Tìm theo
Acetylcysteine
Các tên gọi khác (12 ) :
  • (2R)-2-acetylamino-3-Sulfanylpropanoic acid
  • (R)-2-acetylamino-3-Mercaptopropanoic acid
  • (R)-Mercapturic acid
  • Acetilcisteina
  • Acetylcysteine
  • Acetylcysteinum
  • L-Acetylcysteine
  • L-alpha-acetamido-beta-Mercaptopropionic acid
  • Mercapturic acid
  • N-Acetyl-L-(+)-cysteine
  • N-ACETYL-L-cysteine
  • N-acetylcysteine
Thuốc tác dụng trên đường hô hấp
Thuốc Gốc
Small Molecule
CAS: 616-91-1
ĐG : Amend
CTHH: C5H9NO3S
PTK: 163.195
Acetylcysteine (also known as N-acetylcysteine or N-acetyl-L-cysteine or NAC) is primarily used as a mucolytic agent and in the management of acetaminophen poisoning. It is a derivative of cysteine with an acetyl group attached to the amino group of cysteine. NAC is essentially a prodrug that is converted to cysteine (in the intestine by the enzyme aminoacylase 1) and absorbed in the intestine into the blood stream. Cysteine is a key constituent to glutathione and hence administration of acetylcysteine replenishes glutathione stores. Acetylcysteine can also be used as a general antioxidant which can help mitigate symptoms for a variety of diseases exacerbated by reactive oxygen species (ROS). For instance, acetylcysteine is commonly used in individuals with renal impairment to prevent the precipitation of acute renal failure. Acetylcysteine has been shown to have efficacy in treating mild to moderate traumatic brain injury including ischemic brain injury, particularly in reducing neuronal losses, and also reducing cognitive and neurological symptoms when administered promptly after injury. N-acetylcysteine is now widely used in the treatment of HIV, and it has reported efficacy in chronic obstructive pulmonary disease and contrast-induced nephropathy. Acetylcysteine is also being successfully used to treat a variety of neuropsychiatric and neurodegenerative disorders including cocaine, cannabis, and smoking addictions, Alzheimer's and Parkinson's diseases, autism, compulsive and grooming disorders, schizophrenia, depression, and bipolar disorder. Recent data also shows that N-acetylcysteine inhibits muscle fatigue and can be used to enhance performance in endurance events and in exercise and endurance training.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C5H9NO3S
Phân tử khối
163.195
Monoisotopic mass
163.030313849
InChI
InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1
InChI Key
InChIKey=PWKSKIMOESPYIA-BYPYZUCNSA-N
IUPAC Name
(2R)-2-acetamido-3-sulfanylpropanoic acid
Traditional IUPAC Name
acetylcysteine
SMILES
CC(=O)N[C@@H](CS)C(O)=O
Độ tan chảy
109-110
Độ hòa tan
5.09e+00 g/l
logP
-0.71
logS
-1.5
pKa (strongest acidic)
3.82
pKa (Strongest Basic)
-1.5
PSA
66.4 Å2
Refractivity
37.67 m3·mol-1
Polarizability
15.34 Å3
Rotatable Bond Count
3
H Bond Acceptor Count
3
H Bond Donor Count
3
Physiological Charge
-1
Number of Rings
0
Bioavailability
1
Rule of Five
true
pKa
9.52 (at 25 °C)
Dược Lực Học : Acetylcysteine has been shown to reduce the extent of liver injury following acetaminophen overdose. It is most effective when given early, with benefit seen principally in patients treated within 8-10 hours of the overdose. Acetylcysteine likely protects the liver by maintaining or restoring the glutathione levels, or by acting as an alternate substrate for conjugation with, and thus detoxification of, the reactive metabolite.
