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Basic information

  • Name:
  • Thymidine,3'-azido-3'-deoxy-

  • Superlist Name:
  • Zidovudine
  • CAS No.:
  • 30516-87-1

  • Formula:
  • C10H13N5O4
  • 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;
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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.

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-white crystalline powder which is a dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group.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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