Sildenafil

Identification

Summary

Sildenafil is a phosphodiesterase inhibitor used for the treatment of erectile dysfunction.

Brand Names

Liqrev, Revatio, Viagra, Vizarsin

Generic Name

Sildenafil

DrugBank Accession Number

DB00203

Background

In eliciting its mechanism of action, sildenafil ultimately prevents or minimizes the breakdown of cyclic guanosine monophosphate (cGMP) by inhibiting cGMP specific phosphodiesterase type 5 (PDE5) ^{11,12,13,14,15,16,8,9}. The result of doing so allows cGMP present in both the penis and pulmonary vasculature to elicit smooth muscle relaxation and vasodilation that subsequently facilitates relief in pulmonary arterial hypertension and the increased flow of blood into the spongy erectile tissue of the penis that consequently allows it to grow in size and become erect and rigid ^{11,12,13,14,15,16,8,9}.

Interestingly enough, it is precisely via this mechanism why sildenafil was at first researched as a potential treatment for angina - or chest pain associated with inadequate blood flow to the heart - before being serendipitously indicated for treating erectile dysfunction in the late 1980s ⁷. Nevertheless, it is because of this mechanism that sildenafil is also indicated for treating pulmonary arterial hypertension but is also additionally notorious for interacting with various anti-anginal or anti-hypertensive agents to develop potentially rapid, excessive, and/or fatal hypotensive crises ^4,5,6.

Regardless, sildenafil, among a variety of other similar or related PDE5 inhibitors, has become a common and effective treatment for erectile dysfunction and since its formal approval for medical use in the public in 1998 ⁷, continues to see millions of prescriptions written for it internationally. Although the medication has historically been most popularly recognized as Pfizer's brand name Viagra, sildenafil is currently available generically and even as a non-prescription over the counter medication in some countries ¹⁰.

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Sildenafil (DB00203)

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Weight

Average: 474.576
Monoisotopic: 474.204924168

Chemical Formula

C₂₂H₃₀N₆O₄S

Synonyms

• 1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine
• Sildenafil
• Sildenafilo

External IDs

• HIP-0908
• HIP0908

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Pharmacology

Indication

Sildenafil is a phosphodiesterase-5 (PDE5) inhibitor that is predominantly employed for two primary indications:

(1) the treatment of erectile dysfunction ^5,8,12,13,16; and

(2) treatment of pulmonary hypertension, where: a) the US FDA specifically indicates sildenafil for the treatment of pulmonary arterial hypertension (PAH) (WHO Group I) in adults to improve exercise ability and delay clinical worsening ¹¹. The delay in clinical worsening was demonstrated when sildenafil was added to background epoprostenol therapy ¹¹. Studies establishing effectiveness were short-term (12 to 16 weeks), and included predominately patients with New York Heart Association (NYHA) Functional Class II-III symptoms and idiopathic etiology (71%) or associated with connective tissue disease (CTD) (25%) ¹¹;

b) the Canadian product monograph specifically indicates sildenafil for the treatment of primary pulmonary arterial hypertension (PPH) or pulmonary hypertension secondary to connective tissue disease (CTD) in adult patients with WHO functional class II or III who have not responded to conventional therapy ¹⁴. In addition, improvement in exercise ability and delay in clinical worsening was demonstrated in adult patients who were already stabilized on background epoprostenol therapy ¹⁴; and

c) the EMA product information specifically indicates sildenafil for the treatment of adult patients with pulmonary arterial hypertension classified as WHO functional class II and III, to improve exercise capacity ¹⁵. Efficacy has been shown in primary pulmonary hypertension and pulmonary hypertension associated with connective tissue disease ¹⁵. The EMA label also indicates sildenafil for the treatment of pediatric patients aged 1 year to 17 years old with pulmonary arterial hypertension ¹⁵. Efficacy in terms of improvement of exercise capacity or pulmonary hemodynamics has been shown in primary pulmonary hypertension and pulmonary hypertension associated with congenital heart disease ¹⁵.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to treat	Erectile dysfunction	Combination Product in combination with: Dapoxetine (DB04884)	••••••••••••			••••••
Management of	Erectile dysfunction		••••••••••••
Management of	Nyha functional class ii-iii pulmonary arterial hypertension		••••••••••••
Used in combination to treat	Premature ejaculation	Combination Product in combination with: Dapoxetine (DB04884)	••••••••••••			••••••
Treatment of	Pulmonary arterial hypertension (pah)		••••••••••••			•••••••••• ••••••••••• ••••••

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Contraindications & Blackbox Warnings

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Pharmacodynamics

In vitro studies have shown that sildenafil is selective for phosphodiesterase-5 (PDE5) ^{11,12,13,14,15,16,8,9}. Its effect is more potent on PDE5 than on other known phosphodiesterases ^{11,12,13,14,15,16,8,9}. In particular, there is a 10-times selectivity over PDE6 which is involved in the phototransduction pathway in the retina ^{11,12,13,14,15,16,8,9}. There is an 80-times selectivity over PDE1, and over 700-times over PDE 2, 3, 4, 7, 8, 9, 10 and 11 ^{11,12,13,14,15,16,8,9}. And finally, sildenafil has greater than 4,000-times selectivity for PDE5 over PDE3, the cAMP-specific phosphodiesterase isoform involved in the control of cardiac contractility ^{11,12,13,14,15,16,8,9}.

