Details of the Drug

General Information of Drug (ID: DM9PLRH)

Drug Name

Doxazosin

Synonyms

Doxazosina; Doxazosine; Doxazosinum; Normothen; Doxazosina [Spanish]; Doxazosine [French]; Doxazosinum [Latin]; UK 33274; Cardura (TN); Cardura XL (TN); Cardura-1; Cardura-2; Cardura-4; Carduran (TN); Doxazosin (INN); Doxazosin [INN:BAN]; UK-33274; [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(2,3-dihydro-1,4-benzodioxin-3-yl)methanone; 1-(4-Amino-6,7-Dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcarbonyl)piperazin; 1-(4-Amino-6,7-dimethoxy-2-chinazolinyl)-4-(2,3-dihydro-1,4-benzodioxixin-2-ylcarbonyl)piperazin; 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-[4-(1,4-benzodioxan-2-yl)carpiperazin-1-yl)]-6,7-dimethoxyquinazoline mesylate; 2-[4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperazin-1-yl]-6,7-bis(methyloxy)quinazolin-4-amine; 2-[4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine; 2-{4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]piperazin-1-yl}-6,7-dimethoxyquinazolin-4-amine

Indication

Disease Entry	ICD 11	Status	REF
Benign prostatic hyperplasia	GA90	Approved	[1]
Hypertension	BA00-BA04	Approved	[2]
Malignant essential hypertension	BA00	Approved	[1]
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Therapeutic Class

Antihypertensive Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

451.5

Logarithm of the Partition Coefficient (xlogp)

2.5

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 1: high solubility and high permeability [3]
Bioavailability: The bioavailability of drug is 56%-60% []
Clearance: The clearance of drug is 1-2 mL/min/kg [4]
Elimination: In a pharmacokinetic study using a 1 mg IV radiolabeled dose and a 2 mg oral dose, 63% of the ingested doxazosin was found to be excreted in the feces and about 9% of the dose was found to be excreted in the urine [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 22 hours [5]
Metabolism: The drug is metabolized via the hepatic [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.59138 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.017% [7]
Vd: The volume of distribution (Vd) of drug is 1.0-1.9 L/kg [5]

Chemical Identifiers

Formula: C23H25N5O5
IUPAC Name: [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(2,3-dihydro-1,4-benzodioxin-3-yl)methanone
Canonical SMILES: COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4COC5=CC=CC=C5O4)N)OC
InChI: InChI=1S/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)
InChIKey: RUZYUOTYCVRMRZ-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 3157
ChEBI ID: CHEBI:4708
CAS Number: 74191-85-8
DrugBank ID: DB00590
TTD ID: D03MIR
VARIDT ID: DR00516
INTEDE ID: DR0542
ACDINA ID: D00213

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
Adrenergic receptor alpha-1D (ADRA1D)	TT34BHT	ADA1D_HUMAN	Antagonist	[8]

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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	[9]
Cytochrome P450 2D6 (CYP2D6)	DECB0K3	CP2D6_HUMAN	Substrate	[9]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[10]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Doxazosin

