AVANAFIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H26ClN7O3
Molecular Weight	483.951
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(CNC2=C(C=NC(=N2)N3CCC[C@H]3CO)C(=O)NCC4=NC=CC=N4)C=C1Cl

InChI

InChIKey=WEAJZXNPAWBCOA-INIZCTEOSA-N

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

HIDE SMILES / InChI

Molecular Formula	C23H26ClN7O3
Molecular Weight	483.951
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202276s013lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.fiercepharma.com/marketing/vivus-announces-operational-update; https://www.ncbi.nlm.nih.gov/pubmed/?term=22704456

Avanafil is a PDE5 inhibitor approved for erectile dysfunction by FDA and by EMA. Avanafil is known by the trademark names Stendra and Spedra and was developed by Vivus Inc. Avanafil selectively inhibits PDE5, thus inhibiting the degradation of cyclic guanosine monophosphate (cGMP) found in the smooth muscle of the corpus cavernosa of the penis. The physiologic mechanism of erection of the penis involves release of nitric oxide (NO) in the corpus cavernosum during sexual stimulation. NO then activates the enzyme guanylate cyclase, which results in increased levels of cGMP, producing smooth muscle relaxation in the corpus cavernosum and allowing inflow of blood. Avanafil has no direct relaxant effect on isolated human corpus cavernosum, but enhances the effect of NO by inhibiting PDE5, which is responsible for degradation of cGMP in the corpus cavernosum. Because sexual stimulation is required to initiate the local release of nitric oxide, the inhibition of PDE5 has noeffect in the absence of sexual stimulation. The advantage of avanafil is that it has very fast onset of action compared with other PDE5 inhibitors. It is absorbed quickly, reaching a maximum concentration in about 30–45 minutes. About two-thirds of the participants were able to engage in sexual activity within 15 minutes.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 5A 30 Target ID: CHEMBL1827 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202276s013lbl.pdf	Inhibitor 8297		5.2 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Erectile dysfunction 35 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202276s013lbl.pdf	Curative		Approved 8429	STENDRA Approved Use Indicated for the treatment of erectile dysfunction. Launch Date 2012

C_max

Value	Dose	Co-administered	Analyte	Population
2231.63 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20637970/	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		[NO STEREO] AVANAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2630 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20637970/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		AVANAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
7339.13 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20637970/	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		[NO STEREO] AVANAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7148.67 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20637970/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		AVANAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
8.66 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20637970/	100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	[NO STEREO] AVANAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.53 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20637970/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	AVANAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202276s000lbl.pdf	single, oral	AVANAFIL plasma	Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202276s000lbl.pdf	single, oral		AVANAFIL plasma	Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg 1 times / day steady, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	Disc. AE: Dizziness, Pigmentation disorder... AEs leading to discontinuation/dose reduction: Dizziness (2 patients) Pigmentation disorder (1 patient) Chest discomfort (1 patient) Headache (1 patient) Diarrhea (1 patient) Dyspepsia (1 patient) Pruritus (1 patient) Eye swelling (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	Disc. AE: Back pain, Headache... AEs leading to discontinuation/dose reduction: Back pain (1 patient) Headache (2 patients) Erection increased (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
50 mg 1 times / day steady, oral Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	Disc. AE: Palpitations, Dizziness... AEs leading to discontinuation/dose reduction: Palpitations (1 patient) Dizziness (1 patient) Heart rate increased (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99