In eight double-blind, placebo-controlled crossover studies of patients with either organic or psychogenic erectile dysfunction, sexual stimulation resulted in improved erections, as assessed by an objective measurement of hardness and duration of erections (via the use of RigiScan®), after sildenafil administration compared with placebo ^{11,12,13,14,15,16,8,9}. Most studies assessed the efficacy of sildenafil approximately 60 minutes post-dose ^{11,12,13,14,15,16,8,9}. The erectile response, as assessed by RigiScan®, generally increased with increasing sildenafil dose and plasma concentration ^{11,12,13,14,15,16,8,9}. The time course of effect was examined in one study, showing an effect for up to 4 hours but the response was diminished compared to 2 hours ^{11,12,13,14,15,16,8,9}.

Sildenafil causes mild and transient decreases in systemic blood pressure which, in the majority of cases, do not translate into clinical effects ^{11,12,13,14,15,16,8,9}. After chronic dosing of 80 mg, three times a day to patients with systemic hypertension the mean change from baseline in systolic and diastolic blood pressure was a decrease of 9.4 mmHg and 9.1 mmHg respectively ^{11,12,13,14,15,16,8,9}. After chronic dosing of 80 mg, three times a day to patients with pulmonary arterial hypertension lesser effects in blood pressure reduction were observed (a reduction in both systolic and diastolic pressure of 2 mmHg)^{11,12,13,14,15,16,8,9} . At the recommended dose of 20 mg three times a day no reductions in systolic or diastolic pressure were seen ^{11,12,13,14,15,16,8,9}.

Single oral doses of sildenafil up to 100 mg in healthy volunteers produced no clinically relevant effects on ECG ^{11,12,13,14,15,16,8,9}. After chronic dosing of 80 mg three times a day to patients with pulmonary arterial hypertension no clinically relevant effects on the ECG were reported either ^{11,12,13,14,15,16,8,9}.

In a study of the hemodynamic effects of a single oral 100 mg dose of sildenafil in 14 patients with severe coronary artery disease (CAD) (> 70 % stenosis of at least one coronary artery), the mean resting systolic and diastolic blood pressures decreased by 7 % and 6 % respectively compared to baseline ^{11,12,13,14,15,16,8,9}. Mean pulmonary systolic blood pressure decreased by 9% ^{11,12,13,14,15,16,8,9}. Sildenafil showed no effect on cardiac output and did not impair blood flow through the stenosed coronary arteries ^{11,12,13,14,15,16,8,9}.

Mild and transient differences in color discrimination (blue/green) were detected in some subjects using the Farnsworth-Munsell 100 hue test at 1 hour following a 100 mg dose, with no effects evident after 2 hours post-dose ^{11,12,13,14,15,16,8,9}. The postulated mechanism for this change in color discrimination is related to inhibition of PDE6, which is involved in the phototransduction cascade of the retina ^{11,12,13,14,15,16,8,9}. Sildenafil has no effect on visual acuity or contrast sensitivity. In a small size placebo-controlled study of patients with documented early age-related macular degeneration (n = 9), sildenafil (single dose, 100 mg) demonstrated no significant changes in visual tests conducted (which included visual acuity, Amsler grid, color discrimination simulated traffic light, and the Humphrey perimeter and photostress test) ^{11,12,13,14,15,16,8,9}.

Mechanism of action

Sildenafil is an oral therapy for erectile dysfunction ^5,12,13,16,8. In the natural setting, i.e. with sexual stimulation, it restores impaired erectile function by increasing blood flow to the penis ^5,12,13,16,8.

The physiological mechanism responsible for the erection of the penis involves the release of nitric oxide (NO) in the corpus cavernosum during sexual stimulation ^5,12,13,16,8. Nitric oxide then activates the enzyme guanylate cyclase, which results in increased levels of cyclic guanosine monophosphate (cGMP), producing smooth muscle relaxation in the corpus cavernosum and allowing inflow of blood ^5,12,13,16,8.

Sildenafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) in the corpus cavernosum, where PDE5 is responsible for degradation of cGMP ^5,12,13,16,8. Sildenafil has a peripheral site of action on erections ^5,12,13,16,8. Sildenafil has no direct relaxant effect on isolated human corpus cavernosum but potently enhances the relaxant effect of NO on this tissue ^5,12,13,16,8. When the NO/cGMP pathway is activated, as occurs with sexual stimulation, inhibition of PDE5 by sildenafil results in increased corpus cavernosum levels of cGMP ^5,12,13,16,8. Therefore sexual stimulation is required in order for sildenafil to produce its intended beneficial pharmacological effects ^5,12,13,16,8.

Moreover, apart from the presence of PDE5 in the corpus cavernosum of the penis, PDE5 is also present in the pulmonary vasculature ^4,11,14,15,9. Sildenafil, therefore, increases cGMP within pulmonary vascular smooth muscle cells resulting in relaxation ^4,11,14,15,9. In patients with pulmonary arterial hypertension, this can lead to vasodilation of the pulmonary vascular bed and, to a lesser degree, vasodilatation in the systemic circulation ^4,11,14,15,9.

