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MedKoo Cat#: 318693 | Name: Sildenafil Citrate
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Description:

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

Sildenafil is a selective inhibitor of PDE5 (type 5 cGMP phosphodiesterase) which catalyzes the hydrolysis of 3',5'-cyclic guanosine monophosphate (cGMP). As a PDE5 inhibitor, Sildenafil has been reported to enhance neuro-, synapto- and angiogenesis in rat models of stroke and also is reported to be a mild vasodilator. Sildenafil has also been shown to prevent indomethacin-induced small intestinal ulceration formation through an NO/cGMP- dependent mechanism.

Chemical Structure

Sildenafil Citrate
CAS#171599-83-0 (citrate)

Theoretical Analysis

MedKoo Cat#: 318693

Name: Sildenafil Citrate

CAS#: 171599-83-0 (citrate)

Chemical Formula: C28H38N6O11S

Exact Mass: 0.0000

Molecular Weight: 666.70

Elemental Analysis: C, 50.44; H, 5.75; N, 12.61; O, 26.40; S, 4.81

Price and Availability

Size Price Availability Quantity
500mg USD 150.00 Ready to ship
1g USD 250.00 Ready to ship
2g USD 450.00 Ready to ship
5g USD 850.00 Ready to ship
10g USD 1,250.00 Ready to ship
20g USD 2,150.00 Ready to ship
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Related CAS #
139755-83-2 (free base) 171599-83-0 (citrate) 252951-59-0 (nitrate)
Synonym
Sildenafil Citrate; UK 92480-10; UK-92,480-10. Trade name: Revatio; VIAGRA.
IUPAC/Chemical Name
5-(2-ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 2-hydroxypropane-1,2,3-tricarboxylate
InChi Key
DEIYFTQMQPDXOT-UHFFFAOYSA-N
InChi Code
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;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);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
SMILES Code
CCCC1=NN(C2=C1NC(=NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C.C(C(=O)O)C(CC(=O)O)(C(=O)O)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, not in water
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
Related CAS# CAS#139755-83-2 (Sildenafil [INN:BAN])
Biological target:
Sildenafil citrate is a potent PDE5 inhibitor with an IC50 of 5.22 nM.
In vitro activity:
The specific inhibition of PDE5 by sildenafil citrate may be an effective chemotherapeutic strategy for oral squamous cell carcinoma (OSCC) treatment. Elevated PDE5 expression was observed in all OSCC cell lines. After sildenafil citrate treatment, there was decreased cell viability, invasion rate, and migration. A significant correlation was observed between elevated PDE5 expression and lymphatic infiltration in OSCC tissues. Reference: Anticancer Res. 2021 May;41(5):2297-2306. https://pubmed.ncbi.nlm.nih.gov/33952455/
In vivo activity:
In dogs with congenital idiopathic megaoesophagus (CIM), sildenafil significantly reduced regurgitation episodes and increased weight gain compared to controls. There was a significant decrease in relative oesophageal diameter in the sildenafil group. Sildenafil citrate may offer a novel therapeutic approach for treating dogs with CIM by alleviating clinical and radiographic signs through its effects on lower oesophageal sphincter tone. Reference: Vet Rec. 2017 Apr 22;180(16):404. https://pubmed.ncbi.nlm.nih.gov/28188161/
Solvent mg/mL mM comments
Solubility
DMSO 50.0 89.97
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 666.70 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.

Recalculate based on batch purity %
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. Iwasaki T, Onda T, Honda H, Hayashi K, Shibahara T, Nomura T, Takano M. Over-expression of PDE5 in Oral Squamous Cell Carcinoma - Effect of Sildenafil Citrate. Anticancer Res. 2021 May;41(5):2297-2306. doi: 10.21873/anticanres.15005. PMID: 33952455. 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. 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. 4. 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. Iwasaki T, Onda T, Honda H, Hayashi K, Shibahara T, Nomura T, Takano M. Over-expression of PDE5 in Oral Squamous Cell Carcinoma - Effect of Sildenafil Citrate. Anticancer Res. 2021 May;41(5):2297-2306. doi: 10.21873/anticanres.15005. PMID: 33952455. 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.
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.