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MedKoo Cat#: 317750 | Name: Doxazosin
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Description:

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

Doxazosin is an α-1 adrenergic receptor blocker that inhibits the binding of norepinephrine, which is released from sympathetic nerve terminals, to the α-1 receptors on the membrane of vascular smooth muscle cells. Blockages of the alpha-1 adrenergic action on the vascular smooth muscles lead to a decrease in vascular resistance and antihypertensive activity. This agent also shows high affinity to alpha-1c adrenoceptor, the predominant functional type in the prostate, which may partially attribute to its effect in treatment of benign prostatic hyperplasia.

Chemical Structure

Doxazosin
Doxazosin
CAS#74191-85-8 (free base)

Theoretical Analysis

MedKoo Cat#: 317750

Name: Doxazosin

CAS#: 74191-85-8 (free base)

Chemical Formula: C23H25N5O5

Exact Mass: 451.1856

Molecular Weight: 451.48

Elemental Analysis: C, 61.19; H, 5.58; N, 15.51; O, 17.72

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
250mg USD 450.00 2 Weeks
1g USD 950.00 2 Weeks
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Related CAS #
70918-01-3 (HCl) 77883-43-3 (mesylate) 74191-85-8 (free base)
Synonym
Doxazosin; Doxazosine; Doxazosina; Doxazosinum; UK-33274; UK33274; UK 33274;
IUPAC/Chemical Name
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(2,3-dihydro-1,4-benzodioxin-3-yl)methanone
InChi Key
RUZYUOTYCVRMRZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)
SMILES Code
COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4COC5=CC=CC=C5O4)N)OC
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Doxazosin (UK 33274) is a quinazoline-derivative that selectively antagonizes postsynaptic α1-adrenergic receptors.
In vitro activity:
Expression of Col1α1 was significantly decreased by DX (doxazosin) (10 μmol/L) at mRNA (-30 %) and protein level (-50 %) in TGF-β treated aHSCs. DX significantly reduced aHSCs proliferation and increased expression of senescence and SASP markers. PMA and m-3M3FBS reversed the effect of DX on senescence markers. Reference: Mech Ageing Dev. 2022 Jan;201:111617. https://pubmed.ncbi.nlm.nih.gov/34958827/
In vivo activity:
Doxazosin treatment protected against the rat kidney damage and attenuated the associated biochemical changes. Doxazosin has a direct renoprotective effect possibly by down-regulating SGLT2. Reference: Basic Clin Pharmacol Toxicol. 2020 May;126(5):413-423. https://pubmed.ncbi.nlm.nih.gov/31788938/
Solvent mg/mL mM
Solubility
DMSO 31.0 68.66
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 451.48 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. Serna-Salas SA, Arroyave-Ospina JC, Zhang M, Damba T, Buist-Homan M, Muñoz-Ortega MH, Ventura-Juárez J, Moshage H. α-1 Adrenergic receptor antagonist doxazosin reverses hepatic stellate cells activation via induction of senescence. Mech Ageing Dev. 2022 Jan;201:111617. doi: 10.1016/j.mad.2021.111617. Epub 2021 Dec 24. PMID: 34958827. 2. Xiu AY, Ding Q, Li Z, Zhang CQ. Doxazosin Attenuates Liver Fibrosis by Inhibiting Autophagy in Hepatic Stellate Cells via Activation of the PI3K/Akt/mTOR Signaling Pathway. Drug Des Devel Ther. 2021 Aug 21;15:3643-3659. doi: 10.2147/DDDT.S317701. PMID: 34456560; PMCID: PMC8387324. 3. Rezq S, Nasr AM, Shaheen A, Elshazly SM. Doxazosin down-regulates sodium-glucose cotransporter-2 and exerts a renoprotective effect in rat models of acute renal injury. Basic Clin Pharmacol Toxicol. 2020 May;126(5):413-423. doi: 10.1111/bcpt.13371. Epub 2019 Dec 22. PMID: 31788938. 4. Sun JA, Kong DZ, Zhen YQ, Li Q, Zhang W, Zhang JH, Yin ZW, Ren LM. Stereoselective binding of doxazosin enantiomers to plasma proteins from rats, dogs and humans in vitro. Acta Pharmacol Sin. 2013 Dec;34(12):1568-74. doi: 10.1038/aps.2013.120. Epub 2013 Nov 18. PMID: 24241343; PMCID: PMC4002564.
