English 
Español 
français 
العربية Search
Search
Tadalafil is a potent, selective inhibitor of phosphodiesterase type 5 (PDE5). Its chemical structure is based on a beta-carboline framework, distinct from the purine-based sildenafil.
Its systematic (IUPAC) name is (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.
Key chemical features include:
Fused Polycyclic System: A complex structure integrating piperazinedione, dihydroisoquinoline, and indole rings.
Methylenedioxyphenyl Group: A key substituent attached to the chiral core, contributing to its binding affinity.
Lactam Groups: Two cyclic amide (lactam) groups are critical for its interaction with the PDE5 enzyme.
Chiral Centers: It contains two specific chiral centers (6R and 12aR), which are essential for its high pharmacological activity. The stereochemistry is crucial for its fit within the PDE5 active site.
In summary, tadalafil is a complex, chiral, heterocyclic molecule whose specific three-dimensional shape allows it to competitively inhibit PDE5, leading to vasodilation. It is marketed under the brand name Cialis.
| Items | Specification | RESULT |
| APPEARANCE | White or almost white powder | Alomost white powder |
| Soluble in DMSO, slightly soluble in dichloromethane, almost insoluble in water | Conform |
| Product parameters | |
| Cas number: | 171596-29-5 |
| Appearance: | white or almost white powder |
| Purity: | 97.5%–101.0% |
| Package details: | 1kg/Foil bag; 25kg/Drum |
| Brand: | Fortunachem |
Tadalafil is a potent, selective, and long-acting inhibitor of the enzyme phosphodiesterase type 5 (PDE5). It is a prescription medication used primarily to treat erectile dysfunction (ED) and benign prostatic hyperplasia (BPH). Chemically, it is distinct from other PDE5 inhibitors like sildenafil (Viagra) due to its unique beta-carboline-derived structure, which confers its characteristic long duration of action.
Tadalafil's complex structure is key to its function. Its systematic (IUPAC) name is (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.
Key structural features include:
Fused Heterocyclic Ring System: The core of the molecule is a rigid, multi-ring system that includes:
A dihydro-1H-pyrido[3,4-b]indole unit, which is a beta-carboline framework.
A fused piperazinedione ring, containing the two cyclic amide (lactam) groups.
Methylenedioxyphenyl Group: Attached to the core at a chiral center is a 3,4-methylenedioxyphenyl ring. This aromatic group is a critical pharmacophore that contributes significantly to the molecule's high affinity for the PDE5 enzyme's active site.
Chiral Centers: Tadalafil has two specific chiral centers (at positions 6 and 12a), and it is marketed exclusively as the (6R,12aR) enantiomer. This specific three-dimensional configuration is absolutely essential for its biological activity, as it allows for an optimal "lock-and-key" fit with the PDE5 enzyme.
Lactam Groups: The two carbonyl groups in the piperazinedione ring are crucial for forming hydrogen bonds with the glutamine residue in the PDE5 active site, a key interaction for inhibition.
Tadalafil's primary action is competitive inhibition of PDE5. Here's how it works on a biochemical level:
Natural Process: Sexual stimulation releases nitric oxide (NO) in the erectile tissue. NO activates an enzyme called guanylyl cyclase, which converts GTP to cyclic guanosine monophosphate (cGMP). Elevated cGMP levels cause smooth muscle relaxation in the corpus cavernosum, allowing blood to flow in and produce an erection.
Termination of Signal: The enzyme PDE5 normally breaks down cGMP to GMP, terminating the signal and allowing the erection to subside.
Tadalafil's Intervention: Tadalafil's structure allows it to bind reversibly to the active site of PDE5, blocking it. With PDE5 inhibited, the degradation of cGMP is slowed. This results in elevated cGMP levels in the tissue, enhancing and prolonging the smooth muscle relaxation and blood flow in response to sexual stimulation.
A defining chemical property of tadalafil is its long elimination half-life of approximately 17.5 hours. This is significantly longer than other PDE5 inhibitors, allowing for a sustained therapeutic effect and leading to its branding as "the weekend pill." This long duration is attributed to its specific structure, which results in slower dissociation from the PDE5 enzyme and slower hepatic metabolism.
In summary, Tadalafil is a synthetically designed, chiral, heterocyclic molecule whose precise three-dimensional structure enables it to selectively inhibit PDE5. By doing so, it potentiates the natural nitric oxide/cGMP pathway, leading to vasodilation in specific tissues, which is the basis for its clinical use in erectile dysfunction and BPH. It is marketed under the brand name Cialis.
Fortunachem Provides Not Only Professional Chemical Products But Also Professional Help
Keeping you up-to-date with all the latest information, news, and events about Fortunachem!
Quick Links
Add:
E-mail:
