Cyclocytidine Hydrochloride

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Names

[ CAS No. ]:
10212-25-6

[ 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)

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

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

  • 1-β-D-Arabinofuranosyluracil
  • 2,6-diaminopurine arabinoside
  • Cytarabine

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)


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