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Lamivudine(CAS No. 134678-17-4)

Lamivudine C8H11N3O3S (cas 134678-17-4) Molecular Structure

134678-17-4 Structure

Identification and Related Records

【Name】
Lamivudine
【CAS Registry number】
134678-17-4
【Synonyms】
2(1H)-Pyrimidinone,4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, (2R-cis)-
(-)-2'-Deoxy-3'-thiacytidine
(-)-BCH 189
3TC
BCH189, (-)-
Epivir
Epivir HBV
GR 109714X
Hepitec
Heptodin
Heptovir
L-SddC
Lamivir
Virolam
Zeffix
Zefix
b-L-2',3'-Dideoxy-3'-thiacytidine
【Molecular Formula】
C8H11N3O3S (Products with the same molecular formula)
【Molecular Weight】
229.25624
【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
【InChIKey】
JTEGQNOMFQHVDC-NKWVEPMBSA-N
【Canonical SMILES】
C1C(OC(S1)CO)N2C=CC(=NC2=O)N
【Isomers smiles】
C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N
【MOL File】
134678-17-4.mol

Chemical and Physical Properties

【Appearance】
White Crystalline Powder
【Density】
1.73g/cm3
【Melting Point】
177 °C
【Boiling Point】
475.4°C at 760mmHg
【Refractive Index】
-142 ° (C=1, MeOH)
【Flash Point】
241.3°C
【Water】
soluble
【Solubilities】
soluble
【Color/Form】
Crystals from boiling ethanol
【Storage temp】
Freezer
【Computed Properties】
Molecular Weight:229.25624 [g/mol]
Molecular Formula:C8H11N3O3S
XLogP3:-0.9
H-Bond Donor:2
H-Bond Acceptor:4
Rotatable Bond Count:2
Tautomer Count:3
Exact Mass:229.052112
MonoIsotopic Mass:229.052112
Topological Polar Surface Area:113
Heavy Atom Count:15
Formal Charge:0
Complexity:331
Isotope Atom Count:0
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Donor Count:3
Feature 3D Ring Count:2
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:12

Safety and Handling

【Safety】

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

【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
【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.
【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.

【Octanol/Water Partition Coefficient】
log Kow = -9.54 @ 25 deg C /Estimated/
【Disposal Methods】
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.

Use and Manufacturing

【Usage】

A reverse transcriptase inhibitor

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS.
- Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template.
【Therapeutic Uses】
Lamivudine is indicated in the treatment of chronic hepatitis B associated with evidence of hepatitis B viral replication and active liver inflammation. This use is based on 1-year histologic and serologic responses in patients with compensated chronic hepatitis B. /Included in US product labeling/
Lamivudine is indicated, in combination with zidovudine or other antiretroviral agents, in the treatment of HIV infection or AIDS when therapy is warranted based on clinical and/or immunological evidence of disease progression. /Included in US product labeling/
Lamivudine may be used prophylactically in health care workers at risk of acquiring HIV infection after occupational exposure to the virus. It is being used in combination with zidovudine and, in some cases, a protease inhibitor. /NOT included in US product labeling/
The safety, pharmacokinetics, and antiretroviral activity of lamivudine alone and in combination with zidovudine was studied in pregnant women infected with human immunodeficiency virus type 1 (HIV-1) and their neonates. Women received the drugs orally from week 38 of pregnancy to 1 week after delivery. Neonate therapy began 12 h after delivery and continued for 1 week. Both treatment regimens were well-tolerated in women and newborns. Lamivudine and zidovudine pharmacokinetics in pregnant women were similar to those in nonpregnant adults. Lamivudine and zidovudine freely crossed the placenta and were secreted in breast milk. Neonatal lamivudine clearance was about half that in pediatric patients; zidovudine clearance was consistent with previous reports. HIV-1 RNA could be quantified in 17 of the 20 women. At the onset of labor/delivery, mean virus load had decreased by approximately 1.5 log10 copies/mL in both treatment cohorts. Although not definitive for HIV-1 infection status, all neonates had HIV-1 RNA levels below the limit of quantification at birth and at ages 1 and 2 weeks. [Moodley J et al; J Infect Dis 178 (5): 1327-33 (1998)]
【Biomedical Effects and Toxicity】
Lamivudine crosses the placenta and has been detected in the fetal circulation.
Lamivudine has high oral bioavailability with or without food and reaches peak plasma levels within approximately 1 hour.

Supplier Location

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