Details of the Drug

General Information of Drug (ID: DM75CXN)

Drug Name

Avanafil

Synonyms

Stendra (TN)

Indication

Disease Entry	ICD 11	Status	REF
Erectile dysfunction	HA01.1	Approved	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

483.9

Logarithm of the Partition Coefficient (xlogp)

2.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 30-45 min [2]
Elimination: Approximately 62% of a given dose is excreted as metabolites in the feces and approximately 21% as metabolites in the urine [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 5 - 17 hours [3]
Metabolism: The drug is metabolized via the CYP3A4 and to a lesser extent by CYP2C9 [2]
Vd: The volume of distribution (Vd) of drug is 47-83 L [3]

Chemical Identifiers

Formula: C23H26ClN7O3
IUPAC Name: 4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
Canonical SMILES: COC1=C(C=C(C=C1)CNC2=NC(=NC=C2C(=O)NCC3=NC=CC=N3)N4CCC[C@H]4CO)Cl
InChI: InChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1
InChIKey: WEAJZXNPAWBCOA-INIZCTEOSA-N

Cross-matching ID

PubChem CID: 9869929
ChEBI ID: CHEBI:66876
CAS Number: 330784-47-9
DrugBank ID: DB06237
TTD ID: D0Y5JC
INTEDE ID: DR0159
ACDINA ID: D00052

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
Phosphodiesterase 5A (PDE5A)	TTJ0IQB	PDE5A_HUMAN	Modulator	[4]

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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	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Erectile dysfunction

ICD Disease Classification

HA01.1

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Phosphodiesterase 5A (PDE5A)	DTT	PDE5A	1.60E-01	-0.25	-0.99
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	3.90E-02	-3.45E-01	-1.49E+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 Disease Different from Avanafil (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Ivosidenib	DM8S6T7	Moderate	Increased metabolism of Avanafil caused by Ivosidenib mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[6]
Arn-509	DMT81LZ	Moderate	Increased metabolism of Avanafil caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[6]
Troleandomycin	DMUZNIG	Major	Decreased metabolism of Avanafil caused by Troleandomycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[7]
Pexidartinib	DMS2J0Z	Moderate	Increased metabolism of Avanafil caused by Pexidartinib mediated induction of CYP450 enzyme.	Bone/articular cartilage neoplasm [2F7B]	[6]
Tucatinib	DMBESUA	Major	Decreased metabolism of Avanafil caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[7]
Lumacaftor	DMCLWDJ	Moderate	Increased metabolism of Avanafil caused by Lumacaftor mediated induction of CYP450 enzyme.	Cystic fibrosis [CA25]	[8]
MK-8228	DMOB58Q	Major	Decreased metabolism of Avanafil caused by MK-8228 mediated inhibition of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[6]
Stiripentol	DMMSDOY	Major	Decreased metabolism of Avanafil caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[6]
Eslicarbazepine	DMZREFQ	Moderate	Increased metabolism of Avanafil caused by Eslicarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[6]
Tazemetostat	DMWP1BH	Moderate	Increased metabolism of Avanafil caused by Tazemetostat mediated induction of CYP450 enzyme.	Follicular lymphoma [2A80]	[6]
Boceprevir	DMBSHMF	Major	Decreased metabolism of Avanafil caused by Boceprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[7]
Simeprevir	DMLUA9D	Moderate	Decreased metabolism of Avanafil caused by Simeprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[9]
Cobicistat	DM6L4H2	Major	Decreased metabolism of Avanafil caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[7]
Etravirine	DMGV8QU	Moderate	Increased metabolism of Avanafil caused by Etravirine mediated induction of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[6]
Lesinurad	DMUR64T	Moderate	Increased metabolism of Avanafil caused by Lesinurad mediated induction of CYP450 enzyme.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[6]
Berotralstat	DMWA2DZ	Major	Decreased metabolism of Avanafil caused by Berotralstat mediated inhibition of CYP450 enzyme.	Innate/adaptive immunodeficiency [4A00]	[6]
Crizotinib	DM4F29C	Major	Decreased metabolism of Avanafil caused by Crizotinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[6]
Ceritinib	DMB920Z	Major	Decreased metabolism of Avanafil caused by Ceritinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[7]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Avanafil caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[6]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Avanafil caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[10]
Idelalisib	DM602WT	Major	Decreased metabolism of Avanafil caused by Idelalisib mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[7]
IPI-145	DMWA24P	Major	Decreased metabolism of Avanafil caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[6]
Vemurafenib	DM62UG5	Moderate	Increased metabolism of Avanafil caused by Vemurafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[6]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Avanafil caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[6]
Ozanimod	DMT6AM2	Moderate	Additive hypotensive effects by the combination of Avanafil and Ozanimod.	Multiple sclerosis [8A40]	[11]
Fedratinib	DM4ZBK6	Major	Decreased metabolism of Avanafil caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[6]
Netupitant	DMEKAYI	Major	Decreased metabolism of Avanafil caused by Netupitant mediated inhibition of CYP450 enzyme.	Nausea/vomiting [MD90]	[12]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Avanafil caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[13]
Safinamide	DM0YWJC	Moderate	Additive hypotensive effects by the combination of Avanafil and Safinamide.	Parkinsonism [8A00]	[11]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Avanafil caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[14]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Avanafil caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[15]
Lonafarnib	DMGM2Z6	Major	Decreased metabolism of Avanafil caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[7]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Avanafil caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[6]
Voxelotor	DMCS6M5	Moderate	Decreased metabolism of Avanafil caused by Voxelotor mediated inhibition of CYP450 enzyme.	Sickle-cell disorder [3A51]	[16]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Avanafil caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[10]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Avanafil caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[7]
Armodafinil	DMGB035	Minor	Increased metabolism of Avanafil caused by Armodafinil mediated induction of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[17]
LEE011	DMMX75K	Major	Decreased metabolism of Avanafil caused by LEE011 mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[6]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Avanafil caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[18]
Elagolix	DMB2C0E	Moderate	Increased metabolism of Avanafil caused by Elagolix mediated induction of CYP450 enzyme.	Uterine fibroid [2E86]	[6]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Calcium carbonate	E00198	10112	Binding agent; Buffering agent; Diluent; Opacifying agent
Fumaric acid	E00420	444972	Acidulant; Antioxidant; Complexing agent; Flavoring agent; Solubilizing agent
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Magnesium stearate	E00208	11177	lubricant
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Avanafil 100 mg tablet	100 mg	Oral Tablet	Oral
Avanafil 200 mg tablet	200 mg	Oral Tablet	Oral
Avanafil 50 mg tablet	50 mg	Oral Tablet	Oral

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: 7448).
2	FDA Approved Drug Products: Stendra (avanafil) tablets for oral use
3	EMA CHMP Assessment Report: Avanafil (INN)
4	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
5	An update on pharmacological treatment of erectile dysfunction with phosphodiesterase type 5 inhibitors. Expert Opin Pharmacother. 2013 Jul;14(10):1333-44.
6	Product Information. Stendra (avanafil). Vivus Inc, Mountain View, CA.
7	Cerner Multum, Inc. "Australian Product Information.".
8	Product Information. Kalydeco (ivacaftor). Vertex Pharmaceuticals, Cambridge, MA.
9	Product Information. Olysio (simeprevir). Janssen Pharmaceuticals, Titusville, NJ.
10	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
11	Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
12	Product Information. Cialis (tadalafil). Lilly, Eli and Company, Indianapolis, IN.
13	EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
14	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
15	Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
16	Product Information. Oxbryta (voxelotor). Global Blood Therapeutics, Inc., South San Francisco, CA.
17	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]
18	Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.