Phenobarbital, also known as phenobarbitone or phenobarb, sold under the brand name Luminal among others, is a medication of the barbiturate type.[6] It is recommended by the World Health Organization (WHO) for the treatment of certain types of epilepsy in developing countries.[8] In the developed world, it is commonly used to treat seizures in young children,[9] while other medications are generally used in older children and adults.[10] It is also used for veterinary purposes.[11]
It may be administered by slow intravenous infusion (IV infusion), intramuscularly (IM), or orally (swallowed by mouth). Subcutaneous administration is not recommended.[6] The IV or IM (injectable forms) may be used to treat status epilepticus if other drugs fail to achieve satisfactory results.[6] Phenobarbital is occasionally used to treat insomnia, anxiety, and benzodiazepine withdrawal (as well as withdrawal from certain other drugs in specific circumstances), and prior to surgery as an anxiolytic and to induce sedation.[6] It usually begins working within five minutes when used intravenously and half an hour when administered orally.[6] Its effects last for between four hours and two days.[6][7]
It is pregnancy category D in Australia, meaning that it may cause harm when taken during pregnancy.[6][12] If used during breastfeeding it may result in drowsiness in the baby.[13] Phenobarbital works by increasing the activity of the inhibitory neurotransmitterGABA.[6]
Phenobarbital is the first-line choice for the treatment of neonatal seizures.[24][25][26][27] Concerns that neonatal seizures in themselves could be harmful make most physicians treat them aggressively. No reliable evidence, though, supports this approach.[28]
The synthesis of a photoswitchable analog (DASA-barbital) and phenobarbital has been described for use as a research compound in photopharmacology.[36]
Side effects
Sedation and hypnosis are the principal side effects (occasionally, they are also the intended effects) of phenobarbital. Central nervous system effects, such as dizziness, nystagmus and ataxia, are also common. In elderly patients, it may cause excitement and confusion, while in children, it may result in paradoxical hyperactivity.[37]
Phenobarbital is a cytochrome P450 hepatic enzyme inducer. It binds transcription factor receptors that activate cytochrome P450 transcription, thereby increasing its amount and thus its activity.[38] Caution is to be used with children. Among anti-convulsant drugs, behavioural disturbances occur most frequently with clonazepam and phenobarbital.[39]
The electroencephalogram (EEG) of a person with phenobarbital overdose may show a marked decrease in electrical activity, to the point of mimicking brain death. This is due to profound depression of the central nervous system and is usually reversible.[40]
Treatment of phenobarbital overdose is supportive, and mainly consists of the maintenance of airway patency (through endotracheal intubation and mechanical ventilation), correction of bradycardia and hypotension (with intravenous fluids and vasopressors, if necessary), and removal of as much drug as possible from the body. In very large overdoses, multi-dose activated charcoal is a mainstay of treatment as the drug undergoes enterohepatic recirculation. Urine alkalization (achieved with sodium bicarbonate) enhances renal excretion. Hemodialysis is effective in removing phenobarbital from the body and may reduce its half-life by up to 90%.[40] No specific antidote for barbiturate poisoning is available.[41]
Mechanism of action
Phenobarbital acts as an allosteric modulator which extends the amount of time the chloride ion channel is open by interacting with GABAA receptor subunits. Through this action, phenobarbital increases the flow of chloride ions into the neuron which decreases the excitability of the post-synaptic neuron. Hyperpolarizing this post-synaptic membrane leads to a decrease in the general excitatory aspects of the post-synaptic neuron. By making it harder to depolarize the neuron, the threshold for the action potential of the post-synaptic neuron will be increased.[42]
Direct blockade of glutamatergic AMPA and kainate receptors are also believed to contribute to the hypnotic/anticonvulsant effect that is observed with phenobarbital.[43][44]
The first barbiturate drug, barbital, was synthesized in 1902 by German chemists Emil Fischer and Joseph von Mering and was first marketed as Veronal by Friedr. Bayer et comp. By 1904, several related drugs, including phenobarbital, had been synthesized by Fischer. Phenobarbital was brought to market in 1912 by the drug company Bayer as the brand Luminal. It remained a commonly prescribed sedative and hypnotic until the introduction of benzodiazepines in the 1960s.[46]
Phenobarbital's soporific, sedative and hypnotic properties were well known in 1912, but it was not yet known to be an effective anti-convulsant. The young doctor Alfred Hauptmann[47] gave it to his epilepsy patients as a tranquilizer and discovered their seizures were susceptible to the drug. Hauptmann performed a careful study of his patients over an extended period. Most of these patients were using the only effective drug then available, bromide, which had terrible side effects and limited efficacy. On phenobarbital, their epilepsy was much improved: The worst[clarification needed] patients had fewer and lighter seizures and some patients became seizure-free. In addition, they improved physically and mentally as bromides were removed from their regimen. Patients who had been institutionalised due to the severity of their epilepsy were able to leave and, in some cases, resume employment. Hauptmann dismissed concerns that its effectiveness in stalling seizures could lead to patients developing a build-up that needed to be "discharged". As he expected, withdrawal of the drug led to an increase in seizure frequency – it was not a cure. The drug was quickly adopted as the first widely effective anti-convulsant, though World War I delayed its introduction in the U.S.[48]
In 1939, a German family asked Adolf Hitler to have their disabled son killed; the five-month-old boy was given a lethal dose of Luminal after Hitler sent his own doctor to examine him. A few days later 15 psychiatrists were summoned to Hitler's Chancellery and directed to commence a clandestine program of involuntary euthanasia.[49][50]
In 1940, at a clinic in Ansbach, Germany, around 50 intellectually disabled children were injected with Luminal and killed that way. A plaque was erected in their memory in 1988 in the local hospital at Feuchtwanger Strasse 38, although a newer plaque does not mention that patients were killed using barbiturates on site.[51][52] Luminal was used in the Nazi children's euthanasia program until at least 1943.[53][54]
Phenobarbital was used to treat neonatal jaundice by increasing liver metabolism and thus lowering bilirubin levels. In the 1950s, phototherapy was discovered, and became the standard treatment.[55]
Phenobarbital was used for over 25 years as prophylaxis in the treatment of febrile seizures.[56] Although an effective treatment in preventing recurrent febrile seizures, it had no positive effect on patient outcome or risk of developing epilepsy. The treatment of simple febrile seizures with anticonvulsant prophylaxis is no longer recommended.[57][58]
Society and culture
Names
Phenobarbital is the INN and phenobarbitone is the BAN.
The second approach utilizes diethyl carbonate in the presence of a strong base to give α-phenylcyanoacetic ester.[63][64] Alkylation of this ester using ethyl bromide proceeds via a nitrile anion intermediate to give the α-phenyl-α-ethylcyanoacetic ester.[65] This product is then further converted into the 4-iminoderivative upon condensation with urea. Finally acidic hydrolysis of the resulting product gives phenobarbital.[66]
A new synthetic route based on diethyl 2-ethyl-2-phenylmalonate and urea has been described.[36]
Regulation
The level of regulation includes Schedule IV non-narcotic (depressant) (ACSCN 2285) in the United States under the Controlled Substances Act 1970—but along with a few other barbiturates and at least one benzodiazepine, and codeine, dionine, or dihydrocodeine at low concentrations, it also has exempt prescription and had at least one exempt OTC combination drug now more tightly regulated for its ephedrine content.[67] The phenobarbitone/phenobarbital exists in subtherapeutic doses which add up to an effective dose to counter the overstimulation and possible seizures from a deliberate overdose in ephedrine tablets for asthma, which are now regulated at the federal and state level as: a restricted OTC medicine and/or watched precursor, uncontrolled but watched/restricted prescription drug & watched precursor, a Schedule II, III, IV, or V prescription-only controlled substance & watched precursor, or a Schedule V (which also has possible regulations at the county/parish, town, city, or district as well aside from the fact that the pharmacist can also choose not to sell it, and photo ID and signing a register is required) exempt Non-Narcotic restricted/watched OTC medicine.[68]
Selected overdoses
A mysterious woman, known as the Isdal Woman, was found dead in Bergen, Norway, on 29 November 1970. Her death was caused by some combination of burns, phenobarbital, and carbon monoxide poisoning; many theories about her death have been posited, and it is believed that she may have been a spy.[69]
British veterinarian Donald Sinclair, better known as the character Siegfried Farnon in the "All Creatures Great and Small" book series by James Herriot, committed suicide at the age of 84 by injecting himself with an overdose of phenobarbital. Activist Abbie Hoffman also committed suicide by consuming phenobarbital, combined with alcohol, on 12 April 1989; the residue of around 150 pills was found in his body at autopsy.[70]
Thirty-nine members of the Heaven's Gate UFO cult committed mass suicide in March 1997 by drinking a lethal dose of phenobarbital and vodka "and then lay down to die" hoping to enter an alien spacecraft.[71]
Veterinary uses
Phenobarbital is one of the first-line drugs of choice to treat epilepsy in dogs, as well as cats.[11]
^ abcdefghijklm"Phenobarbital". The American Society of Health-System Pharmacists. Archived from the original on 6 September 2015. Retrieved 14 August 2015.
^ abThomas WB (2003). "Seizures and narcolepsy". In Dewey CW (ed.). A Practical Guide to Canine and Feline Neurology. Ames, Iowa: Iowa State Press. ISBN978-0-8138-1249-6.
^World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
^Nolan SJ, Tudur Smith C, Pulman J, Marson AG (January 2013). "Phenobarbitone versus phenytoin monotherapy for partial onset seizures and generalised onset tonic-clonic seizures". The Cochrane Database of Systematic Reviews (1): CD002217. doi:10.1002/14651858.CD002217.pub2. PMID23440786.
^Kasper D (8 April 2015). Harrison's Principles of Internal Medicine (19th ed.). Mc Graw Hill. p. 2002. ISBN978-0071802154. Bilirubin concentrations during phenobarbital administration do not return to normal but are typically in the range of 51-86 µmol/L (3-5 mg/dL). Although the incidence of kernicterus in CN-II is low, instances have occurred, not only in infants but also in adolescents and adults, often in the setting of an intercurrent illness, fasting, or another factor that temporarily raises the serum bilirubin concentration above baseline and reduces serum albumin levels. For this reason, phenobarbital therapy is highly recommended, a single bedtime dose often suffices to maintain clinically safe serum bilirubin concentrations.
^Tamayo V, Del Valle Díaz S, Durañones Góngora S, Corina Domínguez Cardosa M, del Carmen Clares Pochet P (December 2012). "Pruebas de laboratorio en el síndrome de Gilbert consecutivo a hepatitis" [Laboratory tests in Gilbert's syndrome after hepatitis] (PDF). Medisan (in Spanish). 16 (12): 1823–1830. Archived(PDF) from the original on 30 October 2022. Retrieved 30 October 2022.
^López-Muñoz F, Ucha-Udabe R, Alamo C (December 2005). "The history of barbiturates a century after their clinical introduction". Neuropsychiatric Disease and Treatment. 1 (4): 329–343. PMC2424120. PMID18568113. Despite their widespread use during the first half of the 20th century, no barbiturate succeeded in eliminating the main drawbacks of these drugs, which were the phenomena of dependence and death by overdose
^ abCastagna R, Maleeva G, Pirovano D, Matera C, Gorostiza P (August 2022). "Donor-Acceptor Stenhouse Adduct Displaying Reversible Photoswitching in Water and Neuronal Activity". Journal of the American Chemical Society. 144 (34): 15595–15602. doi:10.1021/jacs.2c04920. hdl:2434/918919. PMID35976640. S2CID251623598.
^Lewis CB, Adams N (2019). "Phenobarbital". StatPearls. StatPearls Publishing. PMID30335310. Archived from the original on 28 August 2021. Retrieved 27 March 2019.
^Scott DF (15 February 1993). The History of Epileptic Therapy. Taylor & Francis. pp. 59–65. ISBN978-1-85070-391-4.
^Zoech I (12 October 2003). "Named: the baby boy who was Nazis' first euthanasia victim". The Telegraph. Archived from the original on 16 December 2013. Retrieved 1 November 2013. The case was to provide the rationale for a secret Nazi decree that led to 'mercy killings' of almost 300,000 mentally and physically handicapped people. The Kretschmars wanted their son dead but most of the other children were forcibly taken from their parents to be killed.
