Nadolol | CAS#42200-33-9

MedKoo Cat#: 318297 | Name: Nadolol

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Description:

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

Nadolol is a non-selective beta blocker used in the treatment of high blood pressure and chest pain. Additionally, it is often prescribed in the treatment of atrial fibrillation, migraine headaches, and complications of cirrhosis.

Chemical Structure

Nadolol

CAS#42200-33-9

Theoretical Analysis

MedKoo Cat#: 318297

Name: Nadolol

CAS#: 42200-33-9

Chemical Formula: C17H27NO4

Exact Mass: 309.1940

Molecular Weight: 309.40

Elemental Analysis: C, 65.99; H, 8.80; N, 4.53; O, 20.68

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 250.00
200mg	USD 450.00
500mg	USD 750.00
1g	USD 1,250.00
2g	USD 2,150.00
5g	USD 4,650.00

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Synonym

Nadolol, Corgard, Solgol, SQ-11725, Anabet

IUPAC/Chemical Name

(2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol

InChi Key

VWPOSFSPZNDTMJ-UCWKZMIHSA-N

InChi Code

InChI=1S/C17H27NO4/c1-17(2,3)18-9-12(19)10-22-16-6-4-5-11-7-14(20)15(21)8-13(11)16/h4-6,12,14-15,18-21H,7-10H2,1-3H3/t12?,14-,15+/m1/s1

SMILES Code

O[C@@H]1CC2=C(C(OCC(O)CNC(C)(C)C)=CC=C2)C[C@@H]1O

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:

Nadolol (SQ-11725) is a non-selective and orally active β-adrenergic receptors blocker.

In vitro activity:

This study examined the effects of nadolol on β(2)AR levels and signaling components downstream of the β(2)AR using a line of HEK293 cells expressing human β(2)ARs. Chronic treatment with NAD (nadolol) increased β(2)AR protein levels and decreased receptor degradation, consistent with receptor stabilization by the inverse agonist. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2011 Feb;383(2):209-16. https://pubmed.ncbi.nlm.nih.gov/21225244/

In vivo activity:

The present study attempted to clarify mechanisms of β-AR up-regulation using mouse cerebral cortical neurons continuously exposed to nadolol (10 nM), a non-selective β-AR antagonist, for 24 h. Nadolol dose-dependently induced both subtypes of β-ARs, β₁- and β₂-ARs, which were not suppressed by protein A kinase inhibition with KT5720. Reference: Brain Res. 2011 Sep 26;1414:10-21. https://pubmed.ncbi.nlm.nih.gov/21871614/

	Solvent	mg/mL	mM
Solubility
	DMSO	55.5	179.38

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 309.40 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.

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. Peng H, Bond RA, Knoll BJ. The effects of acute and chronic nadolol treatment on β2AR signaling in HEK293 cells. Naunyn Schmiedebergs Arch Pharmacol. 2011 Feb;383(2):209-16. doi: 10.1007/s00210-010-0591-9. Epub 2011 Jan 12. PMID: 21225244. 2. Mizuno K, Kurokawa K, Shibasaki M, Ohkuma S. β₁-adrenergic receptor up-regulation induced by nadolol is mediated via signal transduction pathway coupled to α₁-adrenergic receptors. Brain Res. 2011 Sep 26;1414:10-21. doi: 10.1016/j.brainres.2011.07.057. Epub 2011 Aug 2. PMID: 21871614.

In vitro protocol:

In vivo protocol:

1. Mizuno K, Kurokawa K, Shibasaki M, Ohkuma S. β₁-adrenergic receptor up-regulation induced by nadolol is mediated via signal transduction pathway coupled to α₁-adrenergic receptors. Brain Res. 2011 Sep 26;1414:10-21. doi: 10.1016/j.brainres.2011.07.057. Epub 2011 Aug 2. PMID: 21871614.

