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Butabarbital
Also known as: Secbutabarbital, Butatab, Secbutobarbitone, Butabarbitone, Secbubarbital, Medarsed
Molecular Formula
C10H16N2O3
Molecular Weight
212.25  g/mol
InChI Key
ZRIHAIZYIMGOAB-UHFFFAOYSA-N
FDA UNII
P0078O25A9

Butabarbital, or Butisol, is a fast onset barbiturate with short duration of action compared to other barbiturates. This makes butabarbital a useful drug for treating severe insomnia and pre-operative anxiety. Butabarbital is less commonly used in recent years, as more patients are typically prescribed benzodiazepines. Its short duration of action gives butabarbital a high abuse potential, comparable to [secobarbital]. Butabarbital was granted FDA approval on 5 June 1939.
1 2D Structure

Butabarbital

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-butan-2-yl-5-ethyl-1,3-diazinane-2,4,6-trione
2.1.2 InChI
InChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15)
2.1.3 InChI Key
ZRIHAIZYIMGOAB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC(C)C1(C(=O)NC(=O)NC1=O)CC
2.2 Other Identifiers
2.2.1 UNII
P0078O25A9
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2,4,6(1h,3h,5h)-pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)-, Monosodium Salt

2. Butabarbital Sodium

3. Butabarbitone

4. Butisol

5. Butisol Sodium

6. Sarisol

7. Secbutabarbital

8. Secbutabarbital Sodium

9. Secbutobarbitone

10. Secumalum

2.3.2 Depositor-Supplied Synonyms

1. Secbutabarbital

2. Butatab

3. Secbutobarbitone

4. Butabarbitone

5. Secbubarbital

6. Medarsed

7. Unicelles

8. Butisol

9. Nilox

10. Butabarb

11. Butrate

12. Butatal

13. Sec-butobarbitone

14. 125-40-6

15. Buticaps

16. 5-sec-butyl-5-ethylbarbituric Acid

17. 5-ethyl-5-(1-methylpropyl)barbituric Acid

18. 5-sec-butyl-5-ethylmalonyl Urea

19. Barbituric Acid, 5-sec-butyl-5-ethyl-

20. 2,4,6(1h,3h,5h)-pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)-

21. Sodium Butabarbital

22. Butabarbital Ciii

23. Nsc 27517

24. Butabarbital (usp)

25. Butabarbital [usp]

26. 5-ethyl-5-(1-methylpropyl)-2,4,6(1h,3h,5h)-pyrimidinetrione

27. Nsc27517

28. 5-sec-butyl-5-ethyl-2,4,6(1h,3h,5h)-pyrimidinetrione

29. Chebi:3228

30. P0078o25a9

31. 5-sec-butyl-5-ethylpyrimidine-2,4,6(1h,3h,5h)-trione

32. Butabarbital (van)

33. Secbutobarbital

34. Secbutabarbitale

35. Secbutabarbitalum

36. Secbutabarbitale [dcit]

37. Secbutabarbitalum [inn-latin]

38. Secbutabarbital [inn]

39. 5-ethyl-5-(1-methylpropyl)barbiturate

40. Hsdb 3018

41. Wln: T6vmvmv Fhj Fy2 & 1 F2

42. Einecs 204-738-6

43. Brn 0199127

44. 5-butan-2-yl-5-ethyl-1,3-diazinane-2,4,6-trione

45. Unii-p0078o25a9

46. Secbutabarbital (ban)

47. Butabarbital [mi]

48. 5-sec-butyl-5-ethyl-barbituric Acid

49. Pyridium Plus (salt/mix)

50. Chembl449

51. Butabarbital [hsdb]

52. Secbutabarbital [inn:ban]

53. Butabarbital [vandf]

54. Schembl79254

55. Gtpl7137

56. Secbutabarbital [mart.]

57. 5-(butan-2-yl)-5-ethyl-1,3-diazinane-2,4,6-trione

58. Dtxsid2022709

59. Schembl22556204

60. Secbutabarbital [who-dd]

61. 5-(butan-2-yl)-5-ethylpyrimidine-2,4,6(1h,3h,5h)-trione

62. Butabarbital [usp Impurity]

63. Butabarbital Ciii [usp-rs]

64. 5-ethyl-5-(1-methylpropyl)pyrimidine-2,4,6(1h,3h,5h)-trione

65. Butabarbital [usp Monograph]

66. Hy-u00167

67. Nsc-27517

68. Akos015962208

69. Cs-7224

70. Db00237

71. Ac-16078

72. C07827

73. D03180

74. Q410608

75. 5-sec-butyl-5-ethyl-2,4,6(1h,3h,5h)-pyrimidinetrione #

76. 2,6(1h,3h,5h)-pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)-

77. 5-(butan-2-yl)-5-ethyl-4,6-dihydroxy-2,5-dihydropyrimidin-2-one

78. Butabarbital Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 212.25 g/mol
Molecular Formula C10H16N2O3
XLogP31.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass212.11609238 g/mol
Monoisotopic Mass212.11609238 g/mol
