Tìm theo
L-Tryptophan
Các tên gọi khác (14 ) :
  • (-)-Tryptophan
  • (2S)-2-amino-3-(1H-indol-3-yl)Propanoic acid
  • (S)-alpha-amino-1H-indole-3-propanoic acid
  • (S)-alpha-Amino-beta-(3-indolyl)-propionic acid
  • (S)-Tryptophan
  • (S)-α-amino-1H-indole-3-propanoic acid
  • L-(-)-Tryptophan
  • L-(−)-tryptophan
  • L-beta-3-Indolylalanine
  • L-Tryptophan
  • L-β-3-indolylalanine
  • Trp
  • Tryptophan
  • W
Thực phẩm chức năng
Thuốc Gốc
Small Molecule
CAS: 73-22-3
ATC: N06AX02
ĐG : Amend
CTHH: C11H12N2O2
PTK: 204.2252
An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C11H12N2O2
Phân tử khối
204.2252
Monoisotopic mass
204.089877638
InChI
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
InChI Key
InChIKey=QIVBCDIJIAJPQS-VIFPVBQESA-N
IUPAC Name
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional IUPAC Name
L-tryptophan
SMILES
N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O
Độ tan chảy
290.5 dec °C
Độ hòa tan
1.34E+004 mg/L (at 25 °C)
logP
-1.06
logS
-1.23
pKa (strongest acidic)
2.54
pKa (Strongest Basic)
9.4
PSA
79.11 Å2
Refractivity
56.2 m3·mol-1
Polarizability
21.05 Å3
Rotatable Bond Count
3
H Bond Acceptor Count
3
H Bond Donor Count
3
Physiological Charge
0
Number of Rings
2
Bioavailability
1
Rule of Five
true
pKa
7.38 (at 25 °C)
Dược Lực Học : Tryptophan is critical for the production of the body's proteins, enzymes and muscle tissue. It is also essential for the production of niacin, the synthesis of the neurotransmitter serotonin and melatonin. Tryptophan supplements can be used as natural relaxants to help relieve insomnia. Tryptophan can also reduce anxiety and depression and has been shown to reduce the intensity of migraine headaches. Other promising indications include the relief of chronic pain, reduction of impulsivity or mania and the treatment of obsessive or compulsive disorders. Tryptophan also appears to help the immune system and can reduce the risk of cardiac spasms. Tryptophan deficiencies may lead to coronary artery spasms. Tryptophan is used as an essential nutrient in infant formulas and intravenous feeding. Tryptophan is marketed as a prescription drug (Tryptan) for those who do not seem to respond well to conventional antidepressants. It may also be used to treat those afflicted with seasonal affective disorder (a winter-onset depression). Tryptopan serves as the precursor for the synthesis of serotonin (5-hydroxytryptamine, 5-HT) and melatonin (N-acetyl-5-methoxytryptamine).
Cơ Chế Tác Dụng : An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals. [PubChem] A number of important side reactions occur during the catabolism of tryptophan on the pathway to acetoacetate. The first enzyme of the catabolic pathway is an iron porphyrin oxygenase that opens the indole ring. The latter enzyme is highly inducible, its concentration rising almost 10-fold on a diet high in tryptophan. Kynurenine is the first key branch point intermediate in the pathway. Kynurenine undergoes deamniation in a standard transamination reaction yielding kynurenic acid. Kynurenic acid and metabolites have been shown to act as antiexcitotoxics and anticonvulsives. A second side branch reaction produces anthranilic acid plus alanine. Another equivalent of alanine is produced further along the main catabolic pathway, and it is the production of these alanine residues that allows tryptophan to be classified among the glucogenic and ketogenic amino acids. The second important branch point converts kynurenine into 2-amino-3-carboxymuconic semialdehyde, which has two fates. The main flow of carbon elements from this intermediate is to glutarate. An important side reaction in liver is a transamination and several rearrangements to produce limited amounts of nicotinic acid, which leads to production of a small amount of NAD+ and NADP+.
Dược Động Học :

▧ Metabolism :
Hepatic.
Độc Tính : Oral rat LD50: > 16 gm/kg. Investigated as a tumorigen, mutagen, reproductive effector. Symptoms of overdose include agitation, confusion, diarrhea, fever, overactive reflexes, poor coordination, restlessness, shivering, sweating, talking or acting with excitement you cannot control, trembling or shaking, twitching, and vomiting.
Chỉ Định : Tryptophan may be useful in increasing serotonin production, promoting healthy sleep, managing depression by enhancing mental and emotional well-being, managing pain tolerance, and managing weight.
Tương Tác Thuốc :
  • Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Isocarboxazid Possible severe adverse reaction with this combination
  • Vilazodone Due to risks of enhanced serotonin activity and/or adverse reactions (e.g., serotonin syndrome), concomitant use of selective serotonin reuptake inhibitors (SSRIs) and tryptophan is not recommended. Avoid combination.
  • Zolmitriptan Use of two serotonin modulators, such as zolmitriptan and L-tryptophan, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Liều Lượng & Cách Dùng : Capsule - Oral
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Alti-Tryptophan
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00150
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=6305
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508329
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C00078
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00020
ChemSpider
http://www.chemspider.com/Chemical-Structure.6066.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=21974
PharmGKB
http://www.pharmgkb.org/drug/PA10323
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