U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H19N3O4
Molecular Weight 389.4048
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TADALAFIL

SMILES

CN1CC(=O)N2[C@]([H])(Cc3c4ccccc4[nH]c3[C@@]2([H])c5ccc6c(c5)OCO6)C1=O

InChI

InChIKey=WOXKDUGGOYFFRN-IIBYNOLFSA-N
InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021368s20s21lbl.pdf

Tadalafil is used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH). Part of the physiological process of erection involves the release of nitric oxide (NO) in the corpus cavernosum. This then activates the enzyme guanylate cyclase which results in increased levels of cyclic guanosine monophosphate (cGMP), leading to smooth muscle relaxation in the corpus cavernosum, resulting in increased inflow of blood and an erection. Tadalafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum. This means that, with tadalafil on board, normal sexual stimulation leads to increased levels of cGMP in the corpus cavernosum which leads to better erections. Without sexual stimulation and no activation of the NO/cGMP system, tadalafil should not cause an erection.Tadalafil 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 tadalafil enhances erectile function by increasing the amount of cGMP. Tadalafil is used for the treatment of erectile dysfunction.

CNS Activity

CNS Active
1726
Curator's Comment:: Tadalafil crosses the blood-brain barrier and reverses cognitive dysfunction in a mouse model of AD.

Originator

Approval Year

2003
32
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
3315
 100.0 µM [IC50]
Inhibitor
3315
 5.1 µM [IC50]
Inhibitor
3315
 0.05 µM [IC50]
Inhibitor
3315
 5.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
4033
CIALIS

Approved Use

CIALIS® is a phosphodiesterase 5 (PDE5) inhibitor indicated for the treatment of: • erectile dysfunction (ED) • the signs and symptoms of benign prostatic hyperplasia (BPH) • ED and the signs and symptoms of BPH (ED/BPH)

Launch Date

1.06928642E12
Primary
Approved
4033
CIALIS

Approved Use

CIALIS® is a phosphodiesterase 5 (PDE5) inhibitor indicated for the treatment of: • erectile dysfunction (ED) • the signs and symptoms of benign prostatic hyperplasia (BPH) • ED and the signs and symptoms of BPH (ED/BPH)

