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5-Azacytidine

Description Indication Contraindications Dosage Mechanism of Action Elimination Adverse reactions Precautions
5-Azacytidine
5-Azacytidine
CAS No.
320-67-2
Chemical Name:
5-Azacytidine
Synonyms
AzGR;5-AC;5 AZC;Vidaza;u18496;5-AZAC;5-AZCR;mylosar;5-AC-15N4;wr 183027
CBNumber:
CB4383338
Molecular Formula:
C8H12N4O5
Formula Weight:
244.2
MOL File:
320-67-2.mol

5-Azacytidine Properties

Melting point:
226-232 °C (dec.)(lit.)
alpha 
40 º (C=1, H2O 22 ºC)
Boiling point:
387.12°C (rough estimate)
Density 
1.4287 (rough estimate)
refractive index 
1.6590 (estimate)
storage temp. 
2-8°C
form 
lyophilized powder
color 
White to Off-white
Water Solubility 
0.5-1.0 g/100 mL at 21 ºC
Merck 
14,887
BRN 
620461
CAS DataBase Reference
320-67-2(CAS DataBase Reference)
EPA Substance Registry System
1,3,5-Triazin-2( 1H)-one, 4-amino-1-.beta.-D-ribofuranosyl- (320-67-2)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  T
Risk Statements  45-46-22
Safety Statements  53-22-36/37/39-45
WGK Germany  3
RTECS  XZ3017500
10-23
HS Code  29349990
Hazardous Substances Data 320-67-2(Hazardous Substances Data)
Toxicity LD50 in mice (mg/kg): 115.9 i.p.; 572.3 orally (Palm, Kensler)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H340 May cause genetic defects Germ cell mutagenicity Category 1A, 1B Danger
H350 May cause cancer Carcinogenicity Category 1A, 1B Danger
Precautionary statements:
P201 Obtain special instructions before use.
P202 Do not handle until all safety precautions have been read and understood.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P308+P313 IF exposed or concerned: Get medical advice/attention.
P405 Store locked up.
P501 Dispose of contents/container to..…

5-Azacytidine price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A1287 5-Azacytidine Hybri-Max , γ-irradiated, lyophilized powder, BioXtra, suitable for hybridoma 320-67-2 1vl $21.9 2018-11-13 Buy
Sigma-Aldrich 1045520 Azacitidine United States Pharmacopeia (USP) Reference Standard 320-67-2 150mg $352.8 2018-11-13 Buy
TCI Chemical A2033 5-Azacytidine >98.0%(T) 320-67-2 1g $238 2018-11-22 Buy
TCI Chemical A2033 5-Azacytidine >98.0%(T) 320-67-2 100mg $46 2018-11-22 Buy
Alfa Aesar J64159 5-Azacytidine, 98% 320-67-2 1g $55.2 2018-11-13 Buy

5-Azacytidine Chemical Properties,Uses,Production

Description

Azacytidine also referred to as Azacytidine and 5-azacytidine (brand name: Vidaza) is an anti-cancer chemotherapy medication. The drug is classified as demethylation and antimetabolite agent. Azacytidine acts by inhibiting the growth and proliferation of cancer cells in the body. The drug is indicated for the treatment of specific types of blood cell disorders and bone marrow cancers.

Indication

Azacytidine is prescribed for treating patients with secondary types of myelodysplastic syndrome, including refractory anemia that presents in the form of ringed sideroblasts (especially if it necessitates transfusion), or it presents itself alongside thrombocytopenia or neutropenia. Also, it is used in treating refractory anemia accompanied by excess blasts, refractory anemia characterized by excess blasts in transition (currently classified as chronic myelogenous leukemia that is accompanied by multilineage dysplasia), and acute myelomonocytic leukemia.

Contraindications

Azacytidine is contraindicated in patients who have acute malignant hepatic tumors or known hypersensitivity to the drug or mannitol.

Dosage

For treatment of patients with myelodysplastic syndrome, the initial dose is 75mg/m2 administered intravenously or subcutaneously in daily doses for 7 days in 4-week intervals. The recommended maintenance dose may be increased to 100mg/m2 if there are no noteworthy effects after 2 treatment cycles and if the patient does not experience additional toxicity other than vomiting and nausea.
Patients should undergo treatment that lasts for a minimum of 4 cycles. However, a partial or complete response may necessitate additional cycles other than the recommended 4 cycles. Treatment should not be discontinued if the patient is experiencing positive outcomes from the therapy.