1: Arafah RS, Ribeiro AE, Rodrigues AE, Pais LS. Separation of Nadolol Stereoisomers Using Chiralpak IA Chiral Stationary Phase. Chirality. 2016 Mar 1. doi: 10.1002/chir.22590. [Epub ahead of print] PubMed PMID: 26931637. 2: Leren IS, Saberniak J, Majid E, Haland TF, Edvardsen T, Haugaa KH. Nadolol decreases the incidence and severity of ventricular arrhythmias during exercise stress testing compared with β1-selective β-blockers in patients with catecholaminergic polymorphic ventricular tachycardia. Heart Rhythm. 2016 Feb;13(2):433-40. doi: 10.1016/j.hrthm.2015.09.029. Epub 2015 Sep 30. PubMed PMID: 26432584. 3: Misaka S, Knop J, Singer K, Hoier E, Keiser M, Müller F, Glaeser H, König J, Fromm MF. The Nonmetabolized β-Blocker Nadolol Is a Substrate of OCT1, OCT2, MATE1, MATE2-K, and P-Glycoprotein, but Not of OATP1B1 and OATP1B3. Mol Pharm. 2016 Jan 19. [Epub ahead of print] PubMed PMID: 26702643. 4: Bernabeu-Wittel J, Narváez-Moreno B, de la Torre-García JM, Fernández-Pineda I, Domínguez-Cruz JJ, Coserría-Sánchez F, Álvarez-del-Vayo C, Conejo-Mir J. Oral Nadolol for Children with Infantile Hemangiomas and Sleep Disturbances with Oral Propranolol. Pediatr Dermatol. 2015 Nov-Dec;32(6):853-7. doi: 10.1111/pde.12686. Epub 2015 Oct 8. PubMed PMID: 26447831. 5: Randhawa HK, Sibbald C, Garcia Romero MT, Pope E. Oral Nadolol for the Treatment of Infantile Hemangiomas: A Single-Institution Retrospective Cohort Study. Pediatr Dermatol. 2015 Sep-Oct;32(5):690-5. doi: 10.1111/pde.12655. Epub 2015 Jul 27. PubMed PMID: 26215612. 6: Giberson M, Hayes R. Infantile hemangioma in a v2 distribution: treatment with nadolol. J Family Med Prim Care. 2015 Jan-Mar;4(1):135-6. doi: 10.4103/2249-4863.152272. PubMed PMID: 25811006; PubMed Central PMCID: PMC4366987. 7: Villalba-Moreno AM, Cotrina-Luque J, Del Vayo-Benito CA, Flores-Moreno S, Bautista-Paloma FJ. Nadolol for the treatment of infantile hemangioma. Am J Health Syst Pharm. 2015 Jan 1;72(1):44-6. doi: 10.2146/ajhp140097. PubMed PMID: 25511837. 8: Misaka S, Yatabe J, Müller F, Takano K, Glaeser H, Yatabe MS, Onoue S, Werba JP, Watanabe H, Yamada S, Fromm MF, Kimura J. Response to "the effect of green tea with exceptionally high catechin content on nadolol plasma concentration". Clin Pharmacol Ther. 2014 Jun;95(6):589. doi: 10.1038/clpt.2014.61. Epub 2014 Mar 12. PubMed PMID: 24739447. 9: Ide K, Park M, Yamada H. The effect of green tea with exceptionally high catechin content on nadolol plasma concentration. Clin Pharmacol Ther. 2014 Jun;95(6):588. doi: 10.1038/clpt.2014.36. Epub 2014 Feb 19. PubMed PMID: 24553283. 10: Misaka S, Yatabe J, Müller F, Takano K, Kawabe K, Glaeser H, Yatabe MS, Onoue S, Werba JP, Watanabe H, Yamada S, Fromm MF, Kimura J. Green tea ingestion greatly reduces plasma concentrations of nadolol in healthy subjects. Clin Pharmacol Ther. 2014 Apr;95(4):432-8. doi: 10.1038/clpt.2013.241. Epub 2014 Jan 13. PubMed PMID: 24419562. 