Page last updated: 2024-11-06

nipradilol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Nipradilol is a nonselective beta-blocker with vasodilatory properties. It is a racemic mixture of two enantiomers, with the S-enantiomer being more potent in terms of beta-blockade and the R-enantiomer showing stronger vasodilatory effects. Nipradilol was synthesized in the 1970s and has been studied for its potential therapeutic applications in various cardiovascular diseases, including hypertension, angina pectoris, and heart failure. It is believed to exert its effects by blocking beta-adrenergic receptors, which are located in the heart, blood vessels, and other tissues. By blocking these receptors, nipradilol can reduce heart rate, decrease blood pressure, and improve blood flow. However, nipradilol also exhibits alpha-adrenergic blocking activity, which can contribute to its vasodilatory effects. Nipradilol has been investigated for its potential in treating conditions such as hypertension and angina pectoris. It has also been explored for its potential to improve blood flow in patients with peripheral artery disease. While nipradilol has shown promise in preclinical studies, its use in clinical practice has been limited due to concerns about its safety profile. Studies have shown that nipradilol can cause side effects such as dizziness, headache, fatigue, and gastrointestinal disturbances. Additionally, some studies have suggested that nipradilol may have a negative impact on blood sugar levels. Despite these concerns, research on nipradilol is ongoing, and it is still considered a potential therapeutic agent for certain cardiovascular conditions.'

Cross-References

ID SourceID
PubMed CID72006
CHEMBL ID155622
CHEBI ID31682
SCHEMBL ID48884
MeSH IDM0110163

Synonyms (50)

Synonym
nipradilol
nipradolol
kt-210
hypadil
k-351
nipranol
brn 3566879
nipradilolum [latin]
ccris 2515
8-(2-hydroxy-3-(isopropylamino)propoxy)-3-chromanol 3-nitrate
2h-1-benzopyran-3-ol, 3,4-dihydro-8-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-, 3-nitrate
3,4-dihydro-8-(2-hydroxy-3-isopropylamino)propoxy-3-nitroxy-2h-1-benzopyran
3,4-dihydro-8-(2-hydroxy-3-(isopropylamino)propoxy)-2h-1-benzopyran-3-ol 3-nitrate
8-(2-hydroxy-3-(isopropylamino)propoxy)-3-chromanyl nitrat
k 351
nipradilol [inn:jan]
8-(2-hydroxy-3-(isopropylamino)propoxy)-3-chromanol, 3-nitrate
3,4-dihydro-8-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-2h-1-benzopyran-3-ol 3-nitrate
nipradilol (jan/inn)
D01691
hypadil (tn)
81486-22-8
L013397
CHEMBL155622
[8-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3,4-dihydro-2h-chromen-3-yl] nitrate
AKOS016014067
unii-fvm336i71y
nipradilolum
fvm336i71y ,
FT-0630894
nipradilol [inn]
nipradilol [inci]
nipradilol [jan]
nipradilol [mart.]
nipradilol [mi]
nipradolol [who-dd]
SCHEMBL48884
8-[2-hydroxy-3-(isopropylamino)propoxy]-3,4-dihydro-2h-chromen-3-yl nitrate #
3-nitroxy-8-[(2-hydroxy-3-isopropylamino)propoxy]-3,4(2h)-dihydro-1-benzopyran
OMCPLEZZPVJJIS-UHFFFAOYSA-N
8-(2-hydroxy-3-(isopropylamino)propoxy)chroman-3-yl nitrate
CHEBI:31682
8-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-3,4-dihydro-2h-1-benzopyran-3-yl nitrate
3,4-dihydro-8-(2-hydroxy-3-isopropylaminopropoxy)-3-nitroxy-2h-1-benzopyran
BCP04466
Q15634005
hypadil; k 351; kt 210; nipradilo
CS-0025984
HY-106523
DTXSID30868615

Research Excerpts

Overview

Nipradilol is a donor of nitric oxide and an antagonist of alpha-1, beta-1 and -2 adrenoreceptors. It has a propranolol-like structure and contains a nitrate moiety.