Topological Polar Surface Area75.3 Ų
Heavy Atom Count15
Formal Charge0
Complexity292
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameButisol sodium
PubMed HealthButabarbital (By mouth)
Drug ClassesSedative
Drug LabelBUTISOL SODIUM (butabarbital sodium tablets, USP and butabarbital sodium oral solution, USP) is a non-selective central nervous system depressant which is used as a sedative or hypnotic. It is available for oral administration as Tablets containing...
Active IngredientButabarbital sodium
Dosage FormElixir; Tablet
RouteOral
Strength30mg/5ml; 50mg; 30mg
Market StatusPrescription
CompanyMeda Pharms

2 of 2  
Drug NameButisol sodium
PubMed HealthButabarbital (By mouth)
Drug ClassesSedative
Drug LabelBUTISOL SODIUM (butabarbital sodium tablets, USP and butabarbital sodium oral solution, USP) is a non-selective central nervous system depressant which is used as a sedative or hypnotic. It is available for oral administration as Tablets containing...
Active IngredientButabarbital sodium
Dosage FormElixir; Tablet
RouteOral
Strength30mg/5ml; 50mg; 30mg
Market StatusPrescription
CompanyMeda Pharms

4.2 Therapeutic Uses

Adjuvants, Anesthesia; GABA Modulators; Sedatives, Barbiturate

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)


Butabarbital is indicated for use as a sedative or hypnotic. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for BUTISOL SODIUM (butabarbital sodium tablets) (July 2009). Available from, as of March 7, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10579


Butabarbital sodium is used for routine sedation and to relieve anxiety and provide sedation postoperatively. ... Also used as a hypnotic in the short-term treatment of insomnia for periods up to 2 weeks in duration. /Butabarbital sodium/

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 1323


4.3 Drug Warning

Because sleep disturbances may be the presenting manifestation of a physical and/or psychiatric disorder, symptomatic treatment of insomnia should be initiated only after a careful evaluation of the patient. The failure of insomnia to remit after 7 to 10 days of treatment may indicate the presence of a primary psychiatric and/or medical illness that should be evaluated.

US Natl Inst Health; DailyMed. Current Medication Information for BUTISOL SODIUM TABLETS (butabarbital sodium tablets) (July 2009). Available from, as of March 7, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10579


Worsening of insomnia or the emergence of new thinking or behavior abnormalities may be the consequences of an unrecognized psychiatric or physical disorder. Such findings have emerged during the course of treatment with sedative-hypnotic drugs. Because some of the important adverse effects of sedative-hypnotics appear to be dose related, it is important to use the smallest possible effective dose, especially in the elderly.

US Natl Inst Health; DailyMed. Current Medication Information for BUTISOL SODIUM TABLETS (butabarbital sodium tablets) (July 2009). Available from, as of March 7, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10579


Complex behaviors such as "sleep driving" (ie, driving while not fully awake after ingestion of a sedative-hypnotic, with amnesia for the event) have been reported. These events can occur in sedative-hypnotic-naive as well as in sedative-hypnotic-experienced persons. Although behaviors such as sleep-driving may occur with sedative-hypnotics alone at therapeutic doses, the use of alcohol and other CNS depressants with sedative-hypnotics appears to increase the risk of such behaviors, as does the use of sedative-hypnotics at doses exceeding the maximum recommended dose. Due to the risk to the patient and the community, discontinuation of sedative-hypnotics should be strongly considered for patients who report a "sleep driving" episode".

