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Also known as: Cialis, 171596-29-5, Ic351, Tadanafil, Adcirca, Ic 351
Molecular Formula
C22H19N3O4
Molecular Weight
389.4  g/mol
InChI Key
WOXKDUGGOYFFRN-IIBYNOLFSA-N
FDA UNII
742SXX0ICT

Tadalafil
A carboline derivative and PHOSPHODIESTERASE 5 INHIBITOR that is used primarily to treat ERECTILE DYSFUNCTION; BENIGN PROSTATIC HYPERPLASIA and PRIMARY PULMONARY HYPERTENSION.
Tadalafil is a Phosphodiesterase 5 Inhibitor. The mechanism of action of tadalafil is as a Phosphodiesterase 5 Inhibitor.
1 2D Structure

Tadalafil

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R,8R)-2-(1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione
2.1.2 InChI
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
2.1.3 InChI Key
WOXKDUGGOYFFRN-IIBYNOLFSA-N
2.1.4 Canonical SMILES
CN1CC(=O)N2C(C1=O)CC3=C(C2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36
2.1.5 Isomeric SMILES
CN1CC(=O)N2[C@@H](C1=O)CC3=C([C@H]2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36
2.2 Other Identifiers
2.2.1 UNII
742SXX0ICT
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cialis

2. Ic 351

3. Ic-351

4. Ic351

5. 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)-

2.3.2 Depositor-Supplied Synonyms

1. Cialis

2. 171596-29-5

3. Ic351

4. Tadanafil

5. Adcirca

6. Ic 351

7. Icos 351

8. Ic-351

9. Gf 196960

10. (6r,12ar)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4(6h,7h)-dione

11. Tadalafil Mylan

12. Trans-tadalafil

13. Tadalafil(cialis)

14. (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

15. (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

16. Chembl779

17. Nsc-750236

18. Nsc-759172

19. 742sxx0ict

20. Gf-196960

21. Ly-450190

22. (6r,12ar)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

23. Chebi:71940

24. Tadalafil [usan]

25. Ly450190

26. Dsstox_cid_26786

27. Dsstox_rid_81904

28. Dsstox_gsid_46786

29. (6r,12ar)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

30. 6-benzo[1,3]dioxol-5-yl-2-methyl-2,3,6,7,12,12a-hexahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

31. Tadalafil Lilly

32. Smr000466321

33. Cialis (tn)

34. Tildenafil

35. Cas-171596-29-5

36. Hsdb 7303

37. Unii-742sxx0ict

38. Tadalafila

39. Tadalafilo

40. Taldalafil

41. Tadalafil [usan:inn:ban]

42. Tadalafil Solution

43. 1xoz

44. Cialis, Tadalafil

45. Ncgc00168781-01

46. Tadalafil- Bio-x

47. (2r,8r)-2-(1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11,13,15-tetraene-4,7-dione

48. Adcirca (tn)

49. Tadalafil (cialis)

50. Zalutia (tn)

51. (6r,12ar)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione

52. Ks-1117

53. Tadalafil [inn]

54. Tadalafil [jan]

55. Tadalafil [mi]

56. Tadalafil; Cialis

57. Tadalafil [hsdb]

58. Tadalafil [vandf]

59. (-)-tadalafil (6r)

