Tadalafil Citrate Molecular Weight

Sildenafil citrate

Sildenafil citrate Chemical Properties,Usage,Production

Sildenafil is a potent inhibitor of phosphodiesterase 5 (PDE5) with IC₅₀ values of 3.6 and 3 nM for PDE5 activity in isolated rabbit platelets and human corpus cavernosum, respectively. It is selective for PDE5 over PDE1 and PDE3 (IC₅₀s = 0.26 and 65 μM, respectively). Sildenafil reverses glucose-induced decreases in angiopoietin 1 (ANG1) expression and reduction of capillary-like tube formation by mouse dermal endothelial cells in vitro and increases the number of functional blood vessels and regional blood flow in the sciatic nerve in a db/db mouse model of diabetic peripheral neuropathy. It increases the ratio of maximum intracavernosal pressure to mean arterial blood pressure (ICP/MAP), a measure of erectile function, in castrated rats when administered at a dose of 20 mg/kg per day. Sildenafil (0.5 mg/kg) also reduces cardiac arrest and resuscitation-induced increases in angiotensin II , angiotensin converting enzyme (ACE), ACE2, and various angiotensin receptors and increases survival in a porcine model of ischemia/reperfusion injury. Formulations containing sildenafil have been used in the treatment of erectile dysfunction, pulmonary arterial hypertension, and high-altitude pulmonary edema associated with altitude sickness.

Sildenafil Citrate is an orally active selective type 5 cGMP phosphodiesterase inhibitor.

