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Identification
NameSildenafil
Accession NumberDB00203  (APRD00556)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Sildenfail is a vasoactive agent used to treat erectile dysfunction and reduce symptoms in patients with pulmonary arterial hypertension (PAH). Sildenafil elevates levels of the second messenger, cGMP, by inhibiting its breakdown via phosphodiesterase type 5 (PDE5). PDE5 is found in particularly high concentrations in the corpus cavernosum, erectile tissue of the penis. It is also found in the retina and vascular endothelium. Increased cGMP results in vasodilation which facilitates generation and maintenance of an erection. The vasodilatory effects of sildenafil also help reduce symptoms of PAH.

Structure
Thumb
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
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Sildenafiltablet100 mgoralActavis Pharma Company2012-11-08Not applicableCanada
Act Sildenafiltablet50 mgoralActavis Pharma Company2012-11-08Not applicableCanada
Act Sildenafiltablet25 mgoralActavis Pharma Company2012-11-08Not applicableCanada
Auro-sildenafiltablet50 mgoralAuro Pharma IncNot applicableNot applicableCanada
Auro-sildenafiltablet25 mgoralAuro Pharma IncNot applicableNot applicableCanada
Auro-sildenafiltablet100 mgoralAuro Pharma IncNot applicableNot applicableCanada
Dom-sildenafiltablet100 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-sildenafiltablet50 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-sildenafiltablet25 mgoralDominion PharmacalNot applicableNot applicableCanada
Gd-sildenafiltablet25 mgoralGenmed A Division Of Pfizer Canada Inc2012-11-272015-08-03Canada
Gd-sildenafiltablet50 mgoralGenmed A Division Of Pfizer Canada Inc2012-11-272015-08-03Canada
Gd-sildenafiltablet100 mgoralGenmed A Division Of Pfizer Canada Inc2012-11-27Not applicableCanada
Ipg-sildenafiltablet100 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Ipg-sildenafiltablet50 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Ipg-sildenafiltablet25 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Jamp-sildenafiltablet100.0 mgoralJamp Pharma Corporation2014-12-05Not applicableCanada
Jamp-sildenafiltablet50.0 mgoralJamp Pharma Corporation2014-12-05Not applicableCanada
Jamp-sildenafiltablet25.0 mgoralJamp Pharma Corporation2014-12-05Not applicableCanada
M-sildenafiltablet50 mgoralMantra Pharma IncNot applicableNot applicableCanada
M-sildenafiltablet100 mgoralMantra Pharma Inc2015-06-04Not applicableCanada
M-sildenafiltablet25 mgoralMantra Pharma IncNot applicableNot applicableCanada
Mar-sildenafiltablet50.0 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Mar-sildenafiltablet25.0 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Mar-sildenafiltablet100.0 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Mint-sildenafiltablet100 mgoralMint Pharmaceuticals Inc2013-02-15Not applicableCanada
Mint-sildenafiltablet50 mgoralMint Pharmaceuticals Inc2013-02-15Not applicableCanada
Mint-sildenafiltablet25 mgoralMint Pharmaceuticals Inc2013-02-15Not applicableCanada
Myl-sildenafiltablet25 mgoralMylan Pharmaceuticals Ulc2012-11-20Not applicableCanada
Myl-sildenafiltablet100 mgoralMylan Pharmaceuticals Ulc2012-11-20Not applicableCanada
Myl-sildenafiltablet50 mgoralMylan Pharmaceuticals Ulc2012-11-20Not applicableCanada
Mylan-sildenafiltablet100 mgoralMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Mylan-sildenafiltablet50 mgoralMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Mylan-sildenafiltablet25 mgoralMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Pb-sildenafiltablet100.0 mgoralPb Pharma IncNot applicableNot applicableCanada
Pb-sildenafiltablet50.0 mgoralPb Pharma IncNot applicableNot applicableCanada
Pb-sildenafiltablet25.0 mgoralPb Pharma IncNot applicableNot applicableCanada
PMS-sildenafiltablet25 mgoralPharmascience Inc2012-11-14Not applicableCanada
PMS-sildenafiltablet100 mgoralPharmascience Inc2012-11-14Not applicableCanada
PMS-sildenafiltablet50 mgoralPharmascience Inc2012-11-14Not applicableCanada