60. Tadalafil [mart.]

61. Tadalafil [usp-rs]

62. Tadalafil [who-dd]

63. Tadalafil (jan/usp/inn)

64. Schembl33333

65. Tadalafil [ema Epar]

66. Mls000759426

67. Mls001165782

68. Mls001195644

69. Mls001424132

70. Mls006010126

71. Tadalafil Specified Impurity A

72. Gtpl7299

73. Tadalafil [orange Book]

74. Dtxsid9046786

75. Tadalafil [ep Monograph]

76. Bdbm14777

77. Tadalafil (6r ,12as)- Lilly

78. Tadalafil [usp Monograph]

79. Entadfi Component Tadalafil

80. Hms2051n17

81. Hms2235l21

82. Hms3884g19

83. Pharmakon1600-01505639

84. Amy10321

85. Ex-a2644

86. Zinc3993855

87. Tox21_112642

88. Hy-90009a

89. Mfcd07771966

90. Nsc750236

91. Nsc759172

92. S1512

93. Tadalafil 1.0 Mg/ml In Acetonitrile

94. Tadalafil 100 Microg/ml In Methanol

95. Tadalafil Component Of Entadfi

96. Akos015892559

97. Tox21_112642_1

98. Ab42193

99. Ccg-100973

100. Cs-1414

101. Db00820

102. Nc00223

103. Nsc 750236

104. Nsc 759172

105. 1,3-benzodioxol-5-yl(methyl)[?]dione

106. Ncgc00263909-02

107. Tadalafil 100 Microg/ml In Acetonitrile

108. (6r,12ar)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

109. Bt164435

110. Gf196960

111. 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)-

112. 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-trans)-

113. (-)-tadalafil (6r ,12as) Diastereomer

114. Sw197603-2

115. A23556

116. D02008

117. Ab00639969-08

118. Ab00639969_09

119. Ab00639969_10

120. 596t295

121. Ar-270/43507798

122. Q424156

123. Sr-05000001940

124. Sr-05000001940-1

125. Brd-k93645900-001-04-8

126. Tadalafil Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

127. (2r,8r)-2-(1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione

128. (2r,8r)-2-(2h-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11(16),12,14-tetraene-4,7-dione

129. (2r,8r)-2-(2h-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11,13,15-tetraene-4,7-dione

130. (6r,12 Ar)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

131. (6r,12ar) 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino [1',2':1,6] Pyrido[3,4-b]indole-1,4-dione

132. (6r,12ar) 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

133. (6r,12ar)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1,2:1,6]pyrido[3,4-b]indole-1,4-dione

134. (6r,12ar)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1,2,1,6]pyrido[3,4-b]indole-1,4-dione

135. (6r,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

136. 1242099-07-5

137. 171488-03-2

138. 6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

139. 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)-

140. Pyrazino[1',6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12ahexahydro-2-methyl-, (6r,12ar)-

141. Rel-(6r,12ar)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4(6h,7h)-dione

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 389.4 g/mol
Molecular Formula C22H19N3O4
XLogP32.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Exact Mass389.13755610 g/mol
Monoisotopic Mass389.13755610 g/mol
Topological Polar Surface Area74.9 Ų
Heavy Atom Count29
Formal Charge0
Complexity702
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameAdcirca
PubMed HealthTadalafil (By mouth)
Drug ClassesAntihypertensive, Erectile Dysfunction Agent
Drug LabelADCIRCA (tadalafil), an oral treatment for pulmonary arterial hypertension, is a selective inhibitor of cyclic guanosine monophosphate (cGMP)specific phosphodiesterase type 5 (PDE5). Tadalafil has the empirical formula C22H19N3O4 representing a mo...
Active IngredientTadalafil
Dosage FormTablet
RouteOral
Strength20mg
Market StatusPrescription
CompanyEli Lilly

2 of 6  
Drug NameCialis
PubMed HealthTadalafil (By mouth)
Drug ClassesAntihypertensive, Erectile Dysfunction Agent
Drug LabelCIALIS (tadalafil) is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5). Tadalafil has the empirical formula C22H19N3O4 representing a molecular weight of 389.41. The structural formula is: The ch...
Active IngredientTadalafil
Dosage FormTablet
RouteOral
Strength2.5mg; 5mg; 10mg; 20mg
Market StatusPrescription
CompanyLilly

3 of 6  
Drug NameTadalafil
PubMed HealthTadalafil (By mouth)
Drug ClassesAntihypertensive, Erectile Dysfunction Agent
Drug LabelCIALIS (tadalafil) is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5). Tadalafil has the empirical formula C22H19N3O4 representing a molecular weight of 389.41. The structural formula is: The ch...
Active IngredientTadalafil
Dosage FormTablet
Routeoral
Strength20mg
Market StatusTentative Approval
CompanySynthon Pharms

4 of 6  
Drug NameAdcirca
PubMed HealthTadalafil (By mouth)
Drug ClassesAntihypertensive, Erectile Dysfunction Agent
Drug LabelADCIRCA (tadalafil), an oral treatment for pulmonary arterial hypertension, is a selective inhibitor of cyclic guanosine monophosphate (cGMP)specific phosphodiesterase type 5 (PDE5). Tadalafil has the empirical formula C22H19N3O4 representing a mo...
Active IngredientTadalafil
Dosage FormTablet
RouteOral
Strength20mg
Market StatusPrescription
CompanyEli Lilly