ExcerptReferenceRelevance
"Nipradilol is a new antiglaucoma ophthalmic agent used in Japan. "( Vasodilatory effects of nipradilol, an alpha- and beta-adrenergic blocker with nitric oxide releasing action, in rabbit ciliary artery.
Ishikawa, H; Ohnishi, Y; Yamaji, K; Yoshitomi, T, 2002
)
2.06
"Nipradilol is an alpha(1), beta-blocker with milder side effects than other beta-blockers used in humans. "( Effects of topical nipradilol and timolol maleate on intraocular pressure, facility of outflow, arterial blood pressure and pulse rate in dogs.
Ito, N; Izumisawa, Y; Kotani, T; Maehara, S; Ono, K; Seno, T; Tsuzuki, K; Yamashita, K; Yokoyama, T,
)
1.9
"Nipradilol is a donor of nitric oxide and an antagonist of alpha-1, beta-1 and -2 adrenoreceptors, and we therefore examined whether one of these pharmacological effects might be more important in promoting axon regeneration."( Axonal regeneration of cat retinal ganglion cells is promoted by nipradilol, an anti-glaucoma drug.
Tokita, Y; Watanabe, M; Yata, T, 2006
)
1.29
"Nipradilol is a newly synthesized beta-blocker which has a propranolol-like structure and contains a nitrate moiety. "( Effects of nipradilol on venous hemodynamics: evaluation with a Doppler blood flow method.
Haraoka, S; Kobayashi, H; Maekawa, K; Mizuo, K; Obayashi, N; Saito, D; Uchida, S, 1994
)
2.12
"Nipradilol is a beta-adrenoreceptor blocking agent, whose structure contains an NO2 group. "( Nipradilol inhibits rat mesangial cell mitogenesis through the activation of soluble guanylate cyclase.
Haneda, M; Kajiwara, N; Kikkawa, R; Koya, D; Sakamoto, K; Sawada, M; Shigeta, Y; Sugimoto, T; Uzu, T, 1993
)
3.17
"Nipradilol is a new type of beta-blocker which possesses nitroglycerin-like vasodilating action in addition to beta-blocking action. "( Treatment of essential and parkinsonian tremor with nipradilol.
Akiyama, K; Kitagawa, Y; Shinohara, Y; Takeoka, T; Yazaki, K; Yoshii, F, 1996
)
1.99
"Nipradilol is a unique beta-blocker that suppresses PEPCK gene transcription in hepatocytes likely through liberation of nitric oxide and resultant activation of guanylate cyclase."( Effects of nipradilol, a nitric oxide-releasing beta-adrenoceptor blocking agent, on phosphoenolpyruvate carboxykinase gene transcription in a rat hepatoma cell line.
Aizawa, T; Hashizume, K; Ikeo, S; Komatsu, M; Nakajima, K; Nishimura, Y; Yamauchi, K, 2001
)
1.42
"Nipradilol, which is a nonselective beta-adrenergic and nitrate-like vasodilator anti-anginal agent developed in Japan, may ameliorate silent myocardial ischemia, while it also improves exercise tolerance and HRV indices in patients with chronic stable angina."( Effect of nipradilol on silent myocardial ischemia and heart rate variability in chronic stable angina.
Hikita, H; Kurita, A; Mastui, T; Ohsuzu, F; Satomura, K; Takase, B, 2002
)
1.44

Effects

Nipradilol has alpha1- and beta-adrenoceptor-blocking and nitric oxide (NO)-donating properties. It has clinically been used as an anti-glaucomatous agent in Japan.

