MedKoo Cat#: 317173 | Name: Alprenolol HCl
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Description:

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

Alprenolol HCl, or alfeprol, alpheprol, and alprenololum (Gubernal, Regletin, Yobir, Apllobal, Aptine, Aptol Duriles), is a non-selective beta blocker as well as 5-HT1A receptor antagonist, used in the treatment of angina pectoris. It is no longer marketed by AstraZeneca, but may still be available from other pharmaceutical companies or generically.

Chemical Structure

Alprenolol HCl
CAS#13707-88-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 317173

Name: Alprenolol HCl

CAS#: 13707-88-5 (HCl)

Chemical Formula: C15H24ClNO2

Exact Mass: 0.0000

Molecular Weight: 285.82

Elemental Analysis: C, 63.04; H, 8.46; Cl, 12.40; N, 4.90; O, 11.20

Price and Availability

Size Price Availability Quantity
50mg USD 350.00 2 Weeks
100mg USD 550.00 2 Weeks
250mg USD 950.00 2 Weeks
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Synonym
Gubernal; Regletin; Yobir; Apllobal; Alfeprol; Alpheprol; Yobir; Alprenololum; Alpheprol; Aptin; Aptin Duriles; Aptin-Duriles; Aptina; AptinDuriles; Aptine
IUPAC/Chemical Name
1-(propan-2-ylamino)-3-(2-prop-2-enylphenoxy)propan-2-ol hydrochloride
InChi Key
RRCPAXJDDNWJBI-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H23NO2.ClH/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3;/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3;1H
SMILES Code
OC(COC1=CC=CC=C1CC=C)CNC(C)C.[H]Cl
Appearance
White to off-white 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

