolism [BD72]	[10]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Carmellose sodium	E00625	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
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⏷ Show the Full List of 9 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Apixaban 2.5 mg tablet	2.5 mg	Oral Tablet	Oral
Apixaban 5 mg tablet	5 mg	Oral Tablet	Oral

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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: 6390).
2	Apixaban metabolism and pharmacokinetics after oral administration to humans. Drug Metab Dispos. 2009 Jan;37(1):74-81. doi: 10.1124/dmd.108.023143. Epub 2008 Oct 2.
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Pfizer. Product Development Pipeline. March 31 2009.
5	Characterization of efflux transporters involved in distribution and disposition of apixaban. Drug Metab Dispos. 2013 Apr;41(4):827-35.
6	Effect of Rifampin on the Pharmacokinetics of Apixaban, an Oral Direct Inhibitor of Factor Xa. Am J Cardiovasc Drugs. 2016 Apr;16(2):119-27.
7	In vitro assessment of metabolic drug-drug interaction potential of apixaban through cytochrome P450 phenotyping, inhibition, and induction studies. Drug Metab Dispos. 2010 Mar;38(3):448-58.
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11	Product Information. Eliquis (apixaban). Bristol-Myers Squibb Canada Inc, Montreal, IN.
12	Product Information. Balversa (erdafitinib). Janssen Products, LP, Horsham, PA.
13	Cerner Multum, Inc. "Australian Product Information.".
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15	Product Information. Ofev (nintedanib). Boehringer Ingelheim, Ridgefield, CT.
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19	Product Information. Calquence (acalabrutinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
20	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
21	Product Information. Iclusig (ponatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
22	Product Information. Braftovi (encorafenib). Array BioPharma Inc., Boulder, CO.
23	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
24	Product Information. Zontivity (vorapaxar). Merck & Company Inc, Whitehouse Station, NJ.
25	Product Information. Varubi (rolapitant). Tesaro Inc., Waltham, MA.
26	Product Information. Acular (ketorolac). Allergan Inc, Irvine, CA.
27	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
28	Richards JR, Garber D, Laurin EG, et al. Treatment of cocaine cardiovascular toxicity: a systematic review.?Clin Toxicol (Phila). 2016;54(5):345-364. [PMID: 26919414]
29	Abebe W "Herbal medication: potential for adverse interactions with analgesic drugs." J Clin Pharm Ther 27 (2002): 391-401. [PMID: 12472978]
30	Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.