Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D05MQK
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| Former ID |
DAP000615
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| Drug Name |
Tadalafil
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| Synonyms |
ADCIRCA; Acdirca; Cialis; Tadanafil; Lilly brand of tadalafil; Tadalafil [USAN]; GF 196960; IC 351; ICOS 351; Ic351; Cialis (TN); GF-196960; IC-351; KS-1117; Tadalafil (JAN/USAN/INN); Cialis, GF 196960, IC 351, ICOS 351, Tadalafil; (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; (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; (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
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| Drug Type |
Small molecular drug
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| Indication | Erectile dysfunction [ICD-11: HA01.1; ICD-10: N48.4; ICD-9: 302.72, 607.84] | Approved | [1], [2] | |
| Therapeutic Class |
Antiimpotence Agents
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| Company |
Eli Lilly
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| Structure |
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Download2D MOL |
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| Formula |
C22H19N3O4
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| Canonical SMILES |
CN1CC(=O)N2C(C1=O)CC3=C(C2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36
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| 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
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| InChIKey |
WOXKDUGGOYFFRN-IIBYNOLFSA-N
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| CAS Number |
CAS 171596-29-5
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| PubChem Compound ID | ||||
| PubChem Substance ID |
585746, 833257, 7849070, 7980303, 10235225, 12015128, 14756405, 14805118, 26719828, 44439099, 46386604, 46393582, 46507646, 46515102, 48631155, 49665805, 49666420, 49681754, 50070180, 50070554, 50071306, 50930588, 53789230, 57338564, 71826083, 92308507, 103205141, 104253184, 104386552, 118046114, 124658965, 124757304, 124801305, 124976968, 125164108, 126670668, 126730649, 129612837, 131407413, 134337906, 134358339, 135067956, 137002812, 142183965, 144075910, 144206195, 152031978, 152344458, 160709391, 160821591
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| ChEBI ID |
CHEBI:71940
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| ADReCS Drug ID | BADD_D02106 | |||
| SuperDrug ATC ID |
G04BE08
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| SuperDrug CAS ID |
cas=171596295
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroides fragilis HMW 610
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Tadalafil can be metabolized by Bacteroides fragilis HMW 610 (log2FC = -0.523; p = 0.009). | |||
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Studied Microbe: Bacteroides fragilis HMW 615
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|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Tadalafil can be metabolized by Bacteroides fragilis HMW 615 (log2FC = -0.434; p = 0.041). | |||
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Studied Microbe: Bacteroides thetaiotaomicron 3731
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|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Tadalafil can be metabolized by Bacteroides thetaiotaomicron 3731 (log2FC = -0.448; p = 0.023). | |||
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Studied Microbe: Bacteroides thetaiotaomicron 7330
Show/Hide Hierarchy
|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Tadalafil can be metabolized by Bacteroides thetaiotaomicron 7330 (log2FC = -0.547; p = 0.048). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Phosphodiesterase 5A (PDE5A) | Target Info | Inhibitor | [4], [5], [6] |
| KEGG Pathway | Purine metabolism | |||
| cGMP-PKG signaling pathway | ||||
| NetPath Pathway | TGF_beta_Receptor Signaling Pathway | |||
| Reactome | cGMP effects | |||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7299). | |||
| REF 2 | Designing drugs for the treatment of female sexual dysfunction. Drug Discov Today. 2007 Sep;12(17-18):757-66. | |||
| REF 3 | Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467. | |||
| REF 4 | Pulmonary arterial hypertension: the most devastating vascular complication of systemic sclerosis. Rheumatology (Oxford). 2009 Jun;48 Suppl 3:iii25-31. | |||
| REF 5 | Phosphodiesterase type 5 inhibitors for the treatment of erectile dysfunction in patients with diabetes mellitus. Int J Impot Res. 2002 Dec;14(6):466-71. | |||
| REF 6 | Tadalafil (Cialis) for men with erectile dysfunction. Int J Clin Pract. 2002 May;56(4):300-4. | |||
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