Target	Actions	Organism
AcGMP-specific 3',5'-cyclic phosphodiesterase	inhibitor	Humans
NRetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma	inhibitor	Humans
NRetinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma	inhibitor	Humans
UOrnithine decarboxylase	downregulator	Humans
UProgrammed cell death 1 ligand 1	downregulator	Humans

Absorption

Sildenafil is known to be quickly absorbed, with maximum plasma concentrations being observed within 30-120 minutes (with a median of 60 minutes) of oral administration in a fasting patient ^{11,12,13,14,15,16,8,9}. Moreover, the mean absolute bioavailability observed for sildenafil is about 41% (from a range of 25-63%) ^{11,12,13,14,15,16,8,9}. In particular, after oral three times a day dosing of sildenafil, the AUC and Cmax increase in proportion with dose over the recommended dosage range of 25-100 mg ^{11,12,13,14,15,16,8,9}.

When used in pulmonary arterial hypertension patients, however, the oral bioavailability of sildenafil after a dosing regimen of 80 mg three times a day, was on average 43% greater than compared to the lower doses ^{11,12,13,14,15,16,8,9}.

Finally, if sildenafil is administered orally with food, the rate of absorption is observed to be decreased with a mean delay in Tmax of about 60 minutes and a mean decrease in Cmax of approximately 29% ^{11,12,13,14,15,16,8,9}. Regardless, the extent of absorption is not observed to be significantly affected as the recorded AUC decreased by only about 11 % ^{11,12,13,14,15,16,8,9}.

Volume of distribution

The mean steady-state volume of distribution documented for sildenafil is approximately 105 L - a value which suggests the medication undergoes distribution into the tissues ^{11,12,13,14,15,16,8,9}.

Protein binding

It is generally observed that sildenafil and its main circulating N-desmethyl metabolite are both estimated to be about 96% bound to plasma proteins ^{11,12,13,14,15,16,8,9}. Nevertheless, it has been determined that protein binding for sildenafil is independent of total drug concentrations ^{11,12,13,14,15,16,8,9}.

Metabolism

The metabolism of sildenafil is facilitated primarily by the CYP3A4 hepatic microsomal isoenzymes and to a minor extent, via the CYP2C9 hepatic isoenzymes ^{6,11,12,13,14,15,16,8,9}. The predominant circulating metabolite results from the N-demethylation of sildenafil ^{6,11,12,13,14,15,16,8,9}. This particular resultant metabolite possesses a phosphodiesterase selectivity that is similar to the parent sildenafil molecule and a corresponding in vitro potency for PDE5 that is approximately 50% that of the parent drug ^{6,11,12,13,14,15,16,8,9}. Moreover, plasma concentrations of the metabolite are about 40% of those recorded for sildenafil, a percentage that accounts for about 20% of sildenafil’s pharmacologic effects ^{6,11,12,13,14,15,16,8,9}. This primary N-desmethyl metabolite of sildenafil also undergoes further metabolism, with a terminal half-life of about 4 hours ^{6,11,12,13,14,15,16,8,9}.

In patients with pulmonary arterial hypertension, plasma concentrations of the primary N-desmethyl metabolite are about 72% those of the original parent sildenafil molecule after a regimen of 20 mg three times a day - which is consequently responsible for about a 36% contribution to sildenafil’s overall pharmacological effects ^{6,11,12,13,14,15,16,8,9}.

Hover over products below to view reaction partners

• Sildenafil
  • N-Desmethyl sildenafil (UK-103,320)
  • N-Desmethyl sildenafil

Route of elimination

After either oral or intravenous administration, sildenafil is excreted as metabolites predominantly in the feces (approximately 80% of the administered oral dose) and to a lesser extent in the urine (approximately 13% of the administered oral dose) ^{11,12,13,14,15,16,8,9}.

Half-life

The terminal phase half-life observed for sildenafil is approximately 3 to 5 hours ^{11,12,13,14,15,16,8,9}.

Clearance

The total body clearance documented for sildenafil is 41 L/h ^{11,12,13,14,15,16,8,9}.

Adverse Effects

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Toxicity

In single-dose volunteer studies of doses up to 800 mg, adverse reactions were similar to those seen at lower doses, but the incidence rates and severities were increased ^{11,12,13,14,15,16,8,9}. Doses of 200 mg did not result in increased efficacy but the incidence of adverse reaction (headache, flushing, dizziness, dyspepsia, nasal congestion, altered vision) was increased ^{11,12,13,14,15,16,8,9}.

Due to the lack of data on the effect of sildenafil indicated for the treatment of pulmonary arterial hypertension (PAH) in pregnant women, sildenafil is not recommended for women of childbearing potential unless also using appropriate contraceptive measures ^11,14,15,9.

The safety and efficacy of sildenafil indicated for treating PAH in a woman during labor and delivery have not been studied ^11,14,15,9. Caution should ultimately be exercised when sildenafil is administered to nursing women as it is not known if sildenafil or its metabolites are excreted in human breast milk ^11,14,15,9.

The safety and efficacy of sildenafil for the treatment of PAH in children below 1 year of age has not been established as no data is available ¹⁵.

Clinical experience with the elderly population in the use of sildenafil for the treatment of PAH has been varied. Some reports suggest that there are no identified differences in responses between elderly and younger patients ¹¹ while others have documented that clinical efficacy as measured by 6-minute walk distance could be less in elderly patients ⁹. In general, dose selection for an elderly patient should be cautious, reflecting the greater frequency of decreased hepatic, renal, or cardiac function, and of concomitant disease or other drug therapy ¹¹.