PMS-sildenafil Rtablet20 mgoralPharmascience Inc2014-11-14Not applicableCanada
Ran-sildenafiltablet100 mgoralRanbaxy Pharmaceuticals Canada Inc.2012-11-21Not applicableCanada
Ran-sildenafiltablet50 mgoralRanbaxy Pharmaceuticals Canada Inc.2012-11-21Not applicableCanada
Ran-sildenafiltablet25 mgoralRanbaxy Pharmaceuticals Canada Inc.2012-11-21Not applicableCanada
Ratio-sildenafiltablet100 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ratio-sildenafiltablet50 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ratio-sildenafiltablet25 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ratio-sildenafil Rtablet20 mgoralTeva Canada Limited2010-06-09Not applicableCanada
Revatiopowder, for suspension10 mg/mLoralPfizer Laboratories Div Pfizer Inc2014-06-02Not applicableUs
Revatiotablet20 mgoralPfizer Canada Inc2006-06-12Not applicableCanada
Revatiosolution0.8 mgintravenousPfizer Canada Inc2010-08-31Not applicableCanada
Revatiotablet, film coated20 mg/1oralPfizer Laboratories Div Pfizer Inc2005-06-03Not applicableUs
Revatiotablet, film coated20 mg/1oralCardinal Health2005-06-03Not applicableUs
Revatioinjection, solution.8 mg/mLintravenousPfizer Laboratories Div Pfizer Inc2009-11-18Not applicableUs
Riva-sildenafiltablet100 mgoralLaboratoire Riva Inc2016-05-06Not applicableCanada
Riva-sildenafiltablet50 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Riva-sildenafiltablet50 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Riva-sildenafiltablet25 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Riva-sildenafiltablet25 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Riva-sildenafiltablet100 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Sandoz Sildenafiltablet100 mgoralSandoz Canada Incorporated2013-01-31Not applicableCanada
Sandoz Sildenafiltablet50 mgoralSandoz Canada Incorporated2013-01-31Not applicableCanada
Sandoz Sildenafiltablet25 mgoralSandoz Canada Incorporated2013-01-31Not applicableCanada
Sildenafiltablet25 mgoralMethapharm IncNot applicableNot applicableCanada
Sildenafiltablet100.0 mgoralJamp Pharma CorporationNot applicableNot applicableCanada
Sildenafiltablet, film coated20 mg/1oralKAISER FOUNDATION HOSPITALS2014-09-19Not applicableUs
Sildenafiltablet50.0 mgoralJamp Pharma CorporationNot applicableNot applicableCanada
Sildenafiltablet25 mgoralPharmascience Inc2013-08-05Not applicableCanada
Sildenafiltablet100 mgoralPro Doc Limitee2014-10-07Not applicableCanada
Sildenafiltablet25.0 mgoralJamp Pharma CorporationNot applicableNot applicableCanada
Sildenafiltablet25 mgoralPro Doc LimiteeNot applicableNot applicableCanada
Sildenafiltablet100 mgoralSivem Pharmaceuticals UlcNot applicableNot applicableCanada
Sildenafiltablet, film coated20 mg/1oralGreenstone LLC2012-09-27Not applicableUs
Sildenafiltablet50 mgoralPro Doc Limitee2014-10-07Not applicableCanada
Sildenafiltablet100 mgoralActavis Pharma CompanyNot applicableNot applicableCanada
Sildenafiltablet50 mgoralSivem Pharmaceuticals UlcNot applicableNot applicableCanada
Sildenafiltablet100 mgoralPharmascience Inc2013-08-05Not applicableCanada
Sildenafiltablet50 mgoralActavis Pharma CompanyNot applicableNot applicableCanada
Sildenafiltablet25 mgoralSivem Pharmaceuticals UlcNot applicableNot applicableCanada
Sildenafiltablet25 mgoralActavis Pharma CompanyNot applicableNot applicableCanada
Sildenafiltablet100 mgoralMethapharm IncNot applicableNot applicableCanada
Sildenafiltablet, film coated20 mg/1oralPd Rx Pharmaceuticals, Inc.2012-09-27Not applicableUs
Sildenafiltablet50 mgoralPharmascience Inc2013-08-05Not applicableCanada
Sildenafiltablet100 mgoralSanis Health Inc2013-06-21Not applicableCanada
Sildenafiltablet50 mgoralMethapharm IncNot applicableNot applicableCanada
Sildenafiltablet50 mgoralSanis Health Inc2013-06-21Not applicableCanada
Sildenafil Citratetablet100.0 mgoralJubilant Generics LimitedNot applicableNot applicableCanada
Sildenafil Citratetablet50.0 mgoralJubilant Generics LimitedNot applicableNot applicableCanada