AEs

AE	Significance	Dose	Population
Chest discomfort	1 patient Disc. AE	100 mg 1 times / day steady, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Diarrhea	1 patient Disc. AE	100 mg 1 times / day steady, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Dyspepsia	1 patient Disc. AE	100 mg 1 times / day steady, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Eye swelling	1 patient Disc. AE	100 mg 1 times / day steady, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Headache	1 patient Disc. AE	100 mg 1 times / day steady, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Pigmentation disorder	1 patient Disc. AE	100 mg 1 times / day steady, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Pruritus	1 patient Disc. AE	100 mg 1 times / day steady, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Dizziness	2 patients Disc. AE	100 mg 1 times / day steady, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Back pain	1 patient Disc. AE	200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Erection increased	1 patient Disc. AE	200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Headache	2 patients Disc. AE	200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Dizziness	1 patient Disc. AE	50 mg 1 times / day steady, oral Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Heart rate increased	1 patient Disc. AE	50 mg 1 times / day steady, oral Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99
Palpitations	1 patient Disc. AE	50 mg 1 times / day steady, oral Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000MedR.pdf Page: p. 99

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587 inducer 781	substrate 1037 inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A 72 CYP2A6 707 CYP2B6 810 CYP2E1 882 CYP2C8 911 CYP2C19 1478 OCT1 512 OCT2 647 OATP1B1 788 OATP1B3 706 OAT3 642 BSEP 402 BCRP 699	P-gp 1537	CYP1A2 701 CYP2B6 547

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BSEP 403	inhibitor 3277 Sources: https://www.tga.gov.au/sites/default/files/auspar-avanafil-161027-pi.pdf#page=15 Page: 15.0	no
CYP1A 121	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202276s018lbl.pdf#page=9 Page: 9.0	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202276s018lbl.pdf#page=9 Page: 9.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202276s018lbl.pdf#page=9 Page: 9.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202276s018lbl.pdf#page=9 Page: 9.0	no
OAT3 644	inhibitor 3277 Sources: https://www.tga.gov.au/sites/default/files/auspar-avanafil-161027-pi.pdf#page=15 Page: 15.0	no
OATP1B1 803	inhibitor 3277 Sources: https://www.tga.gov.au/sites/default/files/auspar-avanafil-161027-pi.pdf#page=15 Page: 15.0	no
OATP1B3 715	inhibitor 3277 Sources: https://www.tga.gov.au/sites/default/files/auspar-avanafil-161027-pi.pdf#page=15 Page: 15.0	no
OCT1 543	inhibitor 3277 Sources: https://www.tga.gov.au/sites/default/files/auspar-avanafil-161027-pi.pdf#page=15 Page: 15.0	no
OCT2 648	inhibitor 3277 Sources: https://www.tga.gov.au/sites/default/files/auspar-avanafil-161027-pi.pdf#page=15 Page: 15.0	no
CYP1A2 1692	inducer 1573 Sources: https://www.tga.gov.au/sites/default/files/auspar-avanafil-161027-pi.pdf#page=15 Page: 15.0	not significant
CYP2B6 1001	inducer 1573 Sources: https://www.tga.gov.au/sites/default/files/auspar-avanafil-161027-pi.pdf#page=15 Page: 15.0	not significant
BCRP 773	inhibitor 3277 Sources: https://www.tga.gov.au/sites/default/files/auspar-avanafil-161027-pi.pdf#page=15 Page: 15.0	unlikely [IC50 1 uM]
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf#page=138 Page: 138.0	weak [Ki 15.2 uM]	weak (co-administration study) Comment: Increased AUC by 2.0% and decreased Cmax by 14% using rosiglitazone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf#page=138 Page: 138.0
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf#page=138 Page: 138.0	weak [Ki 2.9 uM]	weak (co-administration study) Comment: Increased AUC and Cmax of omeprazole by 5.9% and 8.6%, respectively; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf#page=138 Page: 138.0
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf#page=138 Page: 138.0	weak [Ki 43.9 uM]	weak (co-administration study) Comment: Increased AUC and Cmax of desipramine by 5.7% and 5.2%, respectively; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf#page=138 Page: 138.0
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf#page=138 Page: 138.0	weak
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202276s018lbl.pdf#page=9 Page: 9.0	weak	no (co-administration study) Comment: Did not alter changes in PT, INR, AUC, or Cmax of warfarin Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202276s018lbl.pdf#page=9 Page: 9.0
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf#page=138 Page: 138.0	weak	no (co-administration study) Comment: Did not affect PK of amlodipine; no in vivo study to evaluate CYP3A4 induction by avanafil was conducted by the sponsor Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf#page=138 Page: 138.0