Cơ Chế Tác Dụng : Acetylcysteine (also known as N-acetylcysteine or N-acetyl-L-cysteine or NAC) is primarily used as a mucolytic agent and in the management of acetaminophen poisoning. It is a derivative of cysteine with an acetyl group attached to the amino group of cysteine. NAC is essentially a prodrug that is converted to cysteine (in the intestine by the enzyme aminoacylase 1) and absorbed in the intestine into the blood stream. Cysteine is a key constituent to glutathione and hence administration of acetylcysteine replenishes glutathione stores. Acetylcysteine can also be used as a general antioxidant which can help mitigate symptoms for a variety of diseases exacerbated by reactive oxygen species (ROS). For instance, acetylcysteine is commonly used in individuals with renal impairment to prevent the precipitation of acute renal failure. Acetylcysteine has been shown to have efficacy in treating mild to moderate traumatic brain injury including ischemic brain injury, particularly in reducing neuronal losses, and also reducing cognitive and neurological symptoms when administered promptly after injury. N-acetylcysteine is now widely used in the treatment of HIV, and it has reported efficacy in chronic obstructive pulmonary disease and contrast-induced nephropathy. Acetylcysteine is also being successfully used to treat a variety of neuropsychiatric and neurodegenerative disorders including cocaine, cannabis, and smoking addictions, Alzheimer's and Parkinson's diseases, autism, compulsive and grooming disorders, schizophrenia, depression, and bipolar disorder. Recent data also shows that N-acetylcysteine inhibits muscle fatigue and can be used to enhance performance in endurance events and in exercise and endurance training. Acetylcysteine protects against acetaminophen overdose-induced hepatotoxicity by maintaining or restoring hepatic concentrations of glutathione. It does this by producing the glutathione precursor L-cysteine. Glutathione is required to inactivate an intermediate metabolite (N-acetyl-p-benzoquinoneimine or NAPQI) of acetaminophen that is thought to be hepatotoxic. In acetaminophen overdose cases, excessive quantities of this metabolite are formed because the primary metabolic (glucuronide and sulfate conjugation) pathways become saturated. Acetylcysteine may act by reducing the metabolite to the parent compound and/or by providing sulfhydryl for conjugation of the metabolite. Experimental evidence also suggests that a sulfhydryl-containing compound such as acetylcysteine may also directly inactivate the metabolite. The mechanisms of action for acetylcysteine’s well-known mucolytic effects are different. In particular, when inhaled, acetylcysteine (and its metabolic byproduct cysteine) exerts its mucolytic action through its free sulfhydryl group, which reduces the disulfide bonds in the mucus matrix and lowers mucus viscosity. This action increases with increasing pH and is most significant at pH 7 to 9. The mucolytic action of acetylcysteine is not affected by the presence of DNA. Acetylcysteine is also an antioxidant and reduces oxidative stress. Acetylcysteine serves as a prodrug to L-cysteine which is a precursor to the biologic antioxidant, glutathione and hence administration of acetylcysteine replenishes glutathione stores. L-cysteine also serves as a precursor to cystine which in turn serves as a substrate for the cystine-glutamate antiporter on astrocytes hence increasing glutamate release into the extracellular space. This glutamate in turn acts on mGluR2/3 receptors, and at higher doses of acetylcysteine, mGluR5. Glutathione also modulates the NMDA receptor by acting at the redox site. These effects on glutamate and NMDA signaling appear to explain some of the positive neuropsychotropic effects associated with NAC. Acetylcysteine also possesses some anti-inflammatory effects possibly via inhibiting NF-κB through redox activation of the nuclear factor kappa kinases thereby modulating cytokine synthesis.
Dược Động Học :
▧ Absorption :
Bioavailability is 6–10% following oral administration and less than 3% following topical administration.
▧ Protein binding :
83%
▧ Metabolism :
Hepatic. Deacetylated by the liver to cysteine and subsequently metabolized.
▧ Half Life :
5.6 hours (adults), 11 hours (neonates)
Độc Tính : Single intravenous doses of acetylcysteine at 1000 mg/kg in mice, 2445 mg/kg in rats, 1500 mg/kg in guinea pigs, 1200 mg/kg in rabbits and 500 mg/kg in dogs were lethal. Symptoms of acute toxicity were ataxia, hypoactivity, labored respiration, cyanosis, loss of righting reflex and convulsions.
Chỉ Định : Acetylcysteine is used mainly as a mucolytic and in the management of paracetamol (acetaminophen) overdose.
Liều Lượng & Cách Dùng : Liquid - Respiratory (inhalation)
Solution - Respiratory (inhalation)
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Acetadote
  • Công ty :
    Sản phẩm biệt dược : Fluimucil
  • Công ty :
    Sản phẩm biệt dược : Lysox
  • Công ty : Zambon
    Sản phẩm biệt dược : Mucolysin
  • Công ty : Mead Johnson
    Sản phẩm biệt dược : Mucomyst
  • Công ty :
    Sản phẩm biệt dược : Parvolex
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB06151
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=12035
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=99443235
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06809
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00221
ChemSpider
http://www.chemspider.com/Chemical-Structure.11540.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0517-7604-25
PharmGKB
http://www.pharmgkb.org/drug/PA448033
Wikipedia
http://en.wikipedia.org/wiki/Acetylcysteine
RxList
http://www.rxlist.com/cgi/generic/acetylcysteine.htm
Drugs.com
http://www.drugs.com/cdi/acetylcysteine-solution.html
... loading
... loading