capreomycin

Names

[ Name ]:
capreomycin

[Synonym ]:
3,6-diamino-N-(((8E)-15-amino-3,6,9,12,16-pentahydroxy-8-(((hydroxy(imino)methyl)amino)methylene)-2-(hydroxymethyl)-11-(2-iminohexahydropyrimidin-4-yl)-