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MedKoo Cat#: 318563 | Name: Prazosin Hydrochloride
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Description:

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

Prazosin Hydrochloride is a selective adrenergic alpha-1 antagonist used in the treatment of heart failure, hypertension, pheochromocytoma, Raynaud disease, prostratic hypertrophy and urinary retention.

Chemical Structure

Prazosin Hydrochloride
CAS#19237-84-4 (HCl)

Theoretical Analysis

MedKoo Cat#: 318563

Name: Prazosin Hydrochloride

CAS#: 19237-84-4 (HCl)

Chemical Formula: C19H22ClN5O4

Exact Mass: 0.0000

Molecular Weight: 419.86

Elemental Analysis: C, 54.35; H, 5.28; Cl, 8.44; N, 16.68; O, 15.24

Price and Availability

Size Price Availability Quantity
100mg USD 110.00 Ready to ship
200mg USD 150.00 Ready to ship
500mg USD 250.00 Ready to ship
1g USD 350.00 2 Weeks
2g USD 450.00 2 Weeks
5g USD 750.00 2 Weeks
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Related CAS #
19237-84-4 (HCl) 19216-56-9 (free)
Synonym
Prazosin Hydrochloride, Prazosin HCl, Furazosin hydrochloride, Minipress, Peripress, Prazosin
IUPAC/Chemical Name
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(furan-2-yl)methanone;hydrochloride
InChi Key
WFXFYZULCQKPIP-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H21N5O4.ClH/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14;/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22);1H
SMILES Code
COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4=CC=CO4)N)OC.Cl
Appearance
White to off-white crystalline 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
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#T7C09C26
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Prazosin hydrochloride is an alpha-adrenergic blocker.
In vitro activity:
In order to investigate the effect of prazosin on acute myeloid leukaemia, U937 and HL60 cells were transfected with different concentration of prazosin (5, 10 and 15 μM), and DMSO was used as negative control (NC). The cytotoxicity of prazosin to acute myeloid leukaemia cells was confirmed by CCK8 assay. As indicated in Fig. 1A, compared to NC cells, prazosin treatment significantly reduced cell viability in U937 cells when its concentration was higher than 10 μM. Similar inhibitory effect of prazosin on cell viability were also observed in HL60 cells (Fig. 1B). Moreover, these data showed that the percentage of cells in the G1 phase was significantly increased in prazosin-treated U937 cells compared with the NC group, while the proportions of cells in the S phase was decreased (Fig. 1C and E), suggesting that prazosin induced cell cycle arrest in G1 phase in U937 cells. With the increase of prazosin concentration, cell cycle arrest became more obvious (Fig. 1C and E). Similarly, prazosin also induced cell cycle arrest in G1 phase in HL60 cells (Fig. 1D and E). Reference: Biomed Pharmacother. 2020 Apr;124:109731. https://pubmed.ncbi.nlm.nih.gov/31954876/
In vivo activity:
Infarct volume and functional recovery were analyzed in experimental rats with myocardial ischemia after treatment with prazosin. The results showed that the infarct volume was markedly decreased following prazosin treatment compared to the vehicle determined by the infarct volume analysis (Fig. 1A-B). Prazosin was found to improve the neurological deficits, as determined by the mNSS test (Fig. 1C). Treatment of prazosin also decreased brain water content compared to the vehicle group, as determined by the brain water content assay (Fig. 1D). These results suggested that prazosin may attenuate ischemia-induced brain injury. Reference: Exp Ther Med. 2020 Sep; 20(3): 2577–2584. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7401792/
Solvent mg/mL mM comments
Solubility
Water 0.5 1.20
Methanol 6.0 14.30