Preparing Stock Solutions

The following data is based on the product molecular weight 285.82 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
1: Johnsson G. Alprenolol in hypertension. Acta Med Scand Suppl. 1974;554:5-7. doi: 10.1111/j.0954-6820.1974.tb02507.x. PMID: 4593675. 2: Ekbom K. Alprenolol for migraine prophylaxis. Headache. 1975 Jul;15(2):129-32. doi: 10.1111/j.1526-4610.1975.hed1502129.x. PMID: 1097368. 3: Magnusson B, Rödjer S. Alprenolol-induced thrombocytopenia. Acta Med Scand. 1980;207(3):231-3. doi: 10.1111/j.0954-6820.1980.tb09711.x. PMID: 7368989. 4: Touho H, Karasawa J, Shishido H, Yamada K, Shibamoto K. Continuous alprenolol infusion for control of hypertension in the acute stage of ruptured intracranial aneurysms. Neurol Med Chir (Tokyo). 1991 Jul;31(7):396-400. doi: 10.2176/nmc.31.396. PMID: 1720217. 5: Himori N, Izumi A, Ishimori T. Analysis of the vasodilator action of alprenolol. Eur J Pharmacol. 1978 Feb 1;47(3):341-50. doi: 10.1016/0014-2999(78)90242-x. PMID: 631185. 6: Walle UK, Wilson MJ, Walle T. Propranolol, alprenolol and oxprenolol metabolism in the dog. Identification of N-methylated metabolites. Biomed Mass Spectrom. 1981 Feb;8(2):78-84. doi: 10.1002/bms.1200080206. PMID: 7272467. 7: Kishikawa N, Ohkuma M, Wada M, Ohyama K, Ikeda R, Nakashima K, Kuroda N. Labeling of alprenolol with fluorescent aryl iodide as a reagent based on Mizoroki-Heck coupling reaction. J Chromatogr A. 2011 May 20;1218(20):3002-6. doi: 10.1016/j.chroma.2011.03.030. Epub 2011 Apr 12. PMID: 21489541. 8: Miyazaki Y, Ishikawa T, Kamatari YO, Nakagaki T, Takatsuki H, Ishibashi D, Kuwata K, Nishida N, Atarashi R. Identification of Alprenolol Hydrochloride as an Anti-prion Compound Using Surface Plasmon Resonance Imaging. Mol Neurobiol. 2019 Jan;56(1):367-377. doi: 10.1007/s12035-018-1088-7. Epub 2018 Apr 27. PMID: 29704200. 9: Tuomilehto J. A comparison between metroprolol, alprenolol and oxprenolol in the treatment of hypertension. Acta Med Scand Suppl. 1979;625:74-80. doi: 10.1111/j.0954-6820.1979.tb00746.x. PMID: 373397. 10: Ogrodowczyk M, Dettlaff K, Kachlicki P, Marciniec B. Identification of Radiodegradation Products of Acebutolol and Alprenolol by HPLC/MS/MS. J AOAC Int. 2015 Jan-Feb;98(1):46-50. doi: 10.5740/jaoacint.14-096. PMID: 25857877. 11: Imamura H, Komori T, Ismail A, Suenaga A, Otagiri M. Stereoselective protein binding of alprenolol in the renal diseased state. Chirality. 2002 Jul;14(7):599-603. doi: 10.1002/chir.10097. PMID: 12112335. 12: Alván G, Piafsky K, Lind M, von Bahr C. Effect of pentobarbital on the disposition of alprenolol. Clin Pharmacol Ther. 1977 Sep;22(3):316-21. doi: 10.1002/cpt1977223316. PMID: 891097. 13: Gonçalves VMF, Rodrigues P, Ribeiro C, Tiritan ME. Quantification of alprenolol and propranolol in human plasma using a two-dimensional liquid chromatography (2D-LC). J Pharm Biomed Anal. 2017 Jul 15;141:1-8. doi: 10.1016/j.jpba.2017.03.064. Epub 2017 Apr 2. PMID: 28412606. 14: Mukherjee C, Caron MG, Coverstone M, Lefkowitz RJ. Identification of adenylate cyclase-coupled beta-adrenergic receptors in frog erythrocytes with (minus)-[3-H] alprenolol. J Biol Chem. 1975 Jul 10;250(13):4869-76. PMID: 238972. 15: Jayawickrama DA, Sweedler JV. Chiral separation of nanomole amounts of alprenolol with cITP/NMR. Anal Bioanal Chem. 2004 Mar;378(6):1528-35. doi: 10.1007/s00216-003-2421-0. PMID: 15214413. 16: Rabanes HR, Quirino JP. Sweeping of alprenolol enantiomers with an organic solvent and sulfated β-cyclodextrin in capillary electrophoresis. Electrophoresis. 2013 May;34(9-10):1319-26. doi: 10.1002/elps.201200595. PMID: 23529954. 17: Höld KM, de Boer D, Bos KL, van Ooijen RD, Zuidema J, Maes RA. Enantioselective quantitation of (R)- and (S)-alprenolol by gas chromatography- mass spectrometry in human saliva an plasma. J Chromatogr Sci. 1996 Jan;34(1):13-9. doi: 10.1093/chromsci/34.1.13. PMID: 8586675. 18: Bussy U, Delaforge M, El-Bekkali C, Ferchaud-Roucher V, Krempf M, Tea I, Galland N, Jacquemin D, Boujtita M. Acebutolol and alprenolol metabolism predictions: comparative study of electrochemical and cytochrome P450-catalyzed reactions using liquid chromatography coupled to high-resolution mass spectrometry. Anal Bioanal Chem. 2013 Jul;405(18):6077-85. doi: 10.1007/s00216-013-7050-7. Epub 2013 May 23. PMID: 23700103. 19: Nyberg G, Vedin A, Wilhelmsson C. QT time in patients treated with alprenolol or placebo after myocardial infarction. Br Heart J. 1979 Apr;41(4):452-5. doi: 10.1136/hrt.41.4.452. PMID: 380606; PMCID: PMC514695. 20: Meier KE, Ruoho AE. Formation of complexes between avidin and beta- adrenergic receptors using biotinyl-alprenolol derivatives. Biochim Biophys Acta. 1983 Dec 27;761(3):257-61. doi: 10.1016/0304-4165(83)90074-0. PMID: 6317049.