Butabarbital

Các tên gọi khác (8 ) :

5-Ethyl-5-(1-methylpropyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
5-Ethyl-5-(1-methylpropyl)barbituric acid
5-Sec-butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione
5-Sec-butyl-5-ethylbarbituric acid
5-Sec-butyl-5-ethylpyrimidine-2,4,6(1H,3H,5H)-trione
Butabarbital
Butisol
Secbutabarbital

Thuốc an thần

Thuốc Gốc

Small Molecule

CAS: 125-40-6

ĐG : C.O. Truxton Inc.

CTHH: C₁₀H₁₆N₂O₃

PTK: 212.2456

Butabarbital (trade name Butisol) is a prescription barbiturate sleep aid. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its short duration of action gives butabarbital a high abuse potential, comparable to secobarbital. [Wikipedia]

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₁₀H₁₆N₂O₃

Phân tử khối

212.2456

Monoisotopic mass

212.116092388

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)

InChI Key

InChIKey=ZRIHAIZYIMGOAB-UHFFFAOYSA-N

IUPAC Name

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

Traditional IUPAC Name

butabarbital

SMILES

CCC(C)C1(CC)C(=O)NC(=O)NC1=O

Độ tan chảy

166.5 °C

Độ hòa tan

1360 mg/L

logP

1.65

logS

-2.2

pKa (strongest acidic)

8.48

PSA

75.27 Å²

Refractivity

53.4 m³·mol^-1

Polarizability

21.41 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

Rule of Five

true

Ghose Filter

true

Dược Lực Học : Butabarbital, a barbiturate, is used for the treatment of short term insomnia. It belongs to a group of medicines called central nervous system (CNS) depressants that induce drowsiness and relieve tension or nervousness. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.

Cơ Chế Tác Dụng : Butabarbital (trade name Butisol) is a prescription barbiturate sleep aid. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its short duration of action gives butabarbital a high abuse potential, comparable to secobarbital. [Wikipedia] Butabarbital binds at a distinct binding site associated with a Cl^- ionopore at the GABA_A receptor, increasing the duration of time for which the Cl^- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.

Dược Động Học :

▧ Route of Elimination :
Barbiturates are metabolized primarily by the hepatic microsomal enzyme system, and most metabolic products are excreted in the urine.

Độc Tính : Signs of overdose include confusion (severe), decrease in or loss of reflexes, drowsiness (severe), fever, irritability (continuing), low body temperature, poor judgment, shortness of breath or slow or troubled breathing, slow heartbeat, slurred speech, staggering, trouble in sleeping, unusual movements of the eyes, weakness (severe).

Chỉ Định : For short-term treatment of insomnia and anxiety disorders

Tương Tác Thuốc :