US Natl Inst Health; DailyMed. Current Medication Information for BUTISOL SODIUM TABLETS (butabarbital sodium tablets) (July 2009). Available from, as of March 7, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10579


Allergic reactions that occur especially in persons who tend to have asthma, urticaria, angioedema, and similar conditions. /Barbiturates/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 362


For more Drug Warnings (Complete) data for Butabarbital (29 total), please visit the HSDB record page.


4.4 Minimum/Potential Fatal Human Dose

The toxic dose of barbiturates varies considerably. In general, an oral dose of 1 gram of most barbiturates produces serious poisoning in an adult. Death commonly occurs after 2 to 10 grams of ingested barbiturates.

US Natl Inst Health; DailyMed. Current Medication Information for BUTISOL SODIUM (butabarbital sodium tablets) (July 2009). Available from, as of March 7, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10579


Potentially lethal blood concentrations are those in excess of 80 ug/mL for phenobarbital, 50 ug/mL for amobarbital or butabarbital, and approximately 30 ug/mL for secobarbital or pentobarbital; however, some patients have survived much higher blood concentrations. /Barbiturates General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2578


4.5 Drug Indication

Butabarbital is indicated for use as a sedative or hypnotic. Butabarbital should not be used to treat insomnia for longer than 2 weeks.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Butabarbital potentiates GABAergic neurons while inhibiting neuronal acetylcholine and glutamate receptors to produce sedation. Butabarbital is an intermediate acting barbiturate with a duration of action of approximately 6-8 hours. The therapeutic index is quite wide as doses vary considerably from patient to patient. Patients should be counselled regarding the risk of worsening insomnia, drowsiness, falls, and complex behaviour while not fully awake.


5.2 MeSH Pharmacological Classification

Hypnotics and Sedatives

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)


5.3 Absorption, Distribution and Excretion

Route of Elimination

Barbiturates such as butabarbital are predominantly eliminated in the urine. In dogs, 3-5% of the dose is eliminated in the urine as the unchanged parent compound.


Butabarbital sodium tablets and butabarbital sodium oral solution, is the sodium salt of a weak acid. Barbiturates are weak acids that are absorbed and rapidly distributed to all tissues and fluids with high concentrations in the brain, liver, and kidneys. Barbiturates are bound to plasma and tissue proteins. The rate of absorption is increased if it is ingested as a dilute solution or taken on an empty stomach.

US Natl Inst Health; DailyMed. Current Medication Information for BUTISOL SODIUM TABLETS (butabarbital sodium tablets) (July 2009). Available from, as of March 7, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10579


Butabarbital sodium is absorbed from the GI tract. Peak plasma concentrations are achieved within 3-4 hours following oral administration of the drug. Plasma butabarbital concentrations of 2-3 ug/mL produce sedation, and plasma concentrations of 25 ug/mL produce sleep in most patients. Plasma butabarbital concentrations of greater than 30 ug/mL may produce coma, and those in excess of 50 ug/mL are potentially lethal.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2581


Approximately 1-2% of an oral dose /of butabarbital/ is excreted unchanged in the urine.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2581


Fluid & tissue specimens collected from 30 subjects at autopsy were assayed for amylobarbitone (amobarbital), butobarbitone (butethal), pentobarbitone (pentobarbital), quinalbarbitone (secobarbital) and the corresponding hydroxylated metabolites by gas liquid chromatography. Where one barbiturate was ingested, an inverse relationship between lipid solubility of the drug and the distribution in fluids and tissues was observed. In most cases the liver, and in the remainder the spleen, contained the highest concn of barbiturate. Bile concn were often in excess of those in the corresponding liver. The metabolites of the 4 sedative barbiturates were usually present in lower amounts than the parent drugs in the fluids and tissues of most subjects but urine often contained much higher concn of metabolites, sometimes exceeding that of the parent drug in the liver. Admin of 2 or more barbiturates together did not appear to affect the distribution and metabolism of the individual drugs.

Robinson AE; McDowall RD; J Pharm Pharmacol 31: 357-65 (1979)


For more Absorption, Distribution and Excretion (Complete) data for Butabarbital (13 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

Data regarding the metabolism of butabarbital in humans are not readily available. In dogs, butabarbital undergoes metabolism to a final glucuronide metabolite.


