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  • 134678-17-4 , 拉米夫定, Lamivudine, CAS:134678-17-4
  • 134678-17-4 , 拉米夫定, Lamivudine, CAS:134678-17-4
134678-17-4 , 拉米夫定, Lamivudine, CAS:134678-17-4134678-17-4 , 拉米夫定, Lamivudine, CAS:134678-17-4

134678-17-4 , 拉米夫定, Lamivudine, CAS:134678-17-4

134678-17-4 , 拉米夫定,
Lamivudine,
CAS:134678-17-4
C8H11N3O3S / 229.26
MFCD00869739

拉米夫定, Lamivudine

Lamivudine (commonly called 3TC) is a potent nucleoside analogue reverse transcriptase inhibitor. It is one of the front line treatments for HIV.  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.

A reverse transcriptase inhibitor.

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Lamivudine is a synthetic nucleoside analog that shows potential action against human immunodeficiency virus (HIV). It is one of the front line therapies used to treat HIV infection.

Lamivudine is a synthetic nucleoside analogue with activity against hepatitis B virus (HBV) and HIV. Intracellularly, lamivudine is phosphorylated to its active metabolites, lamiduvine triphosphate (L-TP) and lamiduvine monophosphate (L-MP). In HIV, L-TP inhibits HIV-1 reverse transcriptase (RT) via DNA chain termination after incorporation of the nucleoside analogue into viral DNA. In HBV, incorporation of L-MP into viral DNA by HBV polymerase results in DNA chain termination. L-TP is a weak inhibitor of mammalian DNA polymerases alpha and beta, and mitochondrial DNA polymerase. (NCI04)

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, also known as epivir or 3TC, belongs to the class of organic compounds known as 3'-thia pyrimidine nucleosides. These are nucleoside analogues with a structure that consists of a pyrimidine base, which is N-substituted at the 1-position with a 3'-thia derivative (1, 3-oxazolidine) of the ribose moiety that is characteristic of nucleosides. Lamivudine is a drug which is used for the treatment of hiv infection and chronic hepatitis b (hbv). Lamivudine exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). Lamivudine has been detected in multiple biofluids, such as urine and blood. Within the cell, lamivudine is primarily located in the cytoplasm. Lamivudine participates in a number of enzymatic reactions. In particular, Lamivudine and uridine triphosphate can be biosynthesized from lamivudine-monophosphate and uridine 5'-diphosphate through its interaction with the enzyme 5'(3')-deoxyribonucleotidase, cytosolic type. In addition, Lamivudine can be converted into lamivudine sulfoxide; which is mediated by the enzyme sulfotransferase 1A1. In humans, lamivudine is involved in the lamivudine action pathway and the lamivudine metabolism pathway.

Title: Lamivudine

CAS Registry Number: 134678-17-4

CAS Name: (2R-cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone

Additional Names: (-)-2'-deoxy-3'-thiacytidine; (-)-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cystosine; 3'-thia-2',3'-dideoxycytidine; 3TC

Manufacturers' Codes: (-)-BCH-189; GR-109714X

Trademarks: Epivir (GSK); Zeffix (GSK)

Molecular Formula: C8H11N3O3S

Molecular Weight: 229.26

Percent Composition: C 41.91%, H 4.84%, N 18.33%, O 20.94%, S 13.99%

Literature References: Reverse transcriptase inhibitor. Prepn: J. A. V. Coates et al., WO 9117159 C.A. 117, 111989 (1991). Synthesis of enantiomers: J. W. Beach et al., J. Org. Chem. 57, 2217 (1992); of (-)-enantiomer: D. C. Humber et al., Tetrahedron Lett. 33, 4625 (1992). HPLC determn in urine: D. M. Morris, K. Selinger, J. Pharm. Biomed. Anal. 12, 255 (1994). Clinical trial in hepatitis B: F. Nevens et al., Gastroenterology 113, 1258 (1997). Review of pharmacology and clinical efficacy in HIV infection: C. M. Perry, D. Faulds, Drugs 53, 657-680 (1997).

Properties: Crystals from boiling ethanol. mp 160-162°. [a]D21 -135° (c = 0.38 in methanol). Soly in water (20°): ~70 mg/ml.

Melting point: mp 160-162°

Optical Rotation: [a]D21 -135° (c = 0.38 in methanol)

Therap-Cat: Antiviral.

Keywords: Antiviral; Purines/Pyrimidinones; Reverse Transcriptase Inhibitor.

CAS Number134678-17-4
Product NameLamivudine
IUPAC Name4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
Molecular FormulaC8H11N3O3S
Molecular Weight229.26 g/mol
InChIInChI=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)
InChI KeyJTEGQNOMFQHVDC-NKWVEPMBSA-N
SMILESC1C(OC(S1)CO)N2C=CC(=NC2=O)N
Solubility70 mg/ml
In water, 70,000 mg/L @ 20 °C
2.76e+00 g/L
Synonyms2',3' Dideoxy 3' thiacytidine, 2',3'-Dideoxy-3'-thiacytidine, 3TC, BCH 189, BCH-189, BCH189, Epivir, GR-109714X, GR109714X, Lamivudine, Lamivudine, (2S-cis)-Isomer
Canonical SMILESC1C(OC(S1)CO)N2C=CC(=NC2=O)N
Isomeric SMILESC1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N
CAS No: 134678-17-4 Synonyms: 3TC2',3'-Dideoxy-3'-thiacytidine(-)-BCH-189 MDL No: MFCD00869739 Chemical Formula: C8H11N3O3S Molecular Weight: 229.26

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