5 of 6  
Drug NameCialis
PubMed HealthTadalafil (By mouth)
Drug ClassesAntihypertensive, Erectile Dysfunction Agent
Drug LabelCIALIS (tadalafil) is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5). Tadalafil has the empirical formula C22H19N3O4 representing a molecular weight of 389.41. The structural formula is: The ch...
Active IngredientTadalafil
Dosage FormTablet
RouteOral
Strength2.5mg; 5mg; 10mg; 20mg
Market StatusPrescription
CompanyLilly

6 of 6  
Drug NameTadalafil
PubMed HealthTadalafil (By mouth)
Drug ClassesAntihypertensive, Erectile Dysfunction Agent
Drug LabelCIALIS (tadalafil) is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5). Tadalafil has the empirical formula C22H19N3O4 representing a molecular weight of 389.41. The structural formula is: The ch...
Active IngredientTadalafil
Dosage FormTablet
Routeoral
Strength20mg
Market StatusTentative Approval
CompanySynthon Pharms

4.2 Therapeutic Uses

Tadalafil is indicated for the treatment of erectile dysfunction. /Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004.


4.3 Drug Warning

The Food and Drug Administration ... approved updated labeling for Cialis, Levitra and Viagra to reflect a small number of post-marketing reports of sudden vision loss, attributed to NAION (non arteritic ischemic optic neuropathy), a condition where blood flow is blocked to the optic nerve. FDA advises patients to stop taking these medicines, and call a doctor or healthcare provider right away if they experience sudden or decreased vision loss in one or both eyes. Further, patients taking or considering taking these products should inform their health care professionals if they have ever had severe loss of vision, which might reflect a prior episode of NAION. Such patients are at an increased risk of developing NAION again.

US FDA; FDA Statement. FDA Updates Labeling for Viagra, Cialis and Levitra for Rare Post-Marketing Reports of Eye Problems (July 8, 2005) Available from, as of July 12, 2005: https://www.fda.gov/bbs/topics/NEWS/2005/NEW01201.html


Cardiovascular status of patients should be considered since there is a degree of risk associated with sexual activity; treatments for erectile dysfunction, including tadalafil, should not be used in men for whom sexual activity is inadvisable as a result of their underlying cardiac status.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004.


The following groups of patients with cardiovascular disease were not included in clinical safety and efficacy trials for Cialis, and, therefore, the use of Cialis is not recommended in these groups until further information is available: patients with a myocardial infarction within the last 90 days, patients with unstable angina or angina occurring during sexual intercourse, patients with New York Heart Association Class 2 or greater heart failure in the last 6 months, patients with uncontrolled arrhythmias, hypotension (<90/50 mm Hg), or uncontrolled hypertension (>170/100 mm Hg), and patients with a stroke within the last 6 months. In addition, patients with known hereditary degenerative retinal disorders, including retinitis pigmentosa, were not included in the clinical trials, and use in these patients is not recommended.

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004.


The effect of a 100 mg single dose of tadalafil on the QT interval was evaluated at the time of peak tadalafil concentration in a randomized, double-blinded, placebo, and active (intravenous ibutilide)-controlled crossover study in 90 healthy males aged 18 to 53 years. The mean change in QTc (Fridericia QT correction) for tadalafil, relative to placebo, was 3.5 milliseconds (two-sided 90% CI=1.9, 5.1). The mean change in QTc (Individual QT correction) for tadalafil, relative to placebo, was 2.8 milliseconds (two-sided 90% CI=1.2, 4.4). A 100 mg dose of tadalafil (5 times the highest recommended dose) was chosen because this dose yields exposures covering those observed upon coadministration of tadalafil with potent CYP3A4 inhibitors or those observed in renal impairment. In this study, the mean increase in heart rate associated with /this/ dose of tadalafil compared to placebo was 3.1 beats per minute.

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004.


For more Drug Warnings (Complete) data for TADALAFIL (18 total), please visit the HSDB record page.


4.4 Drug Indication

Tadalafil is indicated for the treatment of erectile dysfunction (ED) and either alone or in combination with [finasteride] for the treatment of benign prostatic hypertrophy (BPH). It is also indicated for the treatment of pulmonary arterial hypertension (PAH) both alone and in combination with [macitentan] or other endothelin-1 antagonists.