ExcerptReferenceRelevance
"Nipradilol has a more potent beta-adrenoceptor blocking action than propranolol, while its vasodilator action is not obvious, at least in rabbits."( Pharmacodynamic and pharmacokinetic studies on prizidilol and nipradilol (K-351), antihypertensive drugs with combined vasodilator and beta-adrenoceptor blocking actions, in rabbits.
Kawashima, K; Sokabe, H; Watanabe, TX, 1984
)
1.23
"Nipradilol (Nip), which has α1- and β-adrenoceptor antagonist and nitric oxide (NO)-donating properties, has clinically been used as an anti-glaucomatous agent in Japan. "( Protective action of nipradilol mediated through S-nitrosylation of Keap1 and HO-1 induction in retinal ganglion cells.
Arai, K; Kamiya, M; Kato, S; Koriyama, Y; Ogai, K; Sugitani, K; Takadera, T, 2012
)
2.14
"Nipradilol has alpha1- and beta-adrenoceptor-blocking and nitric oxide (NO)-donating properties."( Nipradilol inhibits apoptosis by preventing the activation of caspase-3 via S-nitrosylation and the cGMP-dependent pathway.
Abe, T; Nakazawa, T; Sugano, E; Tamai, M; Tomita, H, 2002
)
2.48
"Nipradilol has a more potent beta-adrenoceptor blocking action than propranolol, while its vasodilator action is not obvious, at least in rabbits."( Pharmacodynamic and pharmacokinetic studies on prizidilol and nipradilol (K-351), antihypertensive drugs with combined vasodilator and beta-adrenoceptor blocking actions, in rabbits.
Kawashima, K; Sokabe, H; Watanabe, TX, 1984
)
1.23

Treatment

The nipradilol-treated and captopril-treated rats had significantly smaller LVEDVI than did the vehicle- treated rats with both moderate and large infarction. Pretreatment with nip radilol lessened the decreases in the levels of ATP and CrP and the increases in thelevels of AMP and lactate, caused by 3 min of ischaemia.

ExcerptReferenceRelevance
"The nipradilol-treated rats had a significantly smaller left ventricular volume index than the vehicle-treated rats (2.04 +/- 0.16 ml/kg in the vehicle-treated group vs 1.36 +/- 0.10 ml/kg in the nipradilol-treated group, P < 0.01)."( Chronic therapy with nipradilol, a beta-adrenergic blocker, attenuated left ventricular remodeling following myocardial infarction in rats.
Nakamura, M; Sonoki, H; Takeshita, A, 1997
)
1.1
"The nipradilol-treated and captopril-treated rats had significantly smaller LVEDVI than did the vehicle-treated rats with both moderate and large infarction (large infarct: 2.48 +/- 0.12 ml/kg for the vehicle group, 1.69 +/- 0.10 ml/kg for the nipradilol group, P < 0.01, and 1.79 +/- 0.14 ml/kg for the captopril group, P < 0.01)."( Nipradilol, a new beta-adrenergic blocker, reduces left ventricular remodeling following myocardial infarction in spontaneously hypertensive rats.
Nakamura, M; Sonoki, H; Takeshita, A, 1997
)
2.22
"Nipradilol treatment restored this relaxation."( The beta adrenoreceptor antagonist, nipradilol, preserves the endothelial nitric oxide response in atherosclerotic vessels of rabbit.
Esaki, T; Hayashi, T; Iguchi, A; Muto, E; Yamada, K, 1997
)
1.29
"Pretreatment with nipradilol lessened the decreases in the levels of ATP and CrP and the increases in the levels of AMP and lactate, caused by 3 min of ischaemia, to the same extent as propranolol."( Effect of nipradilol on myocardial energy metabolism in the dog ischaemic heart.
Abiko, Y; Chiba, K; Hayase, N; Ichihara, K; Inagaki, S, 1990
)
1.01

Pharmacokinetics

ExcerptReferenceRelevance
"The pharmacokinetic parameters of nipradilol (NIP), a new potent antihypertensive and antianginal agent, and propranolol were determined after oral, intravenous and intraportal administration to the beagle dog implanted with cannula in portal vein at a dose of 1 mg/kg."( Pharmacokinetics of nipradilol (K-351), a new antihypertensive agent. II. Influence of the route of administration on bioavailability in dogs.
Fujii, M; Ito, T; Kojima, J; Suzuki, J; Yoshimura, M, 1985
)
0.87
" Following oral administration, the systemic availability for all species increased with the oral dose, while the half-life was about 2 h, and was independent of dose."( Pharmacokinetics of nipradilol (K-351), a new antihypertensive agent. I. Studies on interspecies variation in laboratory animals.
Ito, T; Kojima, J; Suzuki, J; Yoshimura, M, 1985
)
0.59
" NP/ml, respectively), whereas unchanged NP levels showed a peak at 30 min and Cmax values at both doses indicated a great difference (70-fold) in comparison with the dose ratio."( Pharmacokinetics of the new antihypertensive agent nipradilol in rats. 2nd communication: A single oral administration of [14C]nipradilol to spontaneously hypertensive rats.
Kabuto, S; Kimata, H; Koide, T; Nakao, H; Suzuki, J; Yonemitsu, M, 1985
)
0.52

