Compounds > avanafil
Page last updated: 2024-11-11

avanafil

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Cross-References

ID SourceID
PubMed CID9869929
CHEMBL ID1963681
CHEBI ID66876
SCHEMBL ID118799
MeSH IDM0551615

Synonyms (72)

Synonym
stendra (tn)
avanafil (usan/inn)
330784-47-9
spedra (tn)
D03217
avanafil ,
stendra
ta-1790
zepeed
vi-0162
dr5s136ivo ,
4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)-1-pyrrolidinyl)-n-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide
ta 1790
5-pyrimidinecarboxamide, 4-(((3-chloro-4-methoxyphenyl)methyl)amino)-2-((2s)-2-(hydroxymethyl)-1-pyrrolidinyl)-n-(2-pyrimidinylmethyl)-
4-((3-chloro-4-methoxybenzyl)amino)-2-((2s)-2-(hydroxymethyl)pyrrolidin-1-yl)-n-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
(s)-4-(3-chloro-4-methoxybenzylamino)-2-(2-hydroxymethylpyrrolidin-1-yl)-n-pyrimidin-2-ylmethyl-5-pyrimidinecarboxamide
avanafil [usan:inn]
unii-dr5s136ivo
S4019
CHEMBL1963681
chebi:66876 ,
(s)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[(2-pyrimidinylmethyl)carbamoyl]pyrimidine
BRD-K65781196-001-01-4
avanafil [usan]
spedra
avanafil [inn]
avanafil [vandf]
avanafil [mi]
avanafil [mart.]
avanafil [orange book]
avanafil [who-dd]
4-[(3-chloro-4-methoxybenzyl)amino]-2-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-n-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
gtpl7448
4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-n-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
DB06237
HY-18252
(s)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[n-(2-pyrimidylmethyl)carbamoyl]-pyrimidine
WEAJZXNPAWBCOA-INIZCTEOSA-N
SCHEMBL118799
(s)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-n-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
AKOS024462448
AB01565827_02
bdbm50036629
CCG-229896
DTXSID50186727 ,
ta1790
c23h26cln7o3
e6l ,
4-[(3-chloranyl-4-methoxy-phenyl)methylamino]-2-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-n-(pyrimidin-2-ylmethyl)pyrimid ine-5-carboxamide
EN300-6481290
4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-n-[(pyrimidin-2-yl)methyl]pyrimidine-5-carboxamide
5-pyrimidinecarboxamide, 4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-2-[(2s)-2-(hydroxymethyl)-1-pyrrolidinyl]-n-(2-pyrimidinylmethyl)-; (s)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[(2-pyrimidinylmethyl)carbamoyl]pyrimidine;
J-019006
mfcd11977961
SW219217-1
(s)-4-[(3-chlor-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1- pyrrolidinyl]-n-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamid
Q2873270
ine-5-carboxamide
4-[(3-chloranyl-4-methoxy-phenyl)methylamino]-2-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-n-(pyrimidin-2-ylmethyl)pyrimid
AS-20106
AMY1794
avanafil; (s)-4-chloro-6-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-n-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
NCGC00386241-01
avanafil 100 microg/ml in acetonitrile:dimethylsulfoxide
(s)-4-[(3-chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]-n-(2pyrimidinylmethyl)-5-pyrimidinecarboxamide
CS1566
dtxcid90109218
g04be10
avanafilo
avanafil (mart.)
avanafilum
Z2235802070

Research Excerpts

Overview

Avanafil (AVA) is a recent FDA approved selective phosphodiesterase type 5 inhibitor used for oral treatment of erectile dysfunction. The drug is a highly selective PDE5 inhibitor that is a competitive antagonist of cyclic guanosine monophosphate.

