Details of the Drug

General Information of Drug (ID: DMXY30O)

Drug Name

Dipyridamole

Synonyms

Agilease; Anginal; Antistenocardin; Apricor; Cardioflux; Cardoxil; Cardoxin; Cerebrovase; Chilcolan; Cleridium; Coribon; Coridil; Coronarine; Corosan; Coroxin; Curantil; Curantyl; Dipiridamol; Dipyramidole; Dipyridamine; Dipyridamol; Dipyridamolum; Dipyridan; Dipyudamine; Dypyridamol; Gulliostin; Justpertin; Kurantil; Miosen; Natyl; Peridamol; Permiltin; Persantin; Persantine; Piroan; Prandiol; Protangix; Stenocardil; Stenocardiol; Stimolcardio; Apotex Brand of Dipyridamole; Ashbourne Brand of Dipyridamole; Belmac Brand of Dipyridamole; Berlin Chemie Brand of Dipyridamole; Boehringer Ingelheim Brand of Dipyridamole; IPRAD Brand of Dipyridamole; Iv Persantine; Novopharm Brand of Dipyridamole; Cleridium 150; D 9766; Prandiol 75; Apo-Dipyridamole; Apo-Dipyridamole Fc; Apo-Dipyridamole Sc; Berlin-Chemie Brand of Dipyridamole; Dipiridamol [INN-Spanish]; Dipyridamolum [INN-Latin]; Novo-Dipiradol; Persantine (TN); RA-8; Usaf Ge-12; Dipyridamole (JP15/USP/INN); Dipyridamole [USAN:INN:BAN:JAN]; Permole, Persantine, Dipyridan, Dipyridamole; 2,6-Bis(diethanolamine)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine; 2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido(5,4-d)pyrimidine; 2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine

Indication

Disease Entry	ICD 11	Status	REF
Atrial fibrillation	BC81.3	Approved	[1]
Chronic heart failure	BD1Z	Approved	[1]
Hypertension	BA00-BA04	Approved	[2]
Malignant essential hypertension	BA00	Approved	[1]
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Therapeutic Class

Vasodilator Agents

Affected Organisms

Humans and other mammals

ATC Code

B01AC07: Dipyridamole

B01AC: Platelet aggregation inhibitors excl. heparin

B01A: ANTITHROMBOTIC AGENTS

B01: ANTITHROMBOTIC AGENTS

B: BLOOD AND BLOOD FORMING ORGANS

B01AC07: Dipyridamole

B01AC: Platelet aggregation inhibitors excl. heparin

B01A: ANTITHROMBOTIC AGENTS

B01: ANTITHROMBOTIC AGENTS

B: BLOOD AND BLOOD FORMING ORGANS

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

504.6

Logarithm of the Partition Coefficient (xlogp)

0.7

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The absorption of drug is 70% []
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Clearance: The clearance of drug is 2.3-3.5 mL/min/kg []
Elimination: 0.1% 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 40 minutes [4]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 13.211 micromolar/kg/day [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.009% [4]
Vd: The volume of distribution (Vd) of drug is 1-2.5 L/kg []
Water Solubility: The ability of drug to dissolve in water is measured as 0.007 mg/mL [3]

Chemical Identifiers

Formula: C24H40N8O4
IUPAC Name: 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
Canonical SMILES: C1CCN(CC1)C2=NC(=NC3=C2N=C(N=C3N4CCCCC4)N(CCO)CCO)N(CCO)CCO
InChI: InChI=1S/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2
InChIKey: IZEKFCXSFNUWAM-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 3108
ChEBI ID: CHEBI:4653
CAS Number: 58-32-2
UNII: 64ALC7F90C
DrugBank ID: DB00975
TTD ID: D0F9GE
VARIDT ID: DR00613
INTEDE ID: DR2282
ACDINA ID: D00204