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 419.86 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. Sun X, Yang S, Song W. Prazosin inhibits the proliferation and survival of acute myeloid leukaemia cells through down-regulating TNS1. Biomed Pharmacother. 2020 Apr;124:109731. doi: 10.1016/j.biopha.2019.109731. Epub 2020 Jan 17. PMID: 31954876. 2. Fuchs R, Schwach G, Stracke A, Meier-Allard N, Absenger M, Ingolic E, Haas HS, Pfragner R, Sadjak A. The anti-hypertensive drug prazosin induces apoptosis in the medullary thyroid carcinoma cell line TT. Anticancer Res. 2015 Jan;35(1):31-38. PMID: 25550532; PMCID: PMC4290659. 3. Qasim S, Alamgeer, Saleem M, Alotaibi NH, Bukhari SNA, Alharbi KS, Irfan HM, Anwar R. Appraisal of the Antiarthritic Potential of Prazosin via Inhibition of Proinflammatory Cytokine TNF-α: A Key Player in Rheumatoid Arthritis. ACS Omega. 2021 Jan 15;6(3):2379-2388. doi: 10.1021/acsomega.0c05698. PMID: 33521476; PMCID: PMC7841939. 4. Liu S, Li W. Prazosin blocks apoptosis of endothelial progenitor cells through downregulating the Akt/NF-κB signaling pathway in a rat cerebral infarction model. Exp Ther Med. 2020 Sep;20(3):2577-2584. doi: 10.3892/etm.2020.9009. Epub 2020 Jul 13. PMID: 32765751; PMCID: PMC7401792.
In vitro protocol:
1. Sun X, Yang S, Song W. Prazosin inhibits the proliferation and survival of acute myeloid leukaemia cells through down-regulating TNS1. Biomed Pharmacother. 2020 Apr;124:109731. doi: 10.1016/j.biopha.2019.109731. Epub 2020 Jan 17. PMID: 31954876. 2. Fuchs R, Schwach G, Stracke A, Meier-Allard N, Absenger M, Ingolic E, Haas HS, Pfragner R, Sadjak A. The anti-hypertensive drug prazosin induces apoptosis in the medullary thyroid carcinoma cell line TT. Anticancer Res. 2015 Jan;35(1):31-38. PMID: 25550532; PMCID: PMC4290659.
In vivo protocol:
1. Qasim S, Alamgeer, Saleem M, Alotaibi NH, Bukhari SNA, Alharbi KS, Irfan HM, Anwar R. Appraisal of the Antiarthritic Potential of Prazosin via Inhibition of Proinflammatory Cytokine TNF-α: A Key Player in Rheumatoid Arthritis. ACS Omega. 2021 Jan 15;6(3):2379-2388. doi: 10.1021/acsomega.0c05698. PMID: 33521476; PMCID: PMC7841939. 2. Liu S, Li W. Prazosin blocks apoptosis of endothelial progenitor cells through downregulating the Akt/NF-κB signaling pathway in a rat cerebral infarction model. Exp Ther Med. 2020 Sep;20(3):2577-2584. doi: 10.3892/etm.2020.9009. Epub 2020 Jul 13. PMID: 32765751; PMCID: PMC7401792.
1: Ansari E, Honarvar B, Sajadian SA, Arab Aboosadi Z, Azizi M. Utilization of RESOLV with polymer to produce prazosin hydrochloride nanoparticles and optimization of the process parameters. Sci Rep. 2024 Aug 7;14(1):18346. doi: 10.1038/s41598-024-69128-6. PMID: 39112728; PMCID: PMC11306599. 2: Sudaki H, Fujimoto K, Wada K, Sugano K. Phosphate buffer interferes dissolution of prazosin hydrochloride in compendial dissolution testing. Drug Metab Pharmacokinet. 2023 Aug;51:100519. doi: 10.1016/j.dmpk.2023.100519. Epub 2023 Jun 10. PMID: 37393739. 3: Dawood DH, Srour AM, Saleh DO, Huff KJ, Greco F, Osborn HMI. New pyridine and chromene scaffolds as potent vasorelaxant and anticancer agents. RSC Adv. 2021 Sep 2;11(47):29441-29452. doi: 10.1039/d1ra04758b. PMID: 35479558; PMCID: PMC9040659. 4: Mazeh AC, Angus JA, Wright CE. Pharmacological characterisation of the CB1 receptor antagonist activity of cannabidiol in the rat vas deferens bioassay. Eur J Pharmacol. 2021 Oct 15;909:174433. doi: 10.1016/j.ejphar.2021.174433. Epub 2021 Aug 17. PMID: 34416240. 5: ALOthman ZA, Alsheetan KM, Aboul-Enein HY, Ali I. Applications of shun shell column and nanocomposite sorbent for analysis of eleven anti-hypertensive in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2020 Jun 1;1146:122125. doi: 10.1016/j.jchromb.2020.122125. Epub 2020 Apr 25. PMID: 32371329. 6: Ibrahim AM, Hendawy HAM, Hassan WS, Shalaby A, ElMasry MS. Determination of terazosin in the presence of prazosin: Different state-of-the-art machine learning algorithms with UV spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2020 Aug 5;236:118349. doi: 10.1016/j.saa.2020.118349. Epub 2020 Apr 8. PMID: 32305835. 