Sildenafil Citratetablet25.0 mgoralJubilant Generics LimitedNot applicableNot applicableCanada
Sildenafil Rtablet20 mgoralMethapharm IncNot applicableNot applicableCanada
Sildenafil Tabletstablet100 mgoralDr Reddys Laboratories LtdNot applicableNot applicableCanada
Sildenafil Tabletstablet50 mgoralDr Reddys Laboratories LtdNot applicableNot applicableCanada
Sildenafil Tabletstablet25 mgoralDr Reddys Laboratories LtdNot applicableNot applicableCanada
Teva-sildenafiltablet25 mgoralTeva Canada Limited2012-11-08Not applicableCanada
Teva-sildenafiltablet50 mgoralTeva Canada Limited2012-11-08Not applicableCanada
Teva-sildenafiltablet100 mgoralTeva Canada Limited2012-11-08Not applicableCanada
Van-sildenafiltablet25.0 mgoralVanc Pharmaceuticals IncNot applicableNot applicableCanada
Van-sildenafiltablet100 mgoralVanc Pharmaceuticals Inc2015-07-22Not applicableCanada
Van-sildenafiltablet50.0 mgoralVanc Pharmaceuticals IncNot applicableNot applicableCanada
Viagratablet, film coated100 mg/1oralbryant ranch prepack1998-03-27Not applicableUs
Viagratablet, film coated25 mg/1oralCardinal Health1998-03-27Not applicableUs
Viagratablet, film coated25 mg/1oralPhysicians Total Care, Inc.1998-03-27Not applicableUs
Viagratablet, film coated100 mg/1oralRebel Distributors Corp2010-02-11Not applicableUs
Viagratablet, film coated100 mg/1oralU.S. Pharmaceuticals1998-03-27Not applicableUs
Viagratablet, film coated100 mg/1oralPhysicians Total Care, Inc.1998-03-27Not applicableUs
Viagratablet, film coated50 mg/1oralRebel Distributors Corp2003-07-17Not applicableUs
Viagratablet, film coated50 mg/1oralPhysicians Total Care, Inc.1998-03-27Not applicableUs
Viagratablet, film coated50 mg/1oralU.S. Pharmaceuticals1998-03-27Not applicableUs
Viagratablet100 mgoralPfizer Canada Inc1999-03-09Not applicableCanada
Viagratablet, film coated100 mg/1oralREMEDYREPACK INC.2013-05-22Not applicableUs
Viagratablet, film coated100 mg/1oralPfizer Laboratories Div Pfizer Inc1998-03-27Not applicableUs
Viagratablet50 mgoralPfizer Canada Inc1999-03-09Not applicableCanada
Viagratablet, film coated50 mg/1oralPd Rx Pharmaceuticals, Inc.1998-03-27Not applicableUs
Viagratablet, film coated100 mg/1oralLake Erie Medical Surgical & Supply DBA Quality Care Products LLC2011-07-13Not applicableUs
Viagratablet, film coated50 mg/1oralPfizer Laboratories Div Pfizer Inc1998-03-27Not applicableUs
Viagratablet, film coated100 mg/1oralAphena Pharma Solutions Tennessee, Llc1998-03-27Not applicableUs
Viagratablet, film coated100 mg/1oralPd Rx Pharmaceuticals, Inc.1998-03-27Not applicableUs
Viagratablet, film coated25 mg/1oralAphena Pharma Solutions Tennessee, Llc1998-03-27Not applicableUs
Viagratablet, film coated25 mg/1oralPfizer Laboratories Div Pfizer Inc1998-03-27Not applicableUs
Viagratablet25 mgoralPfizer Canada Inc1999-03-09Not applicableCanada
Viagratablet, film coated50 mg/1oralAphena Pharma Solutions Tennessee, Llc1998-03-27Not applicableUs
Viagratablet, film coated100 mg/1oralCardinal Health1998-03-27Not applicableUs
Viagratablet, film coated50 mg/1oralbryant ranch prepack1998-03-27Not applicableUs
Viagratablet, film coated25 mg/1oralPd Rx Pharmaceuticals, Inc.1998-03-27Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-sildenafiltablet50 mgoralApotex Inc2012-11-14Not applicableCanada
Apo-sildenafiltablet25 mgoralApotex Inc2012-11-14Not applicableCanada
Apo-sildenafiltablet100 mgoralApotex Inc2012-11-09Not applicableCanada
Apo-sildenafil Rtablet20 mgoralApotex Inc2013-12-23Not applicableCanada
Sildenafiltablet20 mg/1oralAmneal Pharmaceuticals of New York, LLC2012-11-08Not applicableUs
Sildenafiltablet20 mg/1oralbryant ranch prepack2012-11-08Not applicableUs
Sildenafiltablet20 mg/1oralAv Pak2015-05-29Not applicableUs
Sildenafiltablet, film coated20 mg/1oralTeva Pharmaceuticals USA Inc2013-05-31Not applicableUs
Sildenafiltablet, film coated20 mg/1oralDIRECT RX2015-01-01Not applicableUs
Sildenafiltablet, film coated20 mg/1oralAv Kare, Inc.2013-09-17Not applicableUs
Sildenafiltablet, film coated20 mg/1oralREMEDYREPACK INC.2015-12-10Not applicableUs
