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P0884 Sigma

(±)-Propranolol hydrochloride

≥99% (TLC), powder

Synonym: (±)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride, DL-Propranolol hydrochloride

  • CAS Number 318-98-9

  • Empirical Formula (Hill Notation) C16H21NO2 · HCl

  • Molecular Weight 295.80

  •  Beilstein Registry Number 4164259

  •  EC Number 206-268-7

  •  MDL number MFCD00012558

  •  PubChem Substance ID 24277796

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Properties

Related Categories Adrenergics, Adrenergics - Antagonists, Antagonists, Approved Therapeutics/Drug Candidates, AstraZeneca,
assay   ≥99% (TLC)
form   powder
color   white
solubility   ethanol: soluble10 mg/mL
  DMSO: <14.5 mg/mL
  H2O: soluble50 mg/mL (dissolve with heat. Aqueous solutions are most stable at pH 3.0 and decompose rapidly at basic pH. Decomposition is accompanied by discoloration of the solution.)
  45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble8.0 mg/mL
originator   AstraZeneca
storage temp.   2-8°C
Gene Information   human ... ADRB1(153), ADRB2(154), ADRB3(155), HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358)

Description

Biochem/physiol Actions

β-adrenoceptor antagonist; 5-HT1/5-HT2 serotonin receptor antagonist; cardiac depressant (anti-arrhythmic).

Caution

Shelf-life of the solid is at least four years if stored protected from the uptake of moisture.

Packaging

1 g in poly tube

5, 25, 100 g in poly bottle

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound is featured on the β-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

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(<I>S</I>)-(−)-Propranolol hydrochloride

≥98% (TLC), powder

Propranolol hydrochloride

United States Pharmacopeia (USP) Reference Standard

Propranolol hydrochloride

European Pharmacopoeia (EP) Reference Standard

Propranolol hydrochloride

pharmaceutical secondary standard; traceable to USP and PhEur

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
22
WGK Germany 
3
RTECS 
UB7525000

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Protocols & Articles

Articles

Antihypertensive Agents

Download BioFiles v7 n5 (3.18 Mb PDF) Back to Pharmaceutical Drugs and Drug Candidates homepage
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BioFiles v7 n5, 2012, 5–20
Keywords: AGE, Antihypertensives, Biofiles, Cardiovascular, Clinical, Diuretics, Help, Pharmaceutical, Reductions, Tools, Type

Discover Bioactive Small Molecules for Neuroscience

The nervous system, comprised of the brain and spinal cord (central nervous system, or CNS) and network of nerves that connects the CNS to the rest of the body (peripheral nervous system, or PNS) is ...
Keywords: Bioactive small molecules, Central Nervous System, Diseases, Metabolism, Neurodegenerative Diseases, Neuroscience, Neurotransmission, Neurotransmitters

Peer-Reviewed Papers

References

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β-Adrenoceptor regulation in rat heart, lung and skin after chronic treatment with (--)-tertatolol or (--)-propranolol. Tan, Y.Y., and Summers, R.J. J. Auton. Pharmacol. 15, 421-436, (1995)

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Isoproterenol And CAMP Block ERK Phosphorylation And Enhance [Ca2+]i Increases And Oxygen Consumption By Muscarinic Receptor Stimulation In Rat Parotid And Submandibular Acinar Cells. Soltoff, S.P., and Hedden, L. J. Thorac. Cardiovasc. Surg. 285, 13337-48, (2010)

Serotonergic inhibition of rat Leydig cell function by propranolol. Tinajero, J.C., et al. Endocrinology 133, 257-264, (1993)

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Reversal of propranolol blockade of adrenergic receptors and related toxicity with drugs that increase cyclic AMP. Whitehurst, V.E., et al. Proc. Soc. Exp. Biol. Med. 221, 382-385, (1999)

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Stereoselective blockade of central [3H]5-hydroxytryptamine binding to multiple sites (5-HT1A, 5-HT1B and 5-HT1C) by mianserin and propranolol. Alexander, B.S., and Wood, M.D. J. Pharm. Pharmacol. 39, 664-666, (1987)

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The effects of propranolol on heterogeneity of rat cerebral small vein oxygen saturation. Chi, O.Z., et al. Anesth. Analg. 89, 690-695, (1999)

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Effects of cyclosporin on the pharmacokinetics of propranolol after intravenous and oral administration to control rats and to rats with uranyl nitrate-induced acute renal failure. Lee, Y.H. and Ku, Y.S. J. Pharm. Pharmacol. 51, 1149-1154, (1999)

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Structural basis for molecular recognition at serotonin receptors. Wang C, Jiang Y, Ma J, et al. Science 340(6132), 610-4, (2013)

