1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 119449
• Molecular Formular: C10H13N5O4
• Molecular Mass: 267.24132
• Monoisotopic Mass: 267.09675392
• SMILES: n1(c(=O)[nH]c(=O)c(c1)C)[C@@H]1O[C@@H]([C@H](C1)N=[N+]=[N-])CO
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1N=[N+]=[N-])n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=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+/m0/s1
• InChIKey: HBOMLICNUCNMMY-XLPZGREQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione; zidovudine
• Synonyms: 3'-Azido-3'-deoxythymidine; 3'-Azidothymidine; Apovir; Novo-AZT; Zidovir; Zidovudine; Zidovudine; Retrovis; Timazid; Retrovir; NSC 602670; 3'-Azido-3'-deoxythymidine; AZT; ZDV; 3′-Azido-3′-deoxythymidine; 1-((2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione; 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione; 叠氮胸苷; 齐多夫定; 3′-叠氮-3′-脱氧胸苷

Database IDs

• CAS Number: 30516-87-1
• MDL Number: MFCD00006536
• Beilstein Number: 3595791
• PubChem SID: 24278143; 162103188
• PubChem CID: 35370

CALCULATED PROPERTIES

• Acid pKa: 9.960416
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.41276968
• LogD (pH = 7.4): -0.41393453
• Log P: -0.29870915
• Molar Refractivity: 61.7045 cm^3
• Polarizability: 23.694994 Å^3
• Polar Surface Area: 108.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble50 mg/mL; Methanol
• Apperance: White to Off White Solid
• Melting Point: 113-115 °C(lit.); 118-120°C; 122 - 124°C
• Hydrophobicity(logP): 0.044

Safety Information

• Storage Condition: Refrigerator
• RTECS: XP2072000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... HIVE1(3095)mouse ... Slc29a1(63959)
• Mechanism of Action: Nucleoside transporter substrate; Reverse Transcriptase Inhibitor

Product Information

• Purity: ≥98% (HPLC); 95%
• Application(s): Antiviral agent active exclusively against retroviruses, esp. AIDS virus and leukaemias; Drugs of choice for AIDS treatment

DETAILS

Sigma Aldrich - A2169

Biochem/physiol Actions
对 HIV-1 病毒有效的逆转录酶抑制剂。
包装
1 g in glass bottle
100, 250 mg in glass bottle
25 mg in poly bottle

Toronto Research Chemicals - A825000

A potent and selective inhibitor of HIV-1 replication.

REFERENCES

• Mitsuya, H., et al.: Nature, 325, 773 (1987)
• Brehm, J., et al.: Biochem., 47, 14020 (1987)
• Paredes, R., et al.: J. Virol., 83, 2038 (1987)
• Wan, J., et al.: J. Med. Chem., 52, 1144 (1987)
• Mainardes, R., et al.: J. Pharm. Sci., 98, 257 (1987)
• 1. Mitsuya H, Yarchoan R, Broder S: Molecular targets for AIDS therapy. Science. 1990 Sep 28;249(4976):1533-44.
• 2. Mitsuya H, Weinhold KJ, Furman PA, St Clair MH, Lehrman SN, Gallo RC, Bolognesi D, Barry DW, Broder S: 3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and
• cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. Proc Natl Acad Sci U S A. 1985 Oct;82(20):7096-100.
• 3. Yarchoan R, Mitsuya H, Broder S: AIDS therapies. Sci Am. 1988 Oct;259(4):110-9.
• 4. De Clercq E: HIV resistance to reverse transcriptase inhibitors. Biochem Pharmacol. 1994 Jan 20;47(2):155-69.
• 5. Connor EM, Sperling RS, Gelber R, Kiselev P, Scott G, O'Sullivan MJ, VanDyke R, Bey M, Shearer W, Jacobson RL, et al.: Reduction of maternal-infant transmission
• of human immunodeficiency virus type 1 with zidovudine treatment. Pediatric AIDS Clinical Trials Group Protocol 076 Study Group. N Engl J Med. 1994 Nov 3;331(18):1173-80.