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ラミブジン

ラミブジン 化学構造式
134678-17-4
CAS番号.
134678-17-4
化学名:
ラミブジン
别名:
ラミブジン;1-[(2S,5R)-2-ヒドロキシメチル-1,3-オキサチオラン-5-イル]シトシン;1-[(2S)-2α-(ヒドロキシメチル)-1,3-オキサチオラン-5α-イル]-4-アミノピリミジン-2(1H)-オン;2',3'-ジデオキシ-3'-チアシチジン;1-[2α-(ヒドロキシメチル)-1,3-オキサチオラン-5α-イル]シトシン;(+)-1-[(2S,5R)-2-(ヒドロキシメチル)-1,3-オキサチオラン-5-イル]シトシン;1-[(2S,5R)-2-(ヒドロキシメチル)-1,3-オキサチオラン-5-イル]シトシン;1-[2α-(ヒドロキシメチル)-1,3-オキサチオラン-5α-イル]-4-アミノピリミジン-2(1H)-オン;4-アミノ-1-[(2S)-2α-(ヒドロキシメチル)-1,3-オキサチオラン-5α-イル]ピリミジン-2(1H)-オン;(-)-1-[(2R,5S)-2-(ヒドロキシメチル)-1,3-オキサチオラン-5-イル]シトシン;ラミブジン (JAN)
英語化学名:
Lamivudine
英語别名:
3TC;Zefix;3¢Epivir;L-SddC;Zeffix;,3¢Hepitec;Heptivir;Heptovir
CBNumber:
CB1290608
化学式:
C8H11N3O3S
分子量:
229.26
MOL File:
134678-17-4.mol

ラミブジン 物理性質

融点 :
177 °C
比旋光度 :
D21 -135° (c = 0.38 in methanol)
沸点 :
475.4±55.0 °C(Predicted)
比重(密度) :
1.73±0.1 g/cm3(Predicted)
屈折率 :
-142 ° (C=1, MeOH)
闪点 :
9℃
貯蔵温度 :
2-8°C
溶解性:
water: soluble10mg/mL, clear
外見 :
powder
酸解離定数(Pka):
13.83±0.10(Predicted)
色:
white to beige
水溶解度 :
70g/L(temperature not stated)
Merck :
14,5352
InChIKey:
JTEGQNOMFQHVDC-NKWVEPMBSA-N
CAS データベース:
134678-17-4(CAS DataBase Reference)
EPAの化学物質情報:
2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]- (134678-17-4)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
Rフレーズ  63-36/37/38
Sフレーズ  26-36
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
RTECS 番号 UW7361333
HSコード  29349990
有毒物質データの 134678-17-4(Hazardous Substances Data)
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H225 引火性の高い液体および蒸気 引火性液体 2 危険 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H361 生殖能または胎児への悪影響のおそれの疑い 生殖毒性 2 警告 P201, P202, P281, P308+P313, P405,P501
H370 臓器の障害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P307+P311, P321,P405, P501
注意書き
P201 使用前に取扱説明書を入手すること。
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P260 粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P281 指定された個人用保護具を使用すること。
P308+P313 暴露または暴露の懸念がある場合:医師の診断/手当てを 受けること。
P403+P233 換気の良い場所で保管すること。容器を密閉 しておくこと。

ラミブジン 価格 もっと(37)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01TRCL172500
Lamivudine
134678-17-4 1g ¥110000 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01COBQA-4615 ラミブジン
Lamivudine
134678-17-4 1g ¥3600 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01COBQA-4615 ラミブジン
Lamivudine
134678-17-4 5g ¥5100 2021-03-23 購入
東京化成工業 L0217 ラミブジン >98.0%(HPLC)(T)
Lamivudine >98.0%(HPLC)(T)
134678-17-4 100mg ¥5500 2021-03-23 購入
東京化成工業 L0217 ラミブジン >98.0%(HPLC)(T)
Lamivudine >98.0%(HPLC)(T)
134678-17-4 1g ¥30500 2021-03-23 購入

ラミブジン 化学特性,用途語,生産方法

外観

白色〜わずかにうすい褐色, 結晶〜粉末

溶解性

ジメチルスルホキシドに溶けやすく、水にやや溶けやすく、メタノール及びエタノールにやや溶けにくく、ジエチルエーテルにほとんど溶けない。

用途

核酸アナログ逆転写酵素阻害 剤です。ウィルス DNA ポリメラーゼによる 基質の取り込みを競合的に阻害し、DNA 鎖の 伸長を停止することにより、ウィルスの増殖 阻害作用を示します。

用途

核酸アナログ逆転写酵素阻害 剤です。ウイルス DNA ポリメラーゼによる 基質の取り込みを競合的に阻害し、DNA 鎖の 伸長を停止することにより、ウイルス増殖阻 害作用を示します。

効能

抗ウイルス薬, 逆転写酵素阻害薬

商品名

エピビル (ヴィーブヘルスケア); ゼフィックス (グラクソ・スミスクライン)

説明

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.

