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73971-82-1 , Zidovudine, Azitidine, CAS:73971-82-1

73971-82-1 , Zidovudine,
Azitidine,
CAS:73971-82-1
C10H13N5O4 / 267.24
MFCD00006536

Zidovudine, Azitidine,齐多夫定

3'-Azido-3'-deoxythymidine

AZT (threo), also known as Zidovudine (ZDV), is an antiretroviral medication used to prevent and treat HIV/AIDS. AZT inhibits the enzyme Reverse Transcriptase that HIV uses to make DNA. This effectively decreases viral replication.

Title: Zidovudine

CAS Registry Number: 73971-82-1

CAS Name: 3'-Azido-3'-deoxythymidine

Additional Names: azidothymidine; AZT

Manufacturers' Codes: BW-A509U

Trademarks: Retrovir (GSK)

Molecular Formula: C10H13N5O4

Molecular Weight: 267.24

Percent Composition: C 44.94%, H 4.90%, N 26.21%, O 23.95%

Literature References: Pyrimidine nucleoside analog; reverse transcriptase inhibitor. Prepn: J. P. Horwitz et al., J. Org. Chem. 29, 2076 (1964); R. P. Glinski et al., ibid. 38, 4299 (1973). See also: J. L. Rideout et al., US 4724232 (1988 to Burroughs Wellcome). Total synthesis: C. K. Chu et al., Tetrahedron Lett. 29, 5349 (1988). In vitro antiviral and antitumor activity: E. De Clercq et al., Biochem. Pharmacol. 29, 1849 (1980); vs HIV-1 virus: H. Mitsuya et al., Proc. Natl. Acad. Sci. USA 82, 7096 (1985). Clinical pharmacokinetics: R. W. Klecker et al., Clin. Pharmacol. Ther. 41, 407 (1987). Toxicology studies: K. M. Ayers, Am. J. Med. 85, Suppl. 2A, 186 (1988). Comprehensive description: M. L. Sethi, Anal. Profiles Drug Subs. 20, 729-765 (1991). Review of clinical experience: G. X. McLeod, S. M. Hammer, Ann. Intern. Med. 117, 487-501 (1992); in prevention of perinatal HIV transmission: R. Sperling, Infect. Dis. Obstet. Gynecol. 6, 197-203 (1998).

Properties: Needles from petr ether, mp 106-112° (Horwitz). Also reported as crystals from water, mp 120-122° (Glinski). [a]D25 +99° (c = 0.5 in water). Soly in water (25°C): 25 mg/ml. uv max (water): 266.5 nm (e 11650). LD50 in male, female mice, male, female rats (mg/kg): 3568, 3062, 3084, 3683 orally; >750 i.v. (all species) (Ayers).

Melting point: mp 106-112° (Horwitz); mp 120-122° (Glinski)

Optical Rotation: [a]D25 +99° (c = 0.5 in water)

Absorption maximum: uv max (water): 266.5 nm (e 11650)

Toxicity data: LD50 in male, female mice, male, female rats (mg/kg): 3568, 3062, 3084, 3683 orally; >750 i.v. (all species) (Ayers)

Therap-Cat: Antiviral.

Keywords: Antiviral; Purines/Pyrimidinones; Reverse Transcriptase Inhibitor.

CAS Number73971-82-1
Product NameAZT (threo)
IUPAC Name1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
Molecular FormulaC10H13N5O4
Molecular Weight267.24 g/mol
InChIInChI=1S/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-/m1/s1
InChI KeyHBOMLICNUCNMMY-BWZBUEFSSA-N
SMILESCC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)N=[N+]=[N-]
SolubilitySoluble in DMSO
Synonyms5-ethyl-1-aza-3,7-dioxabicyclo-3.3.0-octane, Bioban CS 1246, Bioban CS-1246, CS 1246, CS-1246, oxazolidine E
Canonical SMILESCC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)N=[N+]=[N-]
Isomeric SMILESCC1=CN(C(=O)NC1=O)[C@H]2C[C@H]([C@H](O2)CO)N=[N+]=[N-]
CAS No: 30516-87-1,73971-82-1 Synonyms: AZTZidovudineAzitidine3'-Azido-3'-deoxy-thymidine MDL No: MFCD00006536 Chemical Formula: C10H13N5O4 Molecular Weight: 267.24
References: 1. Mitsuya H, et al., Nature 325, p773, 1987


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