Conversely, when sildenafil was used to treat erectile dysfunction in healthy elderly volunteers (65 years or over), a reduced clearance of sildenafil was observed ^12,8. This reduction resulted in about 90% higher plasma concentrations of sildenafil and the active N-desmethyl metabolite compared to those seen in healthy younger volunteers (18-45 years) ^12,8. Due to age-differences in plasma protein binding, the corresponding increase in free sildenafil plasma concentration was approximately 40% ^12,8.

Sildenafil was not carcinogenic when administered to rats for 24 months at a dose resulting in total systemic drug exposure (AUCs) for unbound sildenafil and its major metabolite of 29- and 42- times, for male and female rats, respectively, the exposures observed in human males given the Maximum Recommended Human Dose (MRHD) of 100 mg ^{11,12,13,14,15,16,8,9}. Sildenafil was not carcinogenic when administered to mice for 18-21 months at dosages up to the Maximum Tolerated Dose (MTD) of 10 mg/kg/day, approximately 0.6 times the MRHD on a mg/m2 basis ^{11,12,13,14,15,16,8,9}.

Sildenafil was negative in in vitro bacterial and Chinese hamster ovary cell assays to detect mutagenicity, and in vitro human lymphocytes and in vivo mouse micronucleus assays to detect clastogenicity ^{11,12,13,14,15,16,8,9}.

There was no impairment of fertility in rats given sildenafil up to 60 mg/kg/day for 36 days to females and 102 days to males, a dose producing an AUC value of more than 25 times the human male AUC ^{11,12,13,14,15,16,8,9}.

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Angiotensin-converting enzyme	---	Not Available	Alu insertions / Alu insertions  … show all	Effect Directly Studied	Patients with this genotype have increased frequency of positive erectile response when using sildenafil to treat erectile dysfunction	Details
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3	---	(T;T)	T allele, homozygote	Effect Directly Studied	Patients with this genotype have increased frequency of positive erectile response when using sildenafil to treat erectile dysfunction	Details

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abaloparatide	The risk or severity of hypotension can be increased when Sildenafil is combined with Abaloparatide.
Abametapir	The serum concentration of Sildenafil can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Sildenafil can be increased when combined with Abatacept.
Abciximab	The risk or severity of hemorrhage can be increased when Abciximab is combined with Sildenafil.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Sildenafil.

Food Interactions

• Take with or without food. If taken with a high-fat meal the medicine may take a little longer to start working.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Sildenafil citrate	BW9B0ZE037	171599-83-0	DEIYFTQMQPDXOT-UHFFFAOYSA-N

Product Images

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Act Sildenafil	Tablet	50 mg	Oral	Actavis Pharma Company	2012-11-08	2018-06-26
Act Sildenafil	Tablet	25 mg	Oral	Actavis Pharma Company	2012-11-08	2018-06-26
Act Sildenafil	Tablet	100 mg	Oral	Actavis Pharma Company	2012-11-08	2018-06-26
Granpidam	Tablet, film coated	20 mg	Oral	Accord Healthcare S.L.U.	2021-01-12	Not applicable
Granpidam	Tablet, film coated	20 mg	Oral	Accord Healthcare S.L.U.	2021-01-12	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Accel-sildenafil	Tablet	100 mg	Oral	Accel Pharma Inc	2019-08-15	Not applicable
Accel-sildenafil	Tablet	50 mg	Oral	Accel Pharma Inc	2019-08-15	Not applicable
Accel-sildenafil	Tablet	25 mg	Oral	Accel Pharma Inc	2019-08-15	Not applicable
Ag-sildenafil	Tablet	100 mg	Oral	Angita Pharma Inc.	2018-12-21	2022-11-15
Ag-sildenafil	Tablet	50 mg	Oral	Angita Pharma Inc.	2018-12-21	2022-11-15

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
DAPOKSEL 30 MG/50 MG FILM TABLET ,3 FILM TABLET	Sildenafil citrate (50 mg) + Dapoxetine hydrochloride (30 mg)	Tablet, film coated	Oral	NOBEL İLAÇ SAN. VE TİC. A.Ş.	2016-05-24	2017-11-14
DAPOKSEL 30 MG/50 MG FILM TABLET ,6 FILM TABLET	Sildenafil citrate (50 mg) + Dapoxetine hydrochloride (30 mg)	Tablet, film coated	Oral	NOBEL İLAÇ SAN. VE TİC. A.Ş.	2016-05-24	2017-11-14
DAPOXIL 30/50 MG FILM KAPLI TABLET, 3 FILM KAPLI TABLET	Sildenafil citrate (50 mg) + Dapoxetine hydrochloride (30 mg)	Tablet, coated	Oral	VİTALİS İLAÇ SAN. TİC. A.Ş.	2020-08-14	2021-02-15
DAPOXIL 30/50 MG FILM KAPLI TABLET, 6 FILM KAPLI TABLET	Sildenafil citrate (50 mg) + Dapoxetine hydrochloride (30 mg)	Tablet, coated	Oral	VİTALİS İLAÇ SAN. TİC. A.Ş.	2020-08-14	2021-02-15
DAPOXIL 30/50 MG FILM KAPLI TABLET,18 FILM KAPLI TABLET	Sildenafil citrate (50 mg) + Dapoxetine hydrochloride (30 mg)	Tablet, coated	Oral	VİTALİS İLAÇ SAN. TİC. A.Ş.	2020-08-14	2021-02-15

