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Basic Information
CAS No.: 55726-47-1
Name: Enocitabine
Article Data: 5
Molecular Structure:
Molecular Structure of 55726-47-1 (Enocitabine)
Formula: C31H55 N3 O6
Molecular Weight: 565.794
Synonyms: BH-AC;Behenoylcytosine arabinoside;Enocitabine;N4-Behenoyl-1-b-D-arabinofuranosylcytosine;N4-Behenoylcytosine arabinoside;NSC 239336;Sunrabin;
EINECS: 1312995-182-4
Density: 1.16g/cm3
Melting Point: 141-142°C
Boiling Point: °Cat760mmHg
Flash Point: °C
Safety: Poison by intravenous route. Moderately toxic by subcutaneous and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx.
PSA: 133.91000
LogP: 5.68820
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Chemistry

Molecular Structure of Enocitabine (55726-47-1):

 IUPAC Name: N-[1-[(2R,3S,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]docosanamide 
Molecular Formula: C31H55N3O6
Molecular Weight: 565.7849 g/mol
XLogP3: 9.2
H-Bond Donor: 4
H-Bond Acceptor: 6
Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N(C=C1)C2C(C(C(O2)CO)O)O
Isomeric SMILES: CCCCCCCCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N(C=C1)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O
InChI: InChI=1S/C31H55N3O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(36)32-26-22-23-34(31(39)33-26)30-29(38)28(37)25(24-35)40-30/h22-23,25,28-30,35,37-38H,2-21,24H2,1H3,(H,32,33,36,39)/t25-,28-,29+,30-/m1/s1
InChIKey: SAMRUMKYXPVKPA-VFKOLLTISA-N
Index of Refraction: 1.554
Molar Refractivity: 155.85 cm3
Molar Volume: 486 cm3
Surface Tension: 44.4 dyne/cm
Density: 1.16 g/cm3
Melting Point: 141-142 °C

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 525mg/kg (525mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 484, 1983.
mouse LD50 intravenous 500mg/kg (500mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 484, 1983.
mouse LD50 oral > 1500mg/kg (1500mg/kg) BLOOD: OTHER CHANGES Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 25, Pg. 691, 1983.
mouse LD50 subcutaneous 810mg/kg (810mg/kg)   Gan to Kagaku Ryoho. Cancer and Chemotherapy. Vol. 10, Pg. 2077, 1983.
rat LD50 intraperitoneal 1100mg/kg (1100mg/kg)   Gan to Kagaku Ryoho. Cancer and Chemotherapy. Vol. 10, Pg. 2077, 1983.
rat LD50 intravenous 380mg/kg (380mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 484, 1983.
rat LD50 oral > 1gm/kg (1000mg/kg) BLOOD: OTHER CHANGES Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 25, Pg. 691, 1983.
rat LD50 subcutaneous > 1352mg/kg (1352mg/kg) BLOOD: OTHER CHANGES Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 25, Pg. 691, 1983.

Safety Profile

Poison by intravenous route. Moderately toxic by subcutaneous and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx.

Specification

   Enocitabine (55726-47-1) is a nucleoside analog which can be used as chemotherapy under the brand name Sunrabin. Sunrabin can cause allergic reactions because it contains the emulsifier HCO-60 . Enocitabine (55726-47-1) is also known as Enocitabine [INN:JAN] ; Behenoylcytosine arabinoside ; Enocitabina ; Enocitabina [INN-Spanish] ; Enocitabinum ; Enocitabinum [INN-Latin] ; N(sup 4)-Behenoyl-1-beta-D-arabinofuranosylcytosine ; N(sup 4)-Behenoylcytosine arabinoside ; N-(1-beta-D-Arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)docosanamide ; Sunrabin ; Docosanamide, N-(1-beta-D-arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)- .