ExcerptReferenceRelevance
"Avanafil is a second-generation phosphodiesterase type 5 inhibitor with a high selectivity for phosphodiesterase type 5 isoform."( Efficacy and safety of avanafil 200 mg versus sildenafil 100 mg in the treatment of erectile dysfunction after robot-assisted unilateral nerve-sparing prostatectomy: A prospective multicentre study.
Altieri, VM; Chini, T; Cito, G; Della Camera, PA; Gacci, M; Maggi, M; Natali, A; Nunzio, C; Rastrelli, G; Serni, S; Tellini, R, 2020)		1.59
"Avanafil (AVA) is a recent FDA approved selective phosphodiesterase type 5 inhibitor used for oral treatment of erectile dysfunction. "( Development of an optimized avanafil-loaded invasomal transdermal film: Ex vivo skin permeation and in vivo evaluation.
Ahmed, OAA; Badr-Eldin, SM, 2019)		2.25
"Avanafil is a highly selective and potent oral phosphodiesterase type 5 inhibitor. "( Evaluation of daily avanafil efficacy in improving the endothelial function in Egyptian males with erectile dysfunction.
Badae, NM; Elkamshoushi, AM; Kabary, MG; Omar, SI, 2021)		2.39
"Avanafil (1) is a PDE5 inhibitor (treatment for erectile dysfunction) discovered by our company."( Discovery of 2-[(E)-2-(7-Fluoro-3-methylquinoxalin-2-yl)vinyl]-6-pyrrolidin-1-yl-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine Hydrochloride as a Highly Selective PDE10A Inhibitor.
Himiyama, T; Hongu, M; Kadoh, Y; Kawanishi, E; Kimura, M; Kobayashi, T; Kojima, K; Kotera, J; Matsumura, T; Miyoshi, H; Omori, K; Sakamoto, T; Sasaki, T; Takedomi, K; Tanaka, Y; Taniguchi, H; Watanabe, Y, 2018)		1.2
"Avanafil is a highly selective PDE5 inhibitor that is a competitive antagonist of cyclic guanosine monophosphate. "( Avanafil for erectile dysfunction.
Brown, DA; Hill, JK; Kyle, JA, 2013)		3.28
"Avanafil is a potent PDE5 inhibitor and is an effective treatment option for ED."( Avanafil for erectile dysfunction.
Brown, DA; Hill, JK; Kyle, JA, 2013)		3.28
"Avanafil is a highly selective phosfosdiesterase 5 inhibitor (PDE5 inhibitor), with rapid onset of action, approved by the Food and Drug Administration (FDA) and the European Medicines Agency for the treatment of erectile dysfunction (ED). "( Avanafil for the treatment of erectile dysfunction. An updated review.
Carballido-Rodríguez, J; Egui-Rojo, MA; Martínez-Salamanca, JI; Moncada-Iribarren, I, 2014)		3.29
"Avanafil is a selective PDE5 inhibitors, that is rapidly absorbed and that has a short time to peak response. "( Avanafil for the treatment of erectile dysfunction. An updated review.
Carballido-Rodríguez, J; Egui-Rojo, MA; Martínez-Salamanca, JI; Moncada-Iribarren, I, 2014)		3.29
"Avanafil is a selective phosphodiesterase type 5 inhibitor being developed for the treatment of erectile dysfunction."( Tolerability and pharmacokinetics of avanafil, a phosphodiesterase type 5 inhibitor: a single- and multiple-dose, double-blind, randomized, placebo-controlled, dose-escalation study in healthy Korean male volunteers.
Bae, KS; Cho, SH; Choi, S; Ghim, JL; Hwang, A; Jung, J; Kim, BS; Kim, U; Koguchi, A; Lim, HS; Miyoshi, S; Okabe, H, 2010)		2.08
"Avanafil is a promising medication for ED due to its favorable pharmacokinetics, safety, and efficacy."( Future prospects in the treatment of erectile dysfunction: focus on avanafil.
Al-Mannie, R; Alwaal, A; Carrier, S, 2011)		1.33
"Avanafil is a novel PDE5 inhibitor with favorable pharmacokinetic and pharmacodynamic profiles with good tolerability and limited adverse events."( Avanafil for the treatment of erectile dysfunction.
Burnett, AL; Segal, R, 2012)		2.54
"• Avanafil is an effective and well-tolerated therapy for ED of broad-spectrum aetiology and severity."( Efficacy and safety of avanafil for treating erectile dysfunction: results of a multicentre, randomized, double-blind, placebo-controlled trial.
Ahn, TY; Chung, WS; Hyun, JS; Kim, JJ; Kim, SW; Lee, SW; Min, KS; Moon, KH; Paick, JS; Park, JK; Park, K; Park, NC; Suh, JK; Yang, DY; Zhao, C, 2012)		1.41
"Avanafil is a medication that was recently approved by the US Food and Drug Administration for the management of erectile dysfunction. "( Avanafil for treatment of erectile dysfunction: review of its potential.
Burke, RM; Evans, JD, 2012)		3.26

Effects

ExcerptReferenceRelevance
"Avanafil has a favorable phosphodiesterase-5 selectivity profile compared to that of marketed phosphodiesterase-5 inhibitors. "( Avanafil, a potent and highly selective phosphodiesterase-5 inhibitor for erectile dysfunction.
Fujishige, K; Inoue, H; Kikkawa, K; Kobayashi, T; Kojima, K; Kotera, J; Mochida, H; Noto, T; Omori, K; Sasaki, T; Yamada, Y; Yee, S, 2012)		3.26

Treatment

ExcerptReferenceRelevance
"Avanafil treatment was generally well tolerated; facial flushing (7-15%) was the most commonly observed AE, and no visual disturbances were reported."( A phase II, single-blind, randomized, crossover evaluation of the safety and efficacy of avanafil using visual sexual stimulation in patients with mild to moderate erectile dysfunction.
DiDonato, K; Freier, MT; Hellstrom, WJ; Lewis, RW; Peterson, CA; Serefoglu, EC, 2013)		1.33

Toxicity

Avanafil, from 50 to 200 mg, is effective and well tolerated for the treatment of ED. An increase in dosage is associated with a significant rise in effectiveness but not with significantly more adverse events.