Categories

ATC Codes

G01AE10 — Combinations of sulfonamides

• G01AE — Sulfonamides
• G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
• G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
• G — GENITO URINARY SYSTEM AND SEX HORMONES

G04BE03 — Sildenafil

• G04BE — Drugs used in erectile dysfunction
• G04B — UROLOGICALS
• G04 — UROLOGICALS
• G — GENITO URINARY SYSTEM AND SEX HORMONES

Drug Categories

• Agents Causing Muscle Toxicity
• Amides
• Cardiovascular Agents
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 Inhibitors (weak)
• Cytochrome P-450 CYP2C19 Substrates
• Cytochrome P-450 CYP2C9 Inhibitors
• Cytochrome P-450 CYP2C9 Inhibitors (weak)
• Cytochrome P-450 CYP2C9 Substrates
• Cytochrome P-450 CYP2D6 Substrates
• Cytochrome P-450 CYP2E1 Inhibitors
• Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2E1 Substrates
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A5 Substrates
• Cytochrome P-450 CYP3A7 Substrates
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Drugs Used in Erectile Dysfunction
• Enzyme Inhibitors
• Genitourinary Agents
• Heterocyclic Compounds, Fused-Ring
• OATP1B1/SLCO1B1 Inhibitors
• P-glycoprotein inhibitors
• P-glycoprotein substrates
• Phosphodiesterase 5 Inhibitors
• Phosphodiesterase Inhibitors
• Piperazines
• Purines
• Sulfonamides
• Sulfones
• Sulfur Compounds
• Urological Agents
• Urologicals
• Vasodilating Agents

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Pyrazolopyrimidines / Benzenesulfonyl compounds / Phenoxy compounds / Phenol ethers / Pyrimidones / Alkyl aryl ethers / N-methylpiperazines / Organosulfonamides / Sulfonyls / Pyrazoles / Heteroaromatic compounds / Trialkylamines / Lactams / Azacyclic compounds / Hydrocarbon derivatives / Organic oxides / Organopnictogen compounds

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Substituents

1,4-diazinane / Alkyl aryl ether / Amine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenesulfonamide / Benzenesulfonyl group / Ether / Heteroaromatic compound / Hydrocarbon derivative / Lactam / N-alkylpiperazine / N-methylpiperazine / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organic sulfonic acid or derivatives / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Organosulfonic acid amide / Organosulfonic acid or derivatives / Organosulfur compound / Phenol ether / Phenoxy compound / Piperazine / Pyrazole / Pyrazolopyrimidine / Pyrimidine / Pyrimidone / Sulfonyl / Tertiary aliphatic amine / Tertiary amine

show 25 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide, piperazines, pyrazolopyrimidine (CHEBI:9139)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

3M7OB98Y7H

CAS number

139755-83-2

InChI Key

BNRNXUUZRGQAQC-UHFFFAOYSA-N

InChI

InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)

IUPAC Name

5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one

SMILES

CCCC1=NN(C)C2=C1N=C(NC2=O)C1=CC(=CC=C1OCC)S(=O)(=O)N1CCN(C)CC1

References

Synthesis Reference

Peter James Dunn, Albert Shaw Wood, "Process for preparing sildenafil." U.S. Patent US5955611, issued December, 1994.

US5955611

General References

1. Boolell M, Allen MJ, Ballard SA, Gepi-Attee S, Muirhead GJ, Naylor AM, Osterloh IH, Gingell C: Sildenafil: an orally active type 5 cyclic GMP-specific phosphodiesterase inhibitor for the treatment of penile erectile dysfunction. Int J Impot Res. 1996 Jun;8(2):47-52. [Article]
2. Cheitlin MD, Hutter AM Jr, Brindis RG, Ganz P, Kaul S, Russell RO Jr, Zusman RM: ACC/AHA expert consensus document. Use of sildenafil (Viagra) in patients with cardiovascular disease. American College of Cardiology/American Heart Association. J Am Coll Cardiol. 1999 Jan;33(1):273-82. [Article]
3. Fries R, Shariat K, von Wilmowsky H, Bohm M: Sildenafil in the treatment of Raynaud's phenomenon resistant to vasodilatory therapy. Circulation. 2005 Nov 8;112(19):2980-5. [Article]
4. Unegbu C, Noje C, Coulson JD, Segal JB, Romer L: Pulmonary Hypertension Therapy and a Systematic Review of Efficacy and Safety of PDE-5 Inhibitors. Pediatrics. 2017 Mar;139(3). pii: peds.2016-1450. doi: 10.1542/peds.2016-1450. [Article]
5. Gong B, Ma M, Xie W, Yang X, Huang Y, Sun T, Luo Y, Huang J: Direct comparison of tadalafil with sildenafil for the treatment of erectile dysfunction: a systematic review and meta-analysis. Int Urol Nephrol. 2017 Oct;49(10):1731-1740. doi: 10.1007/s11255-017-1644-5. Epub 2017 Jul 24. [Article]
6. Nichols DJ, Muirhead GJ, Harness JA: Pharmacokinetics of sildenafil after single oral doses in healthy male subjects: absolute bioavailability, food effects and dose proportionality. Br J Clin Pharmacol. 2002;53 Suppl 1:5S-12S. [Article]
7. Goldstein I, Burnett AL, Rosen RC, Park PW, Stecher VJ: The Serendipitous Story of Sildenafil: An Unexpected Oral Therapy for Erectile Dysfunction. Sex Med Rev. 2019 Jan;7(1):115-128. doi: 10.1016/j.sxmr.2018.06.005. Epub 2018 Oct 6. [Article]
8. Electronic Medicines Compendium: Sildenafil 25mg, 50mg, 100mg film-coated tablets Monograph [Link]
9. Electronic Medicines Compendium: Revatio (sildenafil citrate) 20 mg film-coated tablets Monograph [Link]
10. Forbes: With Viagra Now Available Over-The-Counter In The U.K., Will The U.S. Follow Suit? [Link]
11. Revatio (sildenafil) FDA Label [File]
12. Viagra (sildenafil citrate) FDA Label [File]
13. Viagra (sildenafil citrate) Tablets 25 mg, 50 mg, and 100 mg Canadian Product Monograph [File]
14. Revatio (sildenafil citrate) Canadian Product Monograph [File]
15. Revatio (sildenafil citrate) EMA Label [File]
16. Viagra (sildenafil citrate) EMA Label [File]