FDA Label


Adcirca is indicated in adults for the treatment of pulmonary arterial hypertension (PAH) classified as World Health Organization functional class II and III, to improve exercise capacity (see section 5. 1).

Efficacy has been shown in idiopathic PAH (IPAH) and in PAH related to collagen vascular disease.


Treatment of erectile dysfunction.

In order for tadalafil to be effective, sexual stimulation is required.

Cialis is not indicated for use by women.


Treatment of erectile dysfunction in adult males.

In order for tadalafil to be effective, sexual stimulation is required.

Tadalafil Lilly is not indicated for use by women.

Treatment of the signs and symptoms of benign prostatic hyperplasia in adult males.


Treatment of erectile dysfunction in adult males.

In order for tadalafil to be effective, sexual stimulation is required.

Tadalafil Mylan is not indicated for use by women.


Talmanco is indicated in adults for the treatment of pulmonary arterial hypertension (PAH) classified as WHO functional class II and III, to improve exercise capacity. Efficacy has been shown in idiopathic PAH (IPAH) and in PAH related to collagen vascular disease.


Treatment of pulmonary arterial hypertension


5 Pharmacology and Biochemistry
5.1 Pharmacology

Tadalafil exerts a therapeutic effect in ED by increasing sexual stimulation-dependant smooth muscle relaxation in the penis, allowing the corpus cavernosum to fill with blood to produce an erection. Smooth muscle relaxation in the pulmonary vasculature helps to produce vasodilation in PAH which reduces blood pressure in the pulmonary arteries. In BPH, tadalafil may contribute to decreased smooth muscle cell proliferation which may reduce the size of the prostate and relieve the anatomical obstruction which produces urinary symptoms of BPH. The decreased affinity of tadalafil for PDE6 compared to other PDE5 inhibitors may explain the reduced incidence of visual side effects.


5.2 MeSH Pharmacological Classification

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


Phosphodiesterase 5 Inhibitors

Compounds that specifically inhibit PHOSPHODIESTERASE 5. (See all compounds classified as Phosphodiesterase 5 Inhibitors.)


Urological Agents

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS. (See all compounds classified as Urological Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
TADALAFIL
5.3.2 FDA UNII
742SXX0ICT
5.3.3 Pharmacological Classes
Phosphodiesterase 5 Inhibitors [MoA]; Phosphodiesterase 5 Inhibitor [EPC]
5.4 ATC Code

G04BE08


G04BE08


G04BE08


G04BE08


G04BE08


G04BE08

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


G - Genito urinary system and sex hormones

G04 - Urologicals

G04B - Urologicals

G04BE - Drugs used in erectile dysfunction

G04BE08 - Tadalafil


5.5 Absorption, Distribution and Excretion

Absorption

Tadalafil has a tmax of 0.5-6h with a median of 2h in healthy adults. The tmax in adults with PAH is reported as 2-8h with a median of 4h. There does not appear to be a significant effect on absorption when tadalafil is taken with food.


Route of Elimination

Tadalafil is primarily eliminated via hepatic metabolism. These metabolites are mainly excreted in the feces (61%) and to a lesser extent in the urine (36%)


Volume of Distribution

Tadalafil has a mean apparent volume of distribution of 63L in healthy adults. The mean apparent volume of distribution is reported as 77L in adults with PAH.


Clearance

The mean apparent oral clearance of tadalafil is 2.5-3.4L/h in healthy adults. The mean apparent oral clearance in adults with PAH is reported as 3.5L/h


Tmax: 30 minutes to 6 hours (median 2 hours). Absolute bioavailability has not been determined; rate and extent of absorption are not influenced by food.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004.


Volume of distribution: 63 L; indicating distribution into tissues. Less than 0.0005% of administered dose was found in the semen of healthy subjects. 94% protein bound.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004.


Over a dose range of 2.5 to 20 mg, tadalafil exposure (AUC) increases proportionally with dose in healthy subjects. Steady-state plasma concentrations are attained within 5 days of once-daily dosing, and exposure is approximately 1.6-fold greater than after a single dose.

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004.


Elimination: Mean oral clearance: 2.5 L per hour. Fecal: 61%. Urine: 36%.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004.