ExcerptReferenceRelevance
" The most commonly reported adverse events in subjects taking avanafil included headache, flushing, and nasal congestion; there were no drug-related serious adverse events."( A randomized, double-blind, placebo-controlled evaluation of the safety and efficacy of avanafil in subjects with erectile dysfunction.
Bowden, CH; Day, WW; Didonato, K; Goldstein, I; Hellstrom, WJ; Jones, LA; McCullough, AR; Trask, B, 2012)		0.84
" Preclinical and clinical phase I studies showed that avanafil had enhanced selectivity, faster onset of action and a favourable side-effect profile relative to currently available PDE5 inhibitors."( Efficacy and safety of avanafil for treating erectile dysfunction: results of a multicentre, randomized, double-blind, placebo-controlled trial.
Ahn, TY; Chung, WS; Hyun, JS; Kim, JJ; Kim, SW; Lee, SW; Min, KS; Moon, KH; Paick, JS; Park, JK; Park, K; Park, NC; Suh, JK; Yang, DY; Zhao, C, 2012)		0.94
" • Flushing was the most common treatment-related adverse event."( Efficacy and safety of avanafil for treating erectile dysfunction: results of a multicentre, randomized, double-blind, placebo-controlled trial.
Ahn, TY; Chung, WS; Hyun, JS; Kim, JJ; Kim, SW; Lee, SW; Min, KS; Moon, KH; Paick, JS; Park, JK; Park, K; Park, NC; Suh, JK; Yang, DY; Zhao, C, 2012)		0.69
"A low incidence of some PDE-related adverse events may be reflected by the high selectivity of avanafil against non-PDE5 isozymes."( Selectivity of avanafil, a PDE5 inhibitor for the treatment of erectile dysfunction: implications for clinical safety and improved tolerability.
Burnett, AL; Day, WW; DiDonato, K; Heller, WH; Kikkawa, K; Kotera, J; Omori, K; Peterson, CA; Wang, R; Yee, S, 2012)		0.95
" Lower selectivity against PDE1, PDE6, and PDE11 is consistent with results from randomized, placebo-controlled, phase 3 trials in which musculoskeletal and hemodynamic adverse events were reported in <2% of patients and no color vision-related abnormalities were reported with avanafil doses up to 200 mg once daily."( Selectivity of avanafil, a PDE5 inhibitor for the treatment of erectile dysfunction: implications for clinical safety and improved tolerability.
Burnett, AL; Day, WW; DiDonato, K; Heller, WH; Kikkawa, K; Kotera, J; Omori, K; Peterson, CA; Wang, R; Yee, S, 2012)		0.91
"Data suggest that avanafil may confer a safety benefit, in terms of a lower incidence of specific adverse events, by virtue of its high specificity to PDE5 and its overall selectivity against other PDE isozymes."( Selectivity of avanafil, a PDE5 inhibitor for the treatment of erectile dysfunction: implications for clinical safety and improved tolerability.
Burnett, AL; Day, WW; DiDonato, K; Heller, WH; Kikkawa, K; Kotera, J; Omori, K; Peterson, CA; Wang, R; Yee, S, 2012)		1.07
" Safety assessments included adverse events (AEs), vital sign changes in response to dosing, laboratory results (complete blood counts, chemistry panel, prostate-specific antigen, serum testosterone, prothrombin time and urine analysis) and physical examination findings."( A phase II, single-blind, randomized, crossover evaluation of the safety and efficacy of avanafil using visual sexual stimulation in patients with mild to moderate erectile dysfunction.
DiDonato, K; Freier, MT; Hellstrom, WJ; Lewis, RW; Peterson, CA; Serefoglu, EC, 2013)		0.61
" No serious adverse events were reported and fewer than 2% of patients discontinued the study due to an adverse event."( A phase 3, placebo controlled study of the safety and efficacy of avanafil for the treatment of erectile dysfunction after nerve sparing radical prostatectomy.
Bowden, CH; Burnett, AL; Day, WW; DiDonato, K; McVary, KT; Moul, JW; Mulhall, JP; Shih, W; Wang, R, 2013)		0.63
" The most common (≥ 2%) treatment-emergent adverse events were headache, flushing, nasopharyngitis and nasal congestion; < 3% of patients discontinued therapy because of adverse events."( An open-label, long-term evaluation of the safety, efficacy and tolerability of avanafil in male patients with mild to severe erectile dysfunction.
Belkoff, LH; Bowden, CH; Day, WW; DiDonato, K; Goldstein, I; Jones, L; McCullough, A; Trask, B, 2013)		0.62
" International Index of Erectile Function-Erectile Function domain score (IIEF-EF), Sexual Encounter Profile Question (SEP) questions 2 and 3, and adverse events were considered as the study outcomes."( The effectiveness and safety of avanafil for erectile dysfunction: a systematic review and meta-analysis.
Hu, D; Hu, X; Liu, J; Tao, K; Wang, H; Yuan, J, 2014)		0.69
"Avanafil, from 50 to 200 mg, is effective and well tolerated for the treatment of ED, and an increase in dosage is associated with a significant rise in effectiveness but not with significantly more adverse events."( The effectiveness and safety of avanafil for erectile dysfunction: a systematic review and meta-analysis.
Hu, D; Hu, X; Liu, J; Tao, K; Wang, H; Yuan, J, 2014)		2.13
" Specific adverse events with PDE5 inhibitors included headache (12."( Efficacy and safety of phosphodiesterase type 5 (PDE5) inhibitors in treating erectile dysfunction after bilateral nerve-sparing radical prostatectomy.
Cui, Y; Gao, Z; Liu, X; Shi, L, 2016)		0.43
" Most treatment-associated adverse events were mild and resolved spontaneously."( A Randomized, Placebo-Controlled, Double-Blind, Multi-Center Therapeutic Confirmatory Study to Evaluate the Safety and Efficacy of Avanafil in Korean Patients with Erectile Dysfunction.
Ahn, TY; Kim, JJ; Kim, SW; Lee, SW; Paick, JS; Park, HJ; Park, JK; Park, K; Park, NC, 2017)		0.66
" Adverse events in the Avanafil group occurred in four (5%) patients and in 16 (20%) patients in the Sildenafil group."( Efficacy and safety of avanafil 200 mg versus sildenafil 100 mg in the treatment of erectile dysfunction after robot-assisted unilateral nerve-sparing prostatectomy: A prospective multicentre study.
Altieri, VM; Chini, T; Cito, G; Della Camera, PA; Gacci, M; Maggi, M; Natali, A; Nunzio, C; Rastrelli, G; Serni, S; Tellini, R, 2020)		1.18
" Both avanafil and sildenafil were well tolerated by all the patients in the study; the most common adverse event reported during the study was headache in both the groups."( Efficacy and safety of avanafil as compared with sildenafil in the treatment of erectile dysfunction: A randomized, double blind, multicenter clinical trial.
Goyal, S; Gupta, SV; Kumar, M; Mittal, R; Pathade, AD; Rath, D; Sanmukhani, J; Thakre, M, 2022)		1.51

Pharmacokinetics

Avanafil was generally well tolerated and had linear pharmacokinetic properties at daily doses of 50 to 200 mg over 7 days in these healthy Korean male volunteers.

