<Suppliers Price>

Enocitabine

Names

[ CAS No. ]:
55726-47-1

[ Name ]:
Enocitabine

[Synonym ]:
1-(β-D-Arabinofuranosyl)-4-(docosanoylamino)pyrimidin-2(1H)-one
ENOCITABINE ANTINEOPLASTIC DRUGS
N(4)-Behenoyl-1-b-D-arabinofuranosylcytosine
BH-AC
n(sup4)-behenoylcytosinearabinoside
1-(β-D-Arabinofuranosyl)-4-(docosanoylamino)-2(1H)-pyrimidinone
BEHENOYLCYTOSINE ARABINOSIDE
MFCD00866294
Docosanamide, N-(1-β-D-arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)-
Enocitabine
Sunrabin
2(1H)-Pyrimidinone, 1-β-D-arabinofuranosyl-4-[(1-oxodocosyl)amino]-
N-(1-b-D-Arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)docosanamide
Enocitabine [INN:JAN]
N4-Behenoylcytosine arabinoside

Biological Activity

[Description]:

Enocitabine, a nucleoside analog, is a potent DNA replication inhibitor and a DNA chain terminator. Enocitabine can be used as an effective chemotherapeutic agent for the treatment of acute myelogenous leukaemia and lymphocytic leukaemias[1].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Infection
Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog
Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis
Signaling Pathways >> Anti-infection >> CMV

[Target]

DNA replication[1]; CMV[3]


[In Vitro]

Enocitabine is resistant to deamination because Enocitabine bears a highly lipophilic group at the 4-amino position of the cytosine moiety of cytarabine[1]. The combined effects of Pirarubicin and Enocitabine on HeLa S3 human uterine cervix carcinoma and K562 human myelocytic leukemia cells are determined by enhancement of their cytotoxic activities. Enocitabine or etoposide shows synergistic effects on HeLa S3 and K562 cells[2]. In the presence of Enocitabine, triphosphate forms of the nucleoside analogs are detected in the human cytomegalovirus (HCMV)-infected cells, and synthesis of HCMV DNA is strongly suppressed[3].

[References]

[1]. Hamada A, et al. Clinical pharmacokinetics of cytarabine formulations.Clin Pharmacokinet. 2002;41(10):705-18.

[2]. Nagasawa M, et al.In vitro combined effects of pirarubicin (THP) and various antitumor drugs on human tumor cell lines. Gan To Kagaku Ryoho. 1990 Apr;17(4 Pt 1):633-8.

[3]. Nakamura K, et al. Antiviral effect of antileukemic drugs N4-behenoyl-1-beta-D-arabinofuranosylcytosine (BH-AC) and 2,2'-anhydro-1-beta-D-arabinofuranosylcytosine (cyclo-C) against human cytomegalovirus. J Med Virol. 1990 Jun;31(2):141-7.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Melting Point ]:
141-142ºC

[ Molecular Formula ]:
C31H55N3O6

[ Molecular Weight ]:
565.785

[ Exact Mass ]:
565.409058

[ PSA ]:
133.91000

[ LogP ]:
9.00

[ Index of Refraction ]:
1.554

[ Storage condition ]:
-20°C Freezer

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
JR1230400
CHEMICAL NAME :
Docosanamide, N-(1-beta-D-arabinofuranosyl-1,2-dihydro-2-oxo-4-pyri midinyl)-
CAS REGISTRY NUMBER :
55726-47-1
LAST UPDATED :
199612
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C31-H55-N3-O6
MOLECULAR WEIGHT :
565.89

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Blood - other changes
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 25,691,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
GTKRDX Gan to Kagaku Ryoho. Cancer and Chemotherapy. (1-8-9 Yaesu, Chuo-ku, Tokyo 103, Japan) V.1- 1974- Volume(issue)/page/year: 10,2077,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1352 mg/kg
TOXIC EFFECTS :
Blood - other changes
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 25,691,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
380 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,484,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1500 mg/kg
TOXIC EFFECTS :
Blood - other changes
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 25,691,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
525 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,484,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
810 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
GTKRDX Gan to Kagaku Ryoho. Cancer and Chemotherapy. (1-8-9 Yaesu, Chuo-ku, Tokyo 103, Japan) V.1- 1974- Volume(issue)/page/year: 10,2077,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,484,1983

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds