Penbutolol
Penbutolol is only found in individuals that have used or taken this drug. It is a medication in the class of beta blockers, used in the treatment of high blood pressure. [Wikipedia]Penbutolol competes with adrenergic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart and vascliar smooth muscle and beta(2)-receptors in the bronchial and vascliar smooth muscle. Beta(1)-receptor blockade reslits in a decrease in resting and exercise heart rate and cardiac output, a decrease in both systolic and diastolic blood pressure, and, possibly, a reduction in reflex orthostatic hypotension.
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB15447 (Penbutolol)
C18H29NO2
291.4284
291.219829177
(2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol
(2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol
36507-48-9
CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1
InChI=1S/C18H29NO2/c1-18(2,3)19-12-15(20)13-21-17-11-7-6-10-16(17)14-8-4-5-9-14/h6-7,10-11,14-15,19-20H,4-5,8-9,12-13H2,1-3H3/t15-/m0/s1
KQXKVJAGOJTNJS-HNNXBMFYSA-N
This compound belongs to the class of chemical entities known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Chemical entities
Organic compounds
Benzenoids
Phenol ethers
Phenol ethers
Aromatic homomonocyclic compounds
Expected but not Quantified
Solid
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
Not Available
Not Available
None
None
DB01359
Not Available
Not Available
Not Available
Not Available
Not Available
34369
C07416
Not Available
Not Available
Penbutolol
HMDB15447
HMDB15447
Not Available
37464
Not Available
354975
- Hjorth S: (-)-Penbutolol as a blocker of central 5-HT1A receptor-mediated responses. Eur J Pharmacol. 1992 Nov 3;222(1):121-7. [PubMed:1468487 ]
- Martinez Jorda R, Aguirre C, Calvo R, Rodriguez-Sasiain JM, Erill S: Decrease in penbutolol central response as a cause of changes in its serum protein binding. J Pharm Pharmacol. 1990 Mar;42(3):164-6. [PubMed:1974610 ]
- Frishman WH, Covey S: Penbutolol and carteolol: two new beta-adrenergic blockers with partial agonism. J Clin Pharmacol. 1990 May;30(5):412-21. [PubMed:2189902 ]
- Pepe S, Scalici G, DAngelo A, Curiale B, Corrao S, Agnello C: [Validity of the use of penbutolol in essential arterial hypertension]. Minerva Med. 1990 Jun;81(6):471-3. [PubMed:2359502 ]
- Aguirre C, Rodriguez-Sasiain JM, Calvo R: Decrease in penbutolol protein binding as a consequence of treatment with some alkylating agents. Cancer Chemother Pharmacol. 1994;34(1):86-8. [PubMed:8174208 ]
- Maurer HH, Tenberken O, Kratzsch C, Weber AA, Peters FT: Screening for library-assisted identification and fully validated quantification of 22 beta-blockers in blood plasma by liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization. J Chromatogr A. 2004 Nov 26;1058(1-2):169-81. [PubMed:15595665 ]
Enzymes
- General function:
- Involved in G-protein coupled receptor protein signaling pathway
- Specific function:
- Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
- Gene Name:
- ADRB1
- Uniprot ID:
- P08588
- Molecular weight:
- 51322.1
References
- Venter CP, Joubert PH: Ethnic differences in beta-1-adrenoceptor sensitivity. S Afr Med J. 1982 Nov 27;62(23):849-50. [PubMed:6755764 ]
- Sanchez C: Effect of serotonergic drugs on footshock-induced ultrasonic vocalization in adult male rats. Behav Pharmacol. 1993 Jun;4(3):269-277. [PubMed:11224195 ]
- Doze P, Elsinga PH, Maas B, Van Waarde A, Wegman T, Vaalburg W: Synthesis and evaluation of radiolabeled antagonists for imaging of beta-adrenoceptors in the brain with PET. Neurochem Int. 2002 Feb;40(2):145-55. [PubMed:11738481 ]
- General function:
- Involved in G-protein coupled receptor protein signaling pathway
- Specific function:
- Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
- Gene Name:
- ADRB2
- Uniprot ID:
- P07550
- Molecular weight:
- 46458.3
References
- Kulkarni RD, DaSilva LM, Chabria NL, Chadha DR: Beta-2 adrenoceptor blocking activity of penbutolol and propranolol at very low doses. Clin Pharmacol Ther. 1977 Jun;21(6):685-90. [PubMed:16716 ]
- Hjorth S, Sharp T: In vivo microdialysis evidence for central serotonin1A and serotonin1B autoreceptor blocking properties of the beta adrenoceptor antagonist (-)penbutolol. J Pharmacol Exp Ther. 1993 May;265(2):707-12. [PubMed:8098761 ]
- Hjorth S, Bengtsson HJ, Milano S: Raphe 5-HT1A autoreceptors, but not postsynaptic 5-HT1A receptors or beta-adrenoceptors, restrain the citalopram-induced increase in extracellular 5-hydroxytryptamine in vivo. Eur J Pharmacol. 1996 Nov 28;316(1):43-7. [PubMed:8982649 ]
- Sanchez C: Effect of serotonergic drugs on footshock-induced ultrasonic vocalization in adult male rats. Behav Pharmacol. 1993 Jun;4(3):269-277. [PubMed:11224195 ]
- Ijzerman AP, Nagesser A, Garritsen A: The membrane stabilizing activity of beta-adrenoceptor ligands. Quantitative evaluation of the interaction of phenoxypropanolamines with the [3H]batrachotoxinin A 20-alpha-benzoate binding site on voltage-sensitive sodium channels in rat brain. Biochem Pharmacol. 1987 Dec 15;36(24):4239-44. [PubMed:2446632 ]