^Smith WJ (26 March 2006). "Killing Babies, Compassionately". Weekly Standard. Archived from the original on 3 November 2013. Retrieved 1 November 2013. Hitler later signed a secret decree permitting the euthanasia of disabled infants. Sympathetic physicians and nurses from around the country--many not even Nazi party members--cooperated in the horror that followed. Formal 'protective guidelines' were created, including the creation of a panel of 'expert referees,' which judged which infants were eligible for the program.
^Kaelber L (8 March 2013). "Kinderfachabteilung Ansbach". Sites of Nazi "Children's 'Euthanasia'" Crimes and Their Commemoration in Europe. University of Vermont. Archived from the original on 3 November 2013. Retrieved 1 November 2013. In the late 1980s, important developments occurred at the clinic that led to the first publication on the subject and the display of two plaques. Dr. Reiner Weisenseel wrote his dissertation under Dr. Athen, then the director of the Ansbacher Bezirkskrankenhaus, on the involvement of the clinic in Euthanasia crimes, including the operation of the Kinderfachabteilung. In 1988 two members of the Green Party as well as the regional diet (Bezirkstag) were horrified to find portraits of physicians involved in Nazi euthanasia crimes among the honorary display of medical personnel in the administrative building, and they successfully petitioned to have these portraits removed. Since 1992 a plaque hangs in the entry hallway of the administrative building. It reads: 'In the Third Reich the Ansbach facility delivered to their death more than 2000 of the patients entrusted to it as life unworthy of living: They were transferred to killing facilities or starved to death. In their own way, many people incurred responsibility.' It continues: 'Half a century later full of shame we commemorate the victims and call to remember the Fifth Commandment.' The killing of children specifically transferred to the clinic to be murdered is not noted. The plaque does not address that that euthanasia victims were not only starved or transported to gassing facilities but killed using barbiturates on site.
^Kaelber L (Spring 2013). "Jewish Children with Disabilities and Nazi "Euthanasia" Crimes"(PDF). The Bulletin of the Carolyn and Leonard Miller Center for Holocaust Studies. University of Vermont. Archived(PDF) from the original on 3 November 2013. Retrieved 1 November 2013. Two Polish physicians reported at the time that 235 children from ages up to 14 were listed in the booklet, of whom 221 had died. An investigation revealed that the medical records of the children had been falsified, as those records showed a far lower dosage of Luminal given to them than was entered into the Luminal booklet. For example, the medical records for Marianna N. showed for 16 January 1943 (she died on that day) a dosage of 0.1 g of Luminal, whereas the Luminal booklet showed the actual dosage as 0.4 g, or four times the dosage recommended for her body weight.
^López-Muñoz F, Alamo C, García-García P, Molina JD, Rubio G (December 2008). "The role of psychopharmacology in the medical abuses of the Third Reich: from euthanasia programmes to human experimentation". Brain Research Bulletin. 77 (6): 388–403. doi:10.1016/j.brainresbull.2008.09.002. PMID18848972. S2CID39858807.
^Pepling RS (June 2005). "Phenobarbital". Chemical and Engineering News. 83 (25). Archived from the original on 26 November 2005. Retrieved 6 September 2006.
^Pellock JM, Dodson WE, Bourgeois BF (1 January 2001). Pediatric Epilepsy. Demos Medical Publishing. p. 169. ISBN978-1-888799-30-9.
^Baumann R (14 February 2005). "Febrile Seizures". eMedicine. WebMD. Archived from the original on 6 September 2006. Retrieved 6 September 2006.
^Chamberlain JS, Chap JJ, Doyle JE, Spaulding LB (1935). "The Synthesis of 5,5-Alkylphenylbarbituric Acids". Journal of the American Chemical Society. 57 (2): 352–354. doi:10.1021/ja01305a036.
^Nelson WL, Cretcher LH (1928). "The Preparation of Ethyl Phenylmalonate and of 5-Phenyl-beta-hydroxyethylbarbituric acid". Journal of the American Chemical Society. 50 (10): 2758–2762. doi:10.1021/ja01397a029.
^Makosza M, Jończyk A (1976). "Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile". Organic Syntheses. 55: 91. doi:10.15227/orgsyn.055.0091.
^US 2358072, Inman MT, Bilter WP, "Preparation of Phenobarbital", issued 12 September 1944, assigned to Kay Fries Chemicals, Inc..
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