Isocarboxazid

Các tên gọi khác (4 ) :

Isocarboxazida
Isocarboxazide
Isocarboxazidum
Marplan

antidepressive agents, monoamine oxidase inhibitors

Thuốc Gốc

Small Molecule

CAS: 59-63-2

ATC: N06AF01

ĐG : Oxford Pharmaceutical Services Inc. , http://www.oxfordpharm.com

CTHH: C₁₂H₁₃N₃O₂

PTK: 231.2505

An MAO inhibitor that is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in the treatment of panic disorder and the phobic disorders. (From AMA, Drug Evaluations Annual, 1994, p311)

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₁₂H₁₃N₃O₂

Phân tử khối

231.2505

Monoisotopic mass

231.100776675

InChI

InChI=1S/C12H13N3O2/c1-9-7-11(15-17-9)12(16)14-13-8-10-5-3-2-4-6-10/h2-7,13H,8H2,1H3,(H,14,16)

InChI Key

InChIKey=XKFPYPQQHFEXRZ-UHFFFAOYSA-N

IUPAC Name

N'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide

Traditional IUPAC Name

isocarboxazid

SMILES

CC1=CC(=NO1)C(=O)NNCC1=CC=CC=C1

Độ tan chảy

105-106 °C

Độ hòa tan

1.6 mg/mL at 25 °C

logP

1.49

logS

-3

pKa (strongest acidic)

12.02

pKa (Strongest Basic)

3.12

PSA

67.16 Å²

Refractivity

74.78 m³·mol^-1

Polarizability

24.51 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

pKa

10.4

Dược Lực Học : Isocarboxazid is a non-selective hydrazine monoamine oxidase (MAO) inhibitor used to treat depression. In vivo and in vitro studies demonstrated inhibition of MAO in the brain, heart, and liver. Depression is a complicated disease that is not fully understood. It is thought that depression may be linked to an imbalance of chemicals within the brain. When depression occurs, there may be a decrease in the amount of chemicals released from nerve cells in the brain. These chemicals are called monoamines. Monoamines are broken down by a chemical called monoamine oxidase. Isocarboxazid prevents monoamine oxidase from breaking down the monoamines. This results in an increased amount of active monoamines in the brain. By increasing the amount of monoamines in the brain, the imbalance of chemicals thought to be caused by depression is altered. This helps relieve the symptoms of depression.

Cơ Chế Tác Dụng : An MAO inhibitor that is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in the treatment of panic disorder and the phobic disorders. (From AMA, Drug Evaluations Annual, 1994, p311) Isocarboxazid works by irreversibly blocking the action of a chemical substance known as monoamine oxidase (MAO) in the nervous system. MAO subtypes A and B are involved in the metabolism of serotonin and catecholamine neurotransmitters such as epinephrine, norepinephrine, and dopamine. Isocarboxazid, as a nonselective MAO inhibitor, binds irreversibly to monoamine oxidase–A (MAO-A) and monoamine oxidase–B (MAO-B). The reduced MAO activity results in an increased concentration of these neurotransmitters in storage sites throughout the central nervous system (CNS) and sympathetic nervous system. This increased availability of one or more monoamines is the basis for the antidepressant activity of MAO inhibitors.

Dược Động Học :

▧ Absorption :
Well absorbed from the gastrointestinal tract.
▧ Metabolism :
Hepatic and rapid (by oxidation).

Độc Tính : Signs of overdose include severe anxiety, confusion, convulsions, cool clammy skin, severe dizziness, severe drowsiness, fast and irregular pulse, fever, hallucinations, severe headache, high or low blood pressure, hyperactive reflexes, muscle stiffness, respiratory depression or failure, slowed reflexes, sweating, severe trouble in sleeping, and unusual irritability.

Chỉ Định : May be used to treat major depressive disorder.

Tương Tác Thuốc :