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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Social stress up-regulates inflammatory gene expression in the leukocyte transcriptome via β-adrenergic induction of myelopoiesis. Powell ND, Sloan EK, Bailey MT, et al. Proc. Natl. Acad. Sci. U. S. A. 110(41), 16574-9, (2013)

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Carvedilol for primary prophylaxis of variceal bleeding in cirrhotic patients with haemodynamic non-response to propranolol. Reiberger T, Ulbrich G, Ferlitsch A, et al. Gut 62(11), 1634-41, (2013)

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The mode of action (MOA) approach reveals interactive effects of environmental pharmaceuticals on Mytilus galloprovincialis. Franzellitti S, Buratti S, Valbonesi P, et al. Aquat. Toxicol. 140-141, 249-56, (2013)

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A randomized, controlled trial of oral propranolol in infantile hemangioma. Léauté-Labrèze C, Hoeger P, Mazereeuw-Hautier J, et al. N. Engl. J. Med. 372(8), 735-46, (2015)

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Comprehensive therapy for hemangioma presenting with Kasabach-Merritt syndrome in the maxillofacial region. Su L, Wang D, and Fan X J. Oral Maxillofac. Surg. 73(1), 92-8, (2015)

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Propranolol, but not naloxone, enhances spinal reflex bladder activity and reduces pudendal inhibition in cats. Rogers MJ, Xiao Z, Shen B, et al. Am. J. Physiol. Regul. Integr. Comp. Physiol. 308(1), R42-9, (2015)

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Incidence and treatment of infantile haemangioma in preterm infants. Goelz R and Poets CF Arch. Dis. Child Fetal Neonatal Ed. 100(1), F85-91, (2015)

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How I treat splanchnic vein thrombosis. Ageno W, Dentali F, and Squizzato A Blood 124(25), 3685-91, (2014)

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Efficacy and safety of high-dose propranolol for the management of infant supraventricular tachyarrhythmias. Barton AL, Moffett BS, Valdes SO, et al. J. Pediatr. 166(1), 115-8, (2015)

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Propranolol for infantile haemangiomas: single centre experience of 250 cases and proposed therapeutic protocol. Solman L, Murabit A, Gnarra M, et al. Arch. Dis. Child. 99(12), 1132-6, (2014)

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Ask the doctors. I take the beta blocker propranolol twice a day, once in the morning and again in the evening. The drug information label says I should not take propranolol with alcohol. But I like to have two glasses of wine in the evening. Do I need to change medications, or is there a way to handle the wine and propranolol together? Lee TH and Lee RT Harv. Heart Lett. 24(1), 2, (2013)

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Reply to letter: "propranolol: a novel antihemangioma agent with multiple potential mechanisms of action". Chim H Ann. Surg. 261(2), e53, (2015)

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Propranolol: a novel antihemangioma agent with multiple potential mechanisms of action. Ji Y, Chen S, Li K, et al. Ann. Surg. 261(2), e52-3, (2015)

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[Effect of propranolol on dialysate myoglobin levels evoked by ischemia/reperfusion]. Sawada T, Kitagawa H, and Nosaka S Masui. 62(11), 1351-9, (2013)

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[Propanolol effective treatment for laryngo-tracheal hemangioma]. Granholm M and Hjalmars U Lakartidningen. 110(19-20), 947-8, (2013)

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[Hemangioma can be effectively treated with propranolol. Experiences from twelve cases, with promising results and few side effects]. Rosenkvist CJ, Brudin L, and Jörgensen E Lakartidningen. 110(19-20), 942-5, (2013)

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[Propranolol first choice in infantile hemangiomas. Large randomized trials are needed to determine the dosage and duration of treatment]. Wahlgren CF Lakartidningen. 110(19-20), 938-9, (2013)

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Oral propranolol--efficacy and comparison of two doses for peri-operative anxiolysis. Khadke VV, Khadke SV, and Khare A J. Indian Med. Assoc. 110(7), 457-60, (2012)

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Randomized placebo-controlled trial to evaluate chronic dosing effects of propranolol in asthma. Short PM, Williamson PA, Anderson WJ, et al. Am. J. Respir. Crit. Care Med. 187(12), 1308-14, (2013)

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Treatment of infantile haemangiomas with atenolol: comparison with a historical propranolol group. de Graaf M, Raphael MF, Breugem CC, et al. J. Plast. Reconstr. Aesthet. Surg. 66(12), 1732-40, (2013)

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Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Jing Yuan et al Nat. Chem. Biol. 5, 765-71, (2009)

