Zidovudine

Modify Date: 2024-01-02 18:25:31

Zidovudine Structure
Zidovudine structure
 Common Name Zidovudine
CAS Number 30516-87-1 Molecular Weight 267.241
Density N/A Boiling Point N/A
Molecular Formula C10H13N5O4 Melting Point 113-115 °C(lit.)
MSDS Chinese USA Flash Point N/A
Symbol GHS08
GHS08		 Signal Word Warning

 Use of Zidovudine


Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI), widely used to treat HIV infection. Zidovudine increases CRISPR/Cas9-mediated editing frequency.

 Names

Name zidovudine
Synonym More Synonyms

 Zidovudine Biological Activity

Description Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI), widely used to treat HIV infection. Zidovudine increases CRISPR/Cas9-mediated editing frequency.
Related Catalog
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)
Water Solubility 1-5 g/100 mL at 17 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XP2072000
CHEMICAL NAME :
Thymidine, 3'-azido-3'-deoxy-
CAS REGISTRY NUMBER :
30516-87-1
LAST UPDATED :
199712
DATA ITEMS CITED :
36
MOLECULAR FORMULA :
C10-H13-N5-O4
MOLECULAR WEIGHT :
267.28

HEALTH HAZARD DATA

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

 Safety Information

Symbol GHS08
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

 Synthetic Route

 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
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106060-86-0
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