An orally active selective type 5 cGMP phosphodiesterase inhibitor

A mixture of 3-n-propylpyrazole-5-carboxylic acid ethyl ester (24.1 g, 0.132 mol) (prepared by the method of Chem. Pharm. Bull., 1984, 32, 1568) and dimethyl sulfate (16.8 g, 0.133 mol) were heated to 90°C for 2.5 h. The mixture was dissolved in dichloromethane and the solution washed with sodium carbonate solution. The organic phase was separated, dried (MgSO4) and evaporated under vacuum to give a solid. Chromatography on silica gel (300 g), eluting with dichloromethane gave the 1-methyl-3-n-propylpyrazole- 5-carboxylic acid ethyl ester as a colourless oil (20.4 g, 79%).
1-Methyl-3-n-propylpyrazole-5-carboxylic acid ethyl ester (20.2 g, 0.10 mol) was suspended in 6 N aqueous sodium hydroxide solution (50 ml, 0.30 mol). The mixture was heated to 80°C for 2 h then diluted with water (50 ml) and acidified with concentrated hydrochloric acid (25 ml). Filtration gave the 1- methyl-3-n-propylpyrazole-5-carboxylic acid as pale brown crystals (12.3 g, 71%), melting point 150°-154°C.
1-Methyl-3-n-propylpyrazole-5-carboxylic acid (12.1 g, 0.072 mol) was added portionwise to a mixture of oleum (13 ml) and fuming nitric acid (11 ml), keeping the temperature below 60°C. After the addition, the mixture was heated at 60°C overnight and then cooled to room temperature before being poured onto ice. Filtration of the precipitate gave the 1-methyl-4-nitro-3-npropylpyrazole- 5-carboxylic acid as a white solid (11.5 g, 75%), melting point 124°-127°C.
1-Methyl-4-nitro-3-n-propylpyrazole-5-carboxylic acid (11.3 g, 0.053 mol) was added to thionyl chloride (50 ml) and the resulting mixture heated under reflux for 3 h. The reaction mixture was then cooled and excess thionyl chloride removed by evaporation under vacuum. The oily residue was dissolved in acetone (50 ml) and the solution cautiously added to a mixture of ice (50 g) and concentrated aqueous ammonium hydroxide solution (50 ml). The precipitate was collected by filtration to provide the 1-methyl-4-nitro-3-npropylpyrazole- 5-carboxamide as a pale yellow solid (8.77 g, 78%), melting point 141°-143°C.
1-Methyl-4-nito-3-n-propylpyrazole-5-carboxamide (3.45 g, 16.2 mmol) and stannous chloride dihydrate (18.4 g, 81 mmol) were suspended in ethanol and the mixture heated under reflux for 2 h. The resulting solution was cooled to room temperature, basified to pH 9 by the addition of 2 N aqueous sodium hydroxide solution and extracted with dichloromethane (3 x 150 ml). The organic extracts were combined, dried (MgSO4) and evaporated under vacuum. Trituration of the residue with ether gave the 4-amino-1-methyl-3-npropylpyrazole- 5-carboxamide as an off-white solid (2.77 g, 94%), melting point 98°-101°C.
A solution of 2-ethoxybenzoyl chloride (6.1 g, 33.0 mmol) in dichloromethane (50 ml) was added to a stirred solution of 4-amino-1-methyl-3-npropylpyrazole- 5-carboxamide (3.0 g, 16.4 mmol), 4-dimethylaminopyridine (0.02 g, 0.1 64 mmol) and triethylamine (3.34 g, 33.0 mmol) in dichloromethane (50 ml) at 0°C. The resulting mixture was allowed to warm to room temperature and stirred for a further 2 h. The solvent was evaporated under vacuum, the residue dissolved in a 19:1 mixture of dichloromethane and methanol (250 ml), and then the solution washed with 1 N hydrochloric acid (100 ml), dried (MgSO4) and evaporated under vacuum. The crude material was chromatographed on silica gel (200 g), eluting with a 97:3 mixture of dichloromethane and methanol, to give a pink solid; crystallisation from ethyl acetate-hexane gave the 4-(2-ethoxybenzamido)-1-methyl-3-npropylpyrazole- 5-carboxamide as a pale pink solid (2.2 g, 40%), melting point 153°-155°C.
4-(2-Ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide (223 g, 0.676 mol) was added portionwise to a solution of sodium hydroxide (54 g, 1.35 mol) and 30% hydrogen peroxide solution (224 ml) in water (2000 ml). Ethanol (700 ml) was added and the resulting mixture heated under reflux for 2.5 h, cooled, then evaporated under vacuum. The resulting solid was treated with 2 N hydrochloric acid (380 ml), with external cooling, and the mixture was extracted with dichloromethane (1 x 700 ml, 3 x 200 ml). The combined organic extracts were washed successively with saturated aqueous sodium carbonate solution (3 x 400 ml) and brine (300 ml), then dried (Na2SO4) and evaporated under vacuum. Chromatography of the residue on silica gel (1000 g), using a methanol in dichloromethane elution gradient (0-1%), followed by trituration of the crude product with ether (300 ml), gave the 5-(2- ethoxyphenyl)-1-methyl-3-n-propyl-l,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin- 7-one as a colourless solid (152.2 g, 72%), melting point 143°-146°C.
5-(2-Ethoxyphenyl)-1-methyl-3-n-propyl-l,6-dihydro-7H-pyrazolo[4,3- d]pyrimidin-7-one (10.0 g, 32.1 mmol) was added portionwise to chlorosulfonic acid (20 ml) at 0°C under a nitrogen atmosphere. After being stirred overnight, the reaction solution was cautiously added to ice-water (150ml) and the aqueous mixture extracted with a 9:1 mixture of dichloromethane and methanol (4 x 100 ml). The combined extracts were dried (Na2SO4) and evaporated under vacuum to give the required 5-(5-chlorosulphonyl-2- ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin- 7-one as a white solid (12.8 g, 97%), melting point 179°-181°C.
4-Methylpiperidine was added to a stirred suspension of 5-(5-chlorosulphonyl- 2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3- d]pyrimidin-7-one in ethanol at room temperature. The resulting mixture was stirred for 4 days before removing the solvent by evaporation under vacuum. The residue was dissolved in a 9:1 mixture of dichloromethane and methanol and the solution washed with saturated aqueous sodium carbonate solution. The aqueous phase was further extracted with dichloromethane-methanol mixtures (3 x 100 ml) and all the organic fractions were combined, dried (MgSO4) and evaporated under vacuum to give a solid. Crystallisation from a mixture of methanol-dimethylformamide gave the 5-[2-ethoxy-5-(4- methylpiperidinylsulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7Hpyrazolo[ 4,3-d]-pyrimidin-7-one as an off-white solid, melting point 187°- 189°C.
After addition of citric acid to the 5-[2-ethoxy-5-(4- methylpiperidinylsulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7Hpyrazolo[ 4,3-d]-pyrimidin-7-one (sildenafil) the it’s salt is obtained, namely sildenafil citrate.

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Orally active, potent inhibitor of phosphodiesterase 5 (PDE5) (IC 50 = 4 nM). Enhances nitric oxide-dependent relaxation of human corpus cavernosum in vitro .