Acenocoumarol Barbiturates like butabarbital may increase the metabolism of Vitamin K Antagonists like acenocoumarol. onitor for decreased therapeutic effects of oral anticoagulants if a barbiturate is initiated/dose increased (anticoagulant dosage increases of 30% to 60% may be needed based on monitored PT), or increased effects if a barbiturate is discontinued/dose decreased. An increased frequency of PT monitoring should be considered for the period immediately following barbiturate initiation/dosage changes.
Aminophylline The barbiturate, butabarbital, decreases the effect of aminophylline.
Amitriptyline Barbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like amitriptyline. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
Amoxapine Barbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like amoxipine. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
Bendamustine Decreases levels of bendamustine by affecting CYP1A2 hepatic enzyme metabolism. May increase concentrations of active metabolites.
Betamethasone The barbiturate, butabarbital, may decrease the effect of the corticosteroid, betamethasone.
Clomifene The enzyme inducer, butabarbital, decreases the effect of the hormone agent, clomifene.
Clomipramine Barbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like clomipramine. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
Conjugated Estrogens The enzyme inducer, butabarbital, decreases the effect of the hormone agent, conjugated estrogens.
Cyclosporine The barbiturate, butabarbital, increases the effect of cyclosporine.
Desipramine Barbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like desipramine. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
Dexamethasone The barbiturate, butabarbital, may decrease the effect of the corticosteroid, dexamethasone.
Diethylstilbestrol The enzyme inducer, butabarbital, decreases the effect of the hormone agent, diethylstilbestrol.
Disopyramide arbiturates may increase the metabolism of Disopyramide. Monitor for decreased therapeutic effects of disopyramide if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased.
Doxepin Barbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like doxepin. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
Doxycycline The anticonvulsant, butabarbital, decreases the effect of doxycycline.
Droperidol Droperidol may enhance the CNS depressant effect of CNS Depressants like butabarbital. Consider dose reductions of droperidol or of other CNS agents (e.g., opioids, barbiturates) with concomitant use.
Eltrombopag Affects hepatic CYP1A2 metabolism, will decrease effect/level of eltrombopag. Affects hepatic CYP2C9/10 metabolism, will decrease effect/level of eltrombopag.
Estradiol The enzyme inducer, butabarbital, decreases the effect of the hormone agent, estradiol.
Ethinyl Estradiol This product may cause a slight decrease of contraceptive effect
Felodipine The barbiturate, butabarbital, decreases the effect of felodipine.
Fludrocortisone The barbiturate, butabarbital, may decrease the effect of the corticosteroid, fludrocortisone.
Folic Acid Folic acid decreases the effect of anticonvulsant, butabarbital.
Gefitinib The CYP3A4 inducer, butabarbital, may decrease the serum concentration and therapeutic effects of gefitinib.
Griseofulvin The barbiturate, butabarbital, decreases the effect of griseofulvin.
Hydrocortisone The barbiturate, butabarbital, may decrease the effect of the corticosteroid, hydrocortisone.
Hydroxyzine Hydroxyzine may enhance the CNS depressant effect of barbiturates like butabarbital. Consider a decrease in the barbiturate dose, as appropriate, when used together with hydroxyzine. With concurrent use, monitor patients closely for excessive response to the combination.
Imipramine Barbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like imipramine. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
Lamotrigine Barbiturates like butabarbital may decrease the serum concentration of lamotrigine. There are separate patient management guidelines for patients age 12 and under and for patients older than 12 years of age. Monitor for decreased serum concentrations/therapeutic effects of lamotrigine if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased.
Levonorgestrel Phenobarbital decreases the effect of levonorgestrel
Medroxyprogesterone Acetate The enzyme inducer, butabarbital, decreases the effect of the hormone agent, medroxyprogesterone.
Megestrol acetate The enzyme inducer, butabarbital, decreases the effect of the hormone agent, megestrol.
Methadone The barbiturate, butabarbital, decreases the effect of methadone.
Metronidazole The barbiturate, butabarbital, decreases the effect of metronidazole.
Nifedipine The barbiturate, butabarbital, decreases the effect of the calcium channel blocker, nifedipine.
Norethindrone This product may cause a slight decrease of contraceptive effect
Nortriptyline Barbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like nortriptyline. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
Oxtriphylline The barbiturate, butabarbital, decreases the effect of oxtriphylline.
Prednisolone The barbiturate, butabarbital, may decrease the effect of the corticosteroid, prednisolone.
Prednisone The barbiturate, butabarbital, may decrease the effect of the corticosteroid, prednisone.
Protriptyline Barbiturates like butabarbital may increase the metabolism of tricyclic antidepressants like protriptyline. Monitor for decreased therapeutic effects of tricyclic antidepressants if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. The tricyclic antidepressant dosage will likely need to be increased during concomitant barbiturate therapy, and reduced upon barbiturate discontinuation.
Quinidine The anticonvulsant, butabarbital, decreases the effect of quinidine.
Teniposide Barbiturates like butabarbital may decrease the serum concentration of Teniposide. arbiturates may decrease the serum concentration of Teniposide.
Theophylline The barbiturate, butabarbital, decreases the effect of theophylline.
Triamcinolone The barbiturate, butabarbital, may decrease the effect of the corticosteroid, triamcinolone.
Trimipramine The barbiturate, Butabarbital, may increase the metabolism and clearance of Trimipramine. Monitor for changes in the therapeutics and adverse effects of Trimipramine if Butabarbital is initiated, discontinued or dose changed. Dose adjustments of Trimipramine may be required.
Triprolidine The CNS depressants, Triprolidine and Butabarbital, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Verapamil Butabarbital, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Butabarbital is initiated, discontinued or dose changed.
Voriconazole Butabarbital may reduce serum concentrations and efficacy of voriconazole. Concomitant voriconazole and long-acting barbiturates therapy is contraindicated.
Warfarin Butabarbital may decrease the serum concentration of warfarin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of warfarin if butabarbital is initiated, discontinued or dose changed.

Dữ Kiện Thương Mại

Giá thị trường

Biệt dược thương mại : Butisol sodium 30 mg tablet

Giá bán buôn : USD >1.89

Đơn vị tính : tablet
Biệt dược thương mại : Butisol sodium 50 mg tablet

Giá bán buôn : USD >2.46

Đơn vị tính : tablet

Nhà Sản Xuất

Công ty :

Sản phẩm biệt dược : Butalan
Công ty :

Sản phẩm biệt dược : Butisol
Công ty :

Sản phẩm biệt dược : Sarisol No. 2

Đóng gói

Công ty : C.O. Truxton Inc.
Công ty : Chattem Chemicals Inc.

Website : http://www.chattem.com
Công ty : Meda AB

Website : http://www.meda.se

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB00237

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2479

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505051

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C07827

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D03180

ChemSpider

http://www.chemspider.com/Chemical-Structure.2385.html

National Drug Code Directory

http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0037-0113-60

PharmGKB

http://www.pharmgkb.org/drug/PA164743463

Wikipedia

http://en.wikipedia.org/wiki/Butabarbital

Drugs.com

http://www.drugs.com/cdi/butabarbital.html

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