For more Absorption, Distribution and Excretion (Complete) data for TADALAFIL (11 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Tadalafil undergoes hepatic metabolism via CYP3A4 to a catechol metabolite. This catechol metabolite undergoes subsequent methylation and glucuronidation with the methyl-glucuronide metabolite becoming the primary metabolite in circulation. None of the known metabolites are considered to be active.


Biotransformation: Hepatic metabolism, mainly by CYP3A4. Tadalafil is predominantly metabolized by CYP3A4 to a catechol metabolite. The catechol metabolite undergoes extensive methylation and glucuronidation to form the methylcatechol and methylcatechol glucuronide conjugate, respectively. The major circulating metabolite is the methylcatechol glucuronide. Methylcatechol concentrations are less than 10% of glucuronide concentrations. In vitro data suggests that metabolites are not expected to be pharmacologically active at observed metabolite concentrations.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004.


5.7 Biological Half-Life

The mean half-life of elimination of tadalafil is 15-17.5h in healthy adults. The mean half-life of elimination in adults with PAH is reported as 35h.


Terminal: 17.5 hours

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004.


5.8 Mechanism of Action

Tadalafil is a selective phosphodiesterase-5 (PDE5) inhibitor that produces several downstream effects with the most common therapeutic effect being smooth muscle relaxation. Patients may experience ED due to a variety of causes including psychogenic, neurogenic, vasculogenic, iatrogenic, or endocrine. These causes result in dysfunction of penile smooth muscle relaxation through either disrupted neuronal signaling or direct influence on smooth muscle cells. During sexual arousal, non-adrenergic non-cholinergic (NANC) neurons release nitric oxide (NO). Nitric oxide stimulates guanylate cyclase which converts guanosine triphosphate to cyclic guanosine monophosphate (cGMP). cGMP activates the cGMP-dependent kinase (PKG) in a signal cascade which activates K+ channels leading to inhibition of Ca2+ channels, inhibits platelet activation, and inhibits smooth muscle cell proliferation while inducing apoptosis. This signal cascade is attenuated by PDE5 which breaks the phosphodiester bond of cGMP, converting it to GMP. Inhibition of PDE5 by tadalafil increases signaling via the PKG cascade which supports penile smooth muscle relaxation during sexual arousal by decreasing Ca2+ entry into smooth muscle cells. This smooth muscle relaxation allows blood to fill the corpus cavernosum thereby producing an erection. In PAH, blood pressure in the pulmonary arteries is raised due to a variety of mechanisms stemming from endothelial dysfunction. Decreased production of NO and prostacyclin reduce vasodilatory signaling while overproduction of endothelin-1 and thromboxane increase vasoconstriction. Inflammation, thromboses, and hypoxia later contribute to vascular remodeling which further reduces luminal size. The resultant increase in blood pressure reduces the capacity for gas exchange and increases afterload at the right ventricle, producing symptoms of dyspnea, fatigue, and dizziness as well as leading to right-sided heart failure. Tadalafil exerts its therapeutic effect in PAH through boosting NO-cGMP signaling to contribute to smooth muscle relaxation as with ED. Lastly, tadalafil is used to treat BPH. BPH produces urinary dysfunction through hyperproliferation of the epithelial and smooth muscle layers of the prostate. The increased size of the prostate blocks urine flow through the urethra resulting in higher residual volumes due to incomplete emptying. Tadalafil does not appear to exert its benefit via smooth muscle relaxation of the prostate. It may instead exert its effect through a mix of increased oxygenation and decreased inflammation, which decreases tissue remodeling, and inhibition of cell proliferation through the cGMP cascade. The decreased affinity for PDE6 compared to other PDE5 inhibitors may explain the decreased incidence of visual side effects as PDE6 is present in the eye and contributes to color vision.


In vitro studies have shown that the effect of tadalafil is more potent on phosphodiesterase type 5 (PDE5) than on other phosphodiesterases. These studies have shown that tadalafil is >10,000-fold more potent for PDE5 than for PDE1, PDE2, PDE4, and PDE7 enzymes, which are found in the heart, brain, blood vessels, liver, leukocytes, skeletal muscle, and other organs. Tadalafil is >10,000-fold more potent for PDE5 than for PDE3, an enzyme found in the heart and blood vessels. Additionally, tadalafil is 700-fold more potent for PDE5 than for PDE8, PDE9, PDE10 and 14-fold more potent for PDE5 than for PDE11A1, an enzyme found in human skeletal muscle. Tadalafil inhibits human recombinant PDE11A1 activity at concentrations within the therapeutic range. The physiological role and clinical consequence of PDE11 inhibition in humans have not been defined.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004.


