CAS 30516-87-1|Zidovudine
Introduction：Basic information about CAS 30516-87-1|Zidovudine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Zidovudine | ||
|---|---|---|---|
| CAS Number | 30516-87-1 | Molecular Weight | 267.241 |
| Density | / | Boiling Point | / |
| Molecular Formula | C10H13N5O4 | Melting Point | 113-115 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | / |
| Symbol | GHS08 | Signal Word | Warning |
Names
| Name | zidovudine |
|---|---|
| Synonym | More Synonyms |
Zidovudine BiologicalActivity
| Description | Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI), widely used to treat HIV infection. Zidovudine increases CRISPR/Cas9-mediated editing frequency. |
|---|---|
| Related Catalog | Signaling Pathways >>Cell Cycle/DNA Damage >>CRISPR/Cas9Signaling Pathways >>Anti-infection >>HIVResearch Areas >>Infection |
| Target | HIV-1 CRISPR/Cas9 |
| In Vitro | Zidovudine inhibits SVG, Primary human fetal astrocytes (PFA), peripheral blood mononuclear cells (PBMC), and monocyte-derived macrophages (MDM) with EC50 of 17, 1311, 8, and 5 nM, respectively. Zidovudine inhibits SVG, PFA, PBMC, and MDM with EC90 of 0.205 μM, 44.157 μM, 0.481 μM, and 0.219 μM, respectively[1]. Genome editing via CRISPR/Cas9 has become an efficient and reliable way to make precise, targeted changes to the genome of living cells. CXCR4 is a co-receptor for the human immunodeficiency virus type 1 (HIV-1) infection and has been considered as an important therapeutic target for AIDS. CXCR4 mediates viral entry into human CD4+ cells by binding to envelope protein, gp120. Human CXCR4 gene is efficiently disrupted by CRISPR/Cas9-mediated genome editing, leading to HIV-1 resistance of human primary CD4+ T cells. The Cas9-mediated ablation of CXCR4 demonstrated high specificity and negligible off-target effects without affecting cell division and propagation[2]. |
| In Vivo | Intravitrous injection of the NRTIs Lamivudine (3TC), Zidovudine (AZT), or Abacavir (ABC) suppresses the laser-induced choroidal neovascularization (CNV) in wild-type mice compared to PBS vehicle. The mean level of VEGF-A in the RPE/choroid, which peaks on day 3 after laser injury, is significantly reduced in 3TC-, AZT- and ABC-treated eyes compared with control eyes in wild-type mice, but not inP2rx7-/- mice[3]. |
| Cell Assay | Assays are performed in all cell types in the presence of titrating concentrations of ARV. 5,000 SVG, 2,500 PFA, 200,000 PBMC, or 50,000 MDM cells/well are seeded into triplicate wells of 96-well plates. Twenty-four hours later, the culture medium is removed and replaced with medium containing the ARV or DMSO (0.5% vol/vol), and equivalent TCID50 infectious units of luciferase reporter virus are added to the cells. After a 16 h incubation at 37°C, the initial viral inoculum is removed and replaced with culture medium containing the same antiretroviral drug (ARV) or DMSO (0.5% vol/vol) concentrations. At 72 h post infection, the medium is aspirated, the cells are lysed and HIV-1 infection measured using the Luciferase Assay System. Luminescence is measured using a FLUOStar Optima microplate reader. Inhibition curves and the 50% (EC50) and 90% (EC90) effective concentrations are determined by nonlinear regression analysis, using GraphPad Prism software[1]. |
| Animal Admin | Mice[3] C57BL/6J (wild-type) and P2rx7-/- mice are used. The Nlrp3-/- mice are used. The NRTIs 3TC, AZT, and ABC or the P2X7 antagonist A438079 hydrochloride are dissolved in PBS. For CNV, each group of mice is injected once with 1 μL of NRTIs (3TC, 125 ng/μL; ABC, 183 ng/μL; AZT, 146 ng/μL), 1 μL of A438079 hydrochloride (3, 30, or 300 ng/μL), or the same volume of vehicle (PBS) into the vitreous humor using a 33-gauge needle immediately after laser injury. Another group of mice is injected with 3TC (125 ng) in combination with an anti-mouse VEGF polyclonal antibody (10 ng). Goat whole IgG (10 ng) is used as a biological control for the anti-mouse VEGF antibody. |
| References | [1]. Gray LR, et al. The NRTIs lamivudine, stavudine and zidovudine have reduced HIV-1 inhibitory activity in astrocytes. PLoS One. 2013 Apr 16;8(4):e62196. [2]. Hou P, et al. Genome editing of CXCR4 by CRISPR/cas9 confers cells resistant to HIV-1 infection. Sci Rep. 2015 Oct 20;5:15577. [3]. Mizutani T, et al. Nucleoside Reverse Transcriptase Inhibitors Suppress Laser-Induced Choroidal Neovascularization in Mice. Invest Ophthalmol Vis Sci. 2015 Nov;56(12):7122-9. |
Chemical & Physical Properties
| Melting Point | 113-115 °C(lit.) |
|---|---|
| Molecular Formula | C10H13N5O4 |
| Molecular Weight | 267.241 |
| Exact Mass | 267.096741 |
| PSA | 134.07000 |
| LogP | -0.53 |
| Index of Refraction | 47 ° (C=1, H2O) |
| InChIKey | HBOMLICNUCNMMY-XLPZGREQSA-N |
| SMILES | Cc1cn(C2CC(N=[N+]=[N-])C(CO)O2)c(=O)[nH]c1=O |
| Water Solubility | 1-5 g/100 mL at 17 ºC |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 1 gm/kg/6W-I
- TOXIC EFFECTS :
- Skin and Appendages - nails
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 86 mg/kg/1W-I
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Behavioral - headache
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 434 mg/kg/38D-I
