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Zalcitabine

Product Name
Zalcitabine
CAS No.
7481-89-2
Chemical Name
Zalcitabine
Synonyms
DDC;Hivid;dideoxycytidine;2',3'-DIDEOXYCYTIDINE;D 2C;ddCyd;I-livid;2',3'-ddC;2',3'-ddC;NSC 606170
CBNumber
CB2369466
Molecular Formula
C9H13N3O3
Formula Weight
211.22
MOL File
7481-89-2.mol
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Zalcitabine Property

Melting point:
217-218 °C(lit.)
alpha 
D25 +81° (c = 0.635 in water)
Boiling point:
350.9°C (rough estimate)
Density 
1.2605 (rough estimate)
refractive index 
78 ° (C=0.5, H2O)
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 
DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly, Sonicated)
form 
powder
pka
14.44±0.10(Predicted)
color 
colorless
Water Solubility 
5-10 g/100 mL at 19 ºC
Merck 
14,10109
BRN 
654956
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
WREGKURFCTUGRC-POYBYMJQSA-N
CAS DataBase Reference
7481-89-2(CAS DataBase Reference)
IARC
2B (Vol. 76) 2000
EPA Substance Registry System
Cytidine, 2',3'-dideoxy- (7481-89-2)
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Safety

Hazard Codes 
Xn,C
Risk Statements 
40-36/37-34
Safety Statements 
22-36-45-36/37/39-27-26
WGK Germany 
3
RTECS 
HA3870000
10-23
HS Code 
2934990002
Hazardous Substances Data
7481-89-2(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H351Suspected of causing cancer

Precautionary statements

P281Use personal protective equipment as required.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
R306576
Product name
4-AMINO-1-(5-HYDROXYMETHYL-TETRAHYDRO-FURAN-2-YL)-1H-PYRIMIDIN-2-ONE
Purity
AldrichCPR
Packaging
50MG
Price
$29.8
Updated
2024/03/01
Sigma-Aldrich
Product number
D5782
Product name
2′,3′-Dideoxycytidine
Purity
≥98% (HPLC)
Packaging
100mg
Price
$184
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR3266
Product name
Zalcitabine
Purity
pharmaceutical secondary standard, certified reference material
Packaging
500MG
Price
$201
Updated
2024/03/01
Sigma-Aldrich
Product number
1724306
Product name
Zalcitabine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$400
Updated
2022/05/15
Alfa Aesar
Product number
L10619
Product name
2',3'-Dideoxycytidine, 98+%
Packaging
50mg
Price
$60.65
Updated
2024/03/01
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Zalcitabine Chemical Properties,Usage,Production

Description

Zalcitabine is an orally active dideoxynucleoside andog for combination use with zidovudine in advanced HIV infection and also as monotherapy for AIDS patients who cannot tolerate or have not responded to zidovudine. It has a similar mechanism of action (inhibition of reverse transcriptase) to didanosine. Like didanosine, its side effect profile includes peripheral neuropathy. Unlike zidovudine, zalcitabine does not cause bone marrow suppression.

Description

Zalcitabine is an analog of pyrimidine derived from deoxycytidine with the replacement of the hydroxyl group in position 3’ with a hydrogen. In cells, it is phosphorylated to the active triphosphate form, ddCTP, which acts as a substrate for HIV reverse transcriptase (Ki = 51 nM). It incorporates into viral DNA where it terminates chain elongation when the missing hydroxyl group is encountered. Zalcitabine was the third antiretroviral approved by the FDA for treatment of HIV infection and AIDS.

Chemical Properties

White to Off-White Cyrstalline Powder

Originator

National Cancer Institute (NIH) (U.S.A.)

Uses

ammonia detoxicant, diagnostic aid

Uses

A pyrimidine nucleoside analogue with antiviral activity.

Definition

ChEBI: A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.

