Lamivudine

Iupac Name：4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one

Molecular Weight：229.26

Modify Date.: 2023-02-14 00:48

Introduction: 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 forpatients with HIV infection. Lamivudine is rapidly converted to phosphorylatedmetabolites in the body which act as inhibitors and chain terminators of HIV reversetranscriptase (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 isactive against AZT-resistant strains of HIV. Combination therapy of lamivudine and AZTproduced a large decrease in blood-borne virus with an increase in CD4 cells, an effectthat can be sustained for 2 years. Since hepatitis B virus (HBV) also encodes apolymerase with a RT function necessary for the conversion of a RNA replicativeintermediate to DNA, clinical efficacy has been reported for lamivudine in treatingpatients with HBV infection. It was reported that the enantiomer of lamivudine isequipotent against HIV but with considerably higher cytotoxicity. View more+

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1. Names and Identifiers

1.1 Name: Lamivudine
1.2 Synonyms: (-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cystosine (-)-1-[(2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine (-)-BCH-189 2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]- 2(1H)-Pyrimidinone, 4-amino-1-[(5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]- 2(1H)-Pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl], (-)(2R,5S) 2',3'-Dideoxy-3'-thiacytidine 3&L-SddC 3TC 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 4-AMino-1-[(2R,5S)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyriMidinone 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one 4-Amino-1-[(5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone cent cis-Lamivudine Epivir Hepitec Heptivir Heptodin Heptovir LaMivudine(Epivir) LaMivudine-13C-d2 MFCD00869739 Zeffix Zefix

1.3 CAS No.: 134678-17-4

1.4 CID: 60825

1.5 EINECS(EC#): 603-844-3

1.6 Molecular Formula: C8H11N3O3S (isomer)

1.7 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

1.8 InChkey: JTEGQNOMFQHVDC-NKWVEPMBSA-N

1.9 Canonical Smiles: C1C(OC(S1)CO)N2C=CC(=NC2=O)N

1.10 Isomers Smiles: C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N

2. Properties

2.1 Density: 1.73

2.1 Melting point: 177 °C

2.1 Boiling point: 475.4°C at 760mmHg

2.1 Refractive index: -142 ° (C=1, MeOH)

2.1 Flash Point: 9℃

2.1 Precise Quality: 229.05200

2.1 PSA: 115.67000

2.1 logP: -0.01290

2.1 Solubility: water: soluble10mg/mL, clear

2.2 AnalyticLaboratory Methods: Analyte: lamivudine;; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards

2.3 Appearance: white to beige

2.4 Chemical Properties: White Crystalline Powder

2.5 Color/Form: Powder

2.6 Physical: Solid

2.7 pKa: 13.83±0.10(Predicted)

2.8 Water Solubility: 70g/L(temperature not stated)

2.9 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: 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.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 107 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 107 companies. For more detailed information, please visit ECHA C&L website

Of the 9 notification(s) provided by 106 of 107 companies with hazard statement code(s):

H315 (22.64%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (22.64%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (22.64%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H361 (76.42%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H373 (33.02%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.3 Usage: Lamivudine is a potent nucleoside reverse transcriptase inhibitor. Antiviral. Lamivudine has been used for treatment of chronic hepatitis B.

4. Safety and Handling

4.1 Symbol: GHS08

4.1 Signal Word: Warning

4.1 Risk Statements: 63-36/37/38

4.1 Safety Statements: 26-36

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl lamivudine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

4.2 Octanol/Water Partition Coefficient: log Kow = -9.54 @ 25 deg C /Estimated/

4.3 Hazard Declaration: H361

4.3 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.4 RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution

4.4 Caution Statement: P281

4.4 Formulations/Preparations: Oral: Solution: 5 mg.ml, Epivir-HBV (with parabens and propylene glycol), GlaxoSmithKline; 10 mg/ml, Epivir (with alcohol 6% v/v, parabens, and propylene glycol), GlaxoSmithKline; Tablets, film coathed: 100 mg, Epivir-HBV, GlaxoSmithKline; 150 mg, Epivir, GlaxoSmithKline
Lamivudine combinations: Oral: Tablets, film-coated: 150 mg with Abacavir sulfate, Trizivir, GlaxoSmithKline, 300 mg (of abacavir) and zidovudine 300 mg, Trizivir, GlaxoSmithKline; 150 mg with zidovudine 300 mg, Combivir, GlaxoSmithKline

