Tadalafil | CAS#171596-27-3 | PHOSPHODIESTERASE 5 INHIBITOR| MedKoo

MedKoo Cat#: 591093 | Name: Tadalafil, (6R ,12aS)-

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tadalafil, (6R ,12aS)-, is the cis- form of Tadalafil -- a carboline derivative and Phosphodiesterase 5 Inhibitor that is used primarily to treat Erectile dysfunction, Benign Prostatic Hyperplasia and Primary Pulmonary Hypertension.

Chemical Structure

Tadalafil, (6R ,12aS)-

CAS#171596-27-3 (Cis-isomer)

Theoretical Analysis

MedKoo Cat#: 591093

Name: Tadalafil, (6R ,12aS)-

CAS#: 171596-27-3 (Cis-isomer)

Chemical Formula: C22H19N3O4

Exact Mass: 389.1376

Molecular Weight: 389.41

Elemental Analysis: C, 67.86; H, 4.92; N, 10.79; O, 16.43

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Related CAS #

171596-29-5 171596-27-3 (Cis-isomer)

Synonym

(-)-Tadalafil (6R ,12aS) diastereomer, Tadalafil specified impurity A, Tadalafil (6R ,12aS)-; Tadalafil (6R ,12aS)- Lilly;

IUPAC/Chemical Name

(6R,12aS)-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

InChi Key

WOXKDUGGOYFFRN-IIBYNOLFSA-N

InChi Code

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

SMILES Code

O=C([C@@]1([H])CC2=C([C@@H](C3=CC=C(OCO4)C4=C3)N15)NC6=C2C=CC=C6)N(C)CC5=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 389.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Mehanna MM, Domiati S, Chmaisse HN, El Mallah A. Antinociceptive effect of Tadalafil in various pain models: Involvement of opioid receptors and Nitric oxide cyclic GMP pathways. Toxicol Appl Pharmacol. 2018 May 16. pii: S0041-008X(18)30218-7. doi: 10.1016/j.taap.2018.05.013. [Epub ahead of print] PubMed PMID: 29777732. 2: Pantziarka P, Sukhatme V, Crispino S, Bouche G, Meheus L, Sukhatme VP. Repurposing drugs in oncology (ReDO)-selective PDE5 inhibitors as anti-cancer agents. Ecancermedicalscience. 2018 Apr 11;12:824. doi: 10.3332/ecancer.2018.824. eCollection 2018. PubMed PMID: 29743944; PubMed Central PMCID: PMC5931815. 3: Walton RB, Reed LC, Estrada SM, Schmiedecke SS, Villazana-Kretzer DL, Napolitano PG, Ieronimakis N. Evaluation of Sildenafil and Tadalafil for Reversing Constriction of Fetal Arteries in a Human Placenta Perfusion Model. Hypertension. 2018 May 7. pii: HYPERTENSIONAHA.117.10738. doi: 10.1161/HYPERTENSIONAHA.117.10738. [Epub ahead of print] PubMed PMID: 29735634. 4: Bhattar R, Tomar V, Yadav SS, Dhakad DS. Comparison of safety and efficacy of silodosin, solifenacin, tadalafil and their combinations in the treatment of double-J stent- related lower urinary system symptoms: A prospective randomized trial. Turk J Urol. 2018 May;44(3):228-238. doi: 10.5152/tud.2018.50328. Epub 2018 Mar 6. PubMed PMID: 29733797; PubMed Central PMCID: PMC5937643. 5: Sun X, Guan W, Liu H, Tang K, Yan L, Zhang Y, Zeng J, Chen Z, Xu H, Ye Z. Efficacy and safety of PDE5-Is and α-1 blockers for treating lower ureteric stones or LUTS: a meta-analysis of RCTs. BMC Urol. 2018 May 3;18(1):30. doi: 10.1186/s12894-018-0345-4. PubMed PMID: 29724204; PubMed Central PMCID: PMC5934901. 6: Li WJ, Xu MX, Guo JH, Cai ZK, Jiang YQ, Wang Z. [Effects of different medications with tadalafil on erectile dysfunction in males with primary sexual failure]. Zhonghua Nan Ke Xue. 2017 Jun;23(6):522-526. Chinese. PubMed PMID: 29722944. 7: Teymouri Rad R, Mortazavi SA, Vatanara A, Dadashzadeh S. Enhanced Dissolution Rate of Tadalafil Nanoparticles Prepared by Sonoprecipitation Technique: Optimization and Physicochemical Investigation. Iran J Pharm Res. 2017 Fall;16(4):1335-1348. PubMed PMID: 29721025; PubMed Central PMCID: PMC5843297. 8: Park SI, Heo SH, Kim G, Chang S, Song KH, Kim MG, Jin EH, Kim J, Lee S, Hong JH. Comparison of tadalafil pharmacokinetics after administration of a new orodispersible film versus a film-coated tablet. Drug Des Devel Ther. 2018 Apr 20;12:935-942. doi: 10.2147/DDDT.S155040. eCollection 2018. PubMed PMID: 29719379; PubMed Central PMCID: PMC5916261. 