Studies in vitro have demonstrated that tadalafil is a selective inhibitor of phosphodiesterase type 5 (PDE5). PDE5 is found in corpus cavernosum smooth muscle, vascular and visceral smooth muscle, skeletal muscle, platelets, kidney, lung, cerebellum, and pancreas.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004.


Penile erection during sexual stimulation is caused by increased penile blood flow resulting from the relaxation of penile arteries and corpus cavernosum smooth muscle. This response is mediated by the release of nitric oxide (NO) from nerve terminals and endothelial cells, which stimulates the synthesis of cyclic GMP 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) enhances erectile function by increasing the amount of cyclic GMP. Tadalafil inhibits PDE5. Because sexual stimulation is required to initiate the local release of nitric oxide, the inhibition of PDE5 by tadalafil has no effect on the absence of sexual stimulation.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004.


API Reference Price

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AP.","supplier":"MSN ORGANICS PRIVATE LIMITED","supplierCountry":"INDIA","foreign_port":"BASLE","customer":"AIRPHARM PRATTELN","customerCountry":"SWITZERLAND","quantity":"30.00","actualQuantity":"30","unit":"KGS","unitRateFc":"396","totalValueFC":"11511.8","currency":"USD","unitRateINR":32847.73333333333,"date":"30-Apr-2025","totalValueINR":"985432","totalValueInUsd":"11511.8","indian_port":"Hyderabad Air","hs_no":"29337990","bill_no":"1402376","productDescription":"API","marketType":"REGULATED MARKET","country":"SWITZERLAND","selfForZScoreResived":"Pharma Grade","supplierPort":"Hyderabad Air","supplierAddress":"MSN HOUSE, PLOT NO.C-24,, HYDERABAD. AP.","customerAddress":""},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q2","strtotime":1649269800,"product":"RE-IMPORT TADALAFIL USP (SB NO: 6694631 \/DATE:13.12.2021)","address":"H.NO.8-3-166\/7\/1, HETERO HOUSE, ERRAGADDA Contact No: 919396743330","city":"HYDERABAD","supplier":"APEX PHARMA","supplierCountry":"EGYPT","foreign_port":"NA","customer":"HONOUR LAB LIMITED","customerCountry":"INDIA","quantity":"100.00","actualQuantity":"100","unit":"KGS","unitRateFc":"285","totalValueFC":"29812.2","currency":"USD","unitRateINR":"22493","date":"07-Apr-2022","totalValueINR":"2249300.77","totalValueInUsd":"29812.2","indian_port":"MADRAS AIR","hs_no":"29349990","bill_no":"8173193","productDescription":"API","marketType":"","country":"EGYPT","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"H.NO.8-3-166\/7\/1, HETERO HOUSE, ERRAGADDA Contact No: 919396743330"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q3","strtotime":1663785000,"product":"TADALAFIL-USP BATCH NO.TAD220058 MGF JUNE 2022 EXP MAY 2025(RETURNED GOODS)","address":"309,3RD FLOOR,TIMES TRADE CENTER,B RTS ROAD, PUNAGAM","city":"SURAT,GUJARAT","supplier":"PHYTO ANDRO PTY LTD","supplierCountry":"INDIA","foreign_port":"NA","customer":"ATOM PHARMA","customerCountry":"INDIA","quantity":"30.00","actualQuantity":"30","unit":"KGS","unitRateFc":"250","totalValueFC":"8217.6","currency":"USD","unitRateINR":"21952.2","date":"22-Sep-2022","totalValueINR":"658566.45","totalValueInUsd":"8217.6","indian_port":"AHMEDABAD AIR","hs_no":"29420090","bill_no":"2562102","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"309,3RD FLOOR,TIMES TRADE CENTER,B RTS ROAD, PUNAGAM"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1727461800,"product":"TADALAFIL USP,(PACKING:06 DRUMS X 25 KG) BATCH:TD2311004,MFG:OCT 2023,EX P:SEP 2027(RE-IMPORT