Butabarbital is metabolized in the liver by oxidation of the sec-butyl substituent at C5 to form 5-ethyl-5-(1-methyl-2-carboxyethyl) barbituric acid, an inactive metabolite, which is then excreted in the urine.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2581


Most barbiturates are transformed in body to inactive metabolites. Principal site of biotransformation is liver. /Barbiturates/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 115


Barbiturates are transformed by 4 routes: 1. Oxidation of radical at C5. This is by far most important pathway ... Products are ... polar alcohols, ketones, phenols, or carboxylic acids ... /Barbiturates/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 116


With the exception of the less lipid-soluble aprobarbital and phenobarbital, nearly complete metabolism and/or conjugation of barbiturates in the liver precedes their renal excretion. The oxidation of radicals at C5 is the most important biotransformation responsible for termination of biological activity. Oxidation results in the formation of alcohols, kentones, phenols, or carboxylic acids, which may appear in the urine as such or as glucuronic acid conjugates. In some instances (eg, phenobarbital), N-glucosylation is an important metabolic pathway. Other biotransformations include N-hydroxylation, desulfuration of thiobarbiturates to oxybarbiturates, opening of the barbituric acid ring, and N-dealkylation of N-alkylbarbiturates to active metabolites (eg, mephobarbital to phenobarbital).

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 361


5.5 Biological Half-Life

Butabarbital has a half life of 100 hours but its duration of action is only 6-8 hours.


The average plasma half-life for butabarbital is 100 hours in the adult.

US Natl Inst Health; DailyMed. Current Medication Information for BUTISOL SODIUM TABLETS (butabarbital sodium tablets) (July 2009). Available from, as of March 7, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10579


The elimination half-life of butabarbital was reportedly 34-42 hours in one study; one manufacturer states that the plasma half-life averages 100 hours in adults.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2581


5.6 Mechanism of Action

Barbiturates like butabarbital potentiate GABA-A receptors and inhibit receptors for neuronal acetylcholine, and kainate. GABA-A receptors are predominantly on the post-synaptic membrane, and upon activation, open chloride channels to hyperpolarize the neuron and decreased firing rate. Potentiation of GABAergic neurons produces sedation. Inhibition of neuronal acetylcholine receptors and glutamate receptors of the kainate subtype desensitize their respective neurons, producing sedation.


The exact mechanism(s) by which barbiturates exert their effect on the CNS, has not been fully elucidated. However, it is believed that such effects are related, at least partially, to the drugs' ability to enhance the activity of gamma-aminobutyric acid (GABA), the principal inhibitory neurotransmitter in the CNS, by altering inhibitory synaptic transmissions that are mediated by GABAA receptors. /Barbiturates General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2579


Although the drugs act throughout the CNS, a site of particular sensitivity is the polysynaptic midbrain reticular formation which is concerned with the arousal mechanism. Barbiturates induce an imbalance in central inhibitory and facilitatory mechanisms influencing the cerebral cortex and the reticular formation. The significance of the effect of barbiturates on neurotransmitters is unclear. It appears that the drugs decrease the excitability of both presynaptic and postsynaptic membranes. It has not been determined which of the various actions of barbiturates at cellular and synaptic levels are responsible for their sedative and hypnotic effects. /Barbiturates General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2579


Relatively low doses of the barbiturates depress the sensory cortex, decrease motor activity, and produce sedation and drowsiness. In some patients, however, drowsiness may be preceded by a period of transient elation, confusion, euphoria, or excitement, especially after subhypnotic doses of aprobarbital, pentobarbital, or secobarbital. /Barbiturates General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2579


Larger doses distort judgment, cloud perception, suppress motor activity, and produce drowsiness and sleep. Still larger doses induce anesthesia. Barbiturate-induced sleep differs from physiologic sleep. Barbiturates reduce the rapid eye movement (REM) or dreaming stage of sleep. Stages III and IV sleep are also decreased. Although tolerance develops to the REM-suppressant effects during chronic administration, REM rebound occurs when the drugs are withdrawn, and the patient may experience markedly increased dreaming, nightmares, and/or insomnia. /Barbiturates General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2579


For more Mechanism of Action (Complete) data for Butabarbital (13 total), please visit the HSDB record page.


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