4.5 WGK Germany: 3

4.5 RTECS: UW7361333

4.5 Safety: RTECS: UW7361333
Hazardous Substances Data: 134678-17-4(Hazardous Substances Data)

4.6 Specification: ? Lamivudine ,?its cas register number is 134678-17-4. It also can be called?(-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine ; (-)-2'-Deoxy-3'-thiacytidine ; 3'-Thia-2',3'-dideoxycytidine ; 4-Amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinone ; Epivir ; Epivir-HBV ; GR 109714X ; HSDB 7155 ; Hepitec ;
?Heptovir ; Lamivudine ; UNII-2T8Q726O95 ; Zeffix ; beta-L-2',3'-Dideoxy-3'-thiacytidine ; beta-L-3'-Thia-2',3'-dideoxycytidine .?Lamivudine (CAS NO.134678-17-4) is a?white crystalline powder.

4.7 Toxicity: Oral Toxicity: Not expected to be toxic following ingestion.
Inhalation Toxicity: No studies have been conducted.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

134678-17-4Total: 19 Synthesis Route

147027-10-9 106 Suppliers

134678-17-4 416 Suppliers

Literatures:
Jin, Haolun; Siddiqui, Arshad; Evans, Colleen A.; Tse, H. L. Allan; Mansour, Tarek S.; et al. Journal of Organic Chemistry, 1995 , vol. 60, # 8 p. 2621 - 2623
Yield: ~92%

145985-97-3

134678-17-4 416 Suppliers

Literatures:
Beach; Jeong; Alves; Pohl; Kim; Chang; Doong; Schinazi; Cheng; Chu Journal of Organic Chemistry, 1992 , vol. 57, # 8 p. 2217 - 2219
Yield: ~75%

131086-21-0 6 Suppliers

134678-17-4 416 Suppliers

Literatures:
CHONG KUN DANG PHARMACEUTICAL CORP. Patent: WO2007/91753 A1, 2007 ; Location in patent: Page/Page column 14-15 ;
Yield: ~32%

View all

7. Precursor and Product

precursor:

1287791-56-3

173522-96-8

141434-39-1

143957-12-4

69-72-7

1321928-69-1

1235712-39-6

1091585-31-7

1022193-74-3

145985-97-3

1235712-37-4

139757-74-7

358348-70-6

1346921-53-6

147027-10-9

131086-21-0

View all

product :

173522-96-8

8. Other Information

8.0 Merck: 14,5352

8.1 New antiviral drug: Lamivudine is a new antiviral drug, belonging to nucleoside reverse transcriptase inhibitors, having a strong inhibitory effect in vitro and animal experimental infection of hepatitis B virus (HBV), can inhibit the synthesis of HIV virus; the drug produced by the GlaxoSmithKline Co. In the early 90s, they are used for the treatment of AIDS drugs in Europe and North American countries. In the middle of the 1990 medical experts found that they have inhibition to hepatitis B virus DNA, in 1998 the United States Food and Drug Administration (FDA) approved the first drug for treatment of hepatitis B treatment. In China, the State Food and Drug Administration approved the drug import mainly used as medicine in the treatment of hepatitis B, Chinese product name as "He Puding". In 1999, officially began on the mainland. Chinese sold after 10 years of clinical verification, lamivudine is the only proven to delay Hepatitis cirrhosis progress, fewer side effects, less cost of medication, currently has 2 million of the country's hepatitis B patients are using.
Lamivudine can be metabolized to lamivudine three phosphate in HBV infection cells and normal cells, it is the active form of lamivudine, both inhibitors of HBV polymerase, and is polymerase substrate. Lamivudine three phosphate incorporation into viral DNA chain, can block the synthesis of viral DNA, and does not interfere with normal cell deoxynucleoside metabolism, having weak inhibition to mammalian DNA polymerase alpha and beta, almost no effect on mammalian cell DNA content, and without obvious toxicity to the structure of mitochondria, content and function of DNA. For Serum HBV-DNA detection results of most hepatitis B patients showed that lamivudine can rapidly inhibit the replication of HBV, its inhibitory effect lasted for the entire treatment process. At the same time the serum transaminase decreased to normal, long-term use can significantly improve the liver necrosis and inflammatory changes in relieve or prevent liver fibrosis.