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Oral propranolol for retinopathy of prematurity: risks, safety concerns, and perspectives. Filippi L, Cavallaro G, Bagnoli P, et al. J. Pediatr. 163(6), 1570-1577.e6, (2013)

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Eye drop propranolol administration promotes the recovery of oxygen-induced retinopathy in mice. Dal Monte M, Casini G, la Marca G, et al. Exp. Eye Res. 111, 27-35, (2013)

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Atenolol versus propranolol for the treatment of infantile hemangiomas: a randomized controlled study. Ábarzúa-Araya A, Navarrete-Dechent CP, Heusser F, et al. J. Am. Acad. Dermatol. 70(6), 1045-9, (2014)

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Effect of propranolol on hypertonic saline-evoked masseter muscle pain and autonomic response in healthy women during rest and mental arithmetic task. Bendixen KH, Terkelsen AJ, Baad-Hansen L, et al. J. Orofac. Pain 27(3), 243-55, (2013)

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Therapy for triggered acute risk prevention in subjects at increased cardiovascular risk. Tofler GH, Spinaze M, Shaw E, et al. Am. J. Cardiol. 111(12), 1755-8, (2013)

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Low-dose propranolol and exercise capacity in postural tachycardia syndrome: a randomized study. Arnold AC, Okamoto LE, Diedrich A, et al. Neurology 80(21), 1927-33, (2013)

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Treatment of infantile hemangiomas with propranolol: clinical guidelines. Szychta P, Stewart K, and Anderson W Plast. Reconstr. Surg. 133(4), 852-62, (2014)

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Asymmetric aminolytic kinetic resolution of racemic epoxides using recyclable chiral polymeric Co(III)-salen complexes: a protocol for total utilization of racemic epoxide in the synthesis of (R)-Naftopidil and (S)-Propranolol. Kumar M, Kureshy RI, Shah AK, et al. J. Org. Chem. 78(18), 9076-84, (2013)

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Treatment of comorbid migraine and temporomandibular disorders: a factorial, double-blind, randomized, placebo-controlled study. Goncalves DA, Camparis CM, Speciali JG, et al. J. Orofac. Pain 27(4), 325-35, (2013)

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Propranolol induces apoptosis of human umbilical vein endothelial cells through downregulation of CD147. Xie W, Xie H, Liu F, et al. Br. J. Dermatol. 168(4), 739-48, (2013)

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Propranolol transport across the inner blood-retinal barrier: potential involvement of a novel organic cation transporter. Kubo Y, Shimizu Y, Kusagawa Y, et al. J. Pharm. Sci. 102(9), 3332-42, (2013)

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Coronary responses to cold air inhalation following afferent and efferent blockade. Muller MD, Gao Z, McQuillan PM, et al. Am. J. Physiol. Heart Circ. Physiol. 307(2), H228-35, (2014)

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Treatment of a tongue lymphangioma with sirolimus after failure of surgical resection and propranolol. Akyüz C, Ataş E, and Varan A Pediatr. Blood Cancer 61(5), 931-2, (2014)

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Diagnosis and management of infantile hemangiomas. Püttgen KB Pediatr. Clin. North Am. 61(2), 383-402, (2014)

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Activation of hepatic inflammatory pathways by catecholamines is associated with hepatic insulin resistance in male ischemic stroke rats. Wang YY, Lin SY, Chuang YH, et al. Endocrinology 155(4), 1235-46, (2014)

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A blinded, randomized, controlled trial of three doses of high-dose insulin in poison-induced cardiogenic shock. Cole JB, Stellpflug SJ, Ellsworth H, et al. Clin. Toxicol. (Phila.) 51(4), 201-7, (2013)

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Involvement of transmitters in the anxiolytic action of urocortin 3 in mice. Telegdy G and Adamik A Behav. Brain Res. 252, 88-91, (2013)

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Adenylyl cyclase anchoring by a kinase anchor protein AKAP5 (AKAP79/150) is important for postsynaptic β-adrenergic signaling. Zhang M, Patriarchi T, Stein IS, et al. J. Biol. Chem. 288(24), 17918-31, (2013)

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The therapeutic efficacy of propranolol in children with recurrent primary epistaxis. Bjelakovic B, Bojanovic M, Lukic S, et al. Drug Des. Devel. Ther. 7, 127-9, (2013)

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Regulation of mitochondrial poly(ADP-Ribose) polymerase activation by the β-adrenoceptor/cAMP/protein kinase A axis during oxidative stress. Brunyanszki A, Olah G, Coletta C, et al. Mol. Pharmacol. 86(4), 450-62, (2014)