説明

Lamivudine is a cytidine analog that inhibits the reverse transcriptases of HIV1 (IC50 = 45 nM), HIV2, and hepatitis B. It was one of the first approved nucleoside analog reverse transcriptase inhibitors used to treat viral infections. Following prolonged administration, the efficacy of lamivudine is associated with drug resistance, which may be improved through combination treatments.

化学的特性

White Crystalline Powder

Originator

BioChem Pharma (Canada)

使用

A reverse transcriptase inhibitor. Antiviral.

使用

Lamivudine has been used to deplete the Hepatitis B Virus (HBV) covalently closed circular DNA (cccDNA) forms for the preparation of inverse nested PCR.

定義

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.

適応症

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.

Manufacturing Process

To a solution of potassium t-butoxide (0.11 mol) in 100 ml DMF was added thiobenzoic acid (0.11 mol) and the solution partially evaporated in vacuo, benzene added in two consecutive portions and evaporated in vacuo each time. To the residual DMF solution was added bromoacetaldehyde diethyl acetal (0.1 mol) and the mixture stirred at 120°C for 15 h. After cooling, it was poured onto water (500 ml), the product extracted with ether, the extract washed with aqueous NaHCO3 followed by water, then dried and the solvent removed in vacuo. The residue was distilled in vacuo to give 17.2 g of pure 2- thiobenzoyl acetaldehyde diethyl acetal, boiling point 131-133°C/0.07 mm.
The 2-thiobenzoyl acetaldehyde diethyl acetal (17.2 g) was dissolved in 100 ml THF followed by the addition of 6 g NaOH in 20 ml H2O. The mixture was refluxed under N2 for 15 h, then cooled and diluted with water (200 ml) and the product extracted with ether (3 x 200 ml). The extract was dried, the solvent removed in vacuo and the residue distilled to yield 7.1 g of mercaptoacetaldehyde diethylacetal.
50 g of the 1-benzoyl glycerol in a mixture of 500 ml of CH2Cl2 and 25 ml of H2O was treated portionwise with 80 g of NaIO4 under vigorous stirring at room temperature. After addition, stirring was continued for 2 h after which time 100 g of MgSO4 was added and stirring continued for 30 min. The mixture was filtered, the filtrate evaporated in vacuo and the residue distilled to yield 26 g of pure benzoyloxyacetaldehyde, boiling point 92-94°C/0.25 mm.
2-Benzoyloxymethyl-5-ethoxy-1,3-oxathiolane:
The mercaptoacetaldehyde diethylacetal (7 g) was mixed in 100 ml of toluene with 7 g of the above benzoyloxyacetaldehyde, a few crystals of ptoluenesulfonic acid added and the mixture place in an oil-bath at 120°C under N2. The formed ethanol was allowed to distill over, the mixture kept at 120°C for 30 min longer than cooled and washed with aqueous NaHCO3, dried and evaporated in vacuo. The residue was distilled in vacuo to yield 9.8 g of 2-benzoyloxymethyl-5-ethoxy-1,3-oxathiolane as a mixture of cis- and transisomers, boiling point 140-143°C/0.1 mm.
Cis- and trans-2-benzoyloxymethyl-5-cytosin-1'-yl-1,3-oxathiolane:
A mixture of 2.7 g of cytosine, 30 ml of hexamethyldisilazane (HMDS) and 0.3 ml of trimethylsilyl chloride (TMSCl) was heated under reflux under dry N2 untila clear solution resulted (3 L) and the excess reagents evaporated in vacuo. The remaining volatiles were removed under high vacuum, the solid residue taken up in 250 ml of dichlorethane and 5 g of the 2-benzoyloxymethyl-5-ethoxy-1,3-oxathiolane in 50 ml of dichloroethane added under dry argon followed by 4.7 ml of trimethylsilyl triflate. After 3 days of heating under reflux under argon, it was cooled and poured onto 300 ml of saturated aqueous NaHCO3. The organic layer was collected, the aqueous phase extracted with CH2Cl2and the combined extracts washed with water, dried and evaporated in vacuo. The residue was purified by chromatography on silica gel using CH2Cl2-CH3OH 9:1 as the eluant to give 2.5 g of a pure mixture of cis- and trans-2-benzoyloxymethyl-5-cytosin-1'-yl-1,3-oxathiolane in a 1:1 ratio. These were separated as the N-acetyl derivatives.
The preceding mixture of cis- and trans-2-benzoyloxymethyl-5-cytosin-1'-yl- 1,3-oxathiolane (2.5 g) in 100 ml of dry pyridine containing 0.1 g of 4- dimethylaminopyridine (DMAP) was treated with acetic anhydride (7 ml) at room temperature and after 16 h, the mixture was poured onto cold water followed by extraction with CH2Cl2. The extract was washed with water, dried, and evaporated in vacuo. Toluene was added to the residue, then evaporated in vacuo and the residual oil purified by chromatography on silica gel using EtOAc-CH3OH 99:1 as the eluant to yield 1.35 g of pure trans-2- benzoyloxymethyl-5-(N4-acetyl-cytosin-1'-yl)-1,3-oxathiolaneas the fast moving product and 1.20 g of pure cis-2-benzoyloxymethyl-5-cytosin-1'-yl- 1,3-oxathiolan as the slow moving component, melting point 158-160°C.
Cis- and trans-isomers of 2-hydroxymethyl-5-(cytosin-1'-yl)-1,3-oxathiolane was obtained by action of methanolic ammonia at 24°C.

brand name

Epivir (GlaxoSmithKline).

