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Zidovudine Basic information
Product Name: Zidovudine
Synonyms: 1-(4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione;1-(4-azido-5-methylol-tetrahydrofuran-2-yl)-5-methyl-pyrimidine-2,4-quinone;1-[4-azido-5-(hydroxymethyl)-2-tetrahydrofuranyl]-5-methylpyrimidine-2,4-dione;1-[4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione;1-[4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione;1-[4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione;1-[4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione;3'-Deoxy-3'-azidothymi
CAS: 30516-87-1
MF: C10H13N5O5
MW: 283.24
EINECS: 623-849-4
Product Categories: Amino Acids;Miscellaneous Natural Products;Antivirals for Research and Experimental Use;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;API's;Antiviral;HIV/AIDS/Related Products;API;VIOCIN
Mol File: 30516-87-1.mol
Zidovudine Structure
Zidovudine Chemical Properties
Melting point  113-115 °C(lit.)
alpha  D25 +99° (c = 0.5 in water)
Boiling point  410.43°C (rough estimate)
density  1.3382 (rough estimate)
refractive index  47 ° (C=1, H2O)
Fp  9℃
storage temp.  −20°C
solubility  H2O: 50 mg/mL
pka pKa 9.53(H2O t = 25.0±0.1 I = 0.00) (Uncertain)
form  Powder
color  White to Off-white
Water Solubility  1-5 g/100 mL at 17 ºC
Sensitive  Light Sensitive & Hygroscopic
Merck  14,10123
BRN  3595791
InChIKey HBOMLICNUCNMMY-BWZBUEFSSA-N
CAS DataBase Reference 30516-87-1(CAS DataBase Reference)
EPA Substance Registry System Thymidine, 3'-azido-3'-deoxy- (30516-87-1)
Safety Information
Hazard Codes  Xn
Risk Statements  40-36/37/38-20/21/22
Safety Statements  36/37/39-45-36-26
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
RTECS  XP2072000
F  10
Hazard Note  Harmful
HS Code  29349990
Hazardous Substances Data 30516-87-1(Hazardous Substances Data)
Toxicity LD50 in male, female mice, male, female rats (mg/kg): 3568, 3062, 3084, 3683 orally; >750 i.v. (all species) (Ayers)
MSDS Information
Provider Language
3'-Azido-3'-deoxythymidine English
SigmaAldrich English
Zidovudine Usage And Synthesis
Description Zidovudine, also known as azidothymidine (AZT), is an antiviral agent acting via reverse transcnptase inhibition. It was first launched in the U.K. and subsequently introduced in over a dozen countries for the management of severe manifestations of HIV infection. In patients with AIDS and ARC, zidovudine reduces the risk of opportunistic infections and prolongs survival time. In symptom-free patients it shows promise in halting further immunological deterioration.
Chemical Properties Off White Crystalline Powder
Originator Detroit Inst. Cancer Res. (USA)
Uses A potent and selective inhibitor of HIV-1 replication
Uses antibacterial
Definition ChEBI: A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.
Indications Zidovudine was the first agent to be used to prevent the transmission of HIV from a pregnant woman to her child. It was given to the mother at 14 to 34 weeks’ gestation and to the child for the first 6 weeks of life. Current combination therapies employ zidovudine with another NRTI and a protease inhibitor.
Brand name Retrovir (GlaxoSmithKline).
Antimicrobial activity Zidovudine is active against HIV-1, HIV-2 and HTLV-1.
Acquired resistance As with stavudine, mutations at position 41, 67 and 70, and positions 210, 215 and 219 (the ‘thymidine analog mutations’) of the reverse transcriptase genes are associated with diminished antiretroviral efficacy.
General Description Slightly off-white odorless powdery solid.
General Description Zidovudine, 3'-azido-3'-deoxythymidine or AZT, is ananalog of thymidine that possesses antiviral activityagainst HIV-1, HIV-2, HTLV-1, and several other retroviruses.This nucleoside was synthesized in 1978 by Linand Prusoff as an intermediate in the preparation ofamino acid analogs of thymidine. A screening program directedtoward the identification of agents potentially effectivefor the treatment of patients with AIDS led to the discoveryof its unique antiviral properties 7 years later.
Zidovudine is recommended for the management of adultpatients with symptomatic HIV infection (AIDS or ARC)who have a history of confirmed Pneumocystis carinii pneumoniaor an absolute CD4+(T4 or TH cell) lymphocytecount below 200/mm3 before therapy. The hematologicaltoxicity of the drug precludes its use in asymptomatic patients.Anemia and granulocytopenia are the most commontoxic effects associated with AZT.
Air & Water Reactions Dust may form an explosive mixture in air. Water soluble. Hydrolysis occurs in strongly basic solutions .
Reactivity Profile Zidovudine is a azido compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.
Fire Hazard Flash point data for Zidovudine are not available; however, Zidovudine is probably combustible.
Pharmaceutical Applications An analog of thymidine formulated for oral or intravenous use.
Pharmacokinetics Oral absorption: 65%
Cmax 300 mg twice daily: 2.3 mg/L
Plasma half-life: 1.1 h
Volume of distribution: 1.6 L/kg
Plasma protein binding; 34–38%
Absorption and distribution
It is absorbed rapidly and almost completely following oral administration. Absorption is not significantly affected by food. It appears to undergo widespread body distribution. CNS penetration is fairly good. The semen:plasma ratio varies from 0.95 to 13.5 (mean 5.9). It is secreted into breast milk.
Metabolism and excretion
Following hepatic metabolism (glucuronidation), elimination is primarily renal. After oral administration, urinary recovery of zidovudine and its glucuronide metabolite accounted for 14% and 74% respectively of the dose, with a total urinary recovery of 90%.
In severe renal impairment, clearance was about half that reported in subjects with normal renal function Accumulation may occur in patients with hepatic impairment due to decreased glucuronidation.
Clinical Use Treatment of HIV infection in adults and children (in combination with other antiretroviral drugs)
Reduction of maternal transmission of HIV to the fetus
Side effects In common with other drugs in this class, use has been associated with episodes of fatal and non-fatal lactic acidosis and hepatomegaly with steatosis. Careful clinical evaluation is needed in patients with evidence of hepatic abnormality. Myelosuppression may occur within the first 4–6 weeks of therapy. Hematological parameters should be monitored during this period, with prompt dose modification or switch if abnormalities are observed. Treatment with reduced doses may be attempted in some patients once bone marrow recovery has been observed. Myopathy is rarely seen with the use of the current dosing regimens.
Co-administration with drugs known to cause nephrotoxicity, cytotoxicity or which interfere with red or white blood cell number and function may increase the risk of toxicity. Probenecid and trimethoprim may reduce renal clearance of zidovudine, and other drugs that are metabolized by glucuronidation may interfere with its metabolism.
Safety Profile Moderately toxic by intravenousroute. Human systemic effects by ingestion: aplasticanemia, changes in blood cell count, convulsions or effect on seizure threshold, headache, nails, retinal changes.Human mutation data reported.
Veterinary Drugs and Treatments In veterinary medicine, zidovudine may be useful for treating feline immunodeficiency virus (FIV) or feline leukemia virus (FeLV). While zidovudine can reduce the viral load in infected cats and improve clinical signs, it may not alter the natural course of the disease to a great extent.
Zidovudine Preparation Products And Raw materials
Raw materials Ethyl acetate-->Sodium azide-->Triphenylphosphine-->Formamide-->Anisic acid-->Diethyl azodicarboxylate-->Thymidine