8.2 Methods of production: Select 6-o-sulfo acylation reaction to the compounds (I), then acetylated to obtaine compound (II), the yield was 96.7%. The compound (II) uses acetic acid as solvent, and 3 moL hydrogen bromide/L acid (45%, W/V) reaction, bromination to get compound (III), the yield was 99%. Bromide (III) and 3.3 moI ethyl potassium xanthate, refluxing in acetone, thio and cyclization; then in methanol with ammonia hydrolysis to obtain the compound (IV), the second step yield is 72%. Compounds (IV) is purified by column chromatography, is crystalline solid. Compound (IV) uses 1.4 mol sodium periodate treatment to make 2,3-CIS glycol open; followed by sodium borohydride reduction to aldehydes and shrinkage the keto form to protect the glycol, and obtain compound (V), the yield is 60%. The compound (V) silane to protect the rest of the primary alcohol, and then take off ketal to obtain compound (VI) and yield is 63%.Use lead tetraacetate to oxidize glycol of compounds (VI), and then to use dichromic acid pyridine salt to further oxidation, and obtain compound (VII), the oxidation method does not affect the sulfur. compounds (VII) is oxidized by using lead acetate to obtain compounds (VIII), the yield is 66%[ according to compounds (VI)]. Compounds (VIII) and (IX) are in the dichloroethane,and TMSOTf as a Lewis acid catalyst, condensated to compound (x), the yield is 64%. And the amount of isomers of compounds (x) is half of the compounds (x) and their available silica gel chromatography to isolate. Compounds (x) in ammonia-methanol and acetyl, the yield is 73% ; with Tetrabutylammonium fluoride solution to remove the silylation to obtain lamivudine and yield of 75%.

8.3 What kind of patients suitable for use Lamivudine: Not all patients with hepatitis B are suitable for the use of lamivudine. Lamivudine should be applied in the following cases according to the action characteristics of lamivudine and clinical summary of the experience in the application of lamivudine:
(1) HBVDNA quantitative detection of moderate positive; HBeAg positive; ALT increased 2~10 times.
(2) HBeAg negative, but HBVDNA was moderately positive (do not take the qualitative PCR results as the standard, to do quantitative measurement), ALT increased 2~10 times. The majority of this situation may be the virus gene mutations in the C region.
Not suitable for the use of lamivudine is the main:
(1) HBVDNA negative or quantitative determination of <105copies/ml;
(2)with normal ALT (mainly refers to the virus asymptomatic HBV carriers (ASC); for the past elevated ALT, but now ALT and AST normal patients, can be temporary not treatment, elevated ALT and treated. The patient was not suitable for use, not because lamivudine is harmful to the people, but because of the low effective rate of these patients, does not meet the pharmaceutical economics principle.
Lamivudine, like any other drugs, can be used properly to benefit most patients, and inappropriate use will not produce the desired effect, and inappropriate withdrawal may even lead to exacerbations.

