Basic information
- CAS
30516-87-1- Standard SMILES
Cc1cn(C2CC(N=[N+]=[N-])C(CO)O2)c(=O)[nH]c1=O- InChIKey
HBOMLICNUCNMMY-UHFFFAOYSA-N- Molecular formula
- C10H13N5O4
- Average molar mass
- 267.24 g/mol
Overview
See also: Zidovudine (annotation moved to).
Names & identifiers
- Preferred name
- 1-[(2R,4R,5S)-4-Azido-5-(hydroxymethyl)oxolan-2-YL]-5-methyl-pyrimidine-2,4-dione
- IUPAC
- 1-[4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
- English name
- Zidovudine
- Molecular formula
- C10H13N5O5
- Molecular weight
- 283.24
Names & synonyms
Show more names
Database identifiers
- CAS
30516-87-1- PubChem CID
- 5726
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 93.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 484
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 113 · 113-115 °C (lit.)
- Boiling point
- 410.43 °C · 410.43°C (rough estimate)
- alpha
- 25 · D25 +99° (c = 0.5 in water)
- Density
- 1.3382 · 1.3382 (rough estimate)
- refractive index
- 47 ° · 47 ° (C=1, H2O)
- Flash point
- 9 ℃ · 9℃
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: 50 mg/mL
- form
- Powder
- pka
- 9.53 · pKa 9.53(H2O t = 25.0±0.1 I = 0.00) (Uncertain)
- color
- White to Off-white
- Water Solubility
- 1 · 1-5 g/100 mL at 17 ºC
- Sensitive
- Light Sensitive & Hygroscopic
- Merck
- 14 · 14,10123
- BRN
- 3595791 · 3595791
- BCS Class
- 1 · 1,3
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
- 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-BWZBUEFSSA-N
- SMILES
- CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O
- Toxicology and Carcinogenesis
- Toxicology and Carcinogenesis Studies of AZT (CASRN 30516-87-1) and AZT/ a-Interferon A/D in B6C3F1 Mice (Gavage Studies)Toxicology and Carcinogenesis Studies of Transplacental AZT (CASRN 30516-87-1) in Swiss (CD-1®) Mice (in utero Studies)Toxicology and Carcinogenesis Studies of Mixtures of 3'-Azido-3'-Deoxythymidine (AZT), Lamivudine (3TC), Nevirapine (NVP), and Nelfinavir Mesylate (NFV) (CASRNs 30516-87-1, 134678-17-4, 129618-40-2, 159989-65-8) in B6C3F1 Mice (Transplacental Exposure Studies)
- CAS DataBase Reference
- 30516 · 30516-87-1(CAS DataBase Reference)
- FDA UNII
- 4 B9XT59T7S · 4B9XT59T7S
- NCI Dictionary of Cancer Terms
- AZT; zidovudine
- NCI Drug Dictionary
- Retrovir
- ATC code
- 5 AF01 · J05AF01
- Proposition 65 List
- Zidovudine (AZT)
- IARC
- 2 B · 2B (Vol. 76) 2000
- EPA Substance Registry System
- 3 · Thymidine, 3'-azido-3'-deoxy- (30516-87-1)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Protein binding
- 34 · 34-38%
- Excreted unchanged in urine
- 8 · 8-25%
- Volume of distribution
- 1.6 · 1.6(L/kg)
- Biological half-life
- 1.1 · 1.1 / 1. 4-3
- Symbol(GHS)
- 2 · GHS02,GHS06,GHS08
- Signal word
- Danger
- Hazard statements
- 303 · H303-H225-H301+H311+H331-H370-H351
- Precautionary statements
- 210 · P210-P260-P280-P301+P310-P311-P281-P501a-P201-P202-P308+P313-P405-P501
- PPE
- 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- Xn
- Risk Statements
- 40 · 40-36/37/38-20/21/22
- Safety Statements
- 36 · 36/37/39-45-36-26
- RIDADR
- 1230 · UN1230 - class 3 - PG 2 - Methanol, solution
- WGK Germany
- 3 · 3
- RTECS
- 2072000 · XP2072000
- F
- 10 · 10
- Hazard Note
- Harmful
- HS Code
- 29349990 · 29349990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Muta · Carc. 2Muta. 2
- Hazardous Substances Data
- 30516 · 30516-87-1(Hazardous Substances Data)
- Toxicity
- 50 in · LD50 in male, female mice, male, female rats (mg/kg): 3568, 3062, 3084, 3683 orally; >750 i.v. (all species) (Ayers)
Safety & regulation
Safety data
- F
- 10
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- XP2072000
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- hs_code
- 29349990
- Toxicity
- LD50 in male, female mice, male, female rats (mg/kg): 3568, 3062, 3084, 3683 orally; >750 i.v. (all species) (Ayers)
- risk_code
- 40-36/37/38-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06,GHS08
- hazard_code
- Xn
- hazard_note
- Harmful
- safety_code
- 36/37/39-45-36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H303-H225-H301+H311+H331-H370-H351
- Hazard Classifications
- Carc. 2Muta. 2
- Precautionary statements
- P210-P260-P280-P301+P310-P311-P281-P501a-P201-P202-P308+P313-P405-P501
- Hazardous Substances Data
- 30516-87-1(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionZidovudine, also known as azidothymidine (AZT), is an antiviral agent acting via reverse transcnptase inhibition. It was first launched in the U.K. and subsequently introduced in over a dozen countries for the management of severe manifestations of HIV infection. In patients with AIDS and ARC, zidovudine reduces the risk of opportunistic infections and prolongs survival time. In symptom-free patients it shows promise in halting further immunological deterioration.