Drug as victim

Target	Modality	Activity	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf#page=158 Page: 158.0	weak
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202276s018lbl.pdf#page=8 Page: 8.0	yes	yes (co-administration study) Comment: ritonavir increased Cmax and AUC equal to approximately 2-fold and 13-fold, respectively; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202276s018lbl.pdf#page=8 Page: 8.0
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202276s018lbl.pdf#page=8 Page: 8.0	yes	yes (co-administration study) Comment: Ketoconazole increased systemic exposure (AUC) and maximum concentration (Cmax) equal to 13-fold and 3-fold, respectively; ritonavir increased Cmax and AUC equal to approximately 2-fold and 13-fold, respectively; erythromycin increased STENDRA 200 mg single-dose Cmax and AUC equal to approximately 2-fold and 3-fold, respectively; amlodipine increased the Cmax and AUC of avanafil by approximately 22% and 70%, respectively; The Cmax and AUC of amlodipine decreased by approximately 9% and 4%, respectively; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202276s018lbl.pdf#page=8 Page: 8.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000PharmR.pdf#page=29 Page: 29.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:66876	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66876
MolPort	MolPort-029-944-565	https://www.molport.com/shop/molecule-link/MolPort-029-944-565
Selleck Chemicals	avanafil	http://www.selleckchem.com/products/avanafil.html
ZINC	ZINC000011677857	http://zinc15.docking.org/substances/ZINC000011677857
eMolecules	31592045	https://www.emolecules.com/cgi-bin/more?vid=31592045

PubMed

Title	Date	PubMed
Gateways to clinical trials.	2004 Jul-Aug	15349141
Gateways to clinical trials.	2006 Oct	17136234
Avanafil for the treatment of erectile dysfunction: initial data and clinical key properties.	2013 Feb	23372609
An update on pharmacological treatment of erectile dysfunction with phosphodiesterase type 5 inhibitors.	2013 Jul	23675780

Patents

Sample Use Guides

In Vivo Use Guide

The starting dose is 100 mg taken as early as approximately 15 minutes before sexual activity, on an as needed basis. Take STENDRA no more than once a day. Based on efficacy and/or tolerability, the dose may be increased to 200 mg taken as early as approximately 15 minutes before sexual activity, or decreased to 50 mg taken approximately 30 minutes before sexual activity. Use the lowest dose that provides benefit. May be taken with or without food.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:15:40 GMT 2023` Edited by `admin` on `Sat Dec 16 16:15:40 GMT 2023`
Record UNII	DR5S136IVO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AVANAFIL

Official Name

English

AVANAFIL [MI]

Common Name

English

AVANAFIL [ORANGE BOOK]

Common Name

English

AVANAFIL [VANDF]

Common Name

English

avanafil [INN]

Common Name

English

(S)-4-(3-CHLORO-4-METHOXYBENZYLAMINO)-2-(2-HYDROXYMETHYLPYRROLIDIN-1-YL)-N-PYRIMIDIN-2-YLMETHYL-5-PYRIMIDINECARBOXAMIDE

Systematic Name

English

STENDRA

Brand Name

English

SPEDRA

Brand Name

English

Avanafil [WHO-DD]

Common Name

English

AVANAFIL [USAN]

Common Name

English

AVANAFIL [MART.]

Common Name

English

4-[(3-Chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide

Systematic Name

English

5-PYRIMIDINECARBOXAMIDE, 4-(((3-CHLORO-4-METHOXYPHENYL)METHYL)AMINO)-2-((2S)-2-(HYDROXYMETHYL)-1-PYRROLIDINYL)-N-(2-PYRIMIDINYLMETHYL)-

Systematic Name

English

TA-1790

Code

English

Classification Tree Code System Code

WHO-ATC

G04BE10