Mechanism of Action

5-Azacytidine is a chemical analog that is closely linked with the cytosine nucleoside in ribonucleic acid (RNA) and deoxyribonucleic acid (DNA). Azacytidine influences antineoplastic activity through two main mechanisms; suppression of DNA methyltransferase when administered in low doses, which results in hypomethylation of DNA, and unmediated cytotoxicity in anomalous hematopoietic cells present in the bone marrow by its integration into RNA and DNA at high doses which causes the death of the cells.
Since Azacytidine is considered a ribonucleoside, it integrates itself into RNA to a greater extent than DNA. The integration into RNA results in the dissimulation of malfunctioning methylation, polyribosomes, and recipient function of replicated RNA, and suppression of protein production.
The integration of Azacytidine into DNA results in a covalent bond that is characterized by DNA methyltransferases, which inhibits DNA synthesis and resultant cytotoxicity.

Elimination

Intravenous administration of the radioactive form of the drug to cancer patients results in 85% elimination of Azacytidine through urinary excretion. Fecal excretion of the radioactive dose takes place in <1% of the administered drug in 3 days. The mean elimination of radioactivity through urine accounts for 50% of 14C-azacytidine administration.

Adverse reactions

Common side effects associated with Azacytidine in more than 30% of the patients include low white blood cell count, fever, vomiting, low platelet count, anemia, and nausea. At nadir, 10-17days of chemotherapy cycles, one may also experience petechiae, ecchymosis, constipation, redness at the injection site and fatigue.
Other side effects associated with Azacytidine in about 10-29% of the patients may include insomnia, depression, itching, upper respiratory infection, hypokalemia, anxiety, skin rash, abdominal pain, weight loss, nosebleed, chest pain, swelling on the ankles, dizziness, confusion, back pain, sore throat, poor appetite, headache, myalgia and arthralgia, pain at the injection site, chills, weakness, shortness of breath and coughs.
It is important to contact health care provider if one is experiencing diarrhea (4-6 episodes in 24 hours). A patient should also contact the doctor in case he/she has nausea that interferes with their ability to eat. If one has bloodstained urine, constipation that persists regardless of laxative use, extreme fatigue, tarry or bloodstained stools, vomiting (4-5 episodes in a span of 24 hours), signs of infection such as productive coughs or painful urination, and inability to eat or take fluids for more than 24 hours.

Precautions

A patient should notify their healthcare provider if they are taking any other medications which may include herbal remedies, vitamins, and over-the-counter medications before receiving an Azacytidine prescription. A patient should not receive any vaccination or immunization while they are on Azacytidine treatment.
Breastfeeding is not recommended while one is taking this drug. A patient should also inform their healthcare provider if they are pregnant or intending to get pregnant before starting Azacytidine treatment.
Azacytidine may cause neutropenia, anemia, and thrombocytopenia. Since the drug may result in hepatotoxicity amongst patients with acute hepatic impairment, caution should be taken during the administration of Azacytidine in patients with liver disease.
Renal toxicity that may range from renal failure to increased serum creatinine and death has been reported amongst patients who have been accorded intravenous treatment with Azacytidine in combination treatment with other chemotherapeutic medications for nonMDS cases.
The drug may also result in acute tumor lysis syndrome for patients with MDS. Azacytidine poses a threat to a developing embryo/fetus based on its mechanism of action.

Chemical Properties

White-to-Off-White Crystalline Solid

Chemical Properties

White crystalline solid or powder.

Uses

A potent growth inhibitor and cytotoxic agent. It acts as a demethylating agent by inhibiting DNA methyltransferase

Uses

Antineoplastic;'Antimetabolite

Uses

antianginal

Definition

ChEBI: A N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via a N-glycosidic linkage.

brand name

Vidaza (Pharmion).

General Description

White crystalline powder.

Air & Water Reactions

Slightly water soluble. Unstable in solution.

