Fenfluramine

Các tên gọi khác (2) :

Fenfluramina
Fenfluraminum

serotonin uptake inhibitors, appetite depressants, serotonin receptor agonists, serotonin agents, stimul

Thuốc Gốc

Small Molecule

CAS: 458-24-2

ATC: A08AA02, A08AA04

CTHH: C₁₂H₁₆F₃N

PTK: 231.2573

Fenfluramine was withdrawn from the U.S. market in 1997 after reports of heart valve disease and pulmonary hypertension, including a condition known as cardiac fibrosis.

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₁₂H₁₆F₃N

Phân tử khối

231.2573

Monoisotopic mass

231.123484132

InChI

InChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3

InChI Key

InChIKey=DBGIVFWFUFKIQN-UHFFFAOYSA-N

IUPAC Name

ethyl({1-[3-(trifluoromethyl)phenyl]propan-2-yl})amine

Traditional IUPAC Name

fenfluramine

SMILES

CCNC(C)CC1=CC(=CC=C1)C(F)(F)F

Độ tan chảy

108-112 °C at 1.20E+01 mm Hg

Độ hòa tan

412 mg/L

logP

3.36

logS

-4

pKa (Strongest Basic)

10.22

PSA

12.03 Å²

Refractivity

59.2 m³·mol^-1

Polarizability

22.51 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

Dược Lực Học : Used to treat obesity, Fenfluramine decreases caloric intake by increasing serotonin levels in the brain's synapses. Fenfluramine acts as a serotonin reuptake inhibitor. It also causes release of serotonin from the synaptosomes. This in turn increases serotonin transmission in the feeding centre of the brain which suppresses appetite.

Cơ Chế Tác Dụng : Fenfluramine was withdrawn from the U.S. market in 1997 after reports of heart valve disease and pulmonary hypertension, including a condition known as cardiac fibrosis. Fenfluramine binds to the serotonin reuptake pump. This causes inhbition of serotonin uptake and release of serotonin. The increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates.

Dược Động Học :

▧ Absorption :
Fenfluramine is well-absorbed from the gastrointestinal tract, and a maximal anorectic effect is generally seen after 2 to 4 hours.
▧ Metabolism :
Hepatic.
▧ Half Life :
20 hours

Độc Tính : Agitation and drowsiness, confusion, flushing, tremor (or shivering), fever, sweating, abdominal pain, hyperventilation, and dilated non-reactive pupils seem frequent in fenfluramine overdosage. Reflexes may be either exaggerated or depressed and some patients may have rotary nystagmus. Tachycardia may be present, but blood pressure may be normal or only slightly elevated. Convulsions, coma, and ventricular extrasystoles, culminating in ventricular fibrillation, and cardiac arrest, may occur at higher dosages. Less than 5 mg/kg are toxic to humans. Five-ten mg/kg may produce coma and convulsions. Reported single overdoses have ranged from 300 to 2000 mg; the lowest reported fatal dose was a few hundred mg in a small child, and the highest reported nonfatal dose was 1800 mg in an adult. Most deaths were apparently due to respiratory failure and cardiac arrest. Toxic effects will appear within 30 to 60 minutes and may progress rapidly to potentially fatal complications in 90 to 240 minutes. Symptoms may persist for extended periods depending upon the dose ingested.

Chỉ Định : For the management of exogenous obesity as a short-term (a few weeks) adjunct in a regimen of weight reduction based on caloric restriction.

Tương Tác Thuốc :

Acetophenazine Decreased anorexic effect, may increase psychotic symptoms
Alimemazine Decreased anorexic effect, may increase psychotic symptoms
Chlorpromazine Decreased anorexic effect, may increase psychotic symptoms
Ethopropazine Decreased anorexic effect, may increase psychotic symptoms
Fluoxetine Risk of serotoninergic syndrome
Fluphenazine Decreased anorexic effect, may increase psychotic symptoms
Fluvoxamine Risk of serotoninergic syndrome
Guanethidine Fenfluramine may decrease the effect of guanethidine.
Insulin Aspart Fenfluramine increases the effect of insulin
Insulin Detemir Fenfluramine increases the effect of insulin
Insulin Glulisine Fenfluramine increases the effect of insulin
Isocarboxazid Possible hypertensive crisis
Mesoridazine Decreased anorexic effect, may increase psychotic symptoms
Methdilazine Decreased anorexic effect, may increase psychotic symptoms
Methotrimeprazine Decreased anorexic effect, may increase psychotic symptoms
Paroxetine Risk of serotoninergic syndrome
Perphenazine Decreased anorexic effect, may increase psychotic symptoms
Phenelzine Possible hypertensive crisis
Prochlorperazine Decreased anorexic effect, may increase psychotic symptoms.
Promazine Decreased anorexic effect, may increase psychotic symptoms
Promethazine Decreased anorexic effect, may increase psychotic symptoms.
Propericiazine Decreased anorexic effect, may increase psychotic symptoms.
Propiomazine Decreased anorexic effect, may increase psychotic symptoms
Rasagiline Possible hypertensive crisis
Thiethylperazine Decreased anorexic effect, may increase psychotic symptoms
Thioridazine Decreased anorexic effect, may increase psychotic symptoms
Tranylcypromine Possible hypertensive crisis
Trifluoperazine Decreased anorexic effect, may increase psychotic symptoms
Triflupromazine Decreased anorexic effect, may increase psychotic symptoms
Venlafaxine Risk of serotoninergic syndrome

Liều Lượng & Cách Dùng : Tablet - Oral

Dữ Kiện Thương Mại

Nhà Sản Xuất

Công ty :

Sản phẩm biệt dược : Adifax
Công ty :

Sản phẩm biệt dược : Ponderax
Công ty :

Sản phẩm biệt dược : Pondimin

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB00574

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3337

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506096

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C06996

ChemSpider

http://www.chemspider.com/Chemical-Structure.3220.html

PharmGKB

http://www.pharmgkb.org/drug/PA449592

Wikipedia

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

RxList

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

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