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Lamivudine Produkt Beschreibung

Lamivudine Struktur
Englisch Name:

Lamivudine Eigenschaften

177 °C
D21 -135° (c = 0.38 in methanol)
-142 ° (C=1, MeOH)
storage temp. 
water: soluble10mg/mL, clear
white to beige
CAS Datenbank
134678-17-4(CAS DataBase Reference)
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
R-Sätze: 63-36/37/38
S-Sätze: 26-36
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
RTECS-Nr. UW7361333
HS Code  29349990
Giftige Stoffe Daten 134678-17-4(Hazardous Substances Data)
Bildanzeige (GHS)
Alarmwort Achtung
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H225 Flüssigkeit und Dampf leicht entzündbar. Entzündbare Flüssigkeiten Kategorie 2 Achtung P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H361 Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Reproduktionstoxizität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
H370 Schädigt die Organe. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 1 Achtung P260, P264, P270, P307+P311, P321,P405, P501
P201 Vor Gebrauch besondere Anweisungen einholen.
P210 Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P260 Dampf/Aerosol/Nebel nicht einatmen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P281 Vorgeschriebene persönliche Schutzausrüstung verwenden.
P308+P313 BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.
P403+P233 An einem gut belüfteten Ort aufbewahren. Behälter dicht verschlossen halten.

Lamivudine Chemische Eigenschaften,Einsatz,Produktion Methoden


Lamivudine is a new generation orally active nucleoside analog launched in the U.S.A. for use in combination with zidovudine (AZT) as a first-line therapy for patients with HIV infection. Lamivudine is rapidly converted to phosphorylated metabolites in the body which act as inhibitors and chain terminators of HIV reverse transcriptase (RT), the enzyme required for the replication of the HIV genome. Lamivudine has similar inhibitory potency to RT as AZT but is 10 times less toxic and is active against AZT-resistant strains of HIV. Combination therapy of lamivudine and AZT produced a large decrease in blood-borne virus with an increase in CD4 cells, an effect that can be sustained for 2 years. Since hepatitis B virus (HBV) also encodes a polymerase with a RT function necessary for the conversion of a RNA replicative intermediate to DNA, clinical efficacy has been reported for lamivudine in treating patients with HBV infection. It was reported that the enantiomer of lamivudine is equipotent against HIV but with considerably higher cytotoxicity.

Chemische Eigenschaften

White Crystalline Powder


BioChem Pharma (Canada)


A reverse transcriptase inhibitor. Antiviral.


ChEBI: A monothioacetal that consists of cytosine having a (2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl moiety attached at position 1. An inhibitor of HIV-1 reverse transcriptase.


Lamivudine is a synthetic cytidine analogue used in the treatment of HIV and HBV. Its activation requires phosphorylation by cellular enzymes. Lamivudine triphosphate competitively inhibits HBV DNA polymerase and HIV reverse transcriptase and causes chain termination. It inhibits the activity of mammalian DNA polymerases with a much lower potency.
HIV-1 frequently acquires mutations in reverse transcriptase that result in resistance to lamivudine within 12 weeks of treatment. Mutations in the DNA polymerase of HBV are associated with decreased lamivudine efficacy and have been documented in patients treated with this agent for 6 months or more.


Epivir (GlaxoSmithKline).

Acquired resistance

A single codon change at position 184 in the HIV reverse transcriptase gene confers high-level resistance. The K65R mutation is also associated with resistance. In-vitro data indicate that lamivudine resistance may restore HIV sensitivity to zidovudine- and tenofovir-resistant virus.

Allgemeine Beschreibung

Lamivudine is (-)-2',3'-dideoxy-3'-thiacytidine, (-)-β-L-(2R,5S)-1,3-oxathiolanylcytosine, 3TC, or (-)-(S)-ddC.Lamivudine is a synthetic nucleoside analog that differsfrom 2β,3β-dideoxycytidine (ddC) by the substitution of asulfur atom in place of a methylene group at the 3'-positionof the ribose ring. In early clinical trials, lamivudine exhibitedhighly promising antiretroviral activity against HIVand low toxicity in the dosages studied.Preliminarypharmacokinetic studies indicated that it exhibited goodoral bioavailability (F=~80%) and a plasma half-life of 2to 4 hours.

Pharmazeutische Anwendungen

An analog of cytidine available for oral administration.

Pharmazeutische Anwendungen

An antiretroviral agent that also exhibits activity against hepatitis B virus and duck hepatitis B virus. Its properties are described in Ch. 36 . Use is limited by the development of resistance within 1 year in up to 25% of treated patients. It is likely to be used with other drugs in the future.


Oral absorption: 80–85%
Cmax, 300 mg once daily: 2.0 mg/L
Plasma half-life: 5–7 h
Volume of distribution: 1.3 L/kg
Plasma protein binding: <36%
It is rapidly absorbed and there is no significant difference in bioavailability when taken with food.
It penetrates moderately well into the CNS. The semen:plasma ratio is about 9.1 (2.3–16.1). It is secreted into breast milk.
Metabolism and excretion
Less than 10% of the administered dose undergoes hepatic metabolism. Over 70% of the dose is subject to renal clearance via active tubular secretion. Dosage adjustments are not routinely recommended in the presence of renal or hepatic impairment.