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Cardiovascular and blood glucose parameters in infants during propranolol initiation for treatment of symptomatic infantile hemangiomas. Puttgen KB, Summerer B, Schneider J, et al. Ann. Otol. Rhinol. Laryngol. 122(9), 550-4, (2013)

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Comparative study of the molecularly imprinted polymers prepared by reversible addition-fragmentation chain transfer "bulk" polymerization and traditional radical "bulk" polymerization. Ma Y, Pan G, Zhang Y, et al. J. Mol. Recognit. 26(5), 240-51, (2013)

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[Operational mechanism modification of bone mechanostat in an animal model of nutritional stress: effect of propranolol]. Pintos PM, Lezón CE, Bozzini C, et al. Rev. Invest. Clin. 65(1), 39-51, (2013)

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Adrenergic urticaria: review of the literature and proposed mechanism. Hogan SR, Mandrell J, and Eilers D J. Am. Acad. Dermatol. 70(4), 763-6, (2014)

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What's new in pediatric dermatology?: part II. Treatment. Pride HB, Tollefson M, and Silverman R J. Am. Acad. Dermatol. 68(6), 899.e1-11; quiz 910-2, (2013)

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Low dose of propranolol does not affect rat osteotomy healing and callus strength. Smitham P, Crossfield L, Hughes G, et al. J. Orthop. Res. 32(7), 887-93, (2014)

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Propranolol vs prednisolone for symptomatic proliferating infantile hemangiomas: a randomized clinical trial. Bauman NM, McCarter RJ, Guzzetta PC, et al. JAMA Otolaryngol. Head Neck Surg. 140(4), 323-30, (2014)

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Dispersive liquid-liquid microextraction of propranolol enantiomers from human plasma based on the solidification of a floating organic droplet. Farhadi K, Hatami M, Forough M, et al. Bioanalysis 5(6), 701-10, (2013)

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The inverse agonist propranolol confers no corticosteroid-sparing activity in mild-to-moderate persistent asthma. Anderson WJ, Short PM, Williamson PA, et al. Clin. Sci. 127(11), 635-43, (2014)

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Effects of desialylation on human α1-acid glycoprotein-ligand interactions. Huang RY and Hudgens JW Biochemistry 52(40), 7127-36, (2013)

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A high-speed liquid chromatography/tandem mass spectrometry platform using multiplexed multiple-injection chromatography controlled by single software and its application in discovery ADME screening. Zhang J, Vath M, Ferraro C, et al. Rapid Commun. Mass Spectrom. 27(7), 731-7, (2013)

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Propranolol for infantile hemangioma (PINCH): an open-label trial to assess the efficacy of propranolol for treating infantile hemangiomas and for determining the decline in heart rate to predict response to propranolol. Sondhi V and Patnaik SK J. Pediatr. Hematol. Oncol. 35(7), 493-9, (2013)

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Propranolol responsiveness in vascular tumors is not determined by qualitative differences in adrenergic receptors. Boucek RJ, Kirsh AL, Majesky MW, et al. Otolaryngol. Head Neck Surg. 149(5), 772-6, (2013)

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Epidermal growth factor receptor endocytic traffic perturbation by phosphatidate phosphohydrolase inhibition: new strategy against cancer. Shaughnessy R, Retamal C, Oyanadel C, et al. FEBS J. 281(9), 2172-89, (2014)

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Participation of citral in the bronchodilatory effect of ginger oil and possible mechanism of action. Mangprayool T, Kupittayanant S, and Chudapongse N Fitoterapia 89, 68-73, (2013)

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Early propranolol administration to severely injured patients can improve bone marrow dysfunction. Bible LE, Pasupuleti LV, Alzate WD, et al. J. Trauma Acute Care Surg. 77(1), 54-60; discussion 59-60, (2014)

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Gonadal hormone dependent developmental plasticity of catecholamine:β2-adrenoceptor signaling complex in male rat thymus: putative implications for thymopoiesis. Pilipović I, Radojević K, Kosec D, et al. J. Neuroimmunol. 265(1-2), 20-35, (2013)

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Multiple cutaneous and hepatic infantile hemangiomas having a successful response to propranolol as monotherapy at neonatal period. Cavalli R, Novotna V, Buffon RB, et al. G. Ital. Dermatol. Venereol. 148(5), 525-30, (2013)

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Development of an in silico model for human skin permeation based on a Franz cell skin permeability assay. Pil H Lee et al Bioorg. Med. Chem. Lett. 20, 69-73, (2010)

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Effect of propranolol on the treatment of infantile hemangiomas: a single tertiary center 3-year experience. Park YW, Yeom KB, Choi JW, et al. J. Dermatolog. Treat. 25(5), 391-5, (2014)