Therapeutic Function

Antiviral

獲得抵抗性

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.

一般的な説明

Lamivudine is a nucleoside analogue and reverse transcriptase inhibitor used in the therapy of human immunodeficiency virus (HIV) and hepatitis B virus (HBV) infection. Lamivudine is a very rare cause of clinically apparent drug induced liver injury, but is associated with flares of underlying hepatitis B during therapy or with abrupt withdrawal. Lamivudine (formerly known as 3TC) in combination with zidovudine is indicated for the treatment of HIV infection in patients who experience disease progression as evidenced by clinical and/or immunological test.

一般的な説明

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.

応用例(製薬)

An analog of cytidine available for oral administration.

Biochem/physiol Actions

Lamivudine is a potent nucleoside analog reverse transcriptase inhibitor (nRTI). It is an analogue of cytidine, and can inhibit both types (1 and 2) of HIV reverse transcriptase as well as the reverse transcriptase of hepatitis B. It needs to be phosphorylated to its triphosphate form before it is active. 3TC-triphosphate also inhibits cellular DNA polymerase.

薬物動態学

Lamivudine is rapidly absorbed after oral consumption. Fasted and non-fasted states do not interfere with lamivudine absorption; therefore, lamivudine can be administered with or without food. Binding of lamivudine to plasma proteins is <36%. The primary route of excretion is in the urine. The mean elimination half-life ranges from 5 to 7 hours. Decreased renal function increases the mean elimination half-life of lamivudine. Pharmokinetics effects of impaired renal function in pediatric patients are not known. Pharmokinetic properties of lamivudine have not been studied with respect to race, gender, or geriatrics.

薬物動態学

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%
Absorption
It is rapidly absorbed and there is no significant difference in bioavailability when taken with food.
Distribution
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.

臨床応用

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.

副作用

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.

ラミブジン 上流と下流の製品情報

原材料

準備製品


ラミブジン 生産企業

Global( 502)Suppliers
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134678-17-4(ラミブジン)キーワード:


  • 134678-17-4
  • 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
  • LaMivudine-13C-d2
  • 3TC/Epivir-HBV
  • 4-AMino-1-((2R,5S)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl)pyriMidin-2(1H)-one
  • cis-Lamivudine
  • (-)-BCH-189
  • (-)-BETA-L-2',3'-DIDEOXY-3'-THIACYTIDINE
  • 2''-DEOXY-3''-THIACYTIDINE (LAMIVUDINE)
  • (-)-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
  • 4-aMino-1-[(2R,5S)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyriMidin-2-one
  • Lamivudine CAS 134678-17-4
  • Lamivudine, 98%, a potent nucleoside analog reverse transcriptase inhibitor
  • Lamivudine HCl
  • 4-amino-1-[(2R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2-pyrimidinone
  • LAMIVUDINE (BCH-189)
  • (-)-B-L-2',3'-DIDEOXY-3'-THIACYTIDINE
  • ラミブジン
  • 1-[(2S,5R)-2-ヒドロキシメチル-1,3-オキサチオラン-5-イル]シトシン
  • 1-[(2S)-2α-(ヒドロキシメチル)-1,3-オキサチオラン-5α-イル]-4-アミノピリミジン-2(1H)-オン
  • 2',3'-ジデオキシ-3'-チアシチジン
  • 1-[2α-(ヒドロキシメチル)-1,3-オキサチオラン-5α-イル]シトシン
  • (+)-1-[(2S,5R)-2-(ヒドロキシメチル)-1,3-オキサチオラン-5-イル]シトシン
  • 1-[(2S,5R)-2-(ヒドロキシメチル)-1,3-オキサチオラン-5-イル]シトシン
  • 1-[2α-(ヒドロキシメチル)-1,3-オキサチオラン-5α-イル]-4-アミノピリミジン-2(1H)-オン
  • 4-アミノ-1-[(2S)-2α-(ヒドロキシメチル)-1,3-オキサチオラン-5α-イル]ピリミジン-2(1H)-オン
  • (-)-1-[(2R,5S)-2-(ヒドロキシメチル)-1,3-オキサチオラン-5-イル]シトシン
  • ラミブジン (JAN)
  • 生化学
  • 試験研究用抗ウィルス剤
  • 試験研究用抗菌剤
  • 薬理研究用試薬
  • ヌクレオシド,ヌクレオチド&関連試薬
  • ヌクレオシドと類似体
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