5-Azacytidine

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.	-20°C
solubility	Soluble in DMSO (up to 25 mg/ml), or in Water (up to 12 mg/ml).
pka	13.46±0.70(Predicted)
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
Stability	Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.
InChIKey	NMUSYJAQQFHJEW-WGDKFINWSA-N
LogP	-2.191 (est)
CAS DataBase Reference	320-67-2(CAS DataBase Reference)
IARC	2A (Vol. 50) 1990
EPA Substance Registry System	Azacitidine (320-67-2)

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS07,GHS08,GHS09

Signal word

Danger

Hazard statements

H302-H341-H350-H360FD-H372-H410

Precautionary statements

P202-P260-P264-P273-P301+P312-P308+P313

Hazard Codes

T

Risk Statements

45-46-22

Safety Statements

53-22-36/37/39-45

WGK Germany

3

RTECS

XZ3017500

F

10-23

HS Code

29349990

Toxicity

LD50 in mice (mg/kg): 115.9 i.p.; 572.3 orally (Palm, Kensler)

NFPA 704

	1
2		0

5-Azacytidine price More Price(15)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich(India)	A2385	5-Azacytidine ≥98% (HPLC)	320-67-2	100MG	₹5715.6	2022-06-14	Buy
Sigma-Aldrich(India)	A2385	5-Azacytidine ≥98% (HPLC)	320-67-2	250MG	₹11875.03	2022-06-14	Buy
Sigma-Aldrich(India)	PHR1911	Azacitidine Pharmaceutical Secondary Standard; Certified Reference Material	320-67-2	300MG	₹39576.2	2022-06-14	Buy
Sigma-Aldrich(India)	A2385	5-Azacytidine ≥98% (HPLC)	320-67-2	1G	₹40994.28	2022-06-14	Buy
Sigma-Aldrich(India)	A1287	5-Azacytidine Hybri-Max?, γ-irradiated, lyophilized powder, BioXtra, suitable for hybridoma	320-67-2	1VIAL	₹2478.93	2022-06-14	Buy

Product number	Packaging	Price	Buy
A2385	100MG	₹5715.6	Buy
A2385	250MG	₹11875.03	Buy
PHR1911	300MG	₹39576.2	Buy
A2385	1G	₹40994.28	Buy
A1287	1VIAL	₹2478.93	Buy

5-Azacytidine Chemical Properties,Uses,Production

Description

5-Azacytidine is an analog of the nucleoside cytidine which can be incorporated into DNA and RNA. 5-Azacytidine acts as an epigenetic modifier by incorporating into DNA where it irreversibly binds to DNA methyltransferases, thus inhibiting their activity.
Azacitidine is an antineoplastic agent launched for the treatment of myelodysplastic syndrome (MDS). MDS is a group of closely related diseases caused by abnormal blood-forming stem cells of the bone marrow. Azacitidine is indicated for the treatment of all five subtypes of MDS, which consist of refractory anemia, refractory anemia with ringed sideroblasts, refractory anemia with excess blasts, refractory anemia with excess blasts in transformation, and chronic myelomonocytic leukemia.

Chemical Properties

White crystalline solid or powder. Soluble in dimethyl sulfoxide, slightly soluble in ethanol:water (50:50), propylene glycol, polyethylene glycol; slightly soluble in water, saturated octanol aqueous solution, 5% glucose injection, N-methyl-2-pyrrolidone, 0.9% sodium chloride injection and 5% polysorbate 80 aqueous solution; insoluble in acetone, ethanol and methyl ethyl ketone.

Uses

5-Azacytidine, its incorporation into RNA alters RNA synthesis and processing, and results in inhibition of protein synthesis. It has been used as a cancer chemotherapeutic agent. It is a powerful bacteriostatic, antitumor, and mutagenic agent; it also exhibits immunosuppressive, antimitotic, radioprotective, and virostatic effects.

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.

Biological Functions

Azacitidine is given subcutaneously for the treatment of myelodysplastic syndrome, and serum levels generally are maximized within 30 minutes. The parent drug and its metabolites are excreted in the urine. Azacitidine is carcinogenic and teratogenic in rodents, and leukopenia, thrombocytopenia, and neutropenia are the most common reasons for drug discontinuation or dosage reduction.

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.

