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Azidothymidine

Azidothymidine structure

CAS No:
30516-87-1
Formula:
C10H13N5O4
Chemical Name:
Azidothymidine
Synonyms:
Thymidine,3′-azido-3′-deoxy-;3′-Azido-3′-deoxythymidine;Azidothymidine;3′-Deoxy-3′-azidothymidine;AZT;BW-A 509U;AZT (pharmaceutical);Zidovudine;Retrovir;3′-Azidothymidine;NSC 602670;Azitidin;ZDV;Timazid;Retrovir IV;ZVD;3-Azido-3-deoxythymidine;Compound S;Viro-Z;Zido-H;Retrovis;3′-AZT;399024-19-2;1350915-89-7;1904592-23-9;2471391-52-1
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

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Description

Off White Crystalline Powder

Azidothymidine Basic Attributes

Molecular Weight：

283.24

Exact Mass：

267.097

EC Number：

1308068-626-2

HScode：

29349990

Characteristics

PSA：

93.2

XLogP3：

Appearance：

White to Off-white Powder

Density：

1.3382 (rough estimate)

Melting Point：

106-112 °C

Flash Point：

9℃

Refractive Index：

47 ° (C=1, H2O)

Water Solubility：

H2O: 1-5 g/100 mL at 17 ºC

Storage Conditions：

−20°C

Vapor Pressure：

5.2X10-20 mm Hg @ 25 deg C /Estimated/

Toxicity：

Intravenous-rat LD50: >750 mg/kg; Intravenous-mouse LD50: >750 mg/kg

Flammability characteristics：

Burning produces toxic nitrogen oxide fumes; patient side effects: aplastic anemia, headache, convulsive retinopathy, etc.

Specific rotation：

D25 +99° (c = 0.5 in water)

Odor：

Odorless

Safety Information

Transport codes：

UN1230 - class 3 - PG 2 - Methanol, solution

wgk germany：

hazard class code：

40-36/37/38-20/21/22

safety instructions：

36/37/39-45-36-26

RTECS Number：

XP2072000

Marks：

Storage features：

Ventilated, low temperature and dry

Hazard note：

Harmful

Stability/Shelf Life：

Bulk: AZT is stable, as the bulk, at 60 °C for at least 24 hr. AZT is stable indefinitely at room temperature (25 °C). Solution: AZT is stable in DMSO at 45 °C for at least 20 hr.

Precautionary statement(s)：

P201, P202, P260, P263, P264, P270, P281, P307+P311, P308+P313, P314, P321, P405, P501

Hazard Statements：

H341

Toxicity

Toxicity class：

moderately toxic

Azidothymidine Use and Manufacturing

Methods of Manufacturing

Thymine deoxyribonucleoside and triphenylphosphine are dissolved in dimethylformamide, slowly drop into a solution of p-methoxybenzoic acid and diethyl azodicarboxylate (DEAD) dissolved in dimethylformamide After stirring at room temperature, add triphenylphosphine and DEAD. After stirring the reaction, the reaction solution was poured into ether and left at 0°C overnight. The filtered solid was washed with a small amount of ether and dried to obtain an esterified oxygen bridge with a yield of 84.1%. The oxygen bridge and sodium azide were stirred in dimethylformamide at 125°C. Cool to room temperature, pour it into 5% hydrochloric acid, and extract with ethyl acetate. The extract was washed with 20% sodium chloride solution to neutrality, dried, concentrated, and dried in vacuum to obtain the azide derivative in 81.8% yield. The methanol solution of the azide derivative and sodium methoxide was stirred at room temperature and left overnight. Water was added, the solvent was distilled off under reduced pressure, and then water was added. It was extracted with ether, and saturated sodium chloride was added to the separated aqueous layer, which was left overnight. After cooling to 0°C and filtering, the filter cake was washed with a small amount of ethanol, dissolved in water, and acidified with dilute hydrochloric acid to Ph=2. The water was distilled off under reduced pressure, washed with 20% sodium chloride, and dried to obtain an off-white zidovudine solid with a yield of 89.0% and a melting point of 119.0-122.0°C.

Uses

A potent and selective inhibitor of HIV-1 replication

Computed Properties

Molecular Weight:267.24
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:267.09675391
Monoisotopic Mass:267.09675391
Topological Polar Surface Area:93.2
Heavy Atom Count:19
Complexity:484
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Ethyl acetate

Drug Function and Efficacy

Extract from the above information

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

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Registered Holders

HEC PHARM CO LTD

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