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Acebutolol	DM0TI4U	Moderate	Additive hypotensive effects by the combination of Doxazosin and Acebutolol.	Hypertension [BA00-BA04]	[11]
Moexipril	DM26E4B	Moderate	Additive hypotensive effects by the combination of Doxazosin and Moexipril.	Hypertension [BA00-BA04]	[12]
Bisoprolol	DM3UZ95	Moderate	Additive hypotensive effects by the combination of Doxazosin and Bisoprolol.	Hypertension [BA00-BA04]	[11]
Penbutolol	DM4ES8F	Moderate	Additive hypotensive effects by the combination of Doxazosin and Penbutolol.	Hypertension [BA00-BA04]	[11]
Nebivolol	DM7F1PA	Moderate	Additive hypotensive effects by the combination of Doxazosin and Nebivolol.	Hypertension [BA00-BA04]	[11]
Pindolol	DMD2NV7	Moderate	Additive hypotensive effects by the combination of Doxazosin and Pindolol.	Hypertension [BA00-BA04]	[11]
Labetalol	DMK8U72	Moderate	Additive hypotensive effects by the combination of Doxazosin and Labetalol.	Hypertension [BA00-BA04]	[11]
Perindopril	DMOPZDT	Moderate	Additive hypotensive effects by the combination of Doxazosin and Perindopril.	Hypertension [BA00-BA04]	[12]
Quinapril	DMR8H31	Moderate	Additive hypotensive effects by the combination of Doxazosin and Quinapril.	Hypertension [BA00-BA04]	[12]
Lisinopril	DMUOK4C	Moderate	Additive hypotensive effects by the combination of Doxazosin and Lisinopril.	Hypertension [BA00-BA04]	[12]
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⏷ Show the Full List of 10 DDI Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Posaconazole	DMUL5EW	Moderate	Decreased metabolism of Doxazosin caused by Posaconazole mediated inhibition of CYP450 enzyme.	Aspergillosis [1F20]	[13]
Troleandomycin	DMUZNIG	Moderate	Decreased metabolism of Doxazosin caused by Troleandomycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[13]
Telithromycin	DMZ4P3A	Moderate	Decreased metabolism of Doxazosin caused by Telithromycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[13]
Cariprazine	DMJYDVK	Moderate	Additive hypotensive effects by the combination of Doxazosin and Cariprazine.	Bipolar disorder [6A60]	[14]
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Doxazosin caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[13]
Olopatadine	DMKMWQG	Moderate	Additive CNS depression effects by the combination of Doxazosin and Olopatadine.	Conjunctiva disorder [9A60]	[15]
Selegiline	DM6034S	Moderate	Additive hypotensive effects by the combination of Doxazosin and Selegiline.	Depression [6A70-6A7Z]	[16]
Isocarboxazid	DMAF1NB	Moderate	Additive hypotensive effects by the combination of Doxazosin and Isocarboxazid.	Depression [6A70-6A7Z]	[16]
OPC-34712	DMHG57U	Moderate	Additive hypotensive effects by the combination of Doxazosin and OPC-34712.	Depression [6A70-6A7Z]	[14]
Phenelzine	DMHIDUE	Moderate	Additive hypotensive effects by the combination of Doxazosin and Phenelzine.	Depression [6A70-6A7Z]	[16]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Doxazosin caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[17]
Nadolol	DMW6GVL	Moderate	Additive hypotensive effects by the combination of Doxazosin and Nadolol.	Essential hypertension [BA00]	[11]
Itraconazole	DMCR1MV	Moderate	Decreased metabolism of Doxazosin caused by Itraconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[13]
Ketoconazole	DMPZI3Q	Moderate	Decreased metabolism of Doxazosin caused by Ketoconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[13]
Metipranolol	DMJMVKI	Moderate	Additive hypotensive effects by the combination of Doxazosin and Metipranolol.	Glaucoma [9C61]	[11]
Levobetaxolol	DMSREPX	Moderate	Additive hypotensive effects by the combination of Doxazosin and Levobetaxolol.	Glaucoma [9C61]	[11]
Levobunolol	DMTNFCQ	Moderate	Additive hypotensive effects by the combination of Doxazosin and Levobunolol.	Glaucoma [9C61]	[11]
Carvedilol	DMHTEAO	Moderate	Additive hypotensive effects by the combination of Doxazosin and Carvedilol.	Heart failure [BD10-BD1Z]	[11]
Boceprevir	DMBSHMF	Major	Decreased metabolism of Doxazosin caused by Boceprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[18]
Telaprevir	DMMRV29	Moderate	Decreased metabolism of Doxazosin caused by Telaprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[13]