Sildenafiltablet, film coated20 mg/1oralMacleods Pharmaceuticals Limited2014-01-03Not applicableUs
Sildenafiltablet, film coated20 mg/1oralProficient Rx LP2014-11-26Not applicableUs
Sildenafiltablet20 mg/1oralA S Medication Solutions2012-11-08Not applicableUs
Sildenafiltablet, film coated20 mg/1oralApotex Corp.2012-11-06Not applicableUs
Sildenafiltablet, film coated20 mg/1oralCamber Pharmaceuticals, Inc.2014-11-26Not applicableUs
Sildenafiltablet, film coated20 mg/1oralPreferred Pharmaceuticals Inc.2016-04-14Not applicableUs
Sildenafilinjection, solution10 mg/12.5mLintravenousAuro Medics Pharma Llc2015-04-01Not applicableUs
Sildenafiltablet, film coated20 mg/1oralNorthstar Rx LLC2013-02-26Not applicableUs
Sildenafiltablet, film coated20 mg/1oralPd Rx Pharmaceuticals, Inc.2013-05-31Not applicableUs
Sildenafiltablet20 mg/1oralAmerican Health Packaging2015-02-15Not applicableUs
Sildenafiltablet, film coated20 mg/1oralDr. Reddy's Laboratories Limited2012-11-12Not applicableUs
Sildenafiltablet20 mg/1oralBlue Point Laboratories2014-02-04Not applicableUs
Sildenafiltablet, film coated20 mg/1oralREMEDYREPACK INC.2013-09-19Not applicableUs
Sildenafiltablet, film coated20 mg/1oralActavis Pharma, Inc.2012-11-06Not applicableUs
Sildenafiltablet, film coated20 mg/1oralAurobindo Pharma Limited2015-11-18Not applicableUs
Sildenafiltablet, film coated20 mg/1oralNorthwind Pharmaceuticals, LLC2014-11-06Not applicableUs
Sildenafiltablet, film coated20 mg/1oralMylan Pharmaceuticals Inc.2012-11-09Not applicableUs
Sildenafil Citratetablet, film coated20 mg/1oralAmerican Health Packaging2012-12-142016-01-05Us
Sildenafil Citratetablet20 mg/1oralTorrent Pharmaceuticals Limited2012-11-06Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Sildenafil Citrate
171599-83-0
Thumb
  • InChI Key: DEIYFTQMQPDXOT-UHFFFAOYSA-N
  • Monoisotopic Mass: 666.231926778
  • Average Mass: 666.7
DBSALT000347
Categories
UNII3M7OB98Y7H
CAS number139755-83-2
WeightAverage: 474.576
Monoisotopic: 474.204924168
Chemical FormulaC22H30N6O4S
InChI KeyInChIKey=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=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Pyrazolopyrimidine
  • Phenol ether
  • N-alkylpiperazine
  • N-methylpiperazine
  • Pyrimidone
  • Alkyl aryl ether
  • Pyrimidine
  • Piperazine
  • 1,4-diazinane
  • Heteroaromatic compound
  • Vinylogous amide
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Pyrazole
  • Azole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of erectile dysfunction and to relieve symptoms of pulmonary arterial hypertension (PAH).
PharmacodynamicsErections are controlled by the parasympathetic nervous system. Upon sexual stimulation, a decrease in vascular resistance is mediated by acetylcholine and nitric oxide resulting in vasodilation. The hemodynamic mechanism of an erection is comprised of five stages. During the latent stage, arterial and carvernous smooth muscle relaxation occurs. Vasodilation results in high levels of blood flow causing the penis to grow to its full size. This stage is called tumescence. During the full-erection stage, blood flow fills penis sinusoids and outflow is restricted. This is followed by the rigid-erection phase during which the cavernous muscles contract causing the penis to become rigid. Little blood flow occurs during this stage. During the final stage, detumescence, the cavernous muscles relax and blood flows out of the penis. Erectile dysfunction may occur when there is insufficient blood supply to the penis or when the penis is unable to prevent outflow of blood from the penis. Sildenafil is a specific inhibitor of PDE5, an enzyme responsible for the breakdown of cGMP to 5’-GMP. Increased levels of cGMP stimulate vasodilation and facilitate the generation and maintenance of erections. These vasodilatory effects also help decrease symptoms of PAH. Sildenfail also exhibits some activity against PDE6 (10 times less potentcy compared to PDE5), a PDE isoform found predmoninantly in the retina. This activity is responsible for the blue tinged vision experienced by users of sildenafil.
