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Zidovudine

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Name

Zidovudine

EINECS 623-849-4
CAS No. 30516-87-1 Density 1.3382 (rough estimate)
PSA 134.07000 LogP -0.74354
Solubility 1-5 g/100 mL at 17 °C in water Melting Point 106-112 °C
Formula C10H13N5O4 Boiling Point 410.43°C (rough estimate)
Molecular Weight 267.244 Flash Point 9℃
Transport Information N/A Appearance Off -white crystalline powder
Safety 36/37/39-45-36-26 Risk Codes 40-36/37/38-20/21/22
Molecular Structure Molecular Structure of 30516-87-1 (Zidovudine) Hazard Symbols HarmfulXn
Synonyms

3-Azido-3-deoxythymidine;3'-Azido-3'-deoxythymidine;3'-Azidothymidine;3'-Deoxy-3'-azidothymidine;AZT;AZT (pharmaceutical);Azidothymidine;Azitidin;BW-A 509U;Compound S;NSC602670;Retrovir;Retrovir IV;Retrovis;Timazid;Viro-Z;ZDV;ZVD;Zido-H;

Article Data 72

Zidovudine Synthetic route

106060-78-0

3'-azido-5'-O-benzoyl-3'-deoxythymidine

30516-87-1

3'-azido-2',3'-deoxythymidine

Conditions
ConditionsYield
With sodium methylate In methanol for 24h; Ambient temperature;95%
With ammonia In methanol at 20℃;81%
With sodium methylate In methanol71%
With ammonia In methanol
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

30516-87-1

3'-azido-2',3'-deoxythymidine

Conditions
ConditionsYield
With silica gel; trifluoroacetic acid In methanol; chloroform95%
With hydrogenchloride In methanol; water at 20℃; for 3h;95%
With hydrogenchloride In acetic acid at 20℃; for 2h;49%
With sodium periodate In acetone at 50℃; for 20h;
134077-32-0

3'-Azido-5'-O-(4-methoxybenzoyl)-3'-deoxythymidine

30516-87-1

3'-azido-2',3'-deoxythymidine

Conditions
ConditionsYield
With sodium methylate In methanol for 12h; Ambient temperature;94%
With sodium methylate In methanol
162404-30-0

AZT guanidine salt

30516-87-1

3'-azido-2',3'-deoxythymidine

Conditions
ConditionsYield
With hydrogenchloride In water at 75℃; Large scale reaction;88.5%
126441-74-5

3’-azido-5’-O-(4,4’-dimethoxytrityl)-3’-deoxythymidine

30516-87-1

3'-azido-2',3'-deoxythymidine

Conditions
ConditionsYield
In methanol; tetrachloromethane at 25 - 40℃; for 12h; ultrasonic;87%

3'-azido-3'-deoxy-5'-O-pivaloylthymidine

30516-87-1

3'-azido-2',3'-deoxythymidine

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 1h;86%
52450-18-7

3'-amino-3'-deoxythymidine

30516-87-1

3'-azido-2',3'-deoxythymidine

Conditions
ConditionsYield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 4h;83%
15981-92-7

2,3'-anhydrothymidine

30516-87-1

3'-azido-2',3'-deoxythymidine

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide for 3h; Heating;71%
15981-92-7

2,3'-anhydrothymidine

A

30516-87-1

3'-azido-2',3'-deoxythymidine

B

3-(3-azido-2,3-dideoxy-β-D-ribofuranosyl)thymine

Conditions
ConditionsYield
With lithium azide In N,N-dimethyl-formamide at 110℃; for 24h;A 56%
B n/a
With lithium azide In N,N-dimethyl-formamide at 110℃; for 24h; Title compound not separated from byproducts;

1-[(4S,5S)-4-Azido-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

A

30516-87-1

3'-azido-2',3'-deoxythymidine

B

66323-40-8

alpha-3'-azido-2',3'-dideoxythymidine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.5h; Ambient temperature;A 31%
B 45%
With tetrabutyl ammonium fluoride In tetrahydrofuran Yield given. Yields of byproduct given;
With tetrabutyl ammonium fluoride In tetrahydrofuran Yield given;
With tetrabutyl ammonium fluoride In tetrahydrofuran