UsesA potent and selective inhibitor of HIV-1 replication
UsesZidovudine is an antiretroviral drug that is clinically active against HIV-1 and is intended to treat HIV-infected patients. Zidovudine is an analog of thymidine that inhibits replication of the AIDS virus. It also turned into mono-, di-, and triphosphates by the same cellular enzymes that catalyze phosphorylation of thymidine and thymidine nucleosides. Zidovudine-triphosphate is then included in the terminal fragment of the growing chain of viral DNA by viral reverse transcriptase, thus causing the viral DNA chain to break apart in cells infected with the virus. Zidovudine has been authorized for treating patients with AIDS. It significantly prolongs the life of the patient, although it has a number of toxic effects. Synonyms of this drug are azidothymidine and retrovir.
General DescriptionSlightly off-white odorless powdery solid.
General DescriptionZidovudine, 3'-azido-3'-deoxythymidine or AZT, is ananalog of thymidine that possesses antiviral activityagainst HIV-1, HIV-2, HTLV-1, and several other retroviruses.This nucleoside was synthesized in 1978 by Linand Prusoff as an intermediate in the preparation ofamino acid analogs of thymidine. A screening program directedtoward the identification of agents potentially effectivefor the treatment of patients with AIDS led to the discoveryof its unique antiviral properties 7 years later.Zidovudine is recommended for the management of adultpatients with symptomatic HIV infection (AIDS or ARC)who have a history of confirmed Pneumocystis carinii pneumoniaor an absolute CD4+(T4 or TH cell) lymphocytecount below 200/mm3 before therapy. The hematologicaltoxicity of the drug precludes its use in asymptomatic patients.Anemia and granulocytopenia are the most commontoxic effects associated with AZT.
General DescriptionZidovudine, or 3u-azido-3udeoxythymidine, formerly known as azidothymidine (AZT; BW A509U), is an analog of the nucleoside thymidine. It is an inhibitor of the human immunodeficiency virus (HIV)-encoded enzyme reverse transcriptase. It was the first antiretroviral compound to be licenced for the treatment of people infected with HIV. The compound was synthesized much earlier, however, by Horwitz and colleagues and subsequently used in anticancer research. Zidovudine was developed by Burroughs Wellcome and is now marketed by GlaxoSmithKline under the trade name of Retrovir. Zidovudine is also available in fixed-dose cominations with other nucleoside analog reverse transcriptase inhibitors as Combivir (zidovudine with lamivudine) and Trizivir (zidovudine with lamivudine and abacavir). Generic forms of the drug have been produced by a number of companies and include AVIRO-Z (Ranbaxy Laboratories Ltd) and Zidovir (Cipla Ltd). There are also a number of generic fixed-dose products including zidovudine with lamivudine (e.g. Duovir; Cipla Ltd). Zidovudine is indicated for the treatment and prevention of HIV infection, generally given in combination with other antiretroviral agents.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: Zidovudine is a pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase. It has a role as an antimetabolite, an antiviral drug and a HIV-1 reverse transcriptase inhibitor. It is an azide and a pyrimidine 2',3'-dideoxyribonucleoside.
Related reactions
Compound notes
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