Launch Date

1.06928642E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
308.1 μg/L
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29719379
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TADALAFIL blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
7225 μg × h/L
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29719379
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TADALAFIL blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
17.4 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29719379
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TADALAFIL blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022332lbl.pdf
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TADALAFIL unknown
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
40 mg 1 times / day multiple, oral
MTD
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31131648
pregnant, 28 years (range: 20–39 years)
n = 3
Health Status: pregnant
Age Group: 28 years (range: 20–39 years)
Sex: F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/31131648
Other AEs: Facial flushing, Anorexia...
Other AEs:
Facial flushing (grade 1, 2 patients)
Anorexia (grade 1, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/31131648
20 mg 3 times / week multiple, oral
Dose: 20 mg, 3 times / week
Route: oral
Route: multiple
Dose: 20 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
unhealthy, 54.9 years
n = 4262
Health Status: unhealthy
Condition: Erectile Dysfunction
Age Group: 54.9 years
Sex: M
Population Size: 4262
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
Other AEs: Headache, Dyspepsia...
Other AEs:
Headache (7.7%)
Dyspepsia (7%)
Back pain (2.9%)
Flushing (2.9%)
Myalgia (3%)
Abdominal pain upper (1.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
100 mg 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022332lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: erectile dysfunction
Age Group: adult
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022332lbl.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022332lbl.pdf
500 mg single, oral
Highest studied dose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022332lbl.pdf
healthy, adult
Health Status: healthy
Age Group: adult
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022332lbl.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022332lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Anorexia grade 1, 1 patient
40 mg 1 times / day multiple, oral
MTD
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31131648
pregnant, 28 years (range: 20–39 years)
n = 3
Health Status: pregnant
Age Group: 28 years (range: 20–39 years)
Sex: F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/31131648
Facial flushing grade 1, 2 patients
40 mg 1 times / day multiple, oral
MTD
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31131648
pregnant, 28 years (range: 20–39 years)
n = 3
Health Status: pregnant
Age Group: 28 years (range: 20–39 years)
Sex: F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/31131648
Abdominal pain upper 1.7%
20 mg 3 times / week multiple, oral
Dose: 20 mg, 3 times / week
Route: oral
Route: multiple
Dose: 20 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
unhealthy, 54.9 years
n = 4262
Health Status: unhealthy
Condition: Erectile Dysfunction
Age Group: 54.9 years
Sex: M
Population Size: 4262
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
Back pain 2.9%
20 mg 3 times / week multiple, oral
Dose: 20 mg, 3 times / week
Route: oral
Route: multiple
Dose: 20 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
unhealthy, 54.9 years
n = 4262
Health Status: unhealthy
Condition: Erectile Dysfunction
Age Group: 54.9 years
Sex: M
Population Size: 4262
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
Flushing 2.9%
20 mg 3 times / week multiple, oral
Dose: 20 mg, 3 times / week
Route: oral
Route: multiple
Dose: 20 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
unhealthy, 54.9 years
n = 4262
Health Status: unhealthy
Condition: Erectile Dysfunction
Age Group: 54.9 years
Sex: M
Population Size: 4262
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
Myalgia 3%
20 mg 3 times / week multiple, oral
Dose: 20 mg, 3 times / week
Route: oral
Route: multiple
Dose: 20 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
unhealthy, 54.9 years
n = 4262
Health Status: unhealthy
Condition: Erectile Dysfunction
Age Group: 54.9 years
Sex: M
Population Size: 4262
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
Dyspepsia 7%
20 mg 3 times / week multiple, oral
Dose: 20 mg, 3 times / week
Route: oral
Route: multiple
Dose: 20 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
unhealthy, 54.9 years
n = 4262
Health Status: unhealthy
Condition: Erectile Dysfunction
Age Group: 54.9 years
Sex: M
Population Size: 4262
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
Headache 7.7%
20 mg 3 times / week multiple, oral
Dose: 20 mg, 3 times / week
Route: oral
Route: multiple
Dose: 20 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
unhealthy, 54.9 years
n = 4262
Health Status: unhealthy
Condition: Erectile Dysfunction
Age Group: 54.9 years
Sex: M
Population Size: 4262
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
882

inhibitor
753

inducer
374
inhibitor
825

inducer
191
inhibitor
894

inducer
49
inhibitor
775

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
725

CYP2C19
700

CYP2E1
424
P-gp
724
CYP1A2
329

CYP2C19
145

CYP2E1
63
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C19
738
 no
CYP2D6
908
 no
CYP2D6
908
 no
CYP2E1
467
 no
CYP2E1
467
 no
CYP1A2
805
 no
no (co-administration study)
Comment: taladafil had no clinically significant effect on PK of theophylline
Page: 14.0
CYP1A2
805
 no
no (co-administration study)
Comment: taladafil had no clinically significant effect on PK of theophylline
Page: 14.0
CYP2C9
851
 no
no (co-administration study)
Comment: Tadalafil had no clinically significant effect on exposure (AUC) to S-warfarin or R-warfarin, nor did tadalafil affect changes in prothrombin time induced by warfarin.
Page: 14.0
CYP2C9
851
 no
no (co-administration study)
Comment: Tadalafil had no clinically significant effect on exposure (AUC) to S-warfarin or R-warfarin, nor did tadalafil affect changes in prothrombin time induced by warfarin.
Page: 14.0
CYP3A4
920
 no
no (co-administration study)
Comment: taladafil had no clinically significant effect on exposure (AUC) to midazolam or lovastatin
Page: 14.0
CYP3A4
920
 no
no (co-administration study)
Comment: taladafil had no clinically significant effect on exposure (AUC) to midazolam or lovastatin
Page: 14.0
CYP2C19
738
 not significant [Ki 73 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
882
 major
yes (co-administration study)
Comment: coadministration with ketoconazole (inhibitor) increased tadalafil exposure by 107%; ritonavir (inhibitor) increased tadalafil AUC by 124%; coadministration with rifampin (inducer) reduced taladafil AUC by 88%;
Page: 49.0
P-gp
724
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
796
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:71940
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:71940
ChemicalBook
CB2236841
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2236841
MolPort
MolPort-002-885-864
https://www.molport.com/shop/molecule-link/MolPort-002-885-864
Selleck Chemicals
Tadalafil(Cialis)
http://www.selleckchem.com/products/Tadalafil(Cialis).html
ZINC
ZINC000003993855
http://zinc15.docking.org/substances/ZINC000003993855
eMolecules
29781353
https://www.emolecules.com/cgi-bin/more?vid=29781353
eMolecules
33507691
https://www.emolecules.com/cgi-bin/more?vid=33507691
eMolecules
36754634
https://www.emolecules.com/cgi-bin/more?vid=36754634
PubMed