Zidovudine History

   Usage of Zidovudine  was major breakthrough in AIDS therapy in the 1990s that significantly altered the course of the illness and helped destroy the notion of the 1980s and early 90s that HIV/AIDS was an instant death sentence.
  Jerome Horwitz of Barbara Ann Karmanos Cancer Institute and Wayne State University School of Medicine first synthesized Zidovudine in 1964, under a US National Institutes of Health (NIH) grant. Zidovudine was originally intended as an anticancer drug, but was shelved after it proved insufficiently toxic to cancer tumours in mice.

Zidovudine Specification

The IUPAC name of Zidovudine is 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione. With the CAS registry number 30516-87-1, it is also named as 1-(3-Azido-2,3-dideoxy-beta-D-ribofuranosyl)-5-methylpyrimidine-2,4-(1H,3H)-dione. It is off -white crystalline powder which is a dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. When burns, it will produce toxic nitrogen oxide fumes. Additionally, this chemical should be sealed in the container and stored at -20 °C.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.53; (4)ACD/LogD (pH 7.4): -0.53; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12.29; (8)ACD/KOC (pH 7.4): 12.12; (9)#H bond acceptors: 9; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 71.44 Å2; (13)Rotatable Bond Count: 3; (14)Tautomer: Count 3; (15)Exact Mass: 267.096754; (16)MonoIsotopic Mass: 267.096754; (17)Topological Polar Surface Area: 93.2; (18)Heavy Atom Count: 19; (19)Complexity: 484; (20)Defined Atom StereoCenter Count: 3.

Preparation of Zidovudine: It can be obtained by thymidine, triphenylphosphine, p-methoxybenzo and Diethyl azodicarboxylate.


Uses of Zidovudine: It is a type of antiretroviral drug used for the treatment of HIV/AIDS. Its use was a major breakthrough in AIDS therapy in the 1990s that significantly altered the course of the illness and helped destroy the notion that HIV/AIDS was a death sentence. This drug is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Chronic, high-dose therapy with Zidovudine is associated with significant side effects, including anemia, neutropenia, hepatotoxicity, cardiomyopathy, and myopathy.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. It also has limited evidence of a carcinogenic effect. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure. 
1. Smiles:n1([C@H]2C[C@H](N=[N+]=[N-])[C@H](O2)CO)c([nH]c(=O)c(c1)C)=O
2. InChI:InChI=1/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man LDLo oral 86mg/kg/1W-I (86mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: HEADACHE
Lancet. Vol. 2, Pg. 1392, 1986.
man TDLo oral 434mg/kg/38D- (434mg/kg) BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

BLOOD: APLASTIC ANEMIA
Annals of Internal Medicine. Vol. 107, Pg. 502, 1987.
 
man TDLo unreported 69mg/kg (69mg/kg) SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE" Annals of Internal Medicine. Vol. 114, Pg. 297, 1991.
mouse LD50 intravenous > 70mg/kg (70mg/kg)   United States Patent Document. Vol. #4804651,
mouse LD50 oral 3062mg/kg (3062mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Fundamental and Applied Toxicology. Vol. 32, Pg. 129, 1996.
mouse LD50 unreported > 750mg/kg (750mg/kg)   United States Patent Document. Vol. #4857511,
rat LD50 intravenous > 70mg/kg (70mg/kg)   United States Patent Document. Vol. #4804651,
rat LD50 oral 3084mg/kg (3084mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Fundamental and Applied Toxicology. Vol. 32, Pg. 129, 1996.
rat LD50 unreported > 750mg/kg (750mg/kg)   United States Patent Document. Vol. #4857511,
women TDLo oral 1gm/kg/6W-I (1000mg/kg) SKIN AND APPENDAGES (SKIN): NAILS: OTHER Annals of Internal Medicine. Vol. 107, Pg. 350, 1987.

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