External Links

Human Metabolome Database

HMDB0005039

KEGG Drug

D08514

KEGG Compound

C07259

PubChem Compound

5212

PubChem Substance

46508371

ChemSpider

5023

BindingDB

50238854

RxNav

136411

ChEBI

9139

ChEMBL

CHEMBL192

ZINC

ZINC000019796168

Therapeutic Targets Database

DAP000614

PharmGKB

PA451346

PDBe Ligand

VIA

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Sildenafil

PDB Entries

1tbf / 1udt / 1xos / 2h42 / 3jwq

FDA label

Download (80.5 KB)

MSDS

Download (37.1 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Sexual impotency	1
4	Completed	Basic Science	Emphysema	1
4	Completed	Basic Science	Syndrome, Metabolic	1
4	Completed	Diagnostic	Left Ventricular Dysfunction / Pulmonary Arterial Hypertension (PAH)	1
4	Completed	Educational/Counseling/Training	Blindness	1

Pharmacoeconomics

Manufacturers

• Pfizer inc
• Pfizer ireland pharmaceuticals

Packagers

• A-S Medication Solutions LLC
• Bryant Ranch Prepack
• Cardinal Health
• Direct Dispensing Inc.
• Diversified Healthcare Services Inc.
• Gallipot
• MSN Laboratories Ltd.
• Murfreesboro Pharmaceutical Nursing Supply
• Nucare Pharmaceuticals Inc.
• PD-Rx Pharmaceuticals Inc.
• Pfizer Inc.
• Physicians Total Care Inc.
• Preferred Pharmaceuticals Inc.
• Prepackage Specialists
• Prepak Systems Inc.
• Rebel Distributors Corp.
• Redpharm Drug
• Southwood Pharmaceuticals
• Stat Rx Usa
• US Pharmaceutical Group

Dosage Forms

Form	Route	Strength
Tablet, chewable	Oral	25 MG
Tablet, film coated	Oral	140.5 MG
Tablet	Oral	25 mg
Tablet	Oral	50.000 mg
Tablet	Oral	140.48 mg
Suspension	Oral	25 MG/ML
Injection, suspension
Tablet, chewable	Oral	5000000 mg
Tablet, film coated	Oral	140480 Mg
Tablet, film coated	Oral	70240 Mg
Tablet, film coated	Oral
Tablet, film coated	Oral
Tablet, coated	Oral
Tablet, delayed release	Oral	35.112 mg
Capsule	Oral	50.00 mg
Tablet, film coated	Oral	70.225 mg
Film, soluble	Oral	70241 Mg
Tablet	Oral	100 mg
Tablet	Oral	50 mg
Capsule, liquid filled	Oral	25 mg
Capsule, liquid filled	Oral	50 mg
Tablet, soluble	Oral	50 mg
Tablet	Oral	70.240 mg
Tablet, film coated	Oral	20 MG
Solution	Intravenous	10 mg
Tablet	Oral	100.0 mg
Tablet	Oral	25.0 mg
Tablet	Oral	50.0 mg
Solution	Oral	0.01838 g
Tablet	Oral	140.450 mg
Tablet	Oral	70.225 mg
Suspension	Oral	10 mg/1mL
Solution	Oral	1.838 g
Film	Buccal	70.240 mg
Tablet	Oral	140.480 mg
Tablet, film coated	Oral	70.24 mg
Tablet	Oral	50.00 mg
Gel	Oral	28.100 mg
Tablet	Oral	140.400 mg
Tablet	Oral	100.000 mg
Film, soluble	Oral	100 mg
Film, soluble	Oral	25 MG
Film, soluble	Oral	75 MG
Tablet	Oral	28.090 mg
Injection, solution	Intravenous	0.8 MG/ML
Injection, solution	Intravenous	0.8 mg/1mL
Powder, for suspension	Oral	10 MG/ML
Solution	Intravenous	0.8 mg / mL
Syrup
Tablet	Oral	20 mg
Tablet, coated	Oral	20 mg
Tablet, film coated	Oral	20.0 mg/unit
Tablet	Oral
Suspension	Oral	25.000 mg
Film, soluble	Oral	70.23 MG
Tablet, film coated	Oral	100.0 mg
Tablet, film coated	Oral	50.0 mg
Capsule	Oral	25 mg
Capsule	Oral	50 mg
Tablet, film coated	Oral	25 mg
For suspension	Oral	10 mg/1mL
Injection, solution	Intravenous	10 mg/12.5mL
Tablet	Oral	100 mg/1
Tablet	Oral	20 mg/1
Tablet	Oral	25 mg/1
Tablet	Oral	50 mg/1
Tablet, film coated	Oral	20 mg/1
Tablet, chewable	Buccal	50 mg
Tablet, chewable	Oral	50 mg
Tablet, coated	Oral	5000000 mg
Tablet, coated	Oral	70.24 mg
Tablet, coated	Oral	50 mg
Tablet, chewable	Oral	100 MG
Powder, for suspension	Oral	10 mg/1mL
Tablet, chewable	Oral
Tablet, coated	Oral	2500000 mg
Tablet, film coated	Oral	100 mg
Tablet, film coated	Oral	50 mg
Film	Oral	50 mg
Film, soluble	Oral	50 mg
Tablet, film coated	Oral	100 mg/1
Tablet, film coated	Oral	25 mg/1
Tablet, film coated	Oral	50 mg/1
Tablet, orally disintegrating	Oral	50 mg
Tablet, coated	Oral	100 mg
Tablet, coated	Oral	25 mg
Film, soluble	Oral
Tablet, orally disintegrating	Oral	100 mg
Tablet, orally disintegrating	Oral	25 mg
Tablet	Oral	70.241 mg
Tablet, film coated	Oral	140.48 MG
Film	Buccal	70.230 mg