Sildenafil is a potent, selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5). Sildenafil is used to treat erectile dysfunction and pulmonary arterial hypertension. NO activates guanylate cyclase, which results in increased levels of cGMP, producing smooth muscle relaxation. Sildenafil enhances the effect of NO by inhibiting PDE5, which is responsible for degradation of cGMP.

A poison by ingestion. Human systemic effects. When heated to decomposition it emits toxic vapors of NOx and SOx.

Sildenafil may be of benefit in the adjunctive treatment of pulmonary hypertension in small animals.
In humans, sildenafil is indicated for erectile dysfunction or pulmonary hypertension.

Sildenafil citrate (SC) has been widely used for the treatment of erectile disorder. A detailed study concerning solid-state structure of this compound is very important for understanding enzyme (PDE5)-inhibitor (sildenafil) interaction. It is also of interest to determine sildenafil’s protonation sites, as they may be responsible for its binding to the phosphodiesterase acidic amino acids.
Sildenafil citrate (Viagra) and sildenafil base in pure form were characterized by 1H, 13C, 15N NMR spectroscopy in solution, solid-state, and pharmaceutical dosage forms.42 The analysis of chemical shifts showed that: (i) N6-H forms intramolecular hydrogen bonds, (ii) N25 is protonated in the salt, and (iii) intermolecular OH. . .N hydrogen bonds involving N2 and N4 are present in the solid sildenafil citrate. The 13C CPMAS spectra of the tablets containing different amounts of sildenafil citrate were recorded and showed that chemical shifts of sildenafil citrate in pure form and in pharmaceutical dosage forms are the same. SC is easily detected in the pharmaceutical dosage forms since only two of its carbon resonances (OCH2 and quaternary carbon of the citrate anion) fall into carbohydrate-type region of the excipient.
Solid-state 13C and 15N MAS NMR have recently been used to investigate how water interacts with SC.43 When the humidity is altered, the water concentration in the solid compound changes but does not reach a stoichiometric (e.g., 1:1) ratio to form a true hydrate. Only one set of 15N and 13C signals was observed for each humidity level indicating that water incorporated into the crystal lattice of SC is very mobile and exchanges rapidly between various sites. The 13C data showed the formation of a hydrogen bond between water molecule and one carbonyl of the citrate anion. The spectra also show that the water content affects the conformation of the propyl group. Additionally, 15N dipolar dephasing (DD) experiments confirmed that the sildenafil molecule is only protonated in the piperazine ring.

1) Terrett?et al.?(1996),?Sildenafil (VIAGRATM), a potent and selective inhibitor of type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction; Bioorg. Med. Chem. Lett. 6?1819 2) Ballard?et al.?(1998),?Effects of sildenafil on the relaxation of human corpus cavernosum tissue in vitro and on the activities of cyclic nucleotide phosphodiesterase isozymes; J. Urol. 159?2164 3) Turko?et al.?(1999),?Inhibition of cyclic GMP-binding cyclic GMP-specific phosphodiesterase (Type 5) by sildenafil and related compounds; Mol. Pharmacol. 56?124 4) Teixeira?et al.?(2006),?Differential effects of the phosphodiesterase type 5 inhibitors sildenafil, vardenafil, and tadalafil in rat aorta; J. Pharmacol. Exp. Therap. 316?654 5) Ghofrani?et al.?(2006),?Sildenafil: from angina to erectile dysfunction to pulmonary hypertension and beyond; Nat. Rev. Drug Discov. 5?689

Tadalafil Citrate Molecular Weight

The following data is based on the product molecular weight 666.7 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

