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320-67-2

320-67-2 structure

Name: Azacitidine (5-Azacytidine)
Chemical Name: 5-azacytidine
CAS Number: 320-67-2
Molecular Formula: C₈H₁₂N₄O₅
Molecular Weight: 244.205
Catalog: Biochemical Nucleoside drugs Nucleotides and their analogues
Create Date: 2018-06-07 14:42:30
Modify Date: 2024-01-01 18:10:29
5-Azacytidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases.

Name	5-azacytidine
Synonyms	Vidaza 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyméthyl)tétrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-one EINECS 206-280-2 [14C]-Azacitidine 5 AZC 4-Amino-1-b-D-ribofuranosyl-1,3,5-triazine-2(1H)-one 5-AZCR 1,3,5-Triazin-2(1H)-one, 4-amino-1-β-D-ribofuranosyl- 5'-azacytidine azacytidine Ladakamycin Azacitidine AzGR 5-Azacytidine 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-one 5-AC 4-amino-1-(b-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one 5-AC-15N4 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one 4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1,3,5-triazin-2(1H)-one L-β-Ribofuranosyl-5-azacytosine 4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-on 1,3,5-triazin-2(1H)-one, 4-amino-1-b-D-ribofuranosyl- mylosar Azacytidine, 5- MFCD00006539 5-AZAC

Description	5-Azacytidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases.
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Epigenetics >> DNA Methyltransferase Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Research Areas >> Cancer
Target	DNMT1 Nucleoside Antimetabolite/Analog Autophagy
In Vitro	Unmethylated CpG islands associated with a variety of genes become partially or fully methylated in tumors and can be reactivated by 5-Azacytidine[1]. 5-Azacytidine acts as weak inducers of erythroid differentiation of Friend erythroleukemia cells in the same concentration range where they affect DNA methyltransferase activity[2]. 5-Azacytidine inhibits L1210 cells with ID50 and ID90 values of 0.019 and circa 0.15 μg/mL, respectively[3].
In Vivo	TdR-3H incorporation is significantly inhibited when the animals are exposed to 5-Azacitidine (100 mg/kg, i.p.) for 2 hr or longer[3].
Kinase Assay	A crude cell-free extract is isolated from LI 210 cells in culture by suspension of the cells in a given volume of 0.05mol/LTris-HCl buffer, pH 7.4, and sonic extraction with a Biosonik at 70% maximal output for 30 sec. The supernatant is collected after centrifugation at 105,000 × g for 60 min (4°C) in a Model L Spinco ultracentrifuge. The final protein concentration of the cell-free extracts is approximately 3 mg/mL. The extracts are used as the source of enzymes. Ribonucleotide reductase activity is measured. A unit of enzyme is defined as the amount that catalyzed dCMP synthesis at a rate of 1 mμmole/hr. The assay systems for the measurement of pyrimidine nucleoside (CR) and deoxynucleoside (TdR, CdR) kinases are essentially those described by Chu and Fischer. However, reactions are terminated by heating for 2 min in a boiling water bath, and the phosphorylated derivatives are isolated according to the method of Bach. Fifty-jul aliquots are applied to 1-inch discs of diethylaminoethyl paper, which are then placed in counting vials and eluted with 0.5 mL of 0.5 mol/LPCA. After 1 hr, 12 mL of Diotol are added, and the radioactivity is determined.
Cell Assay	Twenty mL of cells (circa 1×104 cells/mL) are pipetted into sterilized culture tubes with screw caps and incubated at 37°C overnight. The experiment is initiated by the addition of 1 mL of 5-Azacytidine (5-azaCR) or medium for a given period (from 0 to 240 min) prior to the addition of 1 mL of metabolite (or medium). Cell growth is determined twice a day for 3 days by means of a Model A Coulter counter. To determine IDSO and ID90 values, 5 mL of L1210 cells (5×103 cells/mL) are incubated with the drug at 37°C for 3 days, and cell growth is determined.
Animal Admin	For the in vivo experiments, leukemic mice (bearing circa 1×103 cells/animal) are given injections i.p. with 0.2 mL of 5-Azacytidine (5-azaCR) of a given concentration. Two hr later, the reaction is started by injecting 0.5 mL of labeled metabolite (TdR-3H or UR-3H, 10 /μCi/12.5 μg). After 1 hr, animals (3 mice/group) are killed by cervical fracture, and the ascites are treated with heparin, collected, pooled, and then centrifuged immediately in a Sorvall refrigerated centrifuge Model R2C-B at 800×g for 10 min (4°C).
References	[1]. Christman JK. 5-Azacytidine and 5-aza-2'-deoxycytidine as inhibitors of DNA methylation: mechanistic studies and their implications for cancer therapy. Oncogene. 2002 Aug 12;21(35):5483-95. [2]. Creusot F, et al. Inhibition of DNA methyltransferase and induction of Friend erythroleukemia cell differentiation by 5-azacytidineand 5-aza-2'-deoxycytidine. J Biol Chem. 1982 Feb 25;257(4):2041-8. [3]. Li LH,et al. Cytotoxicity and mode of action of 5-azacytidine on L1210 leukemia. Cancer Res. 1970 Nov;30(11):2760-9.