ExcerptReferenceRelevance
" To this end, tolerability and pharmacokinetic properties of single and multiple oral doses of avanafil in healthy Korean male volunteers were assessed."( Tolerability and pharmacokinetics of avanafil, a phosphodiesterase type 5 inhibitor: a single- and multiple-dose, double-blind, randomized, placebo-controlled, dose-escalation study in healthy Korean male volunteers.
Bae, KS; Cho, SH; Choi, S; Ghim, JL; Hwang, A; Jung, J; Kim, BS; Kim, U; Koguchi, A; Lim, HS; Miyoshi, S; Okabe, H, 2010)		0.85
" Pharmacokinetic parameters of avanafil on days 1 and 7 were determined by noncompartmental analysis and compared among the 3 dose groups."( Tolerability and pharmacokinetics of avanafil, a phosphodiesterase type 5 inhibitor: a single- and multiple-dose, double-blind, randomized, placebo-controlled, dose-escalation study in healthy Korean male volunteers.
Bae, KS; Cho, SH; Choi, S; Ghim, JL; Hwang, A; Jung, J; Kim, BS; Kim, U; Koguchi, A; Lim, HS; Miyoshi, S; Okabe, H, 2010)		0.92
"Avanafil was generally well tolerated and had linear pharmacokinetic properties at daily doses of 50 to 200 mg over 7 days in these healthy Korean male volunteers."( Tolerability and pharmacokinetics of avanafil, a phosphodiesterase type 5 inhibitor: a single- and multiple-dose, double-blind, randomized, placebo-controlled, dose-escalation study in healthy Korean male volunteers.
Bae, KS; Cho, SH; Choi, S; Ghim, JL; Hwang, A; Jung, J; Kim, BS; Kim, U; Koguchi, A; Lim, HS; Miyoshi, S; Okabe, H, 2010)		2.08

Compound-Compound Interactions

ExcerptReferenceRelevance
"The main objective of this study was to evaluate the effects of a micronutrient supplementation (MS) combined with avanafil on sperm function."( Effects of a micronutrient supplementation combined with a phosphodiesterase type 5 inhibitor on sperm quantitative and qualitative parameters, percentage of mature spermatozoa and sperm capacity to undergo hyperactivation: A randomised controlled trial.
Dimitriadis, F; Hikita, K; Honda, M; Koukos, S; Sofikitis, N; Takenaka, A; Tsounapi, P; Zachariou, A, 2018)		0.69

Bioavailability

The objective of this work was to improve the solubility and oral bioavailability of Avanafil (AVA), a recently approved second generation type 5 phospodiesterase inhibitor used for erectile dysfunction.

ExcerptReferenceRelevance
" The objective of this work was to improve the solubility and oral bioavailability of Avanafil (AVA), a recently approved second generation type 5 phospodiesterase inhibitor used for erectile dysfunction."( Development and evaluation of avanafil self-nanoemulsifying drug delivery system with rapid onset of action and enhanced bioavailability.
Ahmed, OA; Fahmy, UA; Hosny, KM, 2015)		0.93
" The formula had a relative bioavailability of 125."( Effect of different polymers on avanafil-β-cyclodextrin inclusion complex: in vitro and in vivo evaluation.
Ghorab, MM; Ibrahim, HK; Soliman, KA, 2016)		0.72
"2-fold increase in bioavailability in rabbits, as compared to conventional commercially available avanafil tablets (Spedra(®))."( Formulation of avanafil in a solid self-nanoemulsifying drug delivery system for enhanced oral delivery.
Ghorab, MM; Ibrahim, HK; Soliman, KA, 2016)		1
" The oral bioavailability of the drug is challenged by its reduced water solubility, considerable presystemic metabolism, and altered absorption in the presence of food."( Development of an optimized avanafil-loaded invasomal transdermal film: Ex vivo skin permeation and in vivo evaluation.
Ahmed, OAA; Badr-Eldin, SM, 2019)		0.81
" The drug has poor oral bioavailability and undergoes a significant first-pass metabolism."( Incorporating sodium deoxycholate endorsed the buccal administration of avanafil to heighten the bioavailability and duration of action.
Abd-Allah, FI; Ahmed, TA; Al-Hejaili, OD; Alhakamy, NA; El-Sawy, HS; El-Say, KM; Safo, MK, 2023)		1.14

Dosage Studied

Avanafil, from 50 to 200 mg, is effective and well tolerated for the treatment of ED. An increase in dosage is associated with a significant rise in effectiveness but not with significantly more adverse events.

