Cyclocytidine Hydrochloride

Names

[ Name ]:
Cyclocytidine Hydrochloride

[Synonym ]:
2,2'-Anhydro-1-β-D-arabinofuranosylcytosine hydrochloride
Cyclocytidine Hydrochloride
(2R,3R,3aS,9aR)-3-Hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-6-iminiumchlorid
2,2'-O-Cyclocytidine Hydrochloride
Ancitabine Hydrochloride
(2R,3R,3aS,9aR)-2-(Hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-ol hydrochloride (1:1)
EINECS 233-515-6
MFCD00012636
2,2'-Anhydro-(1-β-D-arabinofuranosyl)cytosine Hydrochloride
(-)-Cyclocytidine hydrochloride
(2R,3R,3aS,9aR)-3-Hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-6-iminium chloride
6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-, (2R,3R,3aS,9aR)-, hydrochloride (1:1)
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride
Ancitabine (hydrochloride)

Biological Activity

[Description]:

Ancitabine (hydrochloride) is an important antileukemia drugs.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Natural Products >> Alkaloid

Research Areas >> Cancer

[References]

[1]. Z Rao, et al. Study on the Synthesis of Cytarabine Hydrochloride and its Intermediate Ancitabine Hydrochloride. Fine Chemical Intermediates, 2013

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.01 g/cm3

[ Boiling Point ]:
442ºC at 760 mmHg

[ Melting Point ]:
269-270ºC

[ Molecular Formula ]:
C₉H₁₂ClN₃O₄

[ Molecular Weight ]:
261.662

[ Flash Point ]:
221.1ºC

[ Exact Mass ]:
261.051636

[ PSA ]:
100.59000

[ Index of Refraction ]:
-21 ° (C=2， H2O)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LV2615000

CAS REGISTRY NUMBER :: 10212-25-6

LAST UPDATED :: 199512

DATA ITEMS CITED :: 21

MOLECULAR FORMULA :: C9-H11-N3-O4.Cl-H

MOLECULAR WEIGHT :: 261.69

WISWESSER LINE NOTATION :: T B555 AN CO GO IN JHTT&J D1Q EQ &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 120 mg/kg

TOXIC EFFECTS :: Vascular - BP lowering not characterized in autonomic section Gastrointestinal - nausea or vomiting Blood - changes in bone marrow (not otherwise specified)

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >7 gm/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 - rat

DOSE/DURATION :: 3800 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 :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5500 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 - rat

DOSE/DURATION :: 820 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 :: >7 gm/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 :: 2528 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 :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4050 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 :: 800 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 :: Mammal - dog

DOSE/DURATION :: 344 mg/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 1045 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Gastrointestinal - changes in structure or function of salivary glands Gastrointestinal - nausea or vomiting

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 560 mg/kg/7D-I

TOXIC EFFECTS :: Blood - changes in leukocyte (WBC) count 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 :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 1120 mg/kg/7D-I

TOXIC EFFECTS :: Behavioral - food intake (animal) Blood - changes in leukocyte (WBC) count Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 400 mg/kg

SEX/DURATION :: female 8-15 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 :: 800 mg/kg

SEX/DURATION :: female 8-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 8250 mg/kg

SEX/DURATION :: male 2 year(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 60 mg/kg

SEX/DURATION :: female 8-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 60 mg/kg

SEX/DURATION :: female 8-17 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 125 mg/kg

SEX/DURATION :: female 8-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - body wall

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Leukocyte

DOSE/DURATION :: 10 mg/L

REFERENCE :: CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 20,2286,1972

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
LV2615000

Precursor & DownStream

Precursor

DownStream

Articles

Cytosine-based nucleoside analogs are selectively lethal to DNA mismatch repair-deficient tumour cells by enhancing levels of intracellular oxidative stress.

Br. J. Cancer 108(4) , 983-92, (2013)

DNA mismatch repair deficiency is present in a significant proportion of a number of solid tumours and is associated with distinct clinical behaviour.To identify the therapeutic agents that might show...

Tyramine-like effect of cyclocytidine (2,2'-anhydro-1-β-arabinofuranosylcytosine hydrochloride), an antineoplastic agent Oguro, K., Hashimoto, K.

J. Exp. Med. 124 , 83-90, (1978)