GOODS)","address":"154, SUKHDEV NAGAR","city":"PANIPAT\/HARYANA","supplier":"SHANGHAI AILINRUI BIOTECHNOLOGY CO LTD","supplierCountry":"INDIA","foreign_port":"GUANGZHOU","customer":"SILVERLINE CHEMICALS","customerCountry":"INDIA","quantity":"150.00","actualQuantity":"150","unit":"KGS","unitRateFc":"173.5","totalValueFC":"26568.6","currency":"USD","unitRateINR":"14843.2","date":"28-Sep-2024","totalValueINR":"2226484.29","totalValueInUsd":"26568.6","indian_port":"Delhi Air","hs_no":"29420090","bill_no":"5861336","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"GUANGZHOU","supplierAddress":"BUILDING C, NO. 888, HUANHU WEST 2ND ROAD.LINGANG NEW AREA CHINA (SHANGHAI) PILOT FREE TRADE ZONE CHINA","customerAddress":"154, SUKHDEV NAGAR"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1733682600,"product":"RE IMPORT OF TADALAFIL EP (EXPORTED VIDE SB NO. 8562601 DT.18.03.2023)RE IMPORT OF TADALAFIL EP (EXPORTED VIDE SB NO. 8562601 DT.","address":"2 FLR.PRESTIGE PLAZA","city":"AKOTA BARODA","supplier":"JSC ALIUM","supplierCountry":"INDIA","foreign_port":"MOSCOW DOMODEDOVO","customer":"AMI LIFESCIENCES PVT LTD","customerCountry":"INDIA","quantity":"20.00","actualQuantity":"20","unit":"KGS","unitRateFc":"800","totalValueFC":"16128.2","currency":"USD","unitRateINR":"68520","date":"09-Dec-2024","totalValueINR":"1370400","totalValueInUsd":"16128.2","indian_port":"Ahmedabad Air","hs_no":"29420090","bill_no":"7124227","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"MOSCOW DOMODEDOVO","supplierAddress":"BLD 2TERRITORY OF BLOCK A OBOLENSET TLEMENT SERPUKHOV MOSCOW REGION 142 279 RUSSIA (IN EUROPE)","customerAddress":"2 FLR.PRESTIGE PLAZA"},{"dataSource":"API Import","activeIngredients":"","year":"2025","qtr":"Q1","strtotime":1740940200,"product":"TADALAFIL (TADALAFIL USP)","address":"PLOT NO 75 INDUSTRIAL AREA PHASE -","city":"CHANDIGARH,CHANDIGARH","supplier":"INTAS PHARMACEUTICALS LTD","supplierCountry":"INDIA","foreign_port":"ZIPL-SEZ AHMEDABAD","customer":"ACME GENERICS PRIVATE LIMITED","customerCountry":"INDIA","quantity":"37.98","actualQuantity":"37.978","unit":"KGS","unitRateFc":"490","totalValueFC":"18853.6","currency":"USD","unitRateINR":"43000","date":"03-Mar-2025","totalValueINR":"1633054","totalValueInUsd":"18853.6","indian_port":"Ahmedabad-ZIPL-SEZ","hs_no":"29337990","bill_no":"8656991","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"ZIPL-SEZ AHMEDABAD","supplierAddress":"Plot No. 5 to 14, PHARMEZ Matoda, Sanand, Ahmedabad SDNF India","customerAddress":"PLOT NO 75 INDUSTRIAL AREA PHASE -"}]
06-Jan-2022
30-Apr-2025
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DOSAGE - TABLET;ORAL - 10MG

USFDA APPLICATION NUMBER - 21368

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DOSAGE - TABLET;ORAL - 2.5MG

USFDA APPLICATION NUMBER - 21368

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DOSAGE - TABLET;ORAL - 20MG

USFDA APPLICATION NUMBER - 21368

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DOSAGE - TABLET;ORAL - 5MG

USFDA APPLICATION NUMBER - 21368

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DOSAGE - TABLET;ORAL - 20MG

USFDA APPLICATION NUMBER - 22332

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ABOUT THIS PAGE

Looking for 171596-29-5 / Tadalafil API manufacturers, exporters & distributors?

Tadalafil manufacturers, exporters & distributors 1

29

PharmaCompass offers a list of Tadalafil API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Tadalafil manufacturer or Tadalafil supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Tadalafil manufacturer or Tadalafil supplier.