PubMed

TitleDatePubMed
On-demand IC351 (Cialis) enhances erectile function in patients with erectile dysfunction.
2001 Feb
Gateways to clinical trials.
2002 Dec
Effects of tadalafil on erectile dysfunction in men with diabetes.
2002 Dec
IC351 (tadalafil, Cialis): update on clinical experience.
2002 Feb
Selective phosphodiesterase type 5 inhibition using tadalafil for the treatment of erectile dysfunction.
2002 Nov
[Erectile dysfunction].
2002 Oct
Gateways to clinical trials.
2002 Oct
Erectile dysfunction: comparison of efficacy and side effects of the PDE-5 inhibitors sildenafil, vardenafil and tadalafil--review of the literature.
2002 Oct 29
Family complains that "love drug'"will smear their name.
2002 Sep 7
Tadalafil.
2003
[How effective are PDE-5 inhibitors?].
2003 Apr
The phosphodiesterase inhibitor 'war'.
2003 Apr
Effects of tadalafil on erectile dysfunction in men with diabetes.
2003 Aug
Coming attractions! New medications on the horizon for erectile dysfunction.
2003 Aug
Tadalafil in the treatment of erectile dysfunction.
2003 Dec
Tadalafil: a new agent for erectile dysfunction.
2003 Feb
New phosphodiesterase type 5 inhibitors in the management of erectile dysfunction.
2003 Jun
[New treatment options for erectile dysfunction. Pharmacologic and nonpharmacologic options].
2003 Jun
Pharmacological management of erectile dysfunction.
2003 Mar
Cardiovascular effects of tadalafil.
2003 Nov 6
Efficacy and tolerability of tadalafil, a novel phosphodiesterase 5 inhibitor, in treatment of erectile dysfunction.
2003 Nov 6
Overview of phosphodiesterase 5 inhibition in erectile dysfunction.
2003 Nov 6
[Drug therapy of erectile dysfunction--the current status].
2003 Oct
Phosphodiesterase type 5 inhibitors: a biochemical and clinical correlation survey.
2003 Oct
The discovery of tadalafil: a novel and highly selective PDE5 inhibitor. 1: 5,6,11,11a-tetrahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indole-1,3(2H)-dione analogues.
2003 Oct 9
Novel PDE5 inhibitors for the treatment of male erectile dysfunction.
2003 Oct-Nov
Novel phosphodiesterase type 5 inhibitors: assessing hemodynamic effects and safety parameters.
2004 Apr
Phosphodiesterase type 5 inhibitor differentiation based on selectivity, pharmacokinetic, and efficacy profiles.
2004 Apr
Pills for erectile dysfunction: now there are three.
2004 Apr
A multicenter, randomized, double-blind, crossover study to evaluate patient preference between tadalafil and sildenafil.
2004 Apr
Cardioprotection with phosphodiesterase-5 inhibition--a novel preconditioning strategy.
2004 Feb
Cialis is here. The soft sell.
2004 Feb 2
Are they better than Viagra? Two new drugs for erectile dysfunction work like Viagra and carry similar risks and benefits. Their subtle differences, however, may make a difference for some men.
2004 Jan
[Erectile dysfunction. New drugs with special consideration of the PDE 5 inhibitors].
2004 Jul
The efficacy and safety of tadalafil: an update.
2004 Jun
Atazanavir (Reyataz): new recommendations if combined with tenofovir (Viread) -- and warning on Viagra, Cialis, and Levitra.
2004 Mar 26
New drugs of 2003.
2004 Mar-Apr
Interactions between cGMP- and cAMP-pathways are involved in the regulation of penile smooth muscle tone.
2004 Oct
Patents