In vitro protocol:
1. Serna-Salas SA, Arroyave-Ospina JC, Zhang M, Damba T, Buist-Homan M, Muñoz-Ortega MH, Ventura-Juárez J, Moshage H. α-1 Adrenergic receptor antagonist doxazosin reverses hepatic stellate cells activation via induction of senescence. Mech Ageing Dev. 2022 Jan;201:111617. doi: 10.1016/j.mad.2021.111617. Epub 2021 Dec 24. PMID: 34958827. 2. Xiu AY, Ding Q, Li Z, Zhang CQ. Doxazosin Attenuates Liver Fibrosis by Inhibiting Autophagy in Hepatic Stellate Cells via Activation of the PI3K/Akt/mTOR Signaling Pathway. Drug Des Devel Ther. 2021 Aug 21;15:3643-3659. doi: 10.2147/DDDT.S317701. PMID: 34456560; PMCID: PMC8387324.
In vivo protocol:
1. Rezq S, Nasr AM, Shaheen A, Elshazly SM. Doxazosin down-regulates sodium-glucose cotransporter-2 and exerts a renoprotective effect in rat models of acute renal injury. Basic Clin Pharmacol Toxicol. 2020 May;126(5):413-423. doi: 10.1111/bcpt.13371. Epub 2019 Dec 22. PMID: 31788938. 2. Sun JA, Kong DZ, Zhen YQ, Li Q, Zhang W, Zhang JH, Yin ZW, Ren LM. Stereoselective binding of doxazosin enantiomers to plasma proteins from rats, dogs and humans in vitro. Acta Pharmacol Sin. 2013 Dec;34(12):1568-74. doi: 10.1038/aps.2013.120. Epub 2013 Nov 18. PMID: 24241343; PMCID: PMC4002564.
1: Paik YH. Reappraisal of Antihypertensive Medicine Doxazosin and Carvedilol as a Potential Therapeutic for Hepatic Fibrosis. Gut Liver. 2016 Jan 23;10(1):10-1. doi: 10.5009/gnl15576. PubMed PMID: 26696027. 2: Muñoz-Ortega MH, Llamas-Ramírez RW, Romero-Delgadillo NI, Elías-Flores TG, Tavares-Rodríguez Ede J, Campos-Esparza Mdel R, Cervantes-García D, Muñoz-Fernández L, Gerardo-Rodríguez M, Ventura-Juárez J. Doxazosin Treatment Attenuates Carbon Tetrachloride-Induced Liver Fibrosis in Hamsters through a Decrease in Transforming Growth Factor β Secretion. Gut Liver. 2016 Jan 23;10(1):101-8. doi: 10.5009/gnl14459. PubMed PMID: 26573293. 3: Manoharan A, Morrison AE, Lipworth BJ. Effects of the inverse alpha agonist doxazosin in allergic rhinitis. Clin Exp Allergy. 2016 Jan 6. doi: 10.1111/cea.12700. [Epub ahead of print] PubMed PMID: 26741127. 4: Kaplan SA, Lee JY, Meehan AG, Kusek JW. Time Course of Incident Adverse Experiences Associated with Doxazosin, Finasteride, and Combination Therapy in Men with Benign Prostatic Hyperplasia: the Medical Therapy of Prostatic Symptoms (MTOPS) Trial. J Urol. 2015 Dec 8. pii: S0022-5347(15)05367-7. doi: 10.1016/j.juro.2015.11.065. [Epub ahead of print] PubMed PMID: 26678956. 5: Omar MA, Hammad MA, Salman BI, Derayea SM. Highly sensitive spectrofluorimetric method for determination of doxazosin through derivatization with fluorescamine; Application to content uniformity testing. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Dec 17;157:55-60. doi: 10.1016/j.saa.2015.12.012. [Epub ahead of print] PubMed PMID: 26716887. 6: Kaplan SA. Re: Comparison of the Efficacy of Isosorbide Mononitrate and Doxazosin in the Treatment of Lower Urinary Tract Symptoms and Benign Prostatic Hyperplasia: A Randomized Clinical Trial. J Urol. 2015 Dec;194(6):1702. doi: 10.1016/j.juro.2015.09.040. Epub 2015 Sep 21. PubMed PMID: 26582690. 7: Mariola C, Joanna RZ, Jadwiga P, Bartosz P, Anna S. Analysis of aged human serum albumin affinity for doxazosin. Curr Protein Pept Sci. 2015 Nov 1. [Epub ahead of print] PubMed PMID: 26521959. 8: Williams B, MacDonald TM, Morant S, Webb DJ, Sever P, McInnes G, Ford I, Cruickshank JK, Caulfield MJ, Salsbury J, Mackenzie I, Padmanabhan S, Brown MJ; British Hypertension Society's PATHWAY Studies Group. Spironolactone versus placebo, bisoprolol, and doxazosin to determine the optimal treatment for drug-resistant hypertension (PATHWAY-2): a randomised, double-blind, crossover trial. Lancet. 