Indications

Zalcitabine (ddC, Hivid) is a cytidine analogue active against HIV-1, HIV-2, and hepatitis B virus. It is used for the treatment of HIV infection in adults and asymptomatic children as part of a multidrug regimen. It may be less effective than the other nucleoside inhibitors and is used less frequently.

Manufacturing Process

Bromoacetylation of N-acetylcytidine with 2-acetoxy-2-methylpropanoyl bromide
A 5 L three-nicked, round-bottomed flask equipped with a mechanical stirrer, thermometer, nitrogen inlet tube, and additional funnel was charge with 142.6 g (0.5 mole) of N-acetylcytidine, and 1.25 L of acetonitrile. The suspension was stirred under nitrogen, cooled to 5°C (ice-bath), and treated dropwise (during 20 min) with 225 ml of 2-acetoxy-2-methylpropanoyl bromide (AIBB) during 30 minutes. At the completion of the addition, a homogeneous solution resulted. It was stirred at room temperature overnight (the reaction was complete within 3 hr), cooled to 5°C, and diluted with 1.25 L of ethyl acetate. After recooling to 5°C, 2.0 L of saturated sodium bicarbonate was added. The mixture was stirred for 5 minutes, the organic phase was separated, and the aqueous phase was back-extracted with 500 ml of ethyl acetate. The combined organic extracts were washed with 1 L of saturated brine, dried (MgSO 4 ), and evaporated to give a gum. Final drying at 40°C (1 mm) for 1 hrgave 264.7 g (102%) of a white solid. High pressure liquid chromatographic analysis gave the following results (major peaks only): 40% of [2R- [2α,3β,4α,5α(S*)]]-N-[1-[3-(acetyloxy)-5-[(2-(acetyloxy)-1-oxopropoxy] methyl]-4-bromotetrahydro-2-furanyl]-1,2-dihydro-2-oxo-4-pyrimidinyl] acetamide (a) and 24% of its regioisomer (b).
Preparation of [2R-[2α,3β,4α,5α(S*)]]-N-[1-[3-(acetyloxy)-5-[(2-(acetyloxy)- 1-oxopropoxy]methyl]-4-bromotetrahydro-2-furanyl]-1,2-dihydro-2-oxo-4- pyrimidinyl]acetamide (a) and its regioisomer (b).
A 1-L, three-necked, round-bottomed flask equipped with a mechanical stirrer and argon inlet was charged with 28.52 g of N-acetylcytidine in 250 ml of acetonitrile. The mixture was cooled to 10°C and treated with 48.75 g of (S)- (-)-2-acetoxypropionyl bromide during 15 minutes. It was stirred at room temperature overnight, cooled to 10°C, treated with 400 ml of cold (0°C) saturated sodium bicarbonate, and extracted with 250 ml of ethyl acetate. The extract was washed with 200 ml of saturated brine, dried (MgSO 4 ) and evaporated to give 45.45 g of a white foam. Reversed phase chromatography (C 18 column) with 40% methanol in water gave a pure sample of (a).
Zinc-copper couple was prepared by the next way:
A 12 L three-necked, round-bottomed flask equipped with a mechanical stirrer was charged with 4.50 kg of zinc dust. The zinc dust was washed with 3.75 L of 3% aqueous hydrochloric acid by stirring for 3 to 5 minutes. The hydrochloric acid was decanted from the solid. This cycle was repeated with 3x3.75 L of 3% hydrochloric acid. The reaction was slightly exothermic and the volume of the zinc dust increased to double its original volume. The zinc dust was then washed with 4x3.0 L of deionized water to remove any residual hydrochloric acid. After all the water was decanted, the spongy zinc layer was treated with a solution made by dissolving 240.0 g of cupric sulfate dihydrate in 7.5 L of deionized water. The suspension was stirred rapidly as the solution was added. The aquamarine color of the cupric sulfate solution was removed almost immediately and the zinc suspension changed in color from gray to black. The near colorless aqueous layer was decanted and the solid was washed with 4x3.0 L of deionized water. The suspension of zinc-copper couple was filtered through a piece of Whatman No. 1 filter paper, then washed with 4x30 L ethanol and 3x3.0 L of ether. The solid was carefully dried at 25°C and 140 mm overnight to remove ether, then for 3 hr at 130°-140°C (0.5 mm). The solid was cooled to room temperature under vacuum and was stored under argon in amber bottles. The procedure yielded 3.84 kg of zinc-copper couple.