Patents

JP2008520751A
1
JP2013241463A
1

Sample Use Guides

In Vivo Use Guide
ED: Starting dose: 10 mg as needed prior to sexual activity. Increase to 20 mg or decrease to 5 mg based upon efficacy/tolerability. Improves erectile function compared to placebo up to 36 hours post dose. Not to be taken more than once per day
Route of Administration: Oral
In Vitro Use Guide
Increasing levels of tadalafil (1–25 uM) attenuated proliferation of human primary prostatic stromal cells (PrSCs) in a dose-dependent manner with concentrations above 5 uM showing highly significant effects
Name Type Language
TADALAFIL
EMA EPAR   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
(6R,12AR)-2,3,6,7,12,12A-HEXAHYDRO-2-METHYL-6-(3,4-(METHYLENEDIOXY)PHENYL) PYRAZINO(1',2':1,6)PYRIDO(3,4-B)INDOLE-1,4-DIONE
Common Name English
TADALAFIL [HSDB]
Common Name English
TRANS-TADALAFIL
Common Name English
TADALAFIL [WHO-DD]
Common Name English
TADALAFIL [MART.]
Common Name English
TADALAFIL [USP MONOGRAPH]
Common Name English
TADALAFIL [JAN]
Common Name English
PYRAZINO(1',2':1,6)PYRIDO(3,4-B)INDOLE-1,4-DIONE, 6-(1,3-BENZODIOXOL-5-YL)-2,3,6,7,12,12A-HEXAHYDRO-2-METHYL-, (6R-12AR)-
Common Name English
CIALIS
Brand Name English
TADALAFIL [MI]
Common Name English
LY-450190
Code English
TADALAFIL [EP MONOGRAPH]
Common Name English
TADALAFIL [EMA EPAR]
Common Name English
LY450190
Code English
TADALAFIL [USP-RS]
Common Name English
NSC-759172
Code English
TADALAFIL MYLAN
Brand Name English
TADALAFIL [USAN]
Common Name English
TADALAFIL [INN]
Common Name English
TADALAFIL [VANDF]
Common Name English
NSC-750236
Code English
(6R-TRANS)-6-(1,3-BENZODIOXOL-5-YL)-2,3,6,7,12,12A-HEXAHYDRO-2-METHYL-PYRAZINO(1',2':1,6)PYRIDO(3,4-B)INDOLE-1,4-DIONE
Common Name English
IC351
Code English
TADALAFIL [ORANGE BOOK]
Common Name English
IC-351
Code English
Classification Tree Code System Code
WHO-ATC C02KX52
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
FDA ORPHAN DRUG 528316
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
EMA ASSESSMENT REPORTS CIALIS (AUTHORIZED: ERECTILE DYSFUNCTIONS)
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
NDF-RT N0000175599
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
EMA ASSESSMENT REPORTS ADCIRCA (AUTHORIZED: HYPERTENSION, PULMONARY)
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
NDF-RT N0000020026
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
FDA ORPHAN DRUG 476415
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
EMA ASSESSMENT REPORTS TADALAFIL MYLAN (AUTHORIZED: ERECTILE DYSFUNCTIONS)
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
FDA ORPHAN DRUG 228206
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
NCI_THESAURUS C2127
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
WHO-VATC QG04BE08
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
FDA ORPHAN DRUG 509615
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
WHO-ATC G04BE08
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
LIVERTOX 920
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
Code System Code Type Description
CAS
171596-29-5
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
INN
8136
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
IUPHAR
7299
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
HSDB
7303
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
RXCUI
358263
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY RxNorm
LACTMED
Tadalafil
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
MESH
C429886
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
FDA UNII
742SXX0ICT
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
USP_CATALOG
1642879
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB00820
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
PUBCHEM
110635
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
EVMPD
SUB12602MIG
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
ChEMBL
CHEMBL779
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
NCI_THESAURUS
C47743
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
MERCK INDEX
M10427
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY Merck Index
EPA CompTox
171596-29-5
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
DRUG CENTRAL
2553
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
WIKIPEDIA
TADALAFIL
Created by admin on Fri Jun 25 21:08:53 UTC 2021 , Edited by admin on Fri Jun 25 21:08:53 UTC 2021
PRIMARY
ACTIVE MOIETY
Structure of TADALAFIL
NIH
NCATS
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DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966