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:: 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
3656
Curator's Comment:: Tadalafil crosses the blood-brain barrier and reverses cognitive dysfunction in a mouse model of AD.

Originator

Approval Year

2003
63
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7701
 100 µM [IC50]
Inhibitor
7701
 5.09999999999999964 µM [IC50]
Inhibitor
7701
 0.0500000000000000028 µM [IC50]
Inhibitor
7701
Benign prostatic hyperplasia
Erectile dysfunction
 5 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phosphodiesterase 5A
Approved
7997
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

1069286400000
Primary
Phosphodiesterase 5A
Approved
7997
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

1069286400000
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)
Health Status: pregnant
Age Group: 28 years (range: 20–39 years)
Sex: F
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
Health Status: unhealthy
Age Group: 54.9 years
Sex: M
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
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)
Health Status: pregnant
Age Group: 28 years (range: 20–39 years)
Sex: F
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)
Health Status: pregnant
Age Group: 28 years (range: 20–39 years)
Sex: F
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
Health Status: unhealthy
Age Group: 54.9 years
Sex: M
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
Health Status: unhealthy
Age Group: 54.9 years
Sex: M
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
Health Status: unhealthy
Age Group: 54.9 years
Sex: M
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
Health Status: unhealthy
Age Group: 54.9 years
Sex: M
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
Health Status: unhealthy
Age Group: 54.9 years
Sex: M
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
Health Status: unhealthy
Age Group: 54.9 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/15925082/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1470

inhibitor
1172

inducer
657
inhibitor
1318

inducer
343
inhibitor
1421

inducer
93
inhibitor
1360

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1268

CYP2C19
1215

CYP2E1
761
P-gp
1223
CYP1A2
618

CYP2C19
260

CYP2E1
116
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C19
1277
 no
CYP2D6
1455
 no
CYP2D6
1455
 no
CYP2E1
841
 no
CYP2E1
841
 no
CYP1A2
1406
 no
no (co-administration study)
Comment: taladafil had no clinically significant effect on PK of theophylline
Page: 14
CYP1A2
1406
 no
no (co-administration study)
Comment: taladafil had no clinically significant effect on PK of theophylline
Page: 14
CYP2C9
1362
 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
CYP2C9
1362
 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
CYP3A4
1462
 no
no (co-administration study)
Comment: taladafil had no clinically significant effect on exposure (AUC) to midazolam or lovastatin
Page: 14
CYP3A4
1462
 no
no (co-administration study)
Comment: taladafil had no clinically significant effect on exposure (AUC) to midazolam or lovastatin
Page: 14
CYP2C19
1277
 not significant [Ki 73 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1470
 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
P-gp
1223
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1392
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:71940
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:71940
MolPort
MolPort-002-885-864
https://www.molport.com/shop/molecule-link/MolPort-002-885-864
ZINC
ZINC000003993855
http://zinc15.docking.org/substances/ZINC000003993855
PubMed

PubMed

TitleDatePubMed
PDE-5 inhibition and sexual response: pharmacological mechanisms and clinical outcomes.
2002
The phosphodiesterase inhibitor 'war'.
2003 Apr
Tadalafil: a new treatment for erectile dysfunction.
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
Hypogonadism and erectile dysfunction: the role for testosterone therapy.
2003 Aug
[Erectile dysfunction to be taken seriously. Otherwise, the psyche becomes limp, too].
2003 Aug 7
Tadalafil: new preparation. Slightly more convenient, but poorly assessed in organic disorders.
2003 Dec
Oral drug treatment of erectile dysfunction.
2003 Dec
Tadalafil for the treatment of erectile dysfunction.
2003 Dec
Tadalafil (cialis) for erectile dysfunction.
2003 Dec 22
Tadalafil, a further innovation in the treatment of sexual dysfunction.
2003 Feb
Tadalafil: a new agent for erectile dysfunction.
2003 Feb
Pharmacology of phosphodiesterase 5 inhibitors.
2003 Feb
[Good sex inspite of erectile dysfunction. A new PDE-5 inhibitor gives more latitude].
2003 Feb 20
Tadalafil Lilly ICOS.
2003 Jan
[Erectile dysfunction and phosphodiesterase type 5 inhibitors].
2003 Jun
[New treatment options for erectile dysfunction. Pharmacologic and nonpharmacologic options].
2003 Jun
[Risk classification assures safety].
2003 Mar 13
[PDE-5 inhibitor with improved pharmacokinetics. Far-reaching return to normality].
2003 Mar 13
Switching patients with erectile dysfunction from sildenafil citrate to tadalafil: results of a European multicenter, open-label study of patient preference.
2003 Nov
Review of tadalafil in the treatment of erectile dysfunction.
2003 Nov
Roundtable discussion: tadalafil study group.
2003 Nov 6
Overview of phosphodiesterase 5 inhibition in erectile dysfunction.
2003 Nov 6
[Efficacy and safety of the application of cialis for erectile dysfunction].
2003 Nov-Dec
Cialis (tadalafil): a new treatment for erectile dysfunction.
2003 Oct
[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. 2: 2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione analogues.
2003 Oct 9
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
[Medication of the month. Vardenafil (Levitra)].
2003 Sep
Phosphodiesterase 5 inhibitors in male sexual dysfunction.
2003 Sep
Tadalafil has no detrimental effect on human spermatogenesis or reproductive hormones.
2003 Sep
Structure of the catalytic domain of human phosphodiesterase 5 with bound drug molecules.
2003 Sep 4
Sexual dysfunction and diabetes.
2004 Apr
[Comparison of efficacy and safety of phosphodiesterase type 5 inhibitors in the treatment of erectile dysfunction].
2004 Apr
Gateways to clinical trials.
2004 Apr
Phosphodiesterase type 5 inhibitor differentiation based on selectivity, pharmacokinetic, and efficacy profiles.
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
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
Third drug for impotence.
2004 Jan-Feb
[Erectile dysfunction. New drugs with special consideration of the PDE 5 inhibitors].
2004 Jul
The efficacy and safety of tadalafil: an update.
2004 Jun
Re: tadalafil has no detrimental effect on human spermatogenesis or reproductive hormones.
2004 Jun
Time course of the interaction between tadalafil and nitrates.
2004 Jun 2
Therapeutic options for patients returning to sexual activity.
2004 Mar
Atazanavir (Reyataz): new recommendations if combined with tenofovir (Viread) -- and warning on Viagra, Cialis, and Levitra.
2004 Mar 26
Emerging oral drugs for erectile dysfunction.
2004 May
Nocturnal electrobioimpedance volumetric assessment in diabetic men with erectile dysfunction before and after tadalafil intake.
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
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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ACCESSIBILITY
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