8.4 Pharmacokinetics: After oral administration of lamivudine, it is well absorbed. And about 0.1 g of adult oral about 1hr reached peak plasma concentration Cmax 1.1-1.5 u g/ml, bioavailability is 80-85%. and at the same time of food taking, the Tmax delayed 0.25-2.5 HR and lower 10-40% of Cmax, but the bioavailability is unchanged. Intravenous administration research results table Ming lamivudine average distribution capacity is 1.3 L/Kg, system average clearance rate of 0.3 L/h/kg, seventy percent by organic cation transport system and renal clearance and elimination half-life is 5-7hr. within the therapeutic dose range and lamivudine pharmacokinetics showed a linear relationship, the plasma protein binding rate is low. In vitro studies have shown that with serum albumin binding rate is <16-36%. It can pass through the blood brain barrier into the cerebrospinal fluid. Mainly the prototype drug excretion by the kidneys, renal excretion accounted for about total removal of 70% or so, only 5-10% is metabolized into Anti sulfur oxide derivatives. For patients with renal insufficiency can affect lamivudine excretion, and for creatinine clearance rate <30mL/ points in patients, does not recommend the use of this product. Liver damage does not affect the metabolism of drugs, due to increased age and decreased renal excretory function in elderly patients, lamivudine metabolism without significant changes, Only in creatinine clear except rate <30mL/ time-sharing, there is influence.

8.5 drug withdrawal: Lamivudine is not hepatitis b curative drugs, can only make it better, and easy to rebound after discontinuation of lamivudine treatment. So how long is more appropriate, should according to the therapeutic effect and It differs from man to man. The most accepted standard of withdrawal is: before treatment, HBVDNA positive, HBeAg positive, ALT increased more than 1 times; treatment after HBVDNA seroconversion, HBeAg seroconversion ("big Sanyang" to "small Sanyang"), ALT normalization, maintain the effect of the above 6 months can be stopped. Of course in this standard withdrawal is not only without recurrence, the recurrence rate is low. It is reported that this group of patients discontinued 21 months still maintain curative effect. The recurrence rate of 81%. Asians is slightly higher, but in a year when the recurrence rate is lower than that of 40%. For example not up to this effect and withdrawal, while the majority of cases in a short period of time to recurrence, even some patients because of inappropriate drug withdrawal and lead to illness. So stoping the drug is a great event, I hope the patients in the decision to stop the medicine to go to the hospital to consult an experienced specialist, and not to stop the medicine.

8.6 New antiviral drug: Lamivudine is the (–) enantiomer of a cytidine analogue with sulfur substituted for the 3'carbon atom in the furanose ring [(–) 2',3'-dideoxy, 3'-thiacytidine]. It has significant activity in vitro against both HIV-1 and HIV-2 as well as HBV. Lamivudine is phosphorylated to the triphosphate metabolite by cellular kinases. The triphosphate derivative is a competitive inhibitor of the viral reverse transcriptase.

The oral bioavailability in adults is >80% for doses between 0.25 and 8.0 mg kg1. Peak serum concentrations of 1.5 mg ml 1 are achieved in 1–1.5 h and the plasma T1/2 is approximately 2–4 h. Lamivudine is eliminated by the kidneys unchanged by both glomerular filtration and tubular excretion, and dosages should be adapted to creatinine clearance.

8.7 Clinical indications: Lamivudine is effective as monotherapy for the treatment of chronic HBV infection and in combination with other antiretroviral drugs for treatment of HIV infection. It is the first line drug for the treatment of HBeAg and anti- HBe positive disease. Elevated serum ALT levels have been shown to predict a higher likelihood of HBeAg loss in patients with chronic hepatitis B treated with lamivudine. Lamivudine is administered orally at 100 mg day1 in the treatment of HBV infections, though the ideal dose could be higher.

8.8 Resistance: Resistance to lamivudine monotherapy develops within 6 months of therapy. The incidence of lamivudine resistance is 15–20% per year, with 70% patients becoming resistant after 5 years of treatment. It will be curious to know if lamivudine at higher doses will affect the incidence of resistance. Lamivudine resistance to HBV is conferred through HBV strains with mutations in the viral polymerase, within the catalytic domain (C domain), which includes the YMDD motif (e.g., M204V or M204I), and within the B domain (e.g., L180M or V173L). These mutants have a reduced replication capacity compared with the wild type HBV virus. Lamivudine resistance is managed by sequential treatment with either adefovir or entecavir. However, the advantage of sequen- tial treatment compared to de novo combination therapy is questionable.