Reactivity Profile

5-Azacytidine is sensitive to light (may discolor). 5-Azacytidine is sensitive to oxidation. 5-Azacytidine is unstable in solution. 5-Azacytidine undergoes hydrolysis in aqueous buffers. 5-Azacytidine is incompatible with strong oxidizers.

Fire Hazard

Flash point data for 5-Azacytidine are not available; however, 5-Azacytidine is probably combustible.

Biological Activity

DNA methyltransferase inhibitor. Incorporates into DNA forming covalent adducts with cellular DNMT1, depleting enzyme activity. Induces demethylation and reactivation of silenced genes. Improves the efficiency of reprogramming of stem cells.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic data. Poison by ingestion, intravenous, and intraperitoneal routes. Human systemic effects by intravenous route: nausea, vomiting and dlarrhea, reduction in white cell count (luekopenia and agranulocytosis). An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. A skin irritant. When heated to decomposition it emits toxic fumes of NOx.

Potential Exposure

A growth inhibitor (DNA methyltransferase inhibitor). A cytotoxic agent and chemotherapeutic agent used to treat angina pectoris, an ischemic heart disease symptom. Occupational exposure to azacitidine could occur among health professionals and support staff (including custodians) by dermal contact, inhalation, or accidental ingestion during drug preparation or administration or cleanup of medical waste, including disposal of excretions from treated patients (Zimmerman et al. 1981, NIOSH 2004). The National Occupational Exposure Survey (conducted from 1981 to 1983) estimated that 1069 healthservices workers, including 698 women, potentially were exposed to azacitidine. Azacitidine may be produced synthetically or isolated from the bacterium Streptoverticillium ladakanus . Incompatibilities: Azacitidine is Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Contact with alkali metals, nitrides, and strong reducing agents such as hydrides may form flammable and/or toxic gases. May react with anhydrides forming acids and esters, generating noticeable heat, and also with oxoacids and carboxylic acids to form esters plus water, but the heat of reaction in the latter case typically is low. Keep away from isocyanates and epoxides; may initiate their polymerization. Azacitidine is sensitive to light and oxidation and unstable in solution. It undergoes hydrolysis in aqueous buffers.

First aid

Eyes: First check the victim for contact lenses and remove if present. Flush victim’s eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim’s eyes without specific instructions from a physician. Immediately transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. Skin: Immediately flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, immediately call a physician and be prepared to transport the victim to a hospital for treatment. Inhalation: Immediately leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, SCBA (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: Do not induce vomiting. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and immediately call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim’s airway is open and lay the victim on his/her side with the head lower than the body. Do not induce vomiting. Immediately transport the victim to a hospital.

Shipping

UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Incompatibilities

Azacitidine is Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Contact with alkali metals, nitrides, and strong reducing agents such as hydrides may form flammable and/or toxic gases. May react with anhydrides forming acids and esters, generating noticeable heat, and also with oxoacids and carboxylic acids to form esters plus water, but the heat of reaction in the latter case typically is low. Keep away from isocyanates and epoxides; may initiate their polymerization. Azacitidine is sensitive to light and oxidation and unstable in solution. It undergoes hydrolysis in aqueous buffers.

Waste Disposal

It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

5-Azacytidine Preparation Products And Raw materials

Raw materials

Preparation Products


5-Azacytidine Suppliers

Global( 314)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Hainan Xiyuan Chemical Technology Co., Ltd.
+86-15008981366
15008981366@163.com CHINA 9 58
Capot Chemical Co.,Ltd.
+86 (0)571-855 867 18
+86 (0)571-858 647 95 sales@capotchem.com China 19958 60
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 22058 58
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 500 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20795 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32764 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070;product@chemlin.com.cn
product@chemlin.com.cn CHINA 3015 60
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 14297 60
Anhui Royal Chemical Co., Ltd.
+86-025-86736275
dana.jiang@royal-chem.com CHINA 477 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 20001 58

View Lastest Price from 5-Azacytidine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-16 5-Azacytidine
320-67-2
US $7.00 / KG 1KG 99% 1000KG career henan chemical co
2018-08-16 5-Azacytidine
320-67-2
US $7.00 / KG 1KG 99% 1000KG career henan chemical co
2018-08-15 5-Azacytidine
320-67-2
US $2.00 / KG 1KG 98% 1ton career henan chemical co

5-Azacytidine Spectrum


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