ExcerptRelevanceReference
" Successful intercourse was observed as early as 15 minutes and >6 hours after dosing in some subjects."( A randomized, double-blind, placebo-controlled evaluation of the safety and efficacy of avanafil in subjects with erectile dysfunction.
Bowden, CH; Day, WW; Didonato, K; Goldstein, I; Hellstrom, WJ; Jones, LA; McCullough, AR; Trask, B, 2012)		0.6
" The medication was studied with on-demand dosing that may occur after food and/or alcohol."( Avanafil for treatment of erectile dysfunction: review of its potential.
Burke, RM; Evans, JD, 2012)		1.82
" Following dosing with avanafil 36."( A phase 3, placebo controlled study of the safety and efficacy of avanafil for the treatment of erectile dysfunction after nerve sparing radical prostatectomy.
Bowden, CH; Burnett, AL; Day, WW; DiDonato, K; McVary, KT; Moul, JW; Mulhall, JP; Shih, W; Wang, R, 2013)		0.94
" Dosage adjustments are not warranted based on renal function, hepatic function, age or gender."( Avanafil for erectile dysfunction.
Brown, DA; Hill, JK; Kyle, JA, 2013)		1.83
"22), with an evident dose-response relationship."( The effectiveness and safety of avanafil for erectile dysfunction: a systematic review and meta-analysis.
Hu, D; Hu, X; Liu, J; Tao, K; Wang, H; Yuan, J, 2014)		0.69
"Avanafil, from 50 to 200 mg, is effective and well tolerated for the treatment of ED, and an increase in dosage is associated with a significant rise in effectiveness but not with significantly more adverse events."( The effectiveness and safety of avanafil for erectile dysfunction: a systematic review and meta-analysis.
Hu, D; Hu, X; Liu, J; Tao, K; Wang, H; Yuan, J, 2014)		2.13
"We examined the therapeutic effects of avanafil 15 minutes after dosing in men with mild to severe erectile dysfunction."( Efficacy of Avanafil 15 Minutes after Dosing in Men with Erectile Dysfunction: A Randomized, Double-Blind, Placebo Controlled Study.
Belkoff, LH; Bowden, CH; Day, WW; Goldstein, I; Hellstrom, WJ; Kaminetsky, J; Peterson, CA; Tursi, JP; Uy, J, 2015)		1.07
" The primary efficacy variable was the per subject proportion of sexual attempts during the treatment period in which subjects achieved erection sufficient for vaginal penetration within approximately 15 minutes after dosing as measured by a stopwatch."( Efficacy of Avanafil 15 Minutes after Dosing in Men with Erectile Dysfunction: A Randomized, Double-Blind, Placebo Controlled Study.
Belkoff, LH; Bowden, CH; Day, WW; Goldstein, I; Hellstrom, WJ; Kaminetsky, J; Peterson, CA; Tursi, JP; Uy, J, 2015)		0.8
"Significantly greater mean per subject percentages of successful intercourse attempts within approximately 15 minutes after dosing were observed for avanafil 100 mg (mean 25."( Efficacy of Avanafil 15 Minutes after Dosing in Men with Erectile Dysfunction: A Randomized, Double-Blind, Placebo Controlled Study.
Belkoff, LH; Bowden, CH; Day, WW; Goldstein, I; Hellstrom, WJ; Kaminetsky, J; Peterson, CA; Tursi, JP; Uy, J, 2015)		1
"Avanafil was efficacious within approximately 15 minutes of dosing compared to placebo."( Efficacy of Avanafil 15 Minutes after Dosing in Men with Erectile Dysfunction: A Randomized, Double-Blind, Placebo Controlled Study.
Belkoff, LH; Bowden, CH; Day, WW; Goldstein, I; Hellstrom, WJ; Kaminetsky, J; Peterson, CA; Tursi, JP; Uy, J, 2015)		2.24
"A rapid, smart and sensitive first derivative spectrofluorimetric method has been carried out for the simultaneous estimation of avanafil and tadalafil either in their pure form, tablet dosage form or spiked human plasma."( D-optimal design as a useful tool response surface methodology for the optimization of signals from synchronous fluorescence prior to simultaneous determination of avanafil and tadalafil.
Abdel-Raoof, AM; Abdelzaher, AM; El-Desouky, EA; Emara, MS; Hasan, MA; Osman, AE; Said, RAM, 2020)		0.96
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
EC 3.1.4.* (phosphoric diester hydrolase) inhibitorAn EC 3.1.* (ester hydrolase) inhibitor that interferes with the action of a phosphoric diester hydrolase (EC 3.1.4.*).
vasodilator agentA drug used to cause dilation of the blood vessels.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (5)