Mechanism of actionSildenafil inhibits the cGMP-specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum located around the penis. Penile erection during sexual stimulation is caused by increased penile blood flow resulting from the relaxation of penile arteries and corpus cavernosal smooth muscle. This response is mediated by the release of nitric oxide (NO) from nerve terminals and endothelial cells, which stimulates the synthesis of cGMP in smooth muscle cells. Cyclic GMP causes smooth muscle relaxation and increased blood flow into the corpus cavernosum. The inhibition of phosphodiesterase type 5 (PDE5) by sildenafil enhances erectile function by increasing the amount of cGMP.
Related Articles
Absorption>90% absorbed with ~40% reaching systemic circulation unchanged following first-pass metabolism
Volume of distribution
  • 105 L
Protein binding96%
Metabolism

Sildenafil appears to be completely metabolized in the liver to 16 metabolites. Its metabolism is mediated mainly by cytochrome P450 microsomal isozymes 3A4 (major route) and 2C9 (minor route). The major circulating metabolite, N-demethylated metabolite, has PDE selectivity similar to the parent drug and ~50% of its in vitro potency. The N-demethylated metabolite is further metabolized to an N-dealkylated N,N-de-ethylated metabolite. Sildenafil also undergoes N-dealkylation followed by N-demethylation of the piperazine ring.

SubstrateEnzymesProduct
Sildenafil
N-Desmethyl sildenafil (UK-103,320)Details
Route of eliminationSildenafil is cleared predominantly by the CYP3A (major route) and cytochrome P450 2C9 (CYP2C9, minor route) hepatic microsomal isoenzymes. 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).
Half life4 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Angiotensin-converting enzyme
Gene symbol: ACE
UniProt: P12821
rs1799752 Not AvailableAlu insertionsBetter response to drug treatment12837457
Angiotensin-converting enzyme
Gene symbol: ACE
UniProt: P12821
rs4340 Not AvailableAlu insertionsBetter response to drug treatment12837457
Angiotensin-converting enzyme
Gene symbol: ACE
UniProt: P12821
rs13447447 Not AvailableAlu insertionsBetter response to drug treatment12837457
Angiotensin-converting enzyme
Gene symbol: ACE
UniProt: P12821
rs4646994 Not AvailableAlu insertionsBetter response to drug treatment12837457
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3
Gene symbol: GNB3
UniProt: P16520
rs5443 Not AvailableT AlleleBetter response to drug treatment12576843
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3
Gene symbol: GNB3
UniProt: P16520
rs5443 Not AvailableTT alleleBetter response to drug treatment. More patients experience a 'postive erectile response'12576843
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.6461
Caco-2 permeable+0.7078
P-glycoprotein substrateSubstrate0.7753
P-glycoprotein inhibitor IInhibitor0.672
P-glycoprotein inhibitor IIInhibitor0.8877
Renal organic cation transporterNon-inhibitor0.648
CYP450 2C9 substrateNon-substrate0.6553
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.7254
CYP450 1A2 substrateNon-inhibitor0.823
CYP450 2C9 inhibitorInhibitor0.6864
CYP450 2D6 inhibitorNon-inhibitor0.8394
CYP450 2C19 inhibitorNon-inhibitor0.8222
CYP450 3A4 inhibitorInhibitor0.849
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5839
Ames testNon AMES toxic0.5683
CarcinogenicityNon-carcinogens0.6658
BiodegradationNot ready biodegradable0.7641
Rat acute toxicity2.6730 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8664
hERG inhibition (predictor II)Inhibitor0.7602
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
Packagers
Dosage forms
FormRouteStrength
Tabletoral25 mg
Tabletoral100.0 mg
Tabletoral25.0 mg
Tabletoral50.0 mg
Injection, solutionintravenous.8 mg/mL
Powder, for suspensionoral10 mg/mL
Solutionintravenous0.8 mg
Tabletoral20 mg
Tablet, film coatedoral20 mg/1
Injection, solutionintravenous10 mg/12.5mL
Tabletoral20 mg/1
Tabletoral100 mg
Tabletoral50 mg
Tablet, film coatedoral100 mg/1
Tablet, film coatedoral25 mg/1
Tablet, film coatedoral50 mg/1
Prices
Unit descriptionCostUnit
Sildenafil citrate powder24.38USD g
Viagra 50 mg tablet19.45USD tablet
Viagra 100 mg tablet19.45USD tablet
Viagra 25 mg tablet19.45USD tablet
Revatio 20 mg tablet17.5USD tablet
Revatio 10 mg/12.5 ml vial9.33USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2044748 No1998-02-032011-06-17Canada
CA2324324 No2005-12-202020-10-26Canada
US5250534 No1995-03-272012-03-27Us