2015 Nov 21;386(10008):2059-68. doi: 10.1016/S0140-6736(15)00257-3. Epub 2015 Sep 20. PubMed PMID: 26414968; PubMed Central PMCID: PMC4655321. 9: Kasacka I, Piotrowska Ż, Filipek A, Majewski M. Influence of doxazosin on biosynthesis of S100A6 and atrial natriuretic factor peptides in the heart of spontaneously hypertensive rats. Exp Biol Med (Maywood). 2015 Oct 28. pii: 1535370215611972. [Epub ahead of print] PubMed PMID: 26515144. 10: Li Q, Kong D, Du Q, Zhao J, Zhen Y, Li T, Ren L. Enantioselective pharmacokinetics of doxazosin and pharmacokinetic interaction between the isomers in rats. Chirality. 2015 Oct;27(10):738-44. doi: 10.1002/chir.22483. Epub 2015 Jul 23. PubMed PMID: 26205661. 11: Kong D, Li Q, Zhang P, Zhang W, Zhen Y, Ren L. The truth about the lower plasma concentration of the (-)-isomer after racemic doxazosin administration in rats: Stereoselective inhibition of the (-)-isomer by the (+)-isomer at CYP3A. Eur J Pharm Sci. 2015 Sep 18;77:238-45. doi: 10.1016/j.ejps.2015.06.022. Epub 2015 Jun 25. PubMed PMID: 26116989. 12: Guha A, Biswas N, Bhattacharjee K, Das P, Kuotsu K. In vitro evaluation of pH responsive doxazosin loaded mesoporous silica nanoparticles: A smart approach in drug delivery. Curr Drug Deliv. 2015 Jul 22. [Epub ahead of print] PubMed PMID: 26201344. 13: Kenna GA, Haass-Koffler CL, Zywiak WH, Edwards SM, Brickley MB, Swift RM, Leggio L. Role of the α(1) blocker doxazosin in alcoholism: a proof-of-concept randomized controlled trial. Addict Biol. 2015 Jun 2. doi: 10.1111/adb.12275. [Epub ahead of print] PubMed PMID: 26037245; PubMed Central PMCID: PMC4668239. 14: Konca C, Tekin M, Turgut M. Doxazosin in the treatment of scorpion envenomation. Indian J Pediatr. 2015 Jun;82(6):499-503. doi: 10.1007/s12098-014-1423-6. Epub 2014 Apr 4. PubMed PMID: 24696312. 15: Chang DG, Li GS, Peng CH, Yu XJ, Zhang PH, Bi MS, Chen DA, You YD, Yang XZ. [Longbishu Capsule combined with mesylate doxazosin: an efficacious therapy for benign prostatic hyperplasia]. Zhonghua Nan Ke Xue. 2015 Feb;21(2):165-9. Chinese. PubMed PMID: 25796693. 16: Kaplan SA. Re: Development of a doxazosin and finasteride transdermal system for combination therapy of benign prostatic hyperplasia. J Urol. 2015 Feb;193(2):731-2. doi: 10.1016/j.juro.2014.11.042. Epub 2014 Nov 15. PubMed PMID: 25617311. 17: Yasuda G, Saka S, Ando D, Hirawa N. Effects of doxazosin as the third agent on morning hypertension and position-related blood pressure changes in diabetic patients with chronic kidney disease. Clin Exp Hypertens. 2015;37(1):75-81. doi: 10.3109/10641963.2014.913599. Epub 2014 May 27. PubMed PMID: 24866870. 18: Keten T, Aslan Y, Balci M, Tuncel A, Bilgin O, Dilmen C, Ozdemir U, Yahsi S, Guzel O, Atan A. Determination of the efficiency of 8 mg doxazosin XL treatment in patients with an inadequate response to 4 mg doxazosin XL treatment for benign prostatic hyperplasia. Urology. 2015 Jan;85(1):189-94. doi: 10.1016/j.urology.2014.10.004. PubMed PMID: 25530384. 19: Biswas N, Guha A, Sahoo RK, Kuotsu K. Pulse release of doxazosin from hydroxyethylcellulose compression coated tablet: mechanistic and in vivo study. Int J Biol Macromol. 2015 Jan;72:537-43. doi: 10.1016/j.ijbiomac.2014.08.028. Epub 2014 Aug 29. PubMed PMID: 25179280. 20: Gao N, Wu H, Chang Y, Guo X, Zhang L, Du L, Fu Y. Mixed micelle cloud point-magnetic dispersive μ-solid phase extraction of doxazosin and alfuzosin. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Jan 5;134:10-6. doi: 10.1016/j.saa.2014.06.095. Epub 2014 Jun 24. PubMed PMID: 24995413.