Preparation of [2R-[2α,5α(S*)]]-N-[1-[5-[[2-(acetyloxy)-1-oxopropoxy] methyl]-2-5-dihydro-2-furanyl]-1,2-dihydro-2-oxo-4-pyrimidinyl]acetamide.
A total of 1.47 g of a mixture of bromoacetates in acetonitril was reduced with 800 mg of zinc-copper couple. The mixture was stirred under argon at room temperature overnight. The mixture was deoxygenated by evacuation followed by filling the reaction vessel with argon (oxygen-free nitrogen may be used); this procedure was repeated three times. It was filtered over Celite, the flask was rinsed out with of acetonitrile, and the rinse was used to wash the Celite. The combined filtrate and washing were evaporated (40°C), and the residue was dissolved in of methylene chloride. This was added to a previously prepared solution of ethylenediaminetetraacetic acid disodium salt dihydrate (Fluka) in deionized water containing of sodium bicarbonate. The mixture was stirred vigorously for 1.5 hr, and filtered over Celite, which was washed with methylene chloride. The organic phase was separated and the aqueous phase was re-extracted with of methylene chloride. The combined organic was washed with of saturated sodium bicarbonate, which was back-extracted with of methylene chloride. The combined organic was dried (MgSO 4 ), filtered, and concentrated. To this was added of acetic anhydride followed by 40 g of poly- 4-vinylpyridine, and the mixture was stirred under nitrogen for 3 hr. It was filtered over Celite, which was washed with methylene chloride. The combined filtrate and washing were evaporated, toluene was added, and the mixture was evaporated again, ether was added with vigorous stirring for 15 minutes. The mixture was filtered (some scraping of the flask was necessary) and washed with ether to give 570 mg of after crystallization from hot tetrahydrofuran, melting point 125°C; [α] D 25 +119.04°(c=0.25, CHCl 3 ).
Preparation of [2R-[2α,5α(S*)]]-N-[1-[5-[[2-(acetyloxy)-1-oxopropoxy] methyl]tetrahydro-2-furanyl]-1,2-dihydro-2-oxo-4-pyrimidinyl]acetamide.
A solution of 720 mg of 2R-[2α,5α(S*)]]-N-[1-[5-[[2-(acetyloxy)-1- oxopropoxy]methyl]-2-5-dihydro-2-furanyl]-1,2-dihydro-2-oxo-4- pyrimidinyl]acetamide set forth in 10 ml L of methanol and 10 ml of tetrahydrofuran was hydrogenated over 200 mg of 10% palladium on charcoal at room temperature and atmospheric pressure until hydrogen uptake ceased (10 ml). The mixture was filtered over Celite and the filtrate was evaporated to give a gum. Chromatography on 10 g of silica (70-230 mesh) with 10% methanol in methylene chloride, gave 290 mg of the product as a foam, [α] D 25 +88.43° (C=0.99, CHCl 3 ).
Preparation of 2',3'-dideoxycytidine.
A solution of 20.7 g of [2R-[2α,5α(S*)]]-N-[1-[5-[[2-(acetyloxy)-1- oxopropoxy]methyl]tetrahydro-2-furanyl]-1,2-dihydro-2-oxo-4-pyrimidinyl] acetamide in 100 ml of ethanol was treated with 10.0 ml of Triton B (N- benzyltrimethyl-ammonium hydroxide), and the mixture was stirred at room temperature overnight. The mixture was concentrated to 20 ml, cooled to 0°C, and the product was collected by filtration. It was washed with 10 ml of cold ethanol to give 4.48 g of 2',3'-dideoxycytidine, melting point 215°-218°C, as an white solid.

brand name

Hivid (Roche).