US6469012 Yes2000-04-222020-04-22Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point189-190 °CNot Available
water solubility3.5 mg/mLNot Available
logP1.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.433 mg/mLALOGPS
logP2.35ALOGPS
logP1.65ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.27ChemAxon
pKa (Strongest Basic)5.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area109.13 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity139.44 m3·mol-1ChemAxon
Polarizability51.18 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0002900000-b281f59f40caaba85ac9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-4436900000-0c5804e76b9d495c76d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0459-6292000000-5a32bfcdda2067978be9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0001900000-51b4957d0b3d25c41773View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vk-0302900000-86c63c2fd17f7c5b7d6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-8916100000-e941afc576d544ed32a7View in MoNA
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. [PubMed:8858389 ]
  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. [PubMed:9935041 ]
  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. [PubMed:16275885 ]
External Links
ATC CodesG04BE03
AHFS Codes
  • 24:12.12
PDB EntriesNot Available
FDA labelDownload (80.5 KB)
MSDSDownload (37.1 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe metabolism of Sildenafil can be decreased when combined with Abiraterone.
AlfuzosinSildenafil may increase the hypotensive activities of Alfuzosin.
AlprostadilThe risk or severity of adverse effects can be increased when Sildenafil is combined with Alprostadil.
AmiodaroneThe metabolism of Sildenafil can be decreased when combined with Amiodarone.
Amyl NitriteSildenafil may increase the vasodilatory activities of Amyl Nitrite.
AprepitantThe serum concentration of Sildenafil can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of Sildenafil can be increased when it is combined with Atazanavir.
BatimastatThe serum concentration of Sildenafil can be increased when it is combined with Batimastat.
BexaroteneThe serum concentration of Sildenafil can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Sildenafil can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Sildenafil can be decreased when it is combined with Bosentan.
CapecitabineThe metabolism of Sildenafil can be decreased when combined with Capecitabine.
CarbamazepineThe metabolism of Sildenafil can be increased when combined with Carbamazepine.
CeritinibThe serum concentration of Sildenafil can be increased when it is combined with Ceritinib.
ClarithromycinThe serum concentration of Sildenafil can be increased when it is combined with Clarithromycin.
CobicistatThe serum concentration of Sildenafil can be increased when it is combined with Cobicistat.
ConivaptanThe serum concentration of Sildenafil can be increased when it is combined with Conivaptan.
DabrafenibThe serum concentration of Sildenafil can be decreased when it is combined with Dabrafenib.
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Sildenafil.
DarunavirThe serum concentration of Sildenafil can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Sildenafil can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Sildenafil can be decreased when it is combined with Deferasirox.
DelavirdineThe metabolism of Sildenafil can be decreased when combined with Delavirdine.
EfavirenzThe metabolism of Sildenafil can be decreased when combined with Efavirenz.
Erythrityl TetranitrateSildenafil may increase the vasodilatory activities of Erythrityl Tetranitrate.
ErythromycinThe serum concentration of Sildenafil can be increased when it is combined with Erythromycin.
EthanolEthanol may increase the hypotensive activities of Sildenafil.
EtravirineThe serum concentration of Sildenafil can be decreased when it is combined with Etravirine.
FloxuridineThe metabolism of Sildenafil can be decreased when combined with Floxuridine.
FluconazoleThe serum concentration of Sildenafil can be increased when it is combined with Fluconazole.
FluorouracilThe metabolism of Sildenafil can be decreased when combined with Fluorouracil.
FluvastatinThe metabolism of Sildenafil can be decreased when combined with Fluvastatin.
FosamprenavirThe serum concentration of Sildenafil can be increased when it is combined with Fosamprenavir.
FosaprepitantThe serum concentration of Sildenafil can be increased when it is combined with Fosaprepitant.