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Phosphodiesterase 5A (PDE5A)	TTJ0IQB	PDE5A_HUMAN	Modulator	[6]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[7]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[8]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Alpha-1-acid glycoprotein 1 (ORM1)	OTZKSBRE	A1AG1_HUMAN	Protein Interaction/Cellular Processes	[9]
ATP-binding cassette sub-family C member 4 (ABCC4)	OTO27PAL	MRP4_HUMAN	Gene/Protein Processing	[10]
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[11]
Calcipressin-1 (RCAN1)	OT1MVXC7	RCAN1_HUMAN	Protein Interaction/Cellular Processes	[12]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[13]
Caspase-7 (CASP7)	OTAPJ040	CASP7_HUMAN	Gene/Protein Processing	[13]
CD40 ligand (CD40LG)	OT75Z6A6	CD40L_HUMAN	Protein Interaction/Cellular Processes	[14]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[15]
cGMP-specific 3',5'-cyclic phosphodiesterase (PDE5A)	OTT8Q1AP	PDE5A_HUMAN	Gene/Protein Processing	[16]
Equilibrative nucleoside transporter 1 (SLC29A1)	OTLOOZZS	S29A1_HUMAN	Gene/Protein Processing	[17]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Atrial fibrillation

ICD Disease Classification

BC81.3

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Phosphodiesterase 5A (PDE5A)	DTT	PDE5A	1.60E-01	-0.25	-0.99
P-glycoprotein 1 (ABCB1)	DTP	P-GP	2.16E-04	-1.07E+00	-2.77E+00
Breast cancer resistance protein (ABCG2)	DTP	BCRP	3.39E-04	-4.15E+00	-3.65E+00