Carcinogenicity

Azacitidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

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

Ammonia Sodium Methoxide Potassium hydroxide

Preparation Products

4-amino-1-[4-(hydroxymethyl)-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl]-1,3,5-triazin-2-one 5,6-dihydro-5-azacytidine

5-Azacytidine Suppliers

Global( 658)Suppliers

Supplier	Tel	Country	ProdList	Advantage	Inquiry
Dr. Reddy's Laboratories Ltd	+91-4049002900 +91-4049002900	Hyderabad, India	165	58	Inquiry
Anant Pharmaceuticals Pvt Ltd	+91-8550986868 +91-9485998001	Haryana, India	461	58	Inquiry
J S LABS	+91-7330612784 +91-7330612784	Tamil Nadu, India	160	58	Inquiry
HRV Global Life Sciences	+91-9820219686 +91-9820219686	Telangana, India	379	58	Inquiry
Shilpa Medicare Limited (SML)	+91-8532238704 +91-9320649838	Karnataka, India	61	58	Inquiry
Svak Life Sciences	+91-9963463333 +91-9705383777	Hyderabad, India	101	58	Inquiry
Basil Drugs AND Pharmaceuticals Pvt Ltd	+91-2249700250 +91-9619320820	Mumbai, India	108	58	Inquiry
Gland Chemicals Pvt Ltd	+91-9492733833 +91-9346729196	Telangana, India	16	58	Inquiry
Laurus Labs Ltd	+91-4066594333 +91-4039804333	Telangana, India	50	58	Inquiry
Sakar Healthcare	+91-8976292690 +91-9967572302	Gujarat, India	47	58	Inquiry

Supplier	Advantage
Dr. Reddy's Laboratories Ltd	58
Anant Pharmaceuticals Pvt Ltd	58
J S LABS	58
HRV Global Life Sciences	58
Shilpa Medicare Limited (SML)	58
Svak Life Sciences	58
Basil Drugs AND Pharmaceuticals Pvt Ltd	58
Gland Chemicals Pvt Ltd	58
Laurus Labs Ltd	58
Sakar Healthcare	58

5-Azacytidine Spectrum

5-Azacytidine(320-67-2)MS 5-Azacytidine(320-67-2)¹HNMR 5-Azacytidine(320-67-2)¹³CNMR 5-Azacytidine(320-67-2)IR1 5-Azacytidine(320-67-2)IR2 5-Azacytidine(320-67-2)Raman

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Antibiotic U 18496-15N4 Azacitidine-15N4 Azacytidine-15N4 LadakaMycin-15N4 LedakaMycin-15N4 Mylosar-15N4 NSC 102816-15N4 NSC 103-627-15N4 U 18496-15N4 Vidaza-15N4 NBC-102816 1,3,5-Triazin-2(1H)-one, 4-amino-1-b-D-ribofuranosyl- s-Triazin-2(1H)-one, 4-amino-1-b-D-ribofuranosyl- 5-AZACYTIDIN 5-Azacytidine ,98% 5-Azacytidine,4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Ladakamycin LedakaMycin NSC 103-627 4-AMino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one-15N4 5-AC-15N4 5-AzaC-15N4 5-AZC-15N4 5-AZCR-15N4 4-amino-1-beta-d-ribofuranosyl-s-triazin-2(1h)-on 5-triazin-2(1h)-one,4-amino-1-beta-d-ribofuranosyl-3 4-aMino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one 5'-azacytidine, β-D-5-azaC, 5-azacytidine, azacitidine, azacytidine, 5-aza-C, 4-aMino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one VIDAZAAZACITIDINEAZACYTIDINE 5-Azacytidine, 99% 50MG wr 183027 2-(beta-D-ribofuranosyl)-4-amino-1,3,5-triazin-2-one 5-AZACYTIDINE (50X) GAMMA-IRRADIATEDCELL CULTURE T 5-AZACYTIDINE CRYSTALLINE 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-t 5-Azacytidine99% Azacitidine, 4-Amino-1-D-ribofuranosyl-1,3,5-triazin-2(1H)-one, 5-AzaC, SEC-TRIAZIN-2-ONE,4-AMINO-1-BETA-D-RIBOFURANOSYL- 5-Azacytidine / 5-Azacytosine 4-amino-1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one Azacitidine (5-Azacytidine) 4-aMino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one Azacitidine(Vidaza) Azacitidine (150 mg) 1,3,5-Triazin-2(1H)-one, 4-aMino-1-β-D-ribofuranosyl- 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one Ladakamycin Azacitidine(5-Azacitidine) 4-Amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1,3,5-triazin-2 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one Ladakamycin 5-AZACYTIDINE extrapure AzGR antibioticu18496 nci-c01569 nsc-102816 u18496 5-AZACYTIDINE 4-AMINO-1-B-D-RIBOFURANOSYL-SYM-TRIAZINE-2(1H)-ONE 4-AMINO-1-BETA-D-RIBOFURANOSYL-5-TRIAZIN-2[1H]-ONE 4-AMINO-1-BETA-D-RIBOFURANOSYL-S-TRIAZIN-2[1H]ONE