FosphenytoinThe metabolism of Sildenafil can be increased when combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Sildenafil can be increased when it is combined with Fusidic Acid.
GemfibrozilThe metabolism of Sildenafil can be decreased when combined with Gemfibrozil.
IdelalisibThe serum concentration of Sildenafil can be increased when it is combined with Idelalisib.
IndinavirThe serum concentration of Sildenafil can be increased when it is combined with Indinavir.
IrbesartanThe metabolism of Sildenafil can be decreased when combined with Irbesartan.
IsoflurophateThe serum concentration of Sildenafil can be increased when it is combined with Isoflurophate.
ItraconazoleThe serum concentration of Sildenafil can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Sildenafil can be increased when it is combined with Ivacaftor.
KetoconazoleThe metabolism of Sildenafil can be decreased when combined with Ketoconazole.
LeflunomideThe metabolism of Sildenafil can be decreased when combined with Leflunomide.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Sildenafil.
LosartanThe metabolism of Sildenafil can be decreased when combined with Losartan.
LuliconazoleThe serum concentration of Sildenafil can be increased when it is combined with Luliconazole.
MifepristoneThe serum concentration of Sildenafil can be increased when it is combined with Mifepristone.
MitotaneThe serum concentration of Sildenafil can be decreased when it is combined with Mitotane.
MolsidomineMolsidomine may increase the hypotensive activities of Sildenafil.
MoxonidineSildenafil may increase the antihypertensive activities of Moxonidine.
NefazodoneThe serum concentration of Sildenafil can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Sildenafil can be increased when it is combined with Nelfinavir.
NetupitantThe serum concentration of Sildenafil can be increased when it is combined with Netupitant.
NicardipineThe metabolism of Sildenafil can be decreased when combined with Nicardipine.
OmeprazoleThe metabolism of Sildenafil can be decreased when combined with Omeprazole.
PalbociclibThe serum concentration of Sildenafil can be increased when it is combined with Palbociclib.
PhenobarbitalThe metabolism of Sildenafil can be increased when combined with Phenobarbital.
PhenytoinThe metabolism of Sildenafil can be increased when combined with Phenytoin.
PosaconazoleThe serum concentration of Sildenafil can be increased when it is combined with Posaconazole.
PrazosinSildenafil may increase the hypotensive activities of Prazosin.
PrimidoneThe metabolism of Sildenafil can be increased when combined with Primidone.
PyrimethamineThe metabolism of Sildenafil can be decreased when combined with Pyrimethamine.
QuinineThe metabolism of Sildenafil can be decreased when combined with Quinine.
RifampicinThe metabolism of Sildenafil can be increased when combined with Rifampicin.
RifapentineThe metabolism of Sildenafil can be increased when combined with Rifapentine.
RiociguatSildenafil may increase the hypotensive activities of Riociguat.
RitonavirThe serum concentration of Sildenafil can be increased when it is combined with Ritonavir.
SapropterinTetrahydrobiopterin may increase the hypotensive activities of Sildenafil.
SaquinavirThe serum concentration of Sildenafil can be increased when it is combined with Saquinavir.
SecobarbitalThe metabolism of Sildenafil can be increased when combined with Secobarbital.
SiltuximabThe serum concentration of Sildenafil can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Sildenafil can be increased when it is combined with Simeprevir.
SorafenibThe metabolism of Sildenafil can be decreased when combined with Sorafenib.
St. John's WortThe serum concentration of Sildenafil can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Sildenafil can be increased when it is combined with Stiripentol.
SulfadiazineThe metabolism of Sildenafil can be decreased when combined with Sulfadiazine.
SulfamethoxazoleThe metabolism of Sildenafil can be decreased when combined with Sulfamethoxazole.
SulfisoxazoleThe metabolism of Sildenafil can be decreased when combined with Sulfisoxazole.
TadalafilThe risk or severity of adverse effects can be increased when Tadalafil is combined with Sildenafil.
TelaprevirThe serum concentration of Sildenafil can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Sildenafil can be increased when it is combined with Telithromycin.
TicagrelorThe metabolism of Sildenafil can be decreased when combined with Ticagrelor.
TipranavirThe serum concentration of Sildenafil can be increased when it is combined with Tipranavir.
TocilizumabThe serum concentration of Sildenafil can be decreased when it is combined with Tocilizumab.
TolbutamideThe metabolism of Sildenafil can be decreased when combined with Tolbutamide.
TrimethoprimThe metabolism of Sildenafil can be decreased when combined with Trimethoprim.
VardenafilThe risk or severity of adverse effects can be increased when Vardenafil is combined with Sildenafil.