9: Dash P, Bala Divya M, Guruprasad L, Guruprasad K. Three-dimensional models of Mycobacterium tuberculosis proteins Rv1555, Rv1554 and their docking analyses with sildenafil, tadalafil, vardenafil drugs, suggest interference with quinol binding likely to affect protein's function. BMC Struct Biol. 2018 Apr 18;18(1):5. doi: 10.1186/s12900-018-0085-4. PubMed PMID: 29669541; PubMed Central PMCID: PMC5907181. 10: Causanilles A, Rojas Cantillano D, Emke E, Bade R, Baz-Lomba JA, Castiglioni S, Castrignanò E, Gracia-Lor E, Hernández F, Kasprzyk-Hordern B, Kinyua J, McCall AK, van Nuijs ALN, Plósz BG, Ramin P, Rousis NI, Ryu Y, Thomas KV, de Voogt P. Comparison of phosphodiesterase type V inhibitors use in eight European cities through analysis of urban wastewater. Environ Int. 2018 Apr 2;115:279-284. doi: 10.1016/j.envint.2018.03.039. [Epub ahead of print] PubMed PMID: 29621715. 11: Ni W, Wang H, Li X, Zheng X, Wang M, Zhang J, Gong Q, Ling D, Mao F, Zhang H, Li J. Novel Tadalafil Derivatives Ameliorates Scopolamine-Induced Cognitive Impairment in Mice via Inhibition of Acetylcholinesterase (AChE) and Phosphodiesterase 5 (PDE5). ACS Chem Neurosci. 2018 Apr 17. doi: 10.1021/acschemneuro.8b00014. [Epub ahead of print] PubMed PMID: 29616790. 12: Kim S, Sung GT. Efficacy and Safety of Tadalafil 5 mg Once Daily for the Treatment of Erectile Dysfunction After Robot-Assisted Laparoscopic Radical Prostatectomy: A 2-Year Follow-Up. Sex Med. 2018 Jun;6(2):108-114. doi: 10.1016/j.esxm.2017.12.005. Epub 2018 Mar 27. PubMed PMID: 29602721. 13: Huang YC, Lee HC, Lin YL, Tsai CF, Cheng HF. Identification of a new type tadalafil analogue in a supplement product. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2018 Mar 30. doi: 10.1080/19440049.2018.1459052. [Epub ahead of print] PubMed PMID: 29601254. 14: Kubo-Kaneda M, Tanaka H, Maki S, Nii M, Umekawa T, Osato K, Kamimoto Y, Kondo E, Ikeda T. Placental growth factor as a predictor of the efficacy of tadalafil treatment for fetal growth restriction. J Matern Fetal Neonatal Med. 2018 Mar 26:1-4. doi: 10.1080/14767058.2018.1450863. [Epub ahead of print] PubMed PMID: 29580120. 15: Okamoto K, Kurita M, Yamaguchi H, Numakura Y, Oka M. Effect of tadalafil on chronic pelvic pain and prostatic inflammation in a rat model of experimental autoimmune prostatitis. Prostate. 2018 Mar 26. doi: 10.1002/pros.23514. [Epub ahead of print] PubMed PMID: 29577372. 16: Margelidon-Cozzolino V, Hodin S, Jacqueroux E, Delézay O, Bertoletti L, Delavenne X. In Vitro Assessment of Pharmacokinetic Drug-Drug Interactions of Direct Oral Anticoagulants: Type 5-Phosphodiesterase Inhibitors Are Inhibitors of Rivaroxaban and Apixaban Efflux by P-Glycoprotein. J Pharmacol Exp Ther. 2018 Jun;365(3):519-525. doi: 10.1124/jpet.117.245993. Epub 2018 Mar 23. PubMed PMID: 29572341. 17: Morgia G, Vespasiani G, Pareo RM, Voce S, Madonia M, Carini M, Ingrassia A, Terrone C, Gentile M, Carrino M, Giannantoni A, Blefari F, Arnone S, Santelli G, Russo GI; SPRITE investigators. Serenoa repens + selenium + lycopene vs tadalafil 5 mg for the treatment of lower urinary tract symptoms secondary to benign prostatic obstruction: a Phase IV, non-inferiority, open-label, clinical study (SPRITE study). BJU Int. 2018 Mar 22. doi: 10.1111/bju.14209. [Epub ahead of print] PubMed PMID: 29569389. 18: Dong X, Nakagomi H, Miyamoto T, Ihara T, Kira S, Sawada N, Mitsui T, Takeda M. Tadalafil attenuates hypotonicity-induced Ca(2+) influx via TRPV2 and TRPV4 in primary rat bladder urothelial cell cultures. Neurourol Urodyn. 2018 Mar 22. doi: 10.1002/nau.23423. [Epub ahead of print] PubMed PMID: 29566267. 19: Agis-Torres Á, Recio P, López-Oliva ME, Martínez MP, Barahona MV, Benedito S, Bustamante S, Jiménez-Cidre MÁ, García-Sacristán A, Prieto D, Fernandes VS, Hernández M. Phosphodiesterase type 4 inhibition enhances nitric oxide- and hydrogen sulfide-mediated bladder neck inhibitory neurotransmission. Sci Rep. 2018 Mar 16;8(1):4711. doi: 10.1038/s41598-018-22934-1. PubMed PMID: 29549279; PubMed Central PMCID: PMC5856743. 20: Abu El-Hamd M. Efficacy and safety of daily use of tadalafil in treatment of patients with premature ejaculation: A randomised placebo-controlled clinical trial. Andrologia. 2018 Mar 12. doi: 10.1111/and.13005. [Epub ahead of print] PubMed PMID: 29527702.