8.9 Uses: Lamivudine is a potent nucleoside reverse transcriptase inhibitor. Antiviral. Lamivudine has been used for treatment of chronic hepatitis B.

8.10 Adverse effects: Lamivudine has an extremely favorable toxicity profile. This may be partly because lamivudine does not affect mitochondrial DNA synthesis and its poor inhibition of human DNA polymerases. At the highest doses of 20 mg kg-1 day-1, neutropenia is encountered but at a low frequency.

8.11 drug withdrawal: Lamivudine is not hepatitis b curative drugs, can only make it better, and easy to rebound after discontinuation of lamivudine treatment. So how long is more appropriate, should according to the therapeutic effect and It differs from man to man. The most accepted standard of withdrawal is: before treatment, HBVDNA positive, HBeAg positive, ALT increased more than 1 times; treatment after HBVDNA seroconversion, HBeAg seroconversion ("big Sanyang" to "small Sanyang"), ALT normalization, maintain the effect of the above 6 months can be stopped. Of course in this standard withdrawal is not only without recurrence, the recurrence rate is low. It is reported that this group of patients discontinued 21 months still maintain curative effect. The recurrence rate of 81%. Asians is slightly higher, but in a year when the recurrence rate is lower than that of 40%. For example not up to this effect and withdrawal, while the majority of cases in a short period of time to recurrence, even some patients because of inappropriate drug withdrawal and lead to illness. So stoping the drug is a great event, I hope the patients in the decision to stop the medicine to go to the hospital to consult an experienced specialist, and not to stop the medicine.

8.12 Disabling condition: 1.Chronic asymptomatic hepatitis B virus carriers were normal and no symptoms, whatever virus replication index or not (both "big Sanyang" and "small Sanyang"), are not taking lamivudine. But it is understood that at present this part of patients taking this medicine is a common phenomenon, which wasted drugs and money. At present the treatment of hepatitis B virus is not resolved, medical scientists is also exploring, the existing methods are not mature. The important reason of lamivudine in treatment of hepatitis B virus are invalid, someone after taking HBVDNA may drop to 103 copies/ml, once the withdrawal and we immediately rebound. We found that people taking more than half a year after discontinuation of HBVDNA negative, less than 1 months back, and HBeAg cannot be negative. Therefore, can't use this medicine to treat hepatitis B virus, unless the liver puncture biopsy confirmed chronic liver. The application can only be considered when the inflammatory pathological changes.
2. Acute severe hepatitis or acute liver failure are in critical condition, the ferocious. At this time the patient's main contradiction is not virus replication, some patients even without virus replication index, threatening the patient's life is liver failure, according to "the government ease the emergency treatment of the subject", then the most important is supportive therapy, such as the input of fresh plasma, albumin, artificial liver support therapy.
3. Acute exacerbation of chronic hepatitis B, if the transaminase is greater than the upper limit of the normal value of 10 times, there are obvious jaundice, or serum bilirubin than 85.5 mmol/L, temporarily not to take lamivudine and other antiviral drugs, and liver, jaundice and reducing enzyme treatment is given priority to, When remission can apply a small amount. Although lamivudine on immune function has strongly influenced not the same interferon but in the acute exacerbation of hepatitis, prevent damage on the immune system. No use is the best policy.
4. Chronic hepatitis B in pregnancy or pregnancy after HBV infection, do not use this product, the main reasons of the effect of lamivudine on the fetus are yet to be elucidated. As both at home and abroad, There are application reports and relatively safe, but experts in China has not yet reached a consensus, as a precaution, temporarily application is a wise choice.