VoriconazoleThe metabolism of Sildenafil can be decreased when combined with Voriconazole.
ZafirlukastThe metabolism of Sildenafil can be decreased when combined with Zafirlukast.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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, PubMed:15489334). Specifically regulates nitric-oxide-generated cGMP (PubMed:15489334).
Gene Name:
PDE5A
Uniprot ID:
O76074
Molecular Weight:
99984.14 Da
References
  1. Carson CC: Long-term use of sildenafil. Expert Opin Pharmacother. 2003 Mar;4(3):397-405. [PubMed:12614192 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  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. [PubMed:12414329 ]
  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. [PubMed:12477710 ]
  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. [PubMed:12554648 ]
  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. [PubMed:16735511 ]
  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. [PubMed:17959709 ]
  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. [PubMed:12567500 ]
  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. [PubMed:17979301 ]
Kind
Protein
Organism
Human
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
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. [PubMed:16815627 ]
Kind
Protein
Organism
Human
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
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. [PubMed:16815627 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Ku HY, Ahn HJ, Seo KA, Kim H, Oh M, Bae SK, Shin JG, Shon JH, Liu KH: The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil. Drug Metab Dispos. 2008 Jun;36(6):986-90. doi: 10.1124/dmd.107.020099. Epub 2008 Feb 28. [PubMed:18308836 ]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  4. Hyland R, Roe EG, Jones BC, Smith DA: Identification of the cytochrome P450 enzymes involved in the N-demethylation of sildenafil. Br J Clin Pharmacol. 2001 Mar;51(3):239-48. [PubMed:11298070 ]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Ku HY, Ahn HJ, Seo KA, Kim H, Oh M, Bae SK, Shin JG, Shon JH, Liu KH: The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil. Drug Metab Dispos. 2008 Jun;36(6):986-90. doi: 10.1124/dmd.107.020099. Epub 2008 Feb 28. [PubMed:18308836 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Hyland R, Roe EG, Jones BC, Smith DA: Identification of the cytochrome P450 enzymes involved in the N-demethylation of sildenafil. Br J Clin Pharmacol. 2001 Mar;51(3):239-48. [PubMed:11298070 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Atpase activity, coupled to transmembrane movement of substances
Specific Function:
May be an organic anion pump relevant to cellular detoxification.
Gene Name:
ABCC4
Uniprot ID:
O15439
Molecular Weight:
149525.33 Da
References
  1. Chen ZS, Lee K, Walther S, Raftogianis RB, Kuwano M, Zeng H, Kruh GD: Analysis of methotrexate and folate transport by multidrug resistance protein 4 (ABCC4): MRP4 is a component of the methotrexate efflux system. Cancer Res. 2002 Jun 1;62(11):3144-50. [PubMed:12036927 ]
  2. Reid G, Wielinga P, Zelcer N, De Haas M, Van Deemter L, Wijnholds J, Balzarini J, Borst P: Characterization of the transport of nucleoside analog drugs by the human multidrug resistance proteins MRP4 and MRP5. Mol Pharmacol. 2003 May;63(5):1094-103. [PubMed:12695538 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Organic anion transmembrane transporter activity
Specific Function:
Acts as a multispecific organic anion pump which can transport nucleotide analogs.
Gene Name:
ABCC5
Uniprot ID:
O15440
Molecular Weight:
160658.8 Da
References
  1. Jedlitschky G, Burchell B, Keppler D: The multidrug resistance protein 5 functions as an ATP-dependent export pump for cyclic nucleotides. J Biol Chem. 2000 Sep 29;275(39):30069-74. [PubMed:10893247 ]
  2. Reid G, Wielinga P, Zelcer N, De Haas M, Van Deemter L, Wijnholds J, Balzarini J, Borst P: Characterization of the transport of nucleoside analog drugs by the human multidrug resistance proteins MRP4 and MRP5. Mol Pharmacol. 2003 May;63(5):1094-103. [PubMed:12695538 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Atpase activity, coupled to transmembrane movement of substances
Specific Function:
ATP-dependent transporter probably involved in cellular detoxification through lipophilic anion extrusion.
Gene Name:
ABCC10
Uniprot ID:
Q5T3U5
Molecular Weight:
161627.375 Da
References
  1. Chen ZS, Hopper-Borge E, Belinsky MG, Shchaveleva I, Kotova E, Kruh GD: Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10). Mol Pharmacol. 2003 Feb;63(2):351-8. [PubMed:12527806 ]
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Drug created on June 13, 2005 07:24 / Updated on June 25, 2016 03:05