11: Misaka S, Miyazaki N, Fukushima T, Yamada S, Kimura J. Effects of green tea extract and (-)-epigallocatechin-3-gallate on pharmacokinetics of nadolol in rats. Phytomedicine. 2013 Nov 15;20(14):1247-50. doi: 10.1016/j.phymed.2013.07.003. Epub 2013 Aug 3. PubMed PMID: 23920278. 12: Misaka S, Miyazaki N, Yatabe MS, Ono T, Shikama Y, Fukushima T, Kimura J. Pharmacokinetic and pharmacodynamic interaction of nadolol with itraconazole, rifampicin and grapefruit juice in healthy volunteers. J Clin Pharmacol. 2013 Jul;53(7):738-45. doi: 10.1002/jcph.95. Epub 2013 May 16. PubMed PMID: 23677858. 13: Ribeiro AE, Rodrigues AE, Pais LS. Separation of nadolol stereoisomers by chiral liquid chromatography at analytical and preparative scales. Chirality. 2013 Mar;25(3):197-205. doi: 10.1002/chir.22132. Epub 2013 Jan 21. PubMed PMID: 23339017. 14: Miyazaki N, Misaka S, Ogata H, Fukushima T, Kimura J. Effects of itraconazole, dexamethasone and naringin on the pharmacokinetics of nadolol in rats. Drug Metab Pharmacokinet. 2013;28(4):356-61. Epub 2013 Feb 19. PubMed PMID: 23419354. 15: Pope E, Chakkittakandiyil A, Lara-Corrales I, Maki E, Weinstein M. Expanding the therapeutic repertoire of infantile haemangiomas: cohort-blinded study of oral nadolol compared with propranolol. Br J Dermatol. 2013 Jan;168(1):222-4. doi: 10.1111/j.1365-2133.2012.11131.x. Epub 2012 Oct 5. PubMed PMID: 22762503. 16: Lo GH, Chen WC, Wang HM, Yu HC. Randomized, controlled trial of carvedilol versus nadolol plus isosorbide mononitrate for the prevention of variceal rebleeding. J Gastroenterol Hepatol. 2012 Nov;27(11):1681-7. doi: 10.1111/j.1440-1746.2012.07244.x. PubMed PMID: 22849337. 17: Gracia-Naya M, Huerta-Villanueva M, Rios C, Garcia-Gomara MJ, Artal-Roy J, Sanchez-Valiente S, Santos-Lasaosa S, Mauri-Llerda JA, Latorre-Jimenez AM. [A study to compare independent groups of patients with episodic migraine who were treated preventively with flunarizine or nadolol]. Rev Neurol. 2012 Mar 1;54(5):277-83. Spanish. PubMed PMID: 22362476. 18: Besana A, Wang DW, George AL Jr, Schwartz PJ. Nadolol block of Nav1.5 does not explain its efficacy in the long QT syndrome. J Cardiovasc Pharmacol. 2012 Mar;59(3):249-53. doi: 10.1097/FJC.0b013e31823d2fd1. PubMed PMID: 22030895; PubMed Central PMCID: PMC3291794. 19: Mizuno K, Kurokawa K, Shibasaki M, Ohkuma S. β₁-adrenergic receptor up-regulation induced by nadolol is mediated via signal transduction pathway coupled to α₁-adrenergic receptors. Brain Res. 2011 Sep 26;1414:10-21. doi: 10.1016/j.brainres.2011.07.057. Epub 2011 Aug 2. PubMed PMID: 21871614. 20: Peng H, Bond RA, Knoll BJ. The effects of acute and chronic nadolol treatment on β2AR signaling in HEK293 cells. Naunyn Schmiedebergs Arch Pharmacol. 2011 Feb;383(2):209-16. doi: 10.1007/s00210-010-0591-9. Epub 2011 Jan 12. PubMed PMID: 21225244.