Density	2.1±0.1 g/cm3
Boiling Point	534.5±60.0 °C at 760 mmHg
Melting Point	226-232 °C (dec.)(lit.)
Molecular Formula	C₈H₁₂N₄O₅
Molecular Weight	244.205
Flash Point	277.0±32.9 °C
Exact Mass	244.080765
PSA	143.72000
LogP	-1.99
Vapour Pressure	0.0±3.2 mmHg at 25°C
Index of Refraction	1.823
Water Solubility	0.5-1.0 g/100 mL at 21 ºC

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XZ3017500

CHEMICAL NAME :: 1,3,5-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 320-67-2

LAST UPDATED :: 199801

DATA ITEMS CITED :: 87

MOLECULAR FORMULA :: C8-H12-N4-O5

MOLECULAR WEIGHT :: 244.24

WISWESSER LINE NOTATION :: T6NVN ENJ DZ A- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Rinsed with water

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 6 mg/kg/10D-I

TOXIC EFFECTS :: Blood - leukopenia Blood - agranulocytosis

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 500 ug/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 572 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 68 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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 229 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 7200 ug/kg

TOXIC EFFECTS :: Blood - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: >100 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 :: Bird - wild bird species

DOSE/DURATION :: 100 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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 32500 ug/kg/5D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - muscle contraction or spasticity Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 30800 ug/kg/14D-I

TOXIC EFFECTS :: Blood - changes in bone marrow (not otherwise specified) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 180 mg/kg/9W-I

TOXIC EFFECTS :: Blood - leukopenia Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 190 mg/kg/38W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Reproductive - Tumorigenic effects - testicular tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg/50W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Blood - lymphoma, including Hodgkin's disease Skin and Appendages - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 mg/kg female 16 day(s) after conception

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Reproductive - Tumorigenic effects - transplacental tumorigenesis Blood - lymphoma, including Hodgkin's disease

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 284 mg/kg/43W-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Blood - lymphoma, including Hodgkin's disease

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg/50W-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 90 mg/kg/8W-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 mg/kg female 12 day(s) after conception

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Blood - lymphoma, including Hodgkin's disease Reproductive - Tumorigenic effects - transplacental tumorigenesis

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 600 ug/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 4 mg/kg

SEX/DURATION :: female 17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 450 ug/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 5 mg/kg

SEX/DURATION :: female 12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 500 ug/kg

SEX/DURATION :: female 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1 mg/kg

SEX/DURATION :: female 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material) Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 500 ug/kg

SEX/DURATION :: female 12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 100 ug/kg

SEX/DURATION :: female 12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - physical

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 500 ug/kg

SEX/DURATION :: female 12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 500 ug/kg

SEX/DURATION :: female 12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 4 mg/kg

SEX/DURATION :: female 15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material)

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: Gene conversion and mitotic recombination

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Unscheduled DNA synthesis

TYPE OF TEST :: Mutation test systems - not otherwise specified

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Unscheduled DNA synthesis

TYPE OF TEST :: DNA inhibition

TYPE OF TEST :: Mutation test systems - not otherwise specified

TYPE OF TEST :: Mutation test systems - not otherwise specified

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 400 nmol/L

REFERENCE :: CGCGBR Cytogenetics and Cell Genetics. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.12- 1973- Volume(issue)/page/year: 41,71,1986 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 26,37,1981 IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,47,1990 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 26,37,1981 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,47,1990 IARC Cancer Review:Group 2A IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,47,1990 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5101 No. of Facilities: 88 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 1069 (estimated) No. of Female Employees: 698 (estimated)

Symbol	GHS07, GHS08
Signal Word	Danger
Hazard Statements	H302-H350
Precautionary Statements	P201-P308 + P313
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	T:Toxic
Risk Phrases	R45;R46;R22
Safety Phrases	S53-S22-S36/37/39-S45
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	XZ3017500
HS Code	2934999090

6974-32-9

52523-35-0

~71%

320-67-2

Literature: ScinoPharm Taiwan Ltd. Patent: US2010/36112 A1, 2010 ; Location in patent: Page/Page column 7 ;

13035-61-5

~40%

320-67-2

Literature: Ionescu, Dumitru; Blumbergs, Peter Patent: US2004/186283 A1, 2004 ; Location in patent: Page 8 ;

10302-78-0

~75%

320-67-2

Literature: SICOR INC.; BIGATTI, Ettore; LUX, Giovanna; PAIOCCHI, Maurizio; GIOLITO, Andrea; TOSI, Simone Patent: WO2010/17374 A1, 2010 ; Location in patent: Page/Page column 18 ;