ClassDescription
pyrimidinesAny compound having a pyrimidine as part of its structure.
aromatic amideAn amide in which the amide linkage is bonded directly to an aromatic system.
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
prolinolsThe class of all compounds which contain a prolinol skeleton.
monocarboxylic acid amideA carboxamide derived from a monocarboxylic acid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency39.81070.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)IC50 (µMol)15.10000.00001.18439.6140AID1720819
cGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)Ki0.00500.00071.07978.5000AID1421850
cGMP-specific 3',5'-cyclic phosphodiesteraseCanis lupus familiaris (dog)IC50 (µMol)0.00520.00101.47198.0600AID1173626
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
positive regulation of cardiac muscle hypertrophycGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
regulation of nitric oxide mediated signal transductioncGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
T cell proliferationcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
negative regulation of T cell proliferationcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cGMP catabolic processcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
oocyte developmentcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
negative regulation of cardiac muscle contractioncGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
relaxation of cardiac musclecGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
positive regulation of oocyte developmentcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cAMP-mediated signalingcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
3',5'-cyclic-nucleotide phosphodiesterase activitycGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
protein bindingcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cGMP bindingcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
metal ion bindingcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
cellular_componentcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cytosolcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID1669363Inhibition of human PDE5A1 M816A mutant expressed in Escherichia coli strain BL21 star (DE3) at 25 uM incubated for up to 60 mins in presence of cGMP by colorimetric assay relative to control2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Structure of Human Phosphodiesterase 5A1 Complexed with Avanafil Reveals Molecular Basis of Isoform Selectivity and Guidelines for Targeting α-Helix Backbone Oxygen by Halogen Bonding.
AID1173628Induction of relaxant effect in rabbit corpus cavernosum after 30 mins2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1173631Selectivity for PDE5 (unknown origin) over PDE1 (unknown origin)2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1173632Selectivity for PDE5 (unknown origin) over PDE2 (unknown origin)2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1669369Inhibition of human PDE5A1 A779V/A783L mutant expressed in Escherichia coli strain BL21 star (DE3) at 25 uM incubated for up to 60 mins in presence of cGMP by colorimetric assay relative to control2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Structure of Human Phosphodiesterase 5A1 Complexed with Avanafil Reveals Molecular Basis of Isoform Selectivity and Guidelines for Targeting α-Helix Backbone Oxygen by Halogen Bonding.
AID1173629Selectivity for PDE5 (unknown origin) over PDE6 (unknown origin)2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1669367Inhibition of human PDE5A1 A783V mutant expressed in Escherichia coli strain BL21 star (DE3) at 25 uM incubated for up to 60 mins in presence of cGMP by colorimetric assay relative to control2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Structure of Human Phosphodiesterase 5A1 Complexed with Avanafil Reveals Molecular Basis of Isoform Selectivity and Guidelines for Targeting α-Helix Backbone Oxygen by Halogen Bonding.
AID1173635Selectivity for PDE5 (unknown origin) over PDE7 (unknown origin)2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1421851Selectivity ratio of Ki for PDE6 (unknown origin) to Ki for PDE5 (unknown origin)2018European journal of medicinal chemistry, Oct-05, Volume: 158Discovery of furyl/thienyl β-carboline derivatives as potent and selective PDE5 inhibitors with excellent vasorelaxant effect.
AID1669368Inhibition of human PDE5A1 A783L mutant expressed in Escherichia coli strain BL21 star (DE3) at 25 uM incubated for up to 60 mins in presence of cGMP by colorimetric assay relative to control2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Structure of Human Phosphodiesterase 5A1 Complexed with Avanafil Reveals Molecular Basis of Isoform Selectivity and Guidelines for Targeting α-Helix Backbone Oxygen by Halogen Bonding.
AID1173638Selectivity for PDE5 (unknown origin) over PDE10 (unknown origin)2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1720819Inhibition of PDE5 (unknown origin)2020Bioorganic & medicinal chemistry letters, 08-15, Volume: 30, Issue:16
Design and synthesis of pyrazolo[3,4-d]pyrimidinone derivatives: Discovery of selective phosphodiesterase-5 inhibitors.
AID1669362Inhibition of human PDE5A1 A783Y mutant expressed in Escherichia coli strain BL21 star (DE3) at 25 uM incubated for up to 60 mins in presence of cGMP by colorimetric assay relative to control2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Structure of Human Phosphodiesterase 5A1 Complexed with Avanafil Reveals Molecular Basis of Isoform Selectivity and Guidelines for Targeting α-Helix Backbone Oxygen by Halogen Bonding.
AID1421850Inhibition of PDE5 (unknown origin)2018European journal of medicinal chemistry, Oct-05, Volume: 158Discovery of furyl/thienyl β-carboline derivatives as potent and selective PDE5 inhibitors with excellent vasorelaxant effect.
AID1669360Inhibition of C-terminal 6x-His-tagged human PDE5A1 catalytic core (535 to 862 residues) expressed in Escherichia coli strain BL21 star (DE3) at 25 uM incubated for up to 60 mins in presence of cGMP by colorimetric assay relative to control2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Structure of Human Phosphodiesterase 5A1 Complexed with Avanafil Reveals Molecular Basis of Isoform Selectivity and Guidelines for Targeting α-Helix Backbone Oxygen by Halogen Bonding.
AID1173633Selectivity for PDE5 (unknown origin) over PDE3 (unknown origin)2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1173626Inhibition of dog lungs PDE5 using [3H]cGMP as substrate after 30 mins by scintillation counting analysis2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1173627Selectivity for dog lungs PDE5 over light-activated bovine retina PDE62014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1669366Inhibition of human PDE5A1 I824F mutant expressed in Escherichia coli strain BL21 star (DE3) at 25 uM incubated for up to 60 mins in presence of cGMP by colorimetric assay relative to control2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Structure of Human Phosphodiesterase 5A1 Complexed with Avanafil Reveals Molecular Basis of Isoform Selectivity and Guidelines for Targeting α-Helix Backbone Oxygen by Halogen Bonding.
AID1173630Selectivity for PDE5 (unknown origin) over PDE11 (unknown origin)2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1173634Selectivity for PDE5 (unknown origin) over PDE4 (unknown origin)2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1669364Inhibition of human PDE5A1 F820W mutant expressed in Escherichia coli strain BL21 star (DE3) at 25 uM incubated for up to 60 mins in presence of cGMP by colorimetric assay relative to control2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Structure of Human Phosphodiesterase 5A1 Complexed with Avanafil Reveals Molecular Basis of Isoform Selectivity and Guidelines for Targeting α-Helix Backbone Oxygen by Halogen Bonding.
AID1173636Selectivity for PDE5 (unknown origin) over PDE8 (unknown origin)2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1173637Selectivity for PDE5 (unknown origin) over PDE9 (unknown origin)2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.
AID1669365Inhibition of human PDE5A1 F787Y mutant expressed in Escherichia coli strain BL21 star (DE3) at 25 uM incubated for up to 60 mins in presence of cGMP by colorimetric assay relative to control2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Structure of Human Phosphodiesterase 5A1 Complexed with Avanafil Reveals Molecular Basis of Isoform Selectivity and Guidelines for Targeting α-Helix Backbone Oxygen by Halogen Bonding.
AID1669361Inhibition of human PDE5A1 A767H mutant expressed in Escherichia coli strain BL21 star (DE3) at 25 uM incubated for up to 60 mins in presence of cGMP by colorimetric assay relative to control2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Structure of Human Phosphodiesterase 5A1 Complexed with Avanafil Reveals Molecular Basis of Isoform Selectivity and Guidelines for Targeting α-Helix Backbone Oxygen by Halogen Bonding.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (65)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's52 (80.00)24.3611
2020's13 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 46.28

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index46.28 (24.57)
Research Supply Index4.42 (2.92)
Research Growth Index6.56 (4.65)
Search Engine Demand Index127.00 (26.88)
Search Engine Supply Index3.79 (0.95)