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Ketoprofen	DMRKXPT	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Ketoprofen.	Chronic pain [MG30]	[18]
Levomilnacipran	DMV26S8	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Levomilnacipran.	Chronic pain [MG30]	[19]
Anisindione	DM2C48U	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Anisindione.	Coagulation defect [3B10]	[20]
Regorafenib	DMHSY1I	Major	Increased risk of bleeding by the combination of Dipyridamole and Regorafenib.	Colorectal cancer [2B91]	[21]
Intedanib	DMSTA36	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Intedanib.	Colorectal cancer [2B91]	[22]
Ardeparin	DMYRX8B	Major	Increased risk of bleeding by the combination of Dipyridamole and Ardeparin.	Coronary thrombosis [BA43]	[23]
Danaparoid	DM6CLBN	Major	Increased risk of bleeding by the combination of Dipyridamole and Danaparoid.	Deep vein thrombosis [BD71]	[23]
Rivaroxaban	DMQMBZ1	Major	Increased risk of bleeding by the combination of Dipyridamole and Rivaroxaban.	Deep vein thrombosis [BD71]	[24]
Sertraline	DM0FB1J	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Sertraline.	Depression [6A70-6A7Z]	[19]
Vilazodone	DM4LECQ	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Vilazodone.	Depression [6A70-6A7Z]	[19]
Vortioxetine	DM6F1PU	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Vortioxetine.	Depression [6A70-6A7Z]	[19]
Milnacipran	DMBFE74	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Milnacipran.	Depression [6A70-6A7Z]	[19]
Escitalopram	DMFK9HG	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Escitalopram.	Depression [6A70-6A7Z]	[19]
Desvenlafaxine	DMHD4PE	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Desvenlafaxine.	Depression [6A70-6A7Z]	[19]
Clomipramine	DMINRKW	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Clomipramine.	Depression [6A70-6A7Z]	[19]
Heme	DMGC287	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Heme.	Discovery agent [N.A.]	[25]
Apigenin	DMI3491	Minor	Increased risk of bleeding by the combination of Dipyridamole and Apigenin.	Discovery agent [N.A.]	[26]
Avapritinib	DMK2GZX	Major	Increased risk of bleeding by the combination of Dipyridamole and Avapritinib.	Gastrointestinal stromal tumour [2B5B]	[21]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[27]
Fludarabine	DMVRLT7	Moderate	Interference of cell/tissue uptake of Dipyridamole by Fludarabine.	Malignant haematopoietic neoplasm [2B33]	[21]
Acalabrutinib	DM7GCVW	Major	Increased risk of bleeding by the combination of Dipyridamole and Acalabrutinib.	Mature B-cell lymphoma [2A85]	[28]
Ibrutinib	DMHZCPO	Major	Increased risk of bleeding by the combination of Dipyridamole and Ibrutinib.	Mature B-cell lymphoma [2A85]	[29]
Ponatinib	DMYGJQO	Major	Increased risk of bleeding by the combination of Dipyridamole and Ponatinib.	Mature B-cell lymphoma [2A85]	[30]
Panobinostat	DM58WKG	Major	Increased risk of bleeding by the combination of Dipyridamole and Panobinostat.	Multiple myeloma [2A83]	[31]
Dasatinib	DMJV2EK	Major	Increased risk of bleeding by the combination of Dipyridamole and Dasatinib.	Myeloproliferative neoplasm [2A20]	[32]
Omacetaxine mepesuccinate	DMPU2WX	Major	Increased risk of bleeding by the combination of Dipyridamole and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[33]
Prasugrel	DM7MT6E	Major	Increased risk of bleeding by the combination of Dipyridamole and Prasugrel.	Myocardial infarction [BA41-BA43]	[21]
Vorapaxar	DMA16BR	Major	Increased risk of bleeding by the combination of Dipyridamole and Vorapaxar.	Myocardial infarction [BA41-BA43]	[34]
Sibutramine	DMFJTDI	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Sibutramine.	Obesity [5B80-5B81]	[19]
Dexfenfluramine	DMJ7YDS	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Dexfenfluramine.	Obesity [5B80-5B81]	[19]
Nepafenac	DMYK490	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Nepafenac.	Osteoarthritis [FA00-FA05]	[18]
MK-4827	DMLYGH4	Moderate	Increased risk of bleeding by the combination of Dipyridamole and MK-4827.	Ovarian cancer [2C73]	[21]
Ibuprofen	DM8VCBE	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Ibuprofen.	Pain [MG30-MG3Z]	[18]
Epoprostenol	DMUTYR2	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Epoprostenol.	Pulmonary hypertension [BB01]	[35]
Iloprost	DMVPZBE	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Iloprost.	Pulmonary hypertension [BB01]	[35]
Oxaprozin	DM9UB0P	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Oxaprozin.	Rheumatoid arthritis [FA20]	[18]
Curcumin	DMQPH29	Minor	Increased risk of bleeding by the combination of Dipyridamole and Curcumin.	Solid tumour/cancer [2A00-2F9Z]	[36]
Caplacizumab	DMPUKA7	Major	Increased risk of bleeding by the combination of Dipyridamole and Caplacizumab.	Thrombocytopenia [3B64]	[31]
Apixaban	DM89JLN	Major	Increased risk of bleeding by the combination of Dipyridamole and Apixaban.	Thrombosis [DB61-GB90]	[21]
Cangrelor	DM8JRH0	Major	Increased risk of bleeding by the combination of Dipyridamole and Cangrelor.	Thrombosis [DB61-GB90]	[21]
Brilinta	DMBR01X	Moderate	Increased risk of bleeding by the combination of Dipyridamole and Brilinta.	Thrombosis [DB61-GB90]	[21]
Cabozantinib	DMIYDT4	Major	Increased risk of bleeding by the combination of Dipyridamole and Cabozantinib.	Thyroid cancer [2D10]	[37]
Betrixaban	DM2C4RF	Major	Increased risk of bleeding by the combination of Dipyridamole and Betrixaban.	Venous thromboembolism [BD72]	[38]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