8.13 Description: 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.

8.14 Description: 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.

8.15 Adverse reactions and side effects: Lamivudine is a kind of nucleoside drugs, by inhibiting or blocking synthesis of the hepatitis B virus DNA to restrain replication of hepatitis B virus, thus gradually clear hepatitis B virus, often are used by doctors to treat acute and chronic hepatitis B.
Common side effects are easy to produce drug resistance, side effects, withdrawal difficult, fever, upper respiratory tract infection symptoms, headache, abdominal pain, physical discomfort, diarrhea and other symptoms, but the symptoms are generally mild and in a short time the ego recede. At the same time the State Food and Drug Administration released Thirtieth phase drug adverse reaction information bulletin also alert our medical workers and drug producers wary of lamivudine and telbivudine may cause the risk of rhabdomyolysis, myalgia, weakness, elevated creatine kinase, blood creatinine rise higher.
Long-term use is easily virus mutates, more performance is after discontinuation of hepatitis B virus DNA positive rotation or is in a cycle of treatment occurs when the hepatitis B virus positive turn, this is the hallmark of virus mutates, indicating that more serious illness, more difficult to treat. Recent studies also suggest, the side effects of lamivudine is also reflected on the damage to the kidney, the majority of patients will have different degrees of renal toxicity, serious and even renal failure.

8.16 Disabling condition: 1.Chronic asymptomatic hepatitis B virus carriers were normal and no symptoms, whatever virus replication index or not (both "big Sanyang" and "small Sanyang"), are not taking lamivudine. But it is understood that at present this part of patients taking this medicine is a common phenomenon, which wasted drugs and money. At present the treatment of hepatitis B virus is not resolved, medical scientists is also exploring, the existing methods are not mature. The important reason of lamivudine in treatment of hepatitis B virus are invalid, someone after taking HBVDNA may drop to 103 copies/ml, once the withdrawal and we immediately rebound. We found that people taking more than half a year after discontinuation of HBVDNA negative, less than 1 months back, and HBeAg cannot be negative. Therefore, can't use this medicine to treat hepatitis B virus, unless the liver puncture biopsy confirmed chronic liver. The application can only be considered when the inflammatory pathological changes.
2. Acute severe hepatitis or acute liver failure are in critical condition, the ferocious. At this time the patient's main contradiction is not virus replication, some patients even without virus replication index, threatening the patient's life is liver failure, according to "the government ease the emergency treatment of the subject", then the most important is supportive therapy, such as the input of fresh plasma, albumin, artificial liver support therapy.
3. Acute exacerbation of chronic hepatitis B, if the transaminase is greater than the upper limit of the normal value of 10 times, there are obvious jaundice, or serum bilirubin than 85.5 mmol/L, temporarily not to take lamivudine and other antiviral drugs, and liver, jaundice and reducing enzyme treatment is given priority to, When remission can apply a small amount. Although lamivudine on immune function has strongly influenced not the same interferon but in the acute exacerbation of hepatitis, prevent damage on the immune system. No use is the best policy.
4. Chronic hepatitis B in pregnancy or pregnancy after HBV infection, do not use this product, the main reasons of the effect of lamivudine on the fetus are yet to be elucidated. As both at home and abroad, There are application reports and relatively safe, but experts in China has not yet reached a consensus, as a precaution, temporarily application is a wise choice.

8.17 Uses: 1. Antiviral drugs for hepatitis B.
2. Antiviral drugs for the treatment of liver and gallbladder diseases.
3. Medicine for liver and gallbladder diseases.

8.18 Chemical Properties: White Crystalline Powder

8.19 Uses: A reverse transcriptase inhibitor. Antiviral.

8.20 Definition: 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.

8.21 Brand name: Epivir (GlaxoSmithKline).

8.22 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.

8.23 Pharmaceutical Applications: An analog of cytidine available for oral administration.

8.24 Pharmaceutical Applications: 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.

8.25 Clinical Use: Therapy of chronic hepatitis B

8.26 Side effects: 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.

8.27 Originator: BioChem Pharma (Canada)

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

9. Computational chemical data

Molecular Weight: 229.26g/mol
Molecular Formula: C₈H₁₁N₃O₃S
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 229.05211239
Monoisotopic Mass: 229.05211239
Complexity: 331
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 113
Heavy Atom Count: 15
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBzMABAAAAAAAAAAAAAAAAAASAAAAAgAAAAAAAAAAAAAAAAHgQQCAAACADlwAaBAANABgioACJmdACAAAEAAhAIAAAYABCBEAAAAAAKAAAAFgIjAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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