Procarbazine	DMIK367	Moderate	Additive hypotensive effects by the combination of Doxazosin and Procarbazine.	Hodgkin lymphoma [2B30]	[16]
Delavirdine	DM3NF5G	Moderate	Decreased metabolism of Doxazosin caused by Delavirdine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
Fosamprenavir	DM4W9B3	Moderate	Decreased metabolism of Doxazosin caused by Fosamprenavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Doxazosin caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
Saquinavir	DMG814N	Moderate	Decreased metabolism of Doxazosin caused by Saquinavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
Amprenavir	DMLMXE0	Moderate	Decreased metabolism of Doxazosin caused by Amprenavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
Atazanavir	DMSYRBX	Moderate	Decreased metabolism of Doxazosin caused by Atazanavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
Conivaptan	DM1V329	Moderate	Decreased metabolism of Doxazosin caused by Conivaptan mediated inhibition of CYP450 enzyme.	Hypo-osmolality/hyponatraemia [5C72]	[13]
Berotralstat	DMWA2DZ	Moderate	Decreased metabolism of Doxazosin caused by Berotralstat mediated inhibition of CYP450 enzyme.	Innate/adaptive immunodeficiency [4A00]	[19]
Propiomazine	DMKY8V1	Moderate	Additive hypotensive effects by the combination of Doxazosin and Propiomazine.	Insomnia [7A00-7A0Z]	[14]
ITI-007	DMUQ1DO	Moderate	Additive hypotensive effects by the combination of Doxazosin and ITI-007.	Insomnia [7A00-7A0Z]	[14]
Ceritinib	DMB920Z	Moderate	Decreased metabolism of Doxazosin caused by Ceritinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[13]
Idelalisib	DM602WT	Moderate	Decreased metabolism of Doxazosin caused by Idelalisib mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[13]
IPI-145	DMWA24P	Moderate	Decreased metabolism of Doxazosin caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[20]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Doxazosin and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[21]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Doxazosin and Lasmiditan.	Migraine [8A80]	[22]
Thalidomide	DM70BU5	Moderate	Increased risk of ventricular arrhythmias by the combination of Doxazosin and Thalidomide.	Multiple myeloma [2A83]	[18]
Ozanimod	DMT6AM2	Moderate	Additive hypotensive effects by the combination of Doxazosin and Ozanimod.	Multiple sclerosis [8A40]	[16]
Promethazine	DM6I5GR	Moderate	Additive hypotensive effects by the combination of Doxazosin and Promethazine.	Nausea/vomiting [MD90]	[14]
Safinamide	DM0YWJC	Moderate	Additive hypotensive effects by the combination of Doxazosin and Safinamide.	Parkinsonism [8A00]	[16]
Rasagiline	DM3WKQ4	Moderate	Additive hypotensive effects by the combination of Doxazosin and Rasagiline.	Parkinsonism [8A00]	[16]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Doxazosin caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[23]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Doxazosin caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[24]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Doxazosin caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[13]
Tamsulosin	DM5QF9V	Moderate	Additive hypotensive effects by the combination of Doxazosin and Tamsulosin.	Prostate hyperplasia [GA90]	[25]
Silodosin	DMJSBT6	Moderate	Additive hypotensive effects by the combination of Doxazosin and Silodosin.	Prostate hyperplasia [GA90]	[25]
Levomepromazine	DMIKFEL	Moderate	Additive hypotensive effects by the combination of Doxazosin and Levomepromazine.	Psychotic disorder [6A20-6A25]	[14]
Fluphenazine	DMIT8LX	Moderate	Additive hypotensive effects by the combination of Doxazosin and Fluphenazine.	Psychotic disorder [6A20-6A25]	[14]
Mesoridazine	DM2ZGAN	Moderate	Additive hypotensive effects by the combination of Doxazosin and Mesoridazine.	Schizophrenia [6A20]	[14]
Thioridazine	DM35M8J	Moderate	Additive hypotensive effects by the combination of Doxazosin and Thioridazine.	Schizophrenia [6A20]	[14]
Aripiprazole	DM3NUMH	Moderate	Additive hypotensive effects by the combination of Doxazosin and Aripiprazole.	Schizophrenia [6A20]	[14]
Iloperidone	DM6AUFY	Moderate	Additive hypotensive effects by the combination of Doxazosin and Iloperidone.	Schizophrenia [6A20]	[14]
Paliperidone	DM7NPJS	Moderate	Additive hypotensive effects by the combination of Doxazosin and Paliperidone.	Schizophrenia [6A20]	[14]