Prices

Unit description	Cost	Unit
Sildenafil citrate powder	24.38USD	g
Viagra 50 mg tablet	19.45USD	tablet
Viagra 100 mg tablet	19.45USD	tablet
Viagra 25 mg tablet	19.45USD	tablet
Revatio 20 mg tablet	17.5USD	tablet
Revatio 10 mg/12.5 ml vial	9.33USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US5250534	No	1993-10-05	2012-03-27
CA2324324	No	2005-12-20	2020-10-26
CA2044748	No	1998-02-03	2011-06-17
US6469012	Yes	2002-10-22	2020-04-22
US11337979	No	2018-12-24	2038-12-24
US11464778	No	2018-12-24	2038-12-24
US11759468	No	2018-12-24	2038-12-24

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	189-190 °C	Not Available
water solubility	3.5 mg/mL	Not Available
logP	1.9	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.46 mg/mL	ALOGPS
logP	1.8	ALOGPS
logP	1.87	Chemaxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.14	Chemaxon
pKa (Strongest Basic)	5.99	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	8	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	109.13 Å2	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	139.44 m3·mol-1	Chemaxon
Polarizability	51.18 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.6461
Caco-2 permeable	+	0.7078
P-glycoprotein substrate	Substrate	0.7753
P-glycoprotein inhibitor I	Inhibitor	0.672
P-glycoprotein inhibitor II	Inhibitor	0.8877
Renal organic cation transporter	Non-inhibitor	0.648
CYP450 2C9 substrate	Non-substrate	0.6553
CYP450 2D6 substrate	Substrate	0.8918
CYP450 3A4 substrate	Substrate	0.7254
CYP450 1A2 substrate	Non-inhibitor	0.823
CYP450 2C9 inhibitor	Inhibitor	0.6864
CYP450 2D6 inhibitor	Non-inhibitor	0.8394
CYP450 2C19 inhibitor	Non-inhibitor	0.8222
CYP450 3A4 inhibitor	Inhibitor	0.849
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.5839
Ames test	Non AMES toxic	0.5683
Carcinogenicity	Non-carcinogens	0.6658
Biodegradation	Not ready biodegradable	0.7641
Rat acute toxicity	2.6730 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8664
hERG inhibition (predictor II)	Inhibitor	0.7602

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-006t-9004300000-55c87eff7b6ad40ea3d5
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-0059-2494500000-e3f8387aee5a0463363c
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-05s0-3892000000-aa19715309275e16a6c0
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0059-2494500000-e3f8387aee5a0463363c
MS/MS Spectrum - , positive	LC-MS/MS	splash10-05s0-3892000000-aa19715309275e16a6c0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0001900000-77fcc940621f3df9617b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-0000900000-ef34b5271da197193eb1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0000900000-51cf0b8d94160875f06f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00r2-0001900000-6c86d10055edeb37fa34
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-7800900000-69fdda5ec4e95d6d367a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-01t9-2010900000-647487ea81f1fab90361
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	233.2005827	predicted	DarkChem Lite v0.1.0
[M-H]-	237.5357827	predicted	DarkChem Lite v0.1.0
[M-H]-	208.75966	predicted	DeepCCS 1.0 (2019)
[M+H]+	233.9926827	predicted	DarkChem Lite v0.1.0
[M+H]+	238.7927827	predicted	DarkChem Lite v0.1.0
[M+H]+	211.15523	predicted	DeepCCS 1.0 (2019)
[M+Na]+	232.9520827	predicted	DarkChem Lite v0.1.0
[M+Na]+	238.0477827	predicted	DarkChem Lite v0.1.0
[M+Na]+	217.06773	predicted	DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.