Compound-Compound Interactions

ExcerptReferenceRelevance
" Thus, the hemodynamic effects of nipradilol, a new beta-adrenergic antagonist combined with a nitroxy base, was studied in conscious and unrestrained rats in two models of portal hypertension."( Hemodynamic effects of nipradilol, a new beta-adrenergic antagonist combined with a nitroxy base, in rats with intra- or extra-hepatic portal hypertension.
Cailmail, S; Lebrec, D; Ohsuga, M, 1993
)
0.88

Bioavailability

ExcerptReferenceRelevance
" Orally administered NIP underwent extensive first-pass metabolism leading to low bioavailability (11%), despite of complete gastrointestinal absorption."( Pharmacokinetics of nipradilol (K-351), a new antihypertensive agent. II. Influence of the route of administration on bioavailability in dogs.
Fujii, M; Ito, T; Kojima, J; Suzuki, J; Yoshimura, M, 1985
)
0.59
" Conclusively, nipradilol, beta-blocker with nitric oxide-releasing action, in contrast to the other beta-blockers and nitric oxide donors, showed a successful anti-atherosclerotic effect through the restoration of nitric oxide bioavailability and possible interaction with oxygen radicals."( Anti-atherosclerotic effect of beta-blocker with nitric oxide-releasing action on the severe atherosclerosis.
Hayashi, T; Iguchi, A; Kano, H; Matsui-Hirai, H; Sumi, D; Thakur, NK; Tsunekawa, T, 2002
)
0.67

Dosage Studied

Two recently-introduced beta-blockers, nipradilol and arotinolol, as well as labetalol shifted the pressor dose-response curve for phenylephrine to the right. New anti-glaucoma drugs, latanoprost and nip radilol, have been shown to effect a reduction in IOP equal to that achieved with the equivalent dosage of timolol. Nip Radilol did not appear to exert a nitrovasodilating effect.

ExcerptRelevanceReference
" Nipradilol, at the dosage used in the present study, did not appear to exert a nitrovasodilating effect to enhance the portal pressure reduction induced by beta-blocking action."( Long-term haemodynamic effects of a 4-week regimen of nipradilol, a new beta-blocker with nitrovasodilating properties, in patients with portal hypertension due to cirrhosis. A comparative study with propranolol.
Aramaki, T; Katsuta, Y; Komeichi, H; Kurokawa, H; Ohsuga, M; Okumura, H; Satomura, K; Sekiyama, T; Terada, H; Tsutsui, H, 1992
)
1.44
"In pithed rats two recently-introduced beta-blockers, nipradilol and arotinolol, as well as labetalol shifted the pressor dose-response curve for phenylephrine to the right."( Alpha-blockade and vasodilatation induced by nipradilol, arotinolol and labetalol in pithed rats.
Chin, WP; Imai, S; Nakagawa, Y; Nakahara, H, 1985
)
0.78
" New anti-glaucoma drugs, latanoprost and nipradilol, have been shown to effect a reduction in IOP equal to that achieved with the equivalent dosage of timolol, with no adverse systemic side effects."( [Current topics in glaucoma].
Masuda, K, 1996
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
organic molecular entityAny molecular entity that contains carbon.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (134)

TimeframeStudies, This Drug (%)All Drugs %
pre-199039 (29.10)18.7374
1990's39 (29.10)18.2507
2000's51 (38.06)29.6817
2010's5 (3.73)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.85

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index23.85 (24.57)
Research Supply Index5.12 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index29.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.85)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials22 (15.17%)5.53%
Reviews3 (2.07%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other120 (82.76%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]