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MedKoo Cat#: 574537 | Name: Thiosildenafil
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Description:

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

Thiosildenafil is a derivative of the phosphodiesterase 5 (PDE5) inhibitor sildenafil.

Chemical Structure

Thiosildenafil
Thiosildenafil
CAS#479073-79-5

Theoretical Analysis

MedKoo Cat#: 574537

Name: Thiosildenafil

CAS#: 479073-79-5

Chemical Formula: C22H30N6O3S2

Exact Mass: 490.1821

Molecular Weight: 490.64

Elemental Analysis: C, 53.86; H, 6.16; N, 17.13; O, 9.78; S, 13.07

Price and Availability

Size Price Availability Quantity
5mg USD 400.00 2 Weeks
10mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
Thiosildenafil
IUPAC/Chemical Name
5-[2-ethoxy-5-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidine-7-thione
InChi Key
LJUBVCQVNMLSTQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H30N6O3S2/c1-5-7-17-19-20(27(4)25-17)22(32)24-21(23-19)16-14-15(8-9-18(16)31-6-2)33(29,30)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,32)
SMILES Code
S=C1C(N(C)N=C2CCC)=C2N=C(C3=CC(S(=O)(N4CCN(C)CC4)=O)=CC=C3OCC)N1
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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 490.64 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
1: Li Y, He H, Luan Y, Huang J. Identification of Phosphodiesterase type 5 inhibitors (PDE5is) analogues using surface-enhanced Raman scattering and machine learning algorithm. Spectrochim Acta A Mol Biomol Spectrosc. 2024 Dec 27;330:125678. doi: 10.1016/j.saa.2024.125678. Epub ahead of print. PMID: 39742621. 2: Xu H, Zhang S, DU R, Zhou J, Weng S. [Ultra-high performance liquid chromatography-orbitrap high-resolution mass spectrometry for rapid screening and identification of 32 illegally added drugs in slimming and anti-impotence health foods]. Se Pu. 2022 Jun;40(6):531-540. Chinese. doi: 10.3724/SP.J.1123.2021.12009. PMID: 35616198; PMCID: PMC9404125. 3: Dong L, Chen Y, Chen S, Hou C, Wang S, Xuan R, Fang K, Wang T, Zhang L, Zhang Y. Novel synthesized attapulgite nanoparticles-based hydrophobic monolithic column for in-tube solid-phase microextraction of thiosildenafil, pseudovardenafil, and norneosildenafil in functional foods. Anal Bioanal Chem. 2021 Mar;413(7):1871-1882. doi: 10.1007/s00216-021-03155-4. Epub 2021 Jan 19. PMID: 33469710. 4: Li J, Roh SH, Shaodong J, Hong JY, Lee DK, Shin BK, Park JH, Lee J, Kwon SW. Solid-phase extraction assisted dispersive liquid-liquid microextraction based on solidification of floating organic droplet to determine sildenafil and its analogues in dietary supplements. J Sep Sci. 2017 Aug;40(15):3120-3129. doi: 10.1002/jssc.201700159. Epub 2017 Jul 5. PMID: 28618213. 5: Ahmed M, Kumari S, Manali P, Sonje S, Malik M. Safety and Quality Concerns Regarding Over-the-Counter Sexual Enhancement Products Sold in the USA Market Pose a Major Health Risk. J Addict Res Ther. 2016 Oct;7(5):299. doi: 10.4172/2155-6105.1000299. Epub 2016 Oct 31. PMID: 29214098; PMCID: PMC5713482. 6: Mokhtar SU, Chin ST, Kee CL, Low MY, Drummer OH, Marriott PJ. Rapid determination of sildenafil and its analogues in dietary supplements using gas chromatography-triple quadrupole mass spectrometry. J Pharm Biomed Anal. 2016 Mar 20;121:188-196. doi: 10.1016/j.jpba.2016.01.034. Epub 2016 Jan 15. PMID: 26808068. 7: Kee CL, Ge X, Low MY. Application of Orbitrap-mass spectrometry to differentiate isomeric sildenafil- and thiosildenafil-like analogues used for the adulteration of dietary supplements. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(10):1737-48. doi: 10.1080/19440049.2015.1062923. Epub 2015 Jul 29. PMID: 26179419. 