Tìm theo
Lamivudine
Các tên gọi khác (12 ) :
  • (-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine
  • (-)-2'-Deoxy-3'-thiacytidine
  • 2',3'-Dideoxy-3'-thiacytidine
  • 3'-Thia-2',3'-dideoxycytidine
  • 3TC
  • beta-L-2',3'-Dideoxy-3'-thiacytidine
  • beta-L-3'-Thia-2',3'-dideoxycytidine
  • Epivir
  • Lamivudin
  • Lamivudina
  • Lamivudine
  • Lamivudinum
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 134678-17-4
ATC: J05AF05
ĐG : Apotheca Inc.
CTHH: C8H11N3O3S
PTK: 229.256
A reverse transcriptase inhibitor and zalcitabine analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV).
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C8H11N3O3S
Phân tử khối
229.256
Monoisotopic mass
229.052111923
InChI
InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1
InChI Key
InChIKey=JTEGQNOMFQHVDC-NKWVEPMBSA-N
IUPAC Name
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
Traditional IUPAC Name
lamivudine
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1CS[C@H](CO)O1
Độ tan chảy
160-162 °C
Độ hòa tan
70 mg/ml
logP
-1.4
logS
-1.9
pKa (strongest acidic)
14.29
pKa (Strongest Basic)
-0.16
PSA
88.15 Å2
Refractivity
55.16 m3·mol-1
Polarizability
21.7 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
5
H Bond Donor Count
2
Physiological Charge
0
Number of Rings
2
Bioavailability
1
Rule of Five
true
Dược Lực Học : Lamivudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV). Lamivudine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated.
Cơ Chế Tác Dụng : A reverse transcriptase inhibitor and zalcitabine analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV). Lamivudine is a synthetic nucleoside analogue and is phosphorylated intracellularly to its active 5'-triphosphate metabolite, lamivudine triphosphate (L-TP). This nucleoside analogue is incorporated into viral DNA by HIV reverse transcriptase and HBV polymerase, resulting in DNA chain termination.
Dược Động Học :
▧ Absorption :
Lamivudine was rapidly absorbed after oral administration in HIV-infected patients. Absolute bioavailability in 12 adult patients was 86% ± 16% (mean ± SD) for the 150-mg tablet and 87% ± 13% for the oral solution. The peak serum lamivudine concentration (Cmax) was 1.5 ± 0.5 mcg/mL when an oral dose of 2 mg/kg twice a day was given to HIV-1 patients. When given with food, absorption is slower, compared to the fasted state.
▧ Volume of Distribution :
Apparent volume of distribution, IV administration = 1.3 ± 0.4 L/kg. Volume of distribution was independent of dose and did not correlate with body weight.
▧ Protein binding :
<36% bound to plasma protein.
▧ Metabolism :
Metabolism of lamivudine is a minor route of elimination. In man, the only known metabolite of lamivudine is the trans-sulfoxide metabolite. This biotransformation is catalyzed by sulfotransferases.
▧ Route of Elimination :
The majority of lamivudine is eliminated unchanged in urine by active organic cationic secretion. 5.2% ± 1.4% (mean ± SD) of the dose was excreted as the trans-sulfoxide metabolite in the urine. Lamivudine is excreted in human breast milk and into the milk of lactating rats.
▧ Half Life :
5 to 7 hours (healthy or HBV-infected patients)
▧ Clearance :
* Renal clearance = 199.7 ± 56.9 mL/min [300 mg oral dose, healthy subjects] * Renal clearance = 280.4 ± 75.2 mL/min [single IV dose, HIV-1-infected patients] * Total clearance = 398.5 ± 69.1 mL/min [HIV-1-infected patients]
Độc Tính : The most common reported adverse reactions (incidence ≥15%) in adults were headache, nausea, malaise and fatigue, nasal signs and symptoms, diarrhea, and cough.
Chỉ Định : For the treatment of HIV infection and chronic hepatitis B (HBV).
Tương Tác Thuốc :
  • Tobramycin Increased risk of nephrotoxicity
  • Valganciclovir The adverse/toxic effects of reverse transcriptase inhibitors (nucleoside), such as Lamivudine, may be enhanced by Valganciclovir. There is a risk of hematologic toxicity. Diligent monitoring during concomitant therapy is recommended.
  • Zalcitabine Lamivudine may reduce the efficacy of zalcitabine. Combination therapy is not recommended.
Liều Lượng & Cách Dùng : Solution - Oral - 5 mg/mL, 10 mg/mL
Tablet - Oral - 100 mg, 150 mg, 300 mg
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Epivir 150 mg tablet
    Giá bán buôn : USD >7.79
    Đơn vị tính : tablet
  • Biệt dược thương mại : Epivir hbv 100 mg tablet
    Giá bán buôn : USD >13.94
    Đơn vị tính : tablet
  • Biệt dược thương mại : Epivir 300 mg tablet
    Giá bán buôn : USD >15.57
    Đơn vị tính : tablet
  • Biệt dược thương mại : Epzicom tablet
    Giá bán buôn : USD >35.78
    Đơn vị tính : tablet
  • Biệt dược thương mại : Epzicom 600-300 mg tablet
    Giá bán buôn : USD >37.21
    Đơn vị tính : tablet
  • Biệt dược thương mại : Epivir 10 mg/ml Solution
    Giá bán buôn : USD >0.53
    Đơn vị tính : ml
Nhà Sản Xuất
  • Công ty : Dosa
    Sản phẩm biệt dược : Amilitrap
  • Công ty : Mebiphar
    Sản phẩm biệt dược : Antiheb
  • Công ty : Beximco
    Sản phẩm biệt dược : Avilam
  • Sản phẩm biệt dược : Avolam
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Epivir
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Epivir-HBV
  • Sản phẩm biệt dược : Flamivud
  • Công ty : Ivax
    Sản phẩm biệt dược : Ganvirel
  • Công ty : Square
    Sản phẩm biệt dược : Hepavir
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Hepitec
  • Công ty : Hetero
    Sản phẩm biệt dược : Heptavir
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Heptodin
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Heptodine
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Heptovir
  • Công ty : Cadila
    Sản phẩm biệt dược : Lamda
  • Công ty : Paylos
    Sản phẩm biệt dược : Lamibergen
  • Công ty : Zydus
    Sản phẩm biệt dược : Lamidac
  • Công ty : Zifam India
    Sản phẩm biệt dược : Lamitec
  • Công ty : Incepta
    Sản phẩm biệt dược : Lamivir
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Zeffix
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00709
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=60825
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507855
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07065
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00353
ChemSpider
http://www.chemspider.com/Chemical-Structure.54812.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50046287
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0173-0742-00
PharmGKB
http://www.pharmgkb.org/drug/PA450163
Wikipedia
http://en.wikipedia.org/wiki/Lamivudine
RxList
http://www.rxlist.com/cgi/generic3/lamivudine.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/com1513.shtml
Drugs.com
http://www.drugs.com/cdi/lamivudine.html
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