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Details1. cGMP-specific 3',5'-cyclic phosphodiesterase

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Metal ion binding

Specific Function

Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, ...

Gene Name

PDE5A

Uniprot ID

O76074

Uniprot Name

cGMP-specific 3',5'-cyclic phosphodiesterase

Molecular Weight

99984.14 Da

References

1. Carson CC: Long-term use of sildenafil. Expert Opin Pharmacother. 2003 Mar;4(3):397-405. [Article]
2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
3. Corbin JD, Francis SH, Webb DJ: Phosphodiesterase type 5 as a pharmacologic target in erectile dysfunction. Urology. 2002 Sep;60(2 Suppl 2):4-11. [Article]
4. Kruuse C, Thomsen LL, Birk S, Olesen J: Migraine can be induced by sildenafil without changes in middle cerebral artery diameter. Brain. 2003 Jan;126(Pt 1):241-7. [Article]
5. Rybalkin SD, Rybalkina IG, Shimizu-Albergine M, Tang XB, Beavo JA: PDE5 is converted to an activated state upon cGMP binding to the GAF A domain. EMBO J. 2003 Feb 3;22(3):469-78. [Article]
6. Wang H, Liu Y, Huai Q, Cai J, Zoraghi R, Francis SH, Corbin JD, Robinson H, Xin Z, Lin G, Ke H: Multiple conformations of phosphodiesterase-5: implications for enzyme function and drug development. J Biol Chem. 2006 Jul 28;281(30):21469-79. Epub 2006 May 30. [Article]
7. Wang H, Ye M, Robinson H, Francis SH, Ke H: Conformational variations of both phosphodiesterase-5 and inhibitors provide the structural basis for the physiological effects of vardenafil and sildenafil. Mol Pharmacol. 2008 Jan;73(1):104-10. Epub 2007 Oct 24. [Article]
8. Wang J, Re J, Wang Z: [Mode of action of sildenafil]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 1999 Dec;21(6):493-6. [Article]
9. Zoraghi R, Francis SH, Corbin JD: Critical amino acids in phosphodiesterase-5 catalytic site that provide for high-affinity interaction with cyclic guanosine monophosphate and inhibitors. Biochemistry. 2007 Nov 27;46(47):13554-63. Epub 2007 Nov 3. [Article]

Details2. Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma

Kind

Protein

Organism

Humans

Pharmacological action

No

Actions

Inhibitor

General Function

Enzyme inhibitor activity

Specific Function

Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.

Gene Name

PDE6G

Uniprot ID

P18545

Uniprot Name

Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma

Molecular Weight

9643.09 Da

References

1. Uckert S, Hedlund P, Andersson KE, Truss MC, Jonas U, Stief CG: Update on phosphodiesterase (PDE) isoenzymes as pharmacologic targets in urology: present and future. Eur Urol. 2006 Dec;50(6):1194-207; discussion 1207. Epub 2006 Jun 6. [Article]

Details3. Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma

Kind

Protein

Organism

Humans

Pharmacological action

No

Actions

Inhibitor

General Function

Enzyme inhibitor activity

Specific Function

Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.

Gene Name

PDE6H

Uniprot ID

Q13956

Uniprot Name

Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma

Molecular Weight

9074.36 Da

References

1. Uckert S, Hedlund P, Andersson KE, Truss MC, Jonas U, Stief CG: Update on phosphodiesterase (PDE) isoenzymes as pharmacologic targets in urology: present and future. Eur Urol. 2006 Dec;50(6):1194-207; discussion 1207. Epub 2006 Jun 6. [Article]

Details4. Ornithine decarboxylase

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Downregulator

General Function

Protein homodimerization activity

Specific Function

Key enzyme of polyamine biosynthesis that converts ornithine into putrescine, which is the precursor for the polyamines, spermidine and spermine.

Gene Name

ODC1

Uniprot ID

P11926

Uniprot Name

Ornithine decarboxylase

Molecular Weight

51147.73 Da

References

1. Booth L, Roberts JL, Poklepovic A, Dent P: [pemetrexed + sildenafil], via autophagy-dependent HDAC downregulation, enhances the immunotherapy response of NSCLC cells. Cancer Biol Ther. 2017 Sep 2;18(9):705-714. doi: 10.1080/15384047.2017.1362511. [Article]

Details5. Programmed cell death 1 ligand 1

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Downregulator

General Function

Not Available

Specific Function

Involved in the costimulatory signal, essential for T-cell proliferation and production of IL10 and IFNG, in an IL2-dependent and a PDCD1-independent manner. Interaction with PDCD1 inhibits T-cell ...

Gene Name

CD274

Uniprot ID

Q9NZQ7

Uniprot Name

Programmed cell death 1 ligand 1

Molecular Weight

33275.095 Da

References

1. Booth L, Roberts JL, Poklepovic A, Dent P: [pemetrexed + sildenafil], via autophagy-dependent HDAC downregulation, enhances the immunotherapy response of NSCLC cells. Cancer Biol Ther. 2017 Sep 2;18(9):705-714. doi: 10.1080/15384047.2017.1362511. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55