Formulation protocol:	1. Quintavalla F, Menozzi A, Pozzoli C, Poli E, Donati P, Wyler DK, Serventi P, Bertini S. Sildenafil improves clinical signs and radiographic features in dogs with congenital idiopathic megaoesophagus: a randomised controlled trial. Vet Rec. 2017 Apr 22;180(16):404. doi: 10.1136/vr.103832. Epub 2017 Feb 10. PMID: 28188161. 2. Mostafa T. In vitro sildenafil citrate use as a sperm motility stimulant. Fertil Steril. 2007 Oct;88(4):994-6. doi: 10.1016/j.fertnstert.2006.11.182. Epub 2007 Feb 20. PMID: 17316632. 3. Soares DM, Ramos-Perez F, Araújo SS, Correia Leite de Marcelos PG, Pontual AA, Perez D. Sildenafil citrate on experimental periodontitis in rats: Microtomographic and histological analyses. Oral Dis. 2018 Sep;24(6):1073-1082. doi: 10.1111/odi.12846. Epub 2018 Jun 7. PMID: 29480944.
In vitro protocol:	1. Quintavalla F, Menozzi A, Pozzoli C, Poli E, Donati P, Wyler DK, Serventi P, Bertini S. Sildenafil improves clinical signs and radiographic features in dogs with congenital idiopathic megaoesophagus: a randomised controlled trial. Vet Rec. 2017 Apr 22;180(16):404. doi: 10.1136/vr.103832. Epub 2017 Feb 10. PMID: 28188161. 2. Mostafa T. In vitro sildenafil citrate use as a sperm motility stimulant. Fertil Steril. 2007 Oct;88(4):994-6. doi: 10.1016/j.fertnstert.2006.11.182. Epub 2007 Feb 20. PMID: 17316632.
In vivo protocol:	1. Quintavalla F, Menozzi A, Pozzoli C, Poli E, Donati P, Wyler DK, Serventi P, Bertini S. Sildenafil improves clinical signs and radiographic features in dogs with congenital idiopathic megaoesophagus: a randomised controlled trial. Vet Rec. 2017 Apr 22;180(16):404. doi: 10.1136/vr.103832. Epub 2017 Feb 10. PMID: 28188161. 2. Soares DM, Ramos-Perez F, Araújo SS, Correia Leite de Marcelos PG, Pontual AA, Perez D. Sildenafil citrate on experimental periodontitis in rats: Microtomographic and histological analyses. Oral Dis. 2018 Sep;24(6):1073-1082. doi: 10.1111/odi.12846. Epub 2018 Jun 7. PMID: 29480944.

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1: Shah PC, Trivedi NA. A meta-analysis on efficacy and tolerability of sildenafil for erectile dysfunction in patients with diabetes mellitus. Indian J Sex Transm Dis AIDS. 2018 Jan-Jun;39(1):1-6. doi: 10.4103/ijstd.IJSTD_99_17. Review. PubMed PMID: 30187018; PubMed Central PMCID: PMC6111643.

2: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK500617/ PubMed PMID: 29999677.

3: Andersson KE. PDE5 inhibitors – pharmacology and clinical applications 20 years after sildenafil discovery. Br J Pharmacol. 2018 Jul;175(13):2554-2565. doi: 10.1111/bph.14205. Epub 2018 Apr 25. Review. PubMed PMID: 29667180; PubMed Central PMCID: PMC6003652.

4: Kelly LE, Ohlsson A, Shah PS. Sildenafil for pulmonary hypertension in neonates. Cochrane Database Syst Rev. 2017 Aug 4;8:CD005494. doi: 10.1002/14651858.CD005494.pub4. Review. PubMed PMID: 28777888.

5: Gong B, Ma M, Xie W, Yang X, Huang Y, Sun T, Luo Y, Huang J. Direct comparison of tadalafil with sildenafil for the treatment of erectile dysfunction: a systematic review and meta-analysis. Int Urol Nephrol. 2017 Oct;49(10):1731-1740. doi: 10.1007/s11255-017-1644-5. Epub 2017 Jul 24. Review. PubMed PMID: 28741090; PubMed Central PMCID: PMC5603624.

6: Simonca L, Tulloh R. Sildenafil in Infants and Children. Children (Basel). 2017 Jul 24;4(7). pii: E60. doi: 10.3390/children4070060. Review. PubMed PMID: 28737730; PubMed Central PMCID: PMC5532552.

7: Sable CA, Ivy DD, Beekman RH 3rd, Clayton-Jeter HD, Jenkins KJ, Mahle WT, Morrow WR, Murphy MD, Nelson RM, Rosenthal GL, Stockbridge N, Wessel DL. 2017 ACC/AAP/AHA Health Policy Statement on Opportunities and Challenges in Pediatric Drug Development: Learning From Sildenafil. Circ Cardiovasc Qual Outcomes. 2017 Jul;10(7). pii: e000026. doi: 10.1161/HCQ.0000000000000026. Review. PubMed PMID: 28663437; PubMed Central PMCID: PMC5614492.

8: Graziano S, Montana A, Zaami S, Rotolo MC, Minutillo A, Busardò FP, Marinelli E. Sildenafil-associated hepatoxicity: a review of the literature. Eur Rev Med Pharmacol Sci. 2017 Mar;21(1 Suppl):17-22. Review. PubMed PMID: 28379598.