Almotriptan The MAO inhibitor, isocarboxazid, may decrease the metabolism and clearance of the serotonin 5-HT receptor agonist, almotriptan. Concomitant therapy is contraindicated.
Altretamine Risk of severe hypotension
Amitriptyline Possibility of severe adverse effects
Amoxapine Possibility of severe adverse effects
Amphetamine Possible hypertensive crisis
Atomoxetine Possible severe adverse reaction with this combination
Benzphetamine MAO Inhibitors may enhance the hypertensive effect of Amphetamines. Concomitant use of amphetamines and monoamine oxidase inhibitors (MAOI) should be avoided. If used concomitantly, careful monitoring of blood pressure must occur. It may take up to 2 weeks after the discontinuation of an MAOI for the effects to dissipate enough to afford safety to the administration of interacting agents.
Bezafibrate MAO Inhibitors may enhance the adverse/toxic effect of Bezafibrate. Avoid concomitant use of bezafibrate with monoamine oxidase inhibitors (MAOIs) like isocarboxazid.
Brimonidine MAO Inhibitors like isocarboxazid may enhance the hypertensive effect of Alpha2-Agonists (Ophthalmic). The concomitant use of monoamine oxidase inhibitors and ophthalmic alpha2 agonists is contraindicated.
Buprenorphine Buprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like isocarboxazid. When possible, avoid use of buprenorphine in patients who have used a monoamine oxidase inhibitor within the past 14 days due to possible severe adverse effects.
Bupropion Possible severe adverse reaction with this combination
Buspirone Possible blood pressure elevation
Citalopram Possible severe adverse reaction with this combination
Clomipramine Possibility of severe adverse effects
Desipramine Possibility of severe adverse effects
Desvenlafaxine Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Dexfenfluramine Risk of hypertensive crisis.
Dextroamphetamine Possible hypertensive crisis
Dextromethorphan Possible severe adverse reaction
Diethylpropion Possible hypertensive crisis
Dobutamine Increased arterial pressure
Donepezil Possible antagonism of action
Dopamine Increased arterial pressure
Doxepin Possibility of severe adverse effects
Duloxetine Possible severe adverse reaction with this combination
Entacapone Possible hypertensive crisis with this combination
Ephedra Increased arterial pressure
Ephedrine Increased arterial pressure
Epinephrine Increased arterial pressure
Escitalopram Possible severe adverse reaction with this combination
Fenfluramine Possible hypertensive crisis
Fenoterol Increased arterial pressure
Fluoxetine Possible severe adverse reaction with this combination
Fluvoxamine Possible severe adverse reaction with this combination
Galantamine Possible antagonism of action
Guanethidine Isocarboxazid may decrease the effect of guanethidine.
Imipramine Possibility of severe adverse effects
Isoprenaline Increased arterial pressure
L-DOPA Possible hypertensive crisis
L-Tryptophan Possible severe adverse reaction with this combination
Mazindol Possible hypertensive crisis
Mephentermine Increased arterial pressure
Metaraminol Increased arterial pressure
Methamphetamine Possible hypertensive crisis
Methotrimeprazine Possible severe adverse reaction with this combination
Methoxamine Increased arterial pressure
Methylphenidate Possible hypertensive crisis with this combination
Midodrine Possible hypertensive crisis with this combination
Milnacipran Increase serotonin levels. Combination therapy is contraindicated.
Mirtazapine Possible severe adverse reaction with this combination
Naratriptan The use of two serotonin modulators increases the risk of serotonin syndrome. Consider alternate therapy or monitor for signs and symptoms of serotonin syndrome.
Nefazodone Possible severe adverse reaction with this combination
Norepinephrine Increased arterial pressure
Nortriptyline Possibility of severe adverse effects
Orciprenaline Increased arterial pressure
Paroxetine Possible severe adverse reaction with this combination
Pethidine Potentially fatal adverse effects
Phendimetrazine Possible hypertensive crisis
Phenmetrazine Possible hypertensive crisis
Phentermine Possible hypertensive crisis
Phenylephrine Increased arterial pressure
Phenylpropanolamine Increased arterial pressure
Pirbuterol Increased arterial pressure
Procaterol Increased arterial pressure
Protriptyline Possibility of severe adverse effects
Pseudoephedrine Increased arterial pressure
Rivastigmine Possible antagonism of action
Rizatriptan The MAO inhibitor, isocarboxazid, may decrease the metabolism and clearance of the serotonin 5-HT receptor agonist, rizatriptan. Concomitant therapy is contraindicated.
Salbutamol Increased arterial pressure
Sertraline Possible severe adverse reaction with this combination
Sibutramine Possible serotoninergic syndrome with this combination
Sumatriptan The MAO inhibitor, isocarboxazid, may decrease the metabolism and clearance of the serotonin 5-HT receptor agonist, sumatriptan. Concomitant therapy is contraindicated.
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Isocarboxazid, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Terbutaline Increased arterial pressure
Tetrabenazine Tetrabenazine may increase the adverse/toxic effects of Isocarboxazid. Concomitant therapy is contraindicated.
Tolcapone Tolcapone and Isocarboxazid decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.
Tramadol Tramadol may increase the risk of serotonin syndrome and seizure induction by the MAO inhibitor, isocarboxazid.
Tranylcypromine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Trazodone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Trimethobenzamide Trimethobenzamide and Isocarboxazid, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trimipramine Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Avoid combination or monitor for symptoms of serotonin syndrome and/or hypertensive crisis.
Triprolidine Triprolidine and Isocarboxazid, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
Trospium Trospium and Isocarboxazid, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Venlafaxine Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Vilazodone MAO Inhibitors may enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This may cause serotonin syndrome. Avoid combination.
Zolmitriptan The MAO inhibitor, isocarboxazid, may increase the serum concentration of zolmitriptan by decreasing its metabolism. Concomitant therapy and use of zolmitriptan within two weeks of discontinuing isocarboxazid are contraindicated.

Liều Lượng & Cách Dùng : Tablet - Oral

Dữ Kiện Thương Mại

Giá thị trường

Biệt dược thương mại : Marplan 10 mg tablet

Giá bán buôn : USD >3.45

Đơn vị tính : tablet

Nhà Sản Xuất

Công ty : Takeda

Sản phẩm biệt dược : Enerzer
Công ty : Alliance

Sản phẩm biệt dược : Isocarboxazid
Công ty : Validus

Sản phẩm biệt dược : Marplan

Đóng gói

Công ty : Oxford Pharmaceutical Services Inc.

Website : http://www.oxfordpharm.com
Công ty : Validus Pharmaceuticals

Website : http://www.validuspharma.com

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB01247

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3759

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505330

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D02580

ChemSpider

http://www.chemspider.com/Chemical-Structure.3628.html

National Drug Code Directory

http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/30698-032-01

PharmGKB

http://www.pharmgkb.org/drug/PA450101

Wikipedia

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

RxList

http://www.rxlist.com/cgi/generic/isocarbo.htm

Drugs.com

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

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