8: Aceña J, Pérez S, Gardinali P, Abad JL, Eichhorn P, Heuett N, Barceló D. Structure elucidation of phototransformation products of unapproved analogs of the erectile dysfunction drug sildenafil in artificial freshwater with UPLC-Q Exactive-MS. J Mass Spectrom. 2014 Dec;49(12):1279-89. doi: 10.1002/jms.3461. PMID: 25476946. 9: Duez M, Etter M, Klinger N, Cirimele V. Synthetic phosphodiesterase-5-inhibitors use/abuse and interest of hair testing: reporting of a rape case. Drug Test Anal. 2014 Jun;6 Suppl 1:17-21. doi: 10.1002/dta.1638. PMID: 24817044. 10: Mustazza C, Borioni A, Rodomonte AL, Bartolomei M, Antoniella E, Di Martino P, Valvo L, Sestili I, Costantini E, Gaudiano MC. Characterization of Sildenafil analogs by MS/MS and NMR: a guidance for detection and structure elucidation of phosphodiesterase-5 inhibitors. J Pharm Biomed Anal. 2014 Aug 5;96:170-86. doi: 10.1016/j.jpba.2014.03.038. Epub 2014 Apr 3. PMID: 24747148. 11: Han KM, Lee JH, Park HJ, Hwang I, Heo OS, Kim WS. Isolation and identification of novel propoxyphenyl thiosildenafil found in natural health food product. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2014;31(1):1-6. doi: 10.1080/19440049.2013.855948. Epub 2014 Jan 2. PMID: 24382302. 12: Tagami T, Takeda A, Asada A, Aoyama A, Doi T, Kajimura K, Sawabe Y. Simultaneous identification of hydroxythiohomosildenafil, aminotadalafil, thiosildenafil, dimethylsildenafil, and thiodimethylsildenafil in dietary supplements using high-performance liquid chromatography-mass spectrometry. Shokuhin Eiseigaku Zasshi. 2013;54(3):232-6. doi: 10.3358/shokueishi.54.232. PMID: 23863369. 13: Kee CL, Ge X, Koh HL, Low MY. Isolation and characterization of propoxyphenyl linked sildenafil and thiosildenafil analogues in health supplements. J Pharm Biomed Anal. 2012 Nov;70:265-72. doi: 10.1016/j.jpba.2012.07.008. Epub 2012 Jul 16. PMID: 22840979. 14: Balayssac S, Gilard V, Zedde C, Martino R, Malet-Martino M. Analysis of herbal dietary supplements for sexual performance enhancement: first characterization of propoxyphenyl-thiohydroxyhomosildenafil and identification of sildenafil, thiosildenafil, phentolamine and tetrahydropalmatine as adulterants. J Pharm Biomed Anal. 2012 Apr 7;63:135-50. doi: 10.1016/j.jpba.2012.01.035. Epub 2012 Feb 4. PMID: 22365331. 15: Vaysse J, Gilard V, Balayssac S, Zedde C, Martino R, Malet-Martino M. Identification of a novel sildenafil analogue in an adulterated herbal supplement. J Pharm Biomed Anal. 2012 Feb 5;59:58-66. doi: 10.1016/j.jpba.2011.10.001. Epub 2011 Oct 7. PMID: 22030075. 16: Man CN, Noor NM, Lajis R. Identification of thioketone analogues of sildenfil using gas chromatography-mass spectrometry. J Chromatogr A. 2011 Sep 28;1218(39):7055-60. doi: 10.1016/j.chroma.2011.08.037. Epub 2011 Aug 17. PMID: 21872876. 17: Nicoletti M. Identification of thiosildenafil in a health supplement. Nat Prod Commun. 2011 Jul;6(7):1003-4. PMID: 21834245. 18: Reepmeyer JC. Direct intramolecular gas-phase transfer reactions during fragmentation of sildenafil and thiosildenafil analogs in electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom. 2009 Mar;23(6):927-36. doi: 10.1002/rcm.3948. PMID: 19222058. 19: Gryniewicz CM, Reepmeyer JC, Kauffman JF, Buhse LF. Detection of undeclared erectile dysfunction drugs and analogues in dietary supplements by ion mobility spectrometry. J Pharm Biomed Anal. 2009 Apr 5;49(3):601-6. doi: 10.1016/j.jpba.2008.12.002. Epub 2008 Dec 11. PMID: 19150190. 20: Balayssac S, Trefi S, Gilard V, Malet-Martino M, Martino R, Delsuc MA. 2D and 3D DOSY 1H NMR, a useful tool for analysis of complex mixtures: application to herbal drugs or dietary supplements for erectile dysfunction. J Pharm Biomed Anal. 2009 Nov 1;50(4):602-12. doi: 10.1016/j.jpba.2008.10.034. Epub 2008 Nov 6. PMID: 19108978.