Clinical Use

Therapy of chronic hepatitis B

Clinical Use

Lamivudine is indicated for the treatment of HIV when used in combination with other antiretroviral agents.A lower dose than that used to treat HIV is approved for the treatment of HBV. Although lamivudine initially improves histological and biochemical measures of hepatic function and reduces HBV DNA to below the limits of detection, withdrawal of the drug usually results in disease recurrence. Resistance appears in up to onethird of patients after 1 year of treatment.


The most common adverse effects of lamivudine seen at doses used to treat HBV are mild; they include headache, malaise, fatigue, fever, insomnia, diarrhea, and upper respiratory infections. Elevated alanine aminotransferase (ALT), serum lipase, and creatine kinase may also occur. The safety and efficacy of lamivudine in patients with decompensated liver disease have not been established. Dosage adjustment is required in individuals with renal impairment. Coadministration of trimethoprim–sulfamethoxazole decreases the renal clearance of lamivudine.


Lamivudine is relatively safe and non-toxic. Animal studies of very high doses did not result in any organ toxicity. In patients co-infected with HIV and HBV, cessation of lamivudine therapy may result in clinical and/or laboratory evidence of recurrent hepatic disease that may be more severe in patients with hepatic decompensation. Tests of liver function and inflammation and markers of HBV replication should be periodically monitored.
Lamivudine competes with emtricitabine for the enzymes involved in intracellular phosphorylation and co-administration is contraindicated.

Lamivudine Upstream-Materialien And Downstream Produkte


Downstream Produkte

Lamivudine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 378)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
Frapp's ChemicalNFTZ Co., Ltd.
+86 (576) 8169-6106
+86 (576) 8169-6105 China 886 50
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 CHINA 3194 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817 CHINA 21707 58
Beijing Cooperate Pharmaceutical Co.,Ltd.
+86-10-60279497 +86(0)15646567669
+86-10-60279497 CHINA 1817 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693 CHINA 20672 55
Mainchem Co., Ltd.
+86-0592-6210733 CHINA 32447 55
020-81716319 CHINA 2543 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682; +8618874586545
02783214688 CHINA 535 55
career henan chemical co
+86-371-86658258 CHINA 30001 58
Shaanxi Yikanglong Biotechnology Co., Ltd.
17791478691 CHINA 297 58

134678-17-4()Verwandte Suche:

  • 恩曲他滨杂质Ⅲ(拉米夫定)(一)-1-[(2R,5S)-2-(羟甲基)-1,3-氧硫杂环戊烷-5-基]胞嘧啶
  • (2r-cis)-4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1h)-pyrimidinone
  • 2'-deoxy-3'-thiacytidine
  • 3TC
  • (-)-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cystosine
  • (-)-2¢
  • (-)NGPB-21
  • (2R-cis)-4-amino-1-
  • ,3¢
  • 2(1H)-Pyrimidinone,4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-,(2R-cis)-
  • 3'-thia-2',3'-dideoxcytidine
  • -deoxy-3¢
  • Epivir
  • GR109714X
  • -thia-2¢
  • -thiacytidine
  • Lamivudine(3Tc)
  • 1,3-Oxathiolan-5-Yl-2-(Lh)-Pyrimidinone,Lamivudine
  • 3TC, (-)-BCH-189, 3Thia-23dideoxycytidine
  • 1,3-Oxathiolane, 2(1H)-pyrimidinone deriv.
  • 2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]- (9CI)
  • b-L-3'-Thia-2',3'-dideoxycytidine
  • Epivir HBV
  • Hepitec
  • Heptovir
  • L-SddC
  • Zeffix
  • Zefix
  • LaMivudine(Epivir)
  • 4-AMino-1-[(2R,5S)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyriMidinone
  • 3TC (-)-1-[(2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
  • 3TC/Epivir-HBV
  • 4-AMino-1-((2R,5S)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl)pyriMidin-2(1H)-one
  • LaMivudine-13C-d2
  • cis-Lamivudine
  • (-)-BCH-189
  • (-)-1-[(2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
  • (-)-ILTI-189
  • (2R-cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-y1]-2(1H)-pyrimidinone
  • 2(1H)-Pyrimidinone, 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)
  • Heptivir
  • (+)-1-[(2S,5R)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
  • (+)-β-D-BCH-189
  • 1-[(2S,5R)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
  • 1-[(2S,5R)-2-Hydroxymethyl-1,3-oxathiolan-5-yl]cytosine
  • Lamivudine
  • Lamivudine (200 mg)
  • Lamivudine Resolution Mixture A (10 mg)
  • LaMivudine Resolution Mixture A
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