D&C red no. 30	E00456	3000709	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
methylparaben	E00149	7456	Antimicrobial preservative
Propyl 4-hydroxybenzoate	E00141	7175	Antimicrobial preservative
Quinoline yellow WS	E00309	24671	Colorant
Sodium benzoate	E00432	517055	Antimicrobial preservative; lubricant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Crospovidone	E00626	Not Available	Disintegrant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Lithol rubin BCA	E00607	135423095	Colorant
Magnesium stearate	E00208	11177	lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Saccharose	E00091	5988	Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Soybean lecithin	E00637	Not Available	Other agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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⏷ Show the Full List of 25 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Dipyridamole 25 mg tablet	25 mg	Oral Tablet	Oral
Dipyridamole 50 mg tablet	50 mg	Oral Tablet	Oral
Dipyridamole 75 mg tablet	75 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Dipyridamole FDA Label
2	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: 4807).
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	Anti-platelet therapy: phosphodiesterase inhibitors.Br J Clin Pharmacol.2011 Oct;72(4):634-46.
7	ABCG2: a perspective. Adv Drug Deliv Rev. 2009 Jan 31;61(1):3-13.
8	Improving the prediction of the brain disposition for orally administered drugs using BDDCS. Adv Drug Deliv Rev. 2012 Jan;64(1):95-109.
9	Binding of disopyramide, methadone, dipyridamole, chlorpromazine, lignocaine and progesterone to the two main genetic variants of human alpha 1-acid glycoprotein: evidence for drug-binding differences between the variants and for the presence of two separate drug-binding sites on alpha 1-acid glycoprotein. Pharmacogenetics. 1996 Oct;6(5):403-15. doi: 10.1097/00008571-199610000-00004.
10	Expression of multidrug transporter MRP4/ABCC4 is a marker of poor prognosis in neuroblastoma and confers resistance to irinotecan in vitro. Mol Cancer Ther. 2005 Apr;4(4):547-53. doi: 10.1158/1535-7163.MCT-04-0161.
11	A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov;136(1):216-41.
12	Inhibiting the calcineurin-NFAT (nuclear factor of activated T cells) signaling pathway with a regulator of calcineurin-derived peptide without affecting general calcineurin phosphatase activity. J Biol Chem. 2009 Apr 3;284(14):9394-401. doi: 10.1074/jbc.M805889200. Epub 2009 Feb 3.
13	Palmitate increases the susceptibility of cells to drug-induced toxicity: an in vitro method to identify drugs with potential contraindications in patients with metabolic disease. Toxicol Sci. 2012 Oct;129(2):346-62. doi: 10.1093/toxsci/kfs208. Epub 2012 Jun 14.
14	The effect of dipyridamole on vascular cell-derived reactive oxygen species. J Pharmacol Exp Ther. 2005 Nov;315(2):494-500. doi: 10.1124/jpet.105.089987. Epub 2005 Jul 26.
15	Identification of environmental chemicals that activate p53 signaling after in vitro metabolic activation. Arch Toxicol. 2022 Jul;96(7):1975-1987. doi: 10.1007/s00204-022-03291-5. Epub 2022 Apr 18.
16	Cyclic GMP mediates apoptosis induced by sulindac derivatives via activation of c-Jun NH2-terminal kinase 1. Clin Cancer Res. 2000 Oct;6(10):4136-41.
17	New role of the human equilibrative nucleoside transporter 1 (hENT1) in epithelial-to-mesenchymal transition in renal tubular cells. J Cell Physiol. 2012 Apr;227(4):1521-8. doi: 10.1002/jcp.22869.
18	Product Information. Acular (ketorolac). Allergan Inc, Irvine, CA.
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21	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
22	Product Information. Ofev (nintedanib). Boehringer Ingelheim, Ridgefield, CT.
23	Price AJ, Frcpath DO "Is there a clinical interaction between low molecular weight heparin and non-steroidal analgesics after total hip replacement?" Ann R Coll Surg Engl 77 (1995): 395. [PMID: 7486773]
24	Product Information. Xarelto (rivaroxaban). Bayer Inc, Toronto, IA.
25	Product Information. Panhematin (hemin). Recordati Rare Diseases Inc, Lebanon, NJ.
26	Heck AM, DeWitt BA, Lukes AL "Potential interactions between alternative therapies and warfarin." Am J Health Syst Pharm 57 (2000): 1221-7 quiz 1228-30. [PMID: 10902065]
27	Caruso V, Iacoviello L, Di Castelnuovo A, et.al "Thrombotic complications in childhood acute lymphoblastic leukemia: a meta-analysis of 17 prospective studies comprising 1752 pediatric patients." Blood 108 (2006): 2216-22. [PMID: 16804111]
28	Product Information. Calquence (acalabrutinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
29	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
30	Product Information. Iclusig (ponatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
31	Cerner Multum, Inc. "Australian Product Information.".
32	Product Information. Sprycel (dasatinib). Bristol-Myers Squibb, Princeton, NJ.
33	Product Information. Brukinsa (zanubrutinib). BeiGene USA, Inc, San Mateo, CA.
34	Product Information. Zontivity (vorapaxar). Merck & Company Inc, Whitehouse Station, NJ.
35	Product Information. Flolan (epoprostenol). Glaxo Wellcome, Research Triangle Park, NC.
36	Abebe W "Herbal medication: potential for adverse interactions with analgesic drugs." J Clin Pharm Ther 27 (2002): 391-401. [PMID: 12472978]
37	Product Information. Cometriq (cabozantinib). Exelixis Inc, S San Francisco, CA.
38	Product Information. Bevyxxa (betrixaban). Portola Pharmaceuticals, South San Francisco, CA.