This Compound (46.28)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials14 (20.59%)5.53%
Reviews15 (22.06%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other39 (57.35%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		2.08106-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
carbamates
[no description available]		2.0810amino-acid anion
thioctic acid
Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.		3.811dithiolanes;
heterocyclic fatty acid;
thia fatty acid		fundamental metabolite;
geroprotector
tazarotene
tazarotene: a topical acetylenic retinoid; a topical kerytolytic. tazarotene : The ethyl ester of tazarotenic acid. A prodrug for tazarotenic acid, it is used for the treatment of psoriasis, acne, and sun-damaged skin.		2.0810acetylenic compound;
ethyl ester;
pyridines;
retinoid;
thiochromane		keratolytic drug;
prodrug;
teratogenic agent
thalidomide
Thalidomide: A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppressive and anti-angiogenic activity. It inhibits release of TUMOR NECROSIS FACTOR-ALPHA from monocytes, and modulates other cytokine action.. thalidomide : A racemate comprising equimolar amounts of R- and S-thalidomide.. 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione : A dicarboximide that is isoindole-1,3(2H)-dione in which the hydrogen attached to the nitrogen is substituted by a 2,6-dioxopiperidin-3-yl group.		2.1110phthalimides;
piperidones
prednisone
Prednisone: A synthetic anti-inflammatory glucocorticoid derived from CORTISONE. It is biologically inert and converted to PREDNISOLONE in the liver.. prednisone : A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.		2.081011-oxo steroid;
17alpha-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(1),Delta(4)-steroid;
C21-steroid;
glucocorticoid;
primary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone		adrenergic agent;
anti-inflammatory drug;
antineoplastic agent;
immunosuppressive agent;
prodrug
carbostyril
Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.		2.0810monohydroxyquinoline;
quinolone		bacterial xenobiotic metabolite
n-vinyl-2-pyrrolidinone
N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source		2.610pyrrolidin-2-ones
quinoxalines
quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.		2.1710mancude organic heterobicyclic parent;
naphthyridine;
ortho-fused heteroarene
quinuclidines
Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.		2.5220quinuclidines;
saturated organic heterobicyclic parent
thiazoles
[no description available]		2.08101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
medroxyprogesterone
[no description available]		2.151017alpha-hydroxy steroid;
20-oxo steroid;
3-oxo-Delta(4) steroid;
tertiary alpha-hydroxy ketone		contraceptive drug;
progestin;
synthetic oral contraceptive
deoxycytidine
[no description available]		2.0810pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
mifepristone
Mifepristone: A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME.		2.08103-oxo-Delta(4) steroid;
acetylenic compound;
tertiary amino compound		abortifacient;
contraceptive drug;
hormone antagonist;
synthetic oral contraceptive
emtricitabine
Emtricitabine: A deoxycytidine analog and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B viruses. It is used to treat HIV INFECTIONS.. emtricitabine : An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection.		2.0810monothioacetal;
nucleoside analogue;
organofluorine compound;
pyrimidone		antiviral drug;
HIV-1 reverse transcriptase inhibitor
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.5220D-glucopyranoseepitope;
mouse metabolite
dapoxetine
[no description available]		7.2510naphthalenes
tadalafil
[no description available]		5.09120benzodioxoles;
pyrazinopyridoindole		EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor;
vasodilator agent
bazedoxifene
[no description available]		2.5220phenylindole
perlolyrine
perlolyrine: structure given in first source		2.1710organic molecular entitymetabolite
organophosphonates
hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.		2.0810divalent inorganic anion;
phosphite ion
eslicarbazepine acetate
eslicarbazepine acetate : The acetate ester, with S configuration, of licarbazepine. An anticonvulsant, it is approved for use in Europe and the United States as an adjunctive therapy for epilepsy.		2.1110acetate ester;
carboxamide;
dibenzoazepine;
ureas		anticonvulsant;
drug allergen
deoxycholic acid
Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.		2.610bile acid;
C24-steroid;
dihydroxy-5beta-cholanic acid		human blood serum metabolite
betadex
beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.		2.1310cyclodextrin
tenofovir
tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.		2.0810nucleoside analogue;
phosphonic acids		antiviral drug;
drug metabolite;
HIV-1 reverse transcriptase inhibitor
toremifene
Toremifene: A first generation selective estrogen receptor modulator (SERM). Like TAMOXIFEN, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue.		2.1510aromatic ether;
organochlorine compound;
tertiary amine		antineoplastic agent;
bone density conservation agent;
estrogen antagonist;
estrogen receptor modulator
jtk-303
[no description available]		2.0810aromatic ether;
monochlorobenzenes;
organofluorine compound;
quinolinemonocarboxylic acid;
quinolone		HIV-1 integrase inhibitor
mirabegron
mirabegron: a beta3-adrenergic receptor agonist; structure in first source. mirabegron : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2-amino-1,3-thiazol-4-ylacetic acid with the anilino group of (1R)-2-{[2-(4-aminophenyl)ethyl]amino}-1-phenylethanol. Used for the treatment of overactive bladder syndrome.		2.08101,3-thiazoles;
aromatic amide;
ethanolamines;
monocarboxylic acid amide		beta-adrenergic agonist
dapagliflozin
[no description available]		2.1110aromatic ether;
C-glycosyl compound;
monochlorobenzenes		hypoglycemic agent;
sodium-glucose transport protein subtype 2 inhibitor
perampanel
perampanel : A member of the class of bipyridines that is 2,3'-bipyridin-6'-one substituted at positions 1' and 5' by phenyl and 2-cyanophenyl groups respectively. Used as an adjunctive therapy for the treatment of partial-onset seizures in patients with epilepsy.		2.1110bipyridines;
nitrile;
pyridone		AMPA receptor antagonist;
anticonvulsant
vortioxetine
Vortioxetine: A piperazine derivative that acts as a serotonin reuptake inhibitor, as a 5-HT3 receptor antagonist, and 5-HT1A receptor agonist. It is used for the treatment of anxiety and depression.. vortioxetine : An N-arylpiperazine in which the aryl group is specified as 2-[(2,4-dimethylphenyl)sulfanyl]phenyl. Used (as its hydrobromide salt) for treatment of major depressive disorder.		2.1110aryl sulfide;