Molindone	DMAH70G	Moderate	Additive hypotensive effects by the combination of Doxazosin and Molindone.	Schizophrenia [6A20]	[14]
Thiothixene	DMDINC4	Moderate	Additive hypotensive effects by the combination of Doxazosin and Thiothixene.	Schizophrenia [6A20]	[14]
Trifluoperazine	DMKBYWI	Moderate	Additive hypotensive effects by the combination of Doxazosin and Trifluoperazine.	Schizophrenia [6A20]	[14]
Amisulpride	DMSJVAM	Moderate	Additive hypotensive effects by the combination of Doxazosin and Amisulpride.	Schizophrenia [6A20]	[14]
Asenapine	DMSQZE2	Moderate	Additive hypotensive effects by the combination of Doxazosin and Asenapine.	Schizophrenia [6A20]	[14]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Doxazosin caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[18]
Methdilazine	DMAUHQX	Moderate	Additive hypotensive effects by the combination of Doxazosin and Methdilazine.	Vasomotor/allergic rhinitis [CA08]	[14]
Trimeprazine	DMEMV9D	Moderate	Additive hypotensive effects by the combination of Doxazosin and Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[26]
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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
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF	E00255	17730	Colorant
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
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium chloride	E00077	5234	Diluent; Tonicity agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Cellulose microcrystalline	E00698	Not Available	Adsorbent; Suspending agent; Diluent
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⏷ Show the Full List of 17 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Doxazosin 2 mg tablet	2 mg	Oral Tablet	Oral
Doxazosin 8 mg tablet	8 mg	Oral Tablet	Oral
Doxazosin 4 mg tablet	4 mg	Oral Tablet	Oral
Doxazosin 1 mg tablet	1 mg	Oral Tablet	Oral
Doxazosin Mesylate eq 2mg base tablet	eq 2mg base	Tablet	Oral
Doxazosin Mesylate eq 1mg base tablet	eq 1mg base	Tablet	Oral
Doxazosin Mesylate eq 4mg base tablet	eq 4mg base	Tablet	Oral
Doxazosin 4 mg tablet	4 mg	24 HR Extended Release Oral Tablet	Oral
Doxazosin 8 mg tablet	8 mg	24 HR Extended Release Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Doxazosin 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: 7170).
3	BDDCS applied to over 900 drugs
4	Kaye B, Cussans NJ, Faulkner JK, Stopher DA, Reid JL: The metabolism and kinetics of doxazosin in man, mouse, rat and dog. Br J Clin Pharmacol. 1986;21 Suppl 1:19S-25S. doi: 10.1111/j.1365-2125.1986.tb02849.x.
5	Doxazosin FDA label
6	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
7	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
8	The role of combination medical therapy in benign prostatic hyperplasia. Int J Impot Res. 2008 Dec;20 Suppl 3:S33-43.
9	Priapism induced by boceprevir-CYP3A4 inhibition and alpha-adrenergic blockade: case report. Clin Infect Dis. 2014 Jan;58(1):e35-8.
10	Product monograph: CARDURA (Doxazosin mesylate).
11	Chrysant SG "Experience with terazosin administered in combination with other antihypertensive agents." Am J Med 80 (1986): 55-61. [PMID: 2872808]
12	Baba T, Tomiyama T, Takebe K "Enhancement by an ACE inhibitor of first-dose hypotension caused by an alpha-blocker." N Engl J Med 322 (1990): 1237. [PMID: 1970122]
13	Canadian Pharmacists Association.
14	Aronowitz JS, Chakos MH, Safferman AZ, Lieberman JA "Syncope associated with the combination of clozapine and enalapril." J Clin Psychopharmacol 14 (1994): 429-30. [PMID: 7884028]
15	Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002]
16	Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
17	EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
18	Cerner Multum, Inc. "Australian Product Information.".
19	Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
20	Product Information. Copiktra (duvelisib). Verastem, Inc., Needham, MA.
21	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
22	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
23	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
24	Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
25	Product Information. Flomax (tamsulosin). Boehringer-Ingelheim, Ridgefield, CT.
26	Product Information. Clozaril (clozapine). Novartis Pharmaceuticals, East Hanover, NJ.