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Zidovudine

Zidovudine
Zidovudine structure
CAS No.
30516-87-1
Chemical Name:
Zidovudine
Synonyms
ZDV;ZVD;AZT;fuseng;Timazid;bwa509u;Azitidin;BE-AS09U;bw-a509u;retrovir
CBNumber:
CB1354971
Molecular Formula:
C10H13N5O5
Formula Weight:
283.24
MOL File:
30516-87-1.mol

Zidovudine 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)
Flash point:
9℃
storage temp. 
2-8°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)
FDA UNII
4B9XT59T7S
NCI Dictionary of Cancer Terms
AZT; zidovudine
NCI Drug Dictionary
Retrovir
Proposition 65 List
Zidovudine (AZT)
IARC
2B (Vol. 76) 2000
EPA Substance Registry System
Thymidine, 3'-azido-3'-deoxy- (30516-87-1)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS02,GHS06,GHS08
Signal word  Danger
Hazard statements  H303-H225-H301+H311+H331-H370-H351
Precautionary statements  P210-P260-P280-P301+P310-P311-P281-P501a-P201-P202-P308+P313-P405-P501
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
10
Hazard Note  Harmful
HS Code  29349990
Toxicity LD50 in male, female mice, male, female rats (mg/kg): 3568, 3062, 3084, 3683 orally; >750 i.v. (all species) (Ayers)

Zidovudine price More Price(22)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich Z-011 Zidovudine solution 1.0?mg/mL in methanol, certified reference material, Cerilliant? 30516-87-1 1 mL $58.6 2021-03-22 Buy
Sigma-Aldrich Z1900000 Zidovudine European Pharmacopoeia (EP) Reference Standard 30516-87-1 $190 2021-03-22 Buy
Sigma-Aldrich BP895 Zidovudine impurity standard British Pharmacopoeia (BP) Reference Standard 30516-87-1 $203 2021-03-22 Buy
Sigma-Aldrich BP803 Zidovudine British Pharmacopoeia (BP) Reference Standard 30516-87-1 $220 2021-03-22 Buy
Sigma-Aldrich 1724500 Zidovudine United States Pharmacopeia (USP) Reference Standard 30516-87-1 400mg $366 2021-03-22 Buy

Zidovudine Chemical Properties,Uses,Production

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

Uses

Zidovudine is an antiretroviral drug that is clinically active against HIV-1 and is intended to treat HIV-infected patients. Zidovudine is an analog of thymidine that inhibits replication of the AIDS virus. It also turned into mono-, di-, and triphosphates by the same cellular enzymes that catalyze phosphorylation of thymidine and thymidine nucleosides. Zidovudine-triphosphate is then included in the terminal fragment of the growing chain of viral DNA by viral reverse transcriptase, thus causing the viral DNA chain to break apart in cells infected with the virus.
Zidovudine has been authorized for treating patients with AIDS. It significantly prolongs the life of the patient, although it has a number of toxic effects. Synonyms of this drug are azidothymidine and retrovir.

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.

Manufacturing Process

Preparation of 2,3'-anhydrothymidine
Thymidine (85.4 g; 0.353 mol) was dissolved in 500 mL dry DMF (dimethyl formamide) and added to N-(2-chloro-1,1,2-trifluoroethyl)diethylamine (100.3 g; 0.529 mol) [prepared according to the method of D. E. Ayer, J. Med. Chem. 6, 608 (1963)]. This solution was heated at 70°C for 30 minutes then poured into 950 mL ethanol with vigorous stirring. The product precipitated from this solution and was filtered. The ethanol supernatant was refrigerated then filtered to yield a total of 47.75 g (0.213 mol; 60.3%) of 2,3'- anhydrothymidine; melting point 228°-230°C.
Preparation for 3'-azido-3'-deoxythymidine
2,3'-Anhydrothymidine (25 g; 0.1115 mol) and NaN 3 (29 g; 0.446 mol) was suspended in a mixture of 250 mL DMF and 38 mL H 2 O. The reaction was refluxed for 5 hours at which time it was poured into 1 liter of H 2 O. This aqueous solution was extracted with ethyl acetate (EtOAc) (3x700 ml). The EtOAc was dried over Na 2 SO 4 , filtered, and then EtOAc was removed in vacuo to yield a viscous oil. This oil was stirred with 200 mL water resulting in a solid, 3'-azido-3'-deoxythymidine, 9.15 g (0.0342 mol); 30.7%; melting point 116°-118°C.

brand name

Retrovir (GlaxoSmithKline).

Therapeutic Function

Antiviral, Antineoplastic

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.

Mechanism of action

Zidovudine (AZT , ZDV) is an analogue of thymidine in which the azido group is substituted at the 3-carbon atom of the dideoxyribose moiety. It is active against RNA tumor viruses (retroviruses) that are the causative agents of AIDS and T-cell leukemia. Retroviruses, by virtue of RT, direct the synthesis of a provirus (DNA copy of a viral RNA genome). Proviral DNA integrates into the normal cell DNA, leading to the HIV infection. Zidovudine is converted to 5′-mono-, di-, and triphosphates by the cellular thymidine kinase. These phosphates are then incorporated into proviral DNA, because RT uses ZDV-triphosphate as a substrate. This process prevents normal 5′,3′-phosphodiester bonding, resulting in termination of DNA chain elongation because of the presence of an azido group in ZDV. The multiplication of HIV is halted by selective inhibition of RT and, thus, viral DNA polymerase by ZDV-triphosphate at the required dose concentration. Zidovudine is a potent inhibitor of HIV-1, but it also inhibits HIV-2 and EBV.

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.

Chemical Synthesis

Zidovudine is 3-azido-3-deoxytimidine (36.1.26), is synthesized from 1-(2-deoxy-5-O-trityl-β-D-lyxosyl)thymine, which is treated with methansulfonyl chloride in pyridine to make the corresponding mesylate 36.1.24. Replacing the methyl group with an azide group using lithium azide in dimethylformamaide makes the product 36.1.25 with inverted configuration at C3 of the furanosyl ring. Heating this in 80% acetic acid removes the trityl protection, giving zidovudine.

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

Preparation Products


Zidovudine Suppliers

Global( 433)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Wuhan Boye Science And Technology Development Co., Ltd.
15387090420 86-27-81625225
86-27-81625225 sumihu@boyechemicals.com CHINA 203 58
Frapp's ChemicalNFTZ Co., Ltd.
+86 (576) 8169-6106
+86 (576) 8169-6105 sales@frappschem.com China 886 50
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 21032 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26734 60
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3623 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29961 58
Shaanxi Yikanglong Biotechnology Co., Ltd.
17791478691
yklbiotech@163.com CHINA 297 58
Shenzhen Nexconn Pharmatechs Ltd
15013857715
admin@nexconn.com CHINA 3004 58

View Lastest Price from Zidovudine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-10-20 Zidovudine
30516-87-1
US $10.00 / KG 1KG 99% 20 tons Wuhan wingroup Pharmaceutical Co., Ltd
2021-10-20 Zidovudine
30516-87-1
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-10-15 Zidovudine
30516-87-1
US $0.00 / Kg/Bag 1Kg/Bag 99% 20tons Wuhan Boye Science And Technology Development Co., Ltd.

Zidovudine Spectrum


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