Sildenafil Citrate
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MedKoo CAT#: 318693

CAS#: 171599-83-0 (citrate)

Description: 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

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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:
Molecular Weight: 666.7
Elemental Analysis: C, 50.44; H, 5.75; N, 12.61; O, 26.40; S, 4.81

Price and Availability

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500.0mg USD 150.0 Ready to ship
1.0g USD 250.0 Ready to ship
2.0g USD 450.0 Ready to ship
5.0g USD 850.0 Ready to ship
10.0g USD 1250.0 Ready to ship
20.0g USD 2150.0 Ready to ship
50.0g USD 3850.0 2 Weeks
100.0g USD 4950.0 2 Weeks
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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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 89.97

Preparing Stock Solutions

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.

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

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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.



Additional Information

Related CAS#
CAS#139755-83-2 (Sildenafil [INN:BAN])