7: Wu J, Ma H, Bu X, Ma C, Zhu L, Hao B, Zhao B, Tian Y. SERS determination of the antihypertensive drugs prazosin and losartan by using silver nanoparticles coated with β-cyclodextrin. Mikrochim Acta. 2019 Nov 18;186(12):801. doi: 10.1007/s00604-019-3946-z. PMID: 31741056. 8: Mazeh AC, Angus JA, Wright CE. The effects of varying Mg2+ ion concentrations on contractions to the cotransmitters ATP and noradrenaline in the rat vas deferens. Auton Neurosci. 2019 Dec;222:102588. doi: 10.1016/j.autneu.2019.102588. Epub 2019 Oct 5. PMID: 31669796. 9: Ramasamy VS, Samidurai M, Park HJ, Wang M, Park RY, Yu SY, Kang HK, Hong S, Choi WS, Lee YY, Kim HS, Jo J. Avenanthramide-C Restores Impaired Plasticity and Cognition in Alzheimer's Disease Model Mice. Mol Neurobiol. 2020 Jan;57(1):315-330. doi: 10.1007/s12035-019-01707-5. Epub 2019 Jul 22. PMID: 31332763. 10: Spencer BH, McDermott CM, Chess-Williams R, Christie D, Anoopkumar-Dukie S. Prazosin but Not Tamsulosin Sensitises PC-3 and LNCaP Prostate Cancer Cells to Docetaxel. Pharmacology. 2018 Apr 17;102(1-2):10-18. doi: 10.1159/000488713. Epub ahead of print. PMID: 29669348. 11: Broadley KJ, Broadley HD. Non-adrenergic vasoconstriction and vasodilatation of guinea-pig aorta by β-phenylethylamine and amphetamine - Role of nitric oxide determined with L-NAME and NO scavengers. Eur J Pharmacol. 2018 Jan 5;818:198-205. doi: 10.1016/j.ejphar.2017.10.038. Epub 2017 Oct 23. PMID: 29074414. 12: Angus JA, Rajasekaran P, Wright CE. Novel technique to determine the pKA of clonidine at prejunctional α2-adrenoceptors in cardiac and vascular sympathetic transmission. Eur J Pharmacol. 2017 Apr 5;800:81-95. doi: 10.1016/j.ejphar.2017.02.030. Epub 2017 Feb 17. PMID: 28219708. 13: Neelannavar R, Patil M, Patil S, Lakhkar B, Shegji V. Lizard Bite Masquerading as Scorpion Sting Envenomation. J Clin Diagn Res. 2016 Nov;10(11):SD05-SD06. doi: 10.7860/JCDR/2016/23047.8858. Epub 2016 Nov 1. PMID: 28050465; PMCID: PMC5198418. 14: Angus JA, Wright CE. Novel α1-adrenoceptor antagonism by the fluroquinolone antibiotic trovafloxacin. Eur J Pharmacol. 2016 Nov 15;791:179-184. doi: 10.1016/j.ejphar.2016.08.035. Epub 2016 Aug 31. PMID: 27590356. 15: Wenner MI, Maker GL, Dawson LF, Drummond PD, Mullaney I. The potential of metabolomic analysis techniques for the characterisation of α1-adrenergic receptors in cultured N1E-115 mouse neuroblastoma cells. Cytotechnology. 2016 Aug;68(4):1561-75. doi: 10.1007/s10616-015-9915-4. Epub 2015 Sep 25. PMID: 26408527; PMCID: PMC4960202. 16: de Souza Rossignoli P, Yamamoto FZ, Pereira OC, Chies AB. Norepinephrine responses in rat renal and femoral veins are reinforced by vasoconstrictor prostanoids. Vascul Pharmacol. 2015 Sep;72:93-100. doi: 10.1016/j.vph.2015.06.017. Epub 2015 Jul 2. PMID: 26141930. 17: Li AP, Peng H, Peng JD, Zhou MQ, Zhang J. Rayleigh light scattering detection of three α1-adrenoceptor antagonists coupled with high performance liquid chromatograph. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Aug 5;147:178-84. doi: 10.1016/j.saa.2015.02.062. Epub 2015 Mar 11. PMID: 25840026. 18: Li X, An YL, Zhang L, Xiao ZH, Liu JY, Zhang Y, Wang J, Yang DF, Wang H. [Regulative effects of vessel active drugs on extremital skin temperature of experimental animals exposed to cold]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2014 Sep;30(5):385-9. Chinese. PMID: 25571625. 19: Cheung L, Yu DM, Neiron Z, Failes TW, Arndt GM, Fletcher JI. Identification of new MRP4 inhibitors from a library of FDA approved drugs using a high- throughput bioluminescence screen. Biochem Pharmacol. 2015 Feb 1;93(3):380-8. doi: 10.1016/j.bcp.2014.11.006. Epub 2014 Nov 22. PMID: 25462817. 20: Mugabo P, Philander A, Raji I, Dietrich D, Green I. Effects of hippadine on the blood pressure and heart rate in male spontaneously hypertensive Wistar rats. J Ethnopharmacol. 2014 Dec 2;158 Pt A:123-31. doi: 10.1016/j.jep.2014.10.011. Epub 2014 Oct 18. PMID: 25456427.4.