55726-47-1 , Enocitabine, 依诺他滨, CAS:55726-47-1

55726-47-1 , Enocitabine,
依诺他滨,
CAS:55726-47-1
C31H55N3O6 / 565.78
MFCD00866294

Enocitabine, 依诺他滨

Nucleoside analog and DNA replication inhibitor. Inhibits replication of human cytomegalovirus in vitro. Antitumor and antiviral agent. Active in vitro and in vivo.

Enocitabine is a cytarabine derivative, cytosine analog and DNA chain terminator. It also inhibits replication and growth of cytomegalovirus.

Title: Enocitabine

CAS Registry Number: 55726-47-1

CAS Name: N-(1-b-D-Arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)docosanamide

Additional Names: N(4)-behenoyl-1-b-D-arabinofuranosylcytosine; behenoylcytosine arabinoside; BH-AC

Manufacturers' Codes: NSC-239336

Trademarks: Sunrabin (Asahi)

Molecular Formula: C31H55N3O6

Molecular Weight: 565.78

Percent Composition: C 65.81%, H 9.80%, N 7.43%, O 16.97%

Literature References: Deriv of cytarabine, q.v. Prepn: T. Ishida et al., DE 2426304; eidem, US 3991045 (1975, 1976 both to Asahi); M. Akiyama et al., Chem. Pharm. Bull. 26, 981 (1978). Antitumor activity: M. Aoshima et al., Cancer Res. 36, 2726 (1976); eidem, ibid. 37, 2481 (1977). Distribution, excretion: M. Fukama et al., Gan to Kagaku Ryoho 7, 2109 (1980), C.A. 95, 35186 (1981). Effect and mode of action: T. Kataoka, Y. Sakurai, Recent Results Cancer Res. 70, 147 (1980). Pharmacological and clinical studies: K. Yamada et al., ibid. 219.

Properties: Crystals from DMSO, mp 141-142°. [a]D +70° (c = 1 in THF, 22°). uv max (isopropyl alcohol): 216, 248, 303 nm (e 16400, 15200, 8200).

Melting point: mp 141-142°

Optical Rotation: [a]D +70° (c = 1 in THF, 22°)

Absorption maximum: uv max (isopropyl alcohol): 216, 248, 303 nm (e 16400, 15200, 8200)

Therap-Cat: Antineoplastic.

Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs.

CAS Number	55726-47-1
Product Name	Enocitabine
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	565.78 g/mol
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
InChI Key	SAMRUMKYXPVKPA-VFKOLLTISA-N
SMILES	CCCCCCCCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N(C=C1)C2C(C(C(O2)CO)O)O
Solubility	Soluble in DMSO
Synonyms	behenoyl ara-C, behenoyl cytarabine, BH-AC, enocitabine, N(4)-behenoyl ara-C, N(4)-behenoyl-1-beta-arabinofuranosylcytosine, N(4)-behenoyl-1-beta-D-arabinofuranosylcytosine, NSC 239336, NSC-239336, sunrabim
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