Therapeutic Function

Antiviral, Immunosuppressive

General Description

Zalcitabine, 2',3'-dideoxycytidine or ddCyd, is an analog ofcytosine that demonstrates activity against HIV-1 and HIV-2,including strains resistant to AZT. The potency (in peripheralblood mononuclear cells) is similar to that of AZT, but thedrug is more active in populations of monocytes andmacrophages as well as in resting cells.
The oral bioavailability of zalcitabine is over 80% in adultsand less in children.The major dose-limiting side effect isperipheral neuropathy, characterized by pain, paresthesias,and hypesthesia, beginning in the distal lower extremities.These side effects are typically evident after several months oftherapy with zalcitabine. A potentially fatal pancreatitis is anothertoxic effect of treatment with ddC. The drug has beenapproved for the treatment of HIV infection in adults with advanceddisease who are intolerant to AZT or who have diseaseprogression while receiving AZT. ddC is combined with AZTfor the treatment of advanced HIV infection.

General Description

White crystalline powder. Odorless.

Air & Water Reactions

Water soluble.

Reactivity Profile

Zalcitabine may be sensitive to prolonged exposure to light.

Fire Hazard

Flash point data for Zalcitabine are not available; however, Zalcitabine is probably combustible.

Pharmacology

Peripheral neuropathy occurs in up to 50% of patients taking zalcitabine. Stomatitis, esophageal ulceration, hepatotoxicity, rash, and pancreatitis may occur. Zalcitabine should be used with caution in individuals with a history of pancreatitis, liver disease, or alcohol abuse. Dosage adjustment is necessary for individuals with renal impairment. Zalcitabine should not be used in combination with didanosine, lamivudine, or stavudine.

Pharmacokinetics

Zalcitabine (ddC) is a useful alternate drug to ZDV and is given in combination with ZDV when CD4 cell counts fall to less than 300 cells/mm3 . Monotherapy with ddC is more active than ZDV. Its oral bioavailability is 87%, and its plasma half-life is approximately 1 hour. In low doses (0.005 mg/kg every 4 hours), ddC produces sustained decrease in p24 antigen level and increase in CD4 cell counts. The CSF fluid/plasma ratio of ddC is 0.2. Following oral administration, bioavailability of ddC is less than 80%, which is further reduced when taken with food. The mean maximum plasma concentration of the drug also is reduced from 25.2 to 15.5 ng/mL when the drug was taken with food.

Side effects

It has side effects, such as stomatitis, rash, fever, malaise, arthritis, and arthralgia.

Metabolism

Dideoxyuridine is the major metabolite in urine and feces. The drug penetrates the blood-brain barrier. The major toxicity of ddC is peripheral neuropathy, in which case it should be discontinued. In some cases, pancreatitis occurs when given alone or in combination with ZDV."

Zalcitabine Preparation Products And Raw materials

Raw materials

Preparation Products

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Zalcitabine Suppliers

Maanshan geneyan biotech Co.,LTD
Tel
18913822354
Email
market@geneyan-bio.com
Country
China
ProdList
299
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Hongene Biotech Corporation
Tel
021-64757213
Fax
86-21-64700613
Email
info@hongene.com
Country
China
ProdList
672
Advantage
61
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44688
Advantage
61
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View Lastest Price from Zalcitabine manufacturers

hebei hongtan Biotechnology Co., Ltd
Product
Zalcitabine 7481-89-2
Price
US $30.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
3000kg
Release date
2024-03-22
Hebei Weibang Biotechnology Co., Ltd
Product
Zalcitabine 7481-89-2
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-28
Hebei Yanxi Chemical Co., Ltd.
Product
Zalcitabine 7481-89-2
Price
US $10.00-1.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-09-08

7481-89-2, ZalcitabineRelated Search:


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