- TOXIC EFFECTS :
- Blood - changes in cell count (unspecified) Blood - aplastic anemia Blood - changes in bone marrow (not otherwise specified)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 69 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - retinal changes (pigmentary depositions, retinitis, other)
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 3084 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity)
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >70 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >750 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 3062 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity)
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >70 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >750 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 54600 mg/kg/1Y-I
- TOXIC EFFECTS :
- Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 91 gm/kg/26W-I
- TOXIC EFFECTS :
- Blood - normocytic anemia
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 47 gm/kg/94D-I
- TOXIC EFFECTS :
- Blood - pigmented or nucleated red blood cells Blood - changes in bone marrow (not otherwise specified) Blood - changes in erythrocyte (RBC) count
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 4700 mg/kg/94D-I
- TOXIC EFFECTS :
- Blood - pigmented or nucleated red blood cells Blood - changes in bone marrow (not otherwise specified) Blood - changes in erythrocyte (RBC) count
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 14500 mg/kg/29D-I
- TOXIC EFFECTS :
- Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 6800 mg/kg/17D-I
- TOXIC EFFECTS :
- Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 7 gm/kg/2W-I
- TOXIC EFFECTS :
- Blood - leukopenia Blood - thrombocytopenia Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Primate - monkey
- DOSE/DURATION :
- 3094 mg/kg/13W-I
- TOXIC EFFECTS :
- Blood - normocytic anemia
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Primate - monkey
- DOSE/DURATION :
- 18200 mg/kg/26W-I
- TOXIC EFFECTS :
- Blood - pigmented or nucleated red blood cells Blood - changes in other cell count (unspecified) Blood - changes in erythrocyte (RBC) count
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Primate - monkey
- DOSE/DURATION :
- 12740 mg/kg/1Y-I
- TOXIC EFFECTS :
- Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count Blood - changes in platelet count
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 4200 mg/kg
- SEX/DURATION :
- male 4 week(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Paternal Effects - other effects on male
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 23 gm/kg
- SEX/DURATION :
- male 85 day(s) pre-mating female 26 day(s) pre-mating - 3 week(s) post-birth
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 69 gm/kg
- SEX/DURATION :
- male 85 day(s) pre-mating female 26 day(s) pre-mating - 3 week(s) post-birth
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - live birth index (measured after birth)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 27900 mg/kg
- SEX/DURATION :
- female 26 day(s) pre-mating - 15 day(s) post-birth
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - live birth index (measured after birth)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 910 mg/kg
- SEX/DURATION :
- female 1-13 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 6500 mg/kg
- SEX/DURATION :
- female 6-18 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
- TYPE OF TEST :
- Micronucleus test
- TYPE OF TEST :
- Cytogenetic analysis
MUTATION DATA - TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Rodent - hamster Ovary
- DOSE/DURATION :
- 500 mg/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 321,113,1994
- TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Rodent - hamster Ovary
- DOSE/DURATION :
- 500 mg/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 321,113,1994
Safety Information
| Symbol | GHS08 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H351 |
| Precautionary Statements | P280 |
| 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 |
| Hazard Codes | Xn:Harmful |
| Risk Phrases | R40 |
| Safety Phrases | S36/37/39-S45 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | XP2072000 |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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Synonyms
| Retrovis |
| bwa509u |
| Azitidin |
| BW-A509U |
| 1-(3-Azido-2,3-dideoxy-β-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione |
| 1-(3-Azido-2,3-dideoxy-β-D-ribofuranosyl)thymine |
| Thymidine, 3'-azido-3'-deoxy- |
| ZVD |
| 3'-azido-3'-droxythymidine |
| retrovir |
| Timazid |
| ZDV |
| 1-(3-Azido-2,3-Dideoxy-Beta-D-Ribofuranosyl)Thymine |
| BE-AS09U |
| Azidothymidine |
| 1-[(2R,4S,5S)-4-Azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidin-2,4(1H,3H)-dion |
| 3'-Azido-3'-deoxythymidine |
| 1-[(2R,4S,5S)-4-azido-5-(hydroxyméthyl)tétrahydrofuran-2-yl]-5-méthylpyrimidine-2,4(1H,3H)-dione |
| AZT |
| MFCD00006536 |
| 2,4(1H,3H)-pyrimidinedione, 1-(3-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl)-5-methyl- |
| Zidovudine |
