阿贝卡星, Arbekacin

Inhibitor of DNA replication; aminoglycoside class.

Arbekacin is a semisynthetic aminoglycoside antibiotic derived from dibekacin with activity against both gram-positive and gram-negative bacteria. Arbekacin is most commonly used in the treatment of multi-resistant bacterial infections.

Arbekacin, also known as ABK or arbekacin sulfATE, belongs to the class of organic compounds known as 4, 6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions. Arbekacin exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Arbekacin has been detected in multiple biofluids, such as urine and blood. Within the cell, arbekacin is primarily located in the cytoplasm. In humans, arbekacin is involved in the arbekacin action pathway.

Arbekacin is a kanamycin that is kanamycin B bearing an N-(2S)-4-amino-2-hydroxybutyryl group on the aminocyclitol ring. It has a role as an antimicrobial agent, a protein synthesis inhibitor, an antibacterial agent and an antibacterial drug. It is a member of kanamycins and an aminoglycoside. It derives from a kanamycin B.

Title: Arbekacin

CAS Registry Number: 51025-85-5

CAS Name: O-3-Amino-3-deoxy-a-D-glucopyranosyl-(1®6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-a-D-erythro-hexopyranosyl-(1®4)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-D-streptamine

Additional Names: 1-N-[(S)-4-amino-2-hydroxybutyryl]dibekacin; 1-N-[(S)-4-amino-2-hydroxybutyryl]-3¢,4¢-dideoxykanamycin B; HBK

Molecular Formula: C22H44N6O10

Molecular Weight: 552.62

Percent Composition: C 47.82%, H 8.03%, N 15.21%, O 28.95%

Literature References: Aminoglycoside antibiotic; derivative of kanamycin B, q.v. Prepn and antibacterial activity: S. Kondo et al., J. Antibiot. 26, 412 (1973); H. Umezawa et al., DE 2350169; eidem, US 4107424 (1974, 1978 both to Microbiochem. Res. Found.). Mechanism of action: N. Tanaka et al., Antimicrob. Agents Chemother. 24, 797 (1983); K. Matsunaga et al., J. Antibiot. 37, 596 (1984). Pharmacology: J. Stewens et al., Arzneim.-Forsch. 35, 1440 (1985); M. Kurebe et al., ibid. 36, 1511 (1986). Series of articles on antibacterial activity, pharmacology, pharmacokinetics, and clinical experience: Chemotherapy 34, Suppl. 1, pp 1-670 (1986). Review: Y. Kobayashi et al., Int. J. Antimicrob. Agents 5, 227-230 (1995).

Derivative Type: Sulfate

CAS Registry Number: 104931-87-5

Manufacturers' Codes: 1665-RB

Trademarks: Habekacin (Meiji Seika)

Molecular Formula: C22H44N6O10.H2SO4

Molecular Weight: 650.70

Percent Composition: C 40.61%, H 7.13%, N 12.92%, O 34.42%, S 4.93%

Derivative Type: Dicarbonate

Molecular Formula: C24H48N6O16

Molecular Weight: 676.67

Percent Composition: C 42.60%, H 7.15%, N 12.42%, O 37.83%

Properties: Colorless, crystalline powder, mp 178° (dec). [a]D24 +86.8° (c = 0.77 in water). LD50 i.v. in mice: >150 mg/kg (Umezawa, 1978).

Melting point: mp 178° (dec)

Optical Rotation: [a]D24 +86.8° (c = 0.77 in water)

Toxicity data: LD50 i.v. in mice: >150 mg/kg (Umezawa, 1978)

Therap-Cat: Antibacterial.

Keywords: Antibacterial (Antibiotics); Aminoglycosides.