Tadalafil

• CAT Number: A000256
• CAS Number: 171596-29-5
• Molecular Formula: C22H19N3O4
• Molecular Weight: 389.40
• Purity: ≥95%
• Synonyms: Cialis; 171596-29-5; Tadanafil; Ic351; ADCIRCA
• Target: PDE
• Solubility: >16.6mg/mL in DMSO
• Storage: -20°C
• Related CAS: 629652-72-8 171596-27-3 171596-28-4 960226-55-5
• 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
• 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
• InChIKey: WOXKDUGGOYFFRN-IIBYNOLFSA-N
• SMILES: CN1CC(=O)N2[C@@H](C1=O)CC3=C([C@H]2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36

Research chemical Tadalafil（CAS 171596-29-5）is a phosphodiesterase type 5 (PDE5) inhibitor commonly used to treat erectile dysfunction (ED), benign prostatic hyperplasia (BPH), and pulmonary arterial hypertension. By inhibiting PDE5, tadalafil increases cyclic GMP levels, promoting smooth muscle relaxation and enhancing blood flow, particularly to the penile and pulmonary arteries. Known for its extended half-life, it provides prolonged effects, making it popular as a once-daily or as-needed treatment for ED. Tadalafil is also studied for its vasodilatory effects in cardiovascular and endothelial health, contributing to its versatility in therapeutic applications.

Reference

1: Yokoyama O, Ozeki A, Suzuki N, Murakami M. Early improvement of storage or
voiding symptoms by tadalafil predicts treatment outcomes in patients with lower
urinary tract symptoms from benign prostatic hyperplasia. Int J Urol. 2017 Nov 1.
doi: 10.1111/iju.13487. [Epub ahead of print] PubMed PMID: 29094398.

2: Salah A, Hassan M, Liu J, Li M, Bo X, Ndamanisha JC, Guo L. Pt nanoparticles
supported on nitrogen-doped porous graphene for sensitive detection of Tadalafil.
J Colloid Interface Sci. 2017 Oct 7;512:379-388. doi: 10.1016/j.jcis.2017.10.022.
[Epub ahead of print] PubMed PMID: 29080533.

3: Zhang T, Li WB, Pan MA. [Oral-appliance combined with tadalafil for erectile
dysfunction induced by severe obstructive sleep apneahypopnea syndrome]. Zhonghua
Nan Ke Xue. 2016 Sep;22(9):792-796. Chinese. PubMed PMID: 29071875.

4: Wood H. Neuromuscular disease: Tadalafil fails to halt the progression of
Duchenne muscular dystrophy. Nat Rev Neurol. 2017 Oct 23. doi:
10.1038/nrneurol.2017.153. [Epub ahead of print] PubMed PMID: 29064468.

5: Sabri MR, Bigdelian H, Hosseinzadeh M, Ahmadi A, Ghaderian M, Shoja M.
Comparison of the therapeutic effects and side effects of tadalafil and
sildenafil after surgery in young infants with pulmonary arterial hypertension
due to systemic-to-pulmonary shunts. Cardiol Young. 2017 Nov;27(9):1686-1693.
doi: 10.1017/S1047951117000981. PubMed PMID: 28994364.

6: Yoshikawa K, Umekawa T, Maki S, Kubo M, Nii M, Tanaka K, Tanaka H, Osato K,
Kamimoto Y, Kondo E, Ikemura K, Okuda M, Katayama K, Miyoshi T, Hosoda H, Ma N,
Yoshida T, Ikeda T. Tadalafil Improves L-NG-Nitroarginine Methyl Ester-Induced
Preeclampsia With Fetal Growth Restriction-Like Symptoms in Pregnant Mice. Am J
Hypertens. 2017 Aug 3. doi: 10.1093/ajh/hpx130. [Epub ahead of print] PubMed
PMID: 28992178.

7: Oliveira GG, Oliveira SAH, Botelho PHH, Oliveira MAB, Bian K, Murad F.
Tadalafil: Protective Action against the Development of Multiple Organ Failure
Syndrome. Braz J Cardiovasc Surg. 2017 Jul-Aug;32(4):312-317. doi:
10.21470/1678-9741-2017-0503. PubMed PMID: 28977204; PubMed Central PMCID:
PMC5613730.

8: Victor RG, Sweeney HL, Finkel R, McDonald CM, Byrne B, Eagle M, Goemans N,
Vandenborne K, Dubrovsky AL, Topaloglu H, Miceli MC, Furlong P, Landry J,
Elashoff R, Cox D; Tadalafil DMD Study Group. A phase 3 randomized
placebo-controlled trial of tadalafil for Duchenne muscular dystrophy. Neurology.
2017 Oct 24;89(17):1811-1820. doi: 10.1212/WNL.0000000000004570. Epub 2017 Sep
29. PubMed PMID: 28972192; PubMed Central PMCID: PMC5664308.

9: Hassel JC, Jiang H, Bender C, Winkler J, Sevko A, Shevchenko I, Halama N,
Dimitrakopoulou-Strauss A, Haefeli WE, Jger D, Enk A, Utikal J, Umansky V.
Tadalafil has biologic activity in human melanoma. Results of a pilot trial with
Tadalafil in patients with metastatic Melanoma (TaMe). Oncoimmunology. 2017 May
16;6(9):e1326440. doi: 10.1080/2162402X.2017.1326440. eCollection 2017. PubMed
PMID: 28932631; PubMed Central PMCID: PMC5599085.

10: Chiu AW, Stenstrom R. A Case Report of Tadalafil-Associated Fixed Drug
Eruption. J Pharm Pract. 2017 Jan 1:897190017731246. doi:
10.1177/0897190017731246. [Epub ahead of print] PubMed PMID: 28925328.