9: Osmonov DK, Jünemann KP, Bannowsky A. The “Kiel Concept” of Long-Term Administration of Daily Low-Dose Sildenafil Initiated in the Immediate Post-Prostatectomy Period: Evaluation and Comparison With the International Literature on Penile Rehabilitation. Sex Med Rev. 2017 Jul;5(3):387-392. doi: 10.1016/j.sxmr.2017.03.002. Epub 2017 Mar 31. Review. PubMed PMID: 28372960.

10: Ohl DA, Carlsson M, Stecher VJ, Rippon GA. Efficacy and Safety of Sildenafil in Men With Sexual Dysfunction and Spinal Cord Injury. Sex Med Rev. 2017 Oct;5(4):521-528. doi: 10.1016/j.sxmr.2017.01.007. Epub 2017 Mar 21. Review. PubMed PMID: 28341580.

11: Kniotek M, Boguska A. Sildenafil Can Affect Innate and Adaptive Immune System in Both Experimental Animals and Patients. J Immunol Res. 2017;2017:4541958. doi: 10.1155/2017/4541958. Epub 2017 Feb 20. Review. PubMed PMID: 28316997; PubMed Central PMCID: PMC5337856.

12: Efremov EA, Kasatonova EV, Melnik YI, Simakov VV. [Contemporary aspects of using sildenafil]. Urologiia. 2016 Nov;(5):120-128. Review. Russian. PubMed PMID: 28248033.

13: Scaglione F, Donde S, Hassan TA, Jannini EA. Phosphodiesterase Type 5 Inhibitors for the Treatment of Erectile Dysfunction: Pharmacology and Clinical Impact of the Sildenafil Citrate Orodispersible Tablet Formulation. Clin Ther. 2017 Feb;39(2):370-377. doi: 10.1016/j.clinthera.2017.01.001. Epub 2017 Jan 28. Review. PubMed PMID: 28139291.

14: Dunn L, Greer R, Flenady V, Kumar S. Sildenafil in Pregnancy: A Systematic Review of Maternal Tolerance and Obstetric and Perinatal Outcomes. Fetal Diagn Ther. 2017;41(2):81-88. doi: 10.1159/000453062. Epub 2016 Dec 8. Review. PubMed PMID: 27926905.

15: Chen J, Gong X, Chen P, Luo K, Zhang X. Effect of L-arginine and sildenafil citrate on intrauterine growth restriction fetuses: a meta-analysis. BMC Pregnancy Childbirth. 2016 Aug 16;16:225. doi: 10.1186/s12884-016-1009-6. Review. PubMed PMID: 27528012; PubMed Central PMCID: PMC4986189.

16: Lu X, Han H, Xing N, Tian L. [Efficacy of sildenafil citrate in men with erectile dysfunction following bilateral nerve-sparing radical prostatectomy: systematic review and meta-analysis]. Zhonghua Yi Xue Za Zhi. 2015 Sep 22;95(36):2964-8. Review. Chinese. PubMed PMID: 26814076.

17: Dodgen AL, Hill KD. Safety and tolerability considerations in the use of sildenafil for children with pulmonary arterial hypertension. Drug Healthc Patient Saf. 2015 Dec 15;7:175-83. doi: 10.2147/DHPS.S65571. eCollection 2015. Review. PubMed PMID: 26719728; PubMed Central PMCID: PMC4687613.

18: Perez KM, Laughon M. Sildenafil in Term and Premature Infants: A Systematic Review. Clin Ther. 2015 Nov 1;37(11):2598-2607.e1. doi: 10.1016/j.clinthera.2015.07.019. Epub 2015 Oct 19. Review. PubMed PMID: 26490498.

19: Efremov EA, Kasatonova EV, Mel’nik JI. [USE OF SILDENAFIL CITRATE FOR TREATMENT OF ERECTILE DYSFUNCTION OF VARIOUS ETIOLOGY]. Urologiia. 2015 Mar-Apr;(2):117-8, 120-1. Review. Russian. PubMed PMID: 26237819.

20: Dhariwal AK, Bavdekar SB. Sildenafil in pediatric pulmonary arterial hypertension. J Postgrad Med. 2015 Jul-Sep;61(3):181-92. doi: 10.4103/0022-3859.159421. Review. PubMed PMID: 26119438; PubMed Central PMCID: PMC4943407.

Sildenafil Citrate

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InChI=1S/C22H30N6O4S.C6H8O7/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28, 13H,1-2H2,(H,7,8)(H,9,10)(H,11,12), 7-3(8)1-6(13,5(11)12)2-4(9)10/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)

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