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Adverse effects of propranolol treatment for infantile hemangiomas in China. Jian D, Chen X, Babajee K, et al. J. Dermatolog. Treat. 25(5), 388-90, (2014)

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Medical management of tumors associated with Kasabach-Merritt phenomenon: an expert survey. Tlougan BE, Lee MT, Drolet BA, et al. J. Pediatr. Hematol. Oncol. 35(8), 618-22, (2013)

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Effects of catecholamines on thymocyte apoptosis and proliferation depend on thymocyte microenvironment. Radojević K, Rakin A, Pilipović I, et al. J. Neuroimmunol. 272(1-2), 16-28, (2014)

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Norepinephrine potentiates proinflammatory responses of human vaginal epithelial cells. Brosnahan AJ, Vulchanova L, Witta SR, et al. J. Neuroimmunol. 259(1-2), 8-16, (2013)

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Propranolol-mediated attenuation of MMP-9 excretion in infants with hemangiomas. Thaivalappil S, Bauman N, Saieg A, et al. JAMA Otolaryngol. Head Neck Surg. 139(10), 1026-31, (2013)

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Assessment of xanthan gum based sustained release matrix tablets containing highly water-soluble propranolol HCl. Ali A, Iqbal M, Akhtar N, et al. Acta Pol. Pharm. 70(2), 283-9, (2013)

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Optimization of propranolol HCl release kinetics from press coated sustained release tablets. Ali AA and Ali AM Pharm. Dev. Technol. 18(5), 1238-46, (2013)

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Role of 17-beta estradiol in baroreflex sensitivity in the nucleus tractus solitarii via the autonomic system in ovariectomized rats. Pourshanazari A, Ciriello J, and Tajadini H Neurosciences (Riyadh.) 18(2), 126-32, (2013)

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Effects of oral propranolol on circumscribed choroidal hemangioma: a pilot study. Tanabe H, Sahashi K, Kitano T, et al. JAMA Ophthalmol. 131(12), 1617-22, (2013)

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Stability of extemporaneous pediatric oral liquids compounded from tablets and drug substance: case of propranolol and theophylline. Muśko M and Sznitowska M Acta Pol. Pharm. 70(1), 137-45, (2013)

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Ghost spell or hematohidrosis. Khalid SR, Maqbool S, Raza N, et al. J. Coll. Physicians Surg. Pak. 23(4), 293-4, (2013)

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Paroxysmal sympathetic hyperactivity, traumatic brain injury, and β-blockers. Godoy DA, Piñero GR, and Masotti L J. Trauma Acute Care Surg. 77(2), 387, (2014)

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Oral propranolol (Hemangeol) for infantile hemangioma. Med. Lett. Drugs Ther. 56(1447), 61-2, (2014)

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Successful treatment of multifocal intracerebral and spinal hemangiomas with propranolol. Miquel J, Bruneau B, and Dupuy A J. Am. Acad. Dermatol. 70(4), e83-4, (2014)

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Propranolol impairs the closure of pressure ulcers in mice. Assis de Brito TL, Monte-Alto-Costa A, and Romana-Souza B Life Sci. 100(2), 138-46, (2014)

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Variable response to propranolol treatment of kaposiform hemangioendothelioma, tufted angioma, and Kasabach-Merritt phenomenon. Wang Z, Li K, Dong K, et al. Pediatr. Blood Cancer 61(8), 1518-9, (2014)

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Stress, β-blockers, and putting. Knight A J. Allergy Clin. Immunol. 132(4), 1014-5, (2013)

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Beta-blockers in cirrhosis patients with refractory ascites. Robins A, Bowden A, Watson W, et al. Hepatology 59(5), 2054-5, (2014)

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What doesn't kill may not make you stronger. β-blockers for asthma. Kazani S and Israel E Am. J. Respir. Crit. Care Med. 187(12), 1281, (2013)

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Practice gaps. Propranolol to treat hemangiomas of infancy: safety and side effect recognition. Dyer JA JAMA Dermatol. 149(4), 485-6, (2013)

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Retrospective review of adverse effects from propranolol in infants. Kwon EK, Joachim S, Siegel DH, et al. JAMA Dermatol. 149(4), 484-5, (2013)

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Oral propranolol versus placebo for retinopathy of prematurity: a pilot, randomised, double-blind prospective study. Makhoul IR, Peleg O, Miller B, et al. Arch. Dis. Child. 98(7), 565-7, (2013)

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Failure of systemic propranolol therapy for choroidal hemangioma of Sturge-Weber syndrome: a report of 2 cases. Krema H, Yousef YA, Durairaj P, et al. JAMA Ophthalmol. 131(5), 681-3, (2013)

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