N-arylpiperazine		antidepressant;
anxiolytic drug;
serotonergic agonist;
serotonergic antagonist
vilanterol
[no description available]		2.1110benzyl alcohols;
dichlorobenzene;
ether;
phenols;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent
gsk573719
GSK573719: Muscarinic Antagonist. umeclidinium : A quaternary ammonium ion that is quinuclidine substituted at positions 1 and 4 by 2-(benzyloxy)ethyl and hydroxy(diphenyl)methyl groups respectively.		2.5220
apremilast
[no description available]		2.1110aromatic ether;
N-acetylarylamine;
phthalimides;
sulfone		non-steroidal anti-inflammatory drug;
phosphodiesterase IV inhibitor
lorcaserin
lorcaserin: orally active, small-molecule 5-hydroxytryptamine 2C agonist for the potential treatment of obesity and diabetes. lorcaserin : A benzazepine that is 2,3,4,5-tetrahydro-3-benzazepine substituted at position 1 by a methyl group and a t position 6 by a chloro group.		2.0810benzazepine;
organochlorine compound		anti-obesity agent;
appetite depressant
empagliflozin
[no description available]		2.1110aromatic ether;
C-glycosyl compound;
monochlorobenzenes;
tetrahydrofuryl ether		hypoglycemic agent;
sodium-glucose transport protein subtype 2 inhibitor
glucagon-like peptide 1
Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.		2.1110
cobicistat
[no description available]		2.08101,3-thiazoles;
carbamate ester;
monocarboxylic acid amide;
morpholines;
ureas		P450 inhibitor
quad pill
Elvitegravir, Cobicistat, Emtricitabine, Tenofovir Disoproxil Fumarate Drug Combination: A pharmaceutical preparation of the ANTI-HIV AGENTS elvitegravir, cobicistat, emtricitabine, and tenofovir disoproxil fumarate that is used in the treatment of HIV INFECTIONS.		2.0810
cyclic gmp
Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.		2.11103',5'-cyclic purine nucleotide;
guanyl ribonucleotide		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
sildenafil
sildenafil : A pyrazolo[4,3-d]pyrimidin-7-one having a methyl substituent at the 1-position, a propyl substituent at the 3-position and a 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl group at the 5-position.		2.8530piperazines;
pyrazolopyrimidine;
sulfonamide		EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor;
vasodilator agent
zaprinast
zaprinast: anaphylaxis inhibitor; structure		2.6620triazolopyrimidines
vardenafil
vardenafil : The sulfonamide resulting from formal condensation of the sulfo group of 4-ethoxy-3-(5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one-2-yl)benzenesulfonic acid and the secondary amino group of 4-ethylpiperazine.		2.5320imidazotriazine;
N-alkylpiperazine;
N-sulfonylpiperazine		EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
vasodilator agent
sildenafil citrate
Sildenafil Citrate: A PHOSPHODIESTERASE TYPE-5 INHIBITOR; VASODILATOR AGENT and UROLOGICAL AGENT that is used in the treatment of ERECTILE DYSFUNCTION and PRIMARY PULMONARY HYPERTENSION.. sildenafil citrate : The citrate salt of sildenafil.		6.4111citrate saltEC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor;
vasodilator agent
vardenafil dihydrochloride
Vardenafil Dihydrochloride: A piperazine derivative, PHOSPHODIESTERASE 5 INHIBITOR and VASODILATOR AGENT that is used as a UROLOGICAL AGENT in the treatment of ERECTILE DYSFUNCTION.		4.5970
lucinactant
lucinactant: a pulmonary surfactant composed of sinapultide, colfosceril palmitate, palmitoyloleaoylphosphatidylglycerol, and palmitic acid		2.0810
ConditionIndicatedRelationship StrengthStudiesTrials
Impotence
[description not available]		013.763811
Erectile Dysfunction
The inability in the male to have a PENILE ERECTION due to psychological or organ dysfunction.		115.763811
Diabetes Mellitus, Adult-Onset
[description not available]		03.9721
Diabetes Mellitus, Type 2
A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.		03.9721
Lung Injury, Acute
[description not available]		02.4110
Acute Lung Injury
A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).		07.4110
Acute Confusional Senile Dementia
[description not available]		02.610
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		02.610
Complication, Postoperative
[description not available]		03.520
Cancer of Prostate
[description not available]		02.2510
Postoperative Complications
Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.		03.520
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.1710
Age-Related Osteoporosis
[description not available]		02.1710
Osteoporosis
Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.		07.1710
Sterility, Male
[description not available]		03.5611
Infertility, Male
The inability of the male to effect FERTILIZATION of an OVUM after a specified period of unprotected intercourse. Male sterility is permanent infertility.		03.5611
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		03.5611
Complications of Diabetes Mellitus
[description not available]		02.110
Alloxan Diabetes
[description not available]		02.110
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		03.0410
Adverse Drug Event
[description not available]		02.1310
Branch Vein Occlusion
[description not available]		02.1310
Branch Retinal Artery Occlusion
[description not available]		02.1310
Retinal Vein Occlusion
Blockage of the RETINAL VEIN. Those at high risk for this condition include patients with HYPERTENSION; DIABETES MELLITUS; ATHEROSCLEROSIS; and other CARDIOVASCULAR DISEASES.		02.1310
Retinal Artery Occlusion
Sudden ISCHEMIA in the RETINA due to blocked blood flow through the CENTRAL RETINAL ARTERY or its branches leading to sudden complete or partial loss of vision, respectively, in the eye.		02.1310
Drug-Related Side Effects and Adverse Reactions
Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.		02.1310
Pulmonary Hypertension
[description not available]		02.9810
Hypertension, Pulmonary
Increased VASCULAR RESISTANCE in the PULMONARY CIRCULATION, usually secondary to HEART DISEASES or LUNG DISEASES.		02.9810
Impotence, Arteriogenic
[description not available]		04.3711
Diabetes Mellitus
A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.		09.3711
Blood Pressure, Low
[description not available]		02.0810
Hypotension
Abnormally low BLOOD PRESSURE that can result in inadequate blood flow to the brain and other vital organs. Common symptom is DIZZINESS but greater negative impacts on the body occur when there is prolonged depravation of oxygen and nutrients.		02.0810