PharmaCompass also assists you with knowing the Tadalafil API Price utilized in the formulation of products. Tadalafil API Price is not always fixed or binding as the Tadalafil Price is obtained through a variety of data sources. The Tadalafil Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Tadalafil

Synonyms

Cialis, 171596-29-5, Ic351, Tadanafil, Adcirca, Ic 351

Cas Number

171596-29-5

Unique Ingredient Identifier (UNII)

742SXX0ICT

About Tadalafil

A carboline derivative and PHOSPHODIESTERASE 5 INHIBITOR that is used primarily to treat ERECTILE DYSFUNCTION; BENIGN PROSTATIC HYPERPLASIA and PRIMARY PULMONARY HYPERTENSION.

Tadalafil Manufacturers

A Tadalafil manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Tadalafil, including repackagers and relabelers. The FDA regulates Tadalafil manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Tadalafil API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Tadalafil manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Tadalafil Suppliers

A Tadalafil supplier is an individual or a company that provides Tadalafil active pharmaceutical ingredient (API) or Tadalafil finished formulations upon request. The Tadalafil suppliers may include Tadalafil API manufacturers, exporters, distributors and traders.

click here to find a list of Tadalafil suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Tadalafil USDMF

A Tadalafil DMF (Drug Master File) is a document detailing the whole manufacturing process of Tadalafil active pharmaceutical ingredient (API) in detail. Different forms of Tadalafil DMFs exist exist since differing nations have different regulations, such as Tadalafil USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Tadalafil DMF submitted to regulatory agencies in the US is known as a USDMF. Tadalafil USDMF includes data on Tadalafil's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Tadalafil USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Tadalafil suppliers with USDMF on PharmaCompass.

Tadalafil JDMF

The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

The Tadalafil Drug Master File in Japan (Tadalafil JDMF) empowers Tadalafil API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

PMDA reviews the Tadalafil JDMF during the approval evaluation for pharmaceutical products. At the time of Tadalafil JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

click here to find a list of Tadalafil suppliers with JDMF on PharmaCompass.

Tadalafil KDMF

In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

Pharmaceutical companies submit a Tadalafil Drug Master File in Korea (Tadalafil KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of Tadalafil. The MFDS reviews the Tadalafil KDMF as part of the drug registration process and uses the information provided in the Tadalafil KDMF to evaluate the safety and efficacy of the drug.

After submitting a Tadalafil KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their Tadalafil API can apply through the Korea Drug Master File (KDMF).

click here to find a list of Tadalafil suppliers with KDMF on PharmaCompass.

Tadalafil CEP

A Tadalafil CEP of the European Pharmacopoeia monograph is often referred to as a Tadalafil Certificate of Suitability (COS). The purpose of a Tadalafil CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Tadalafil EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Tadalafil to their clients by showing that a Tadalafil CEP has been issued for it. The manufacturer submits a Tadalafil CEP (COS) as part of the market authorization procedure, and it takes on the role of a Tadalafil CEP holder for the record. Additionally, the data presented in the Tadalafil CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Tadalafil DMF.

A Tadalafil CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Tadalafil CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Tadalafil suppliers with CEP (COS) on PharmaCompass.

Tadalafil WC

A Tadalafil written confirmation (Tadalafil WC) is an official document issued by a regulatory agency to a Tadalafil manufacturer, verifying that the manufacturing facility of a Tadalafil active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Tadalafil APIs or Tadalafil finished pharmaceutical products to another nation, regulatory agencies frequently require a Tadalafil WC (written confirmation) as part of the regulatory process.

click here to find a list of Tadalafil suppliers with Written Confirmation (WC) on PharmaCompass.

Tadalafil NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Tadalafil as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Tadalafil API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Tadalafil as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Tadalafil and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Tadalafil NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Tadalafil suppliers with NDC on PharmaCompass.

Tadalafil GMP

Tadalafil Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Tadalafil GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Tadalafil GMP manufacturer or Tadalafil GMP API supplier for your needs.

Tadalafil CoA

A Tadalafil CoA (Certificate of Analysis) is a formal document that attests to Tadalafil's compliance with Tadalafil specifications and serves as a tool for batch-level quality control.

Tadalafil CoA mostly includes findings from lab analyses of a specific batch. For each Tadalafil CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Tadalafil may be tested according to a variety of international standards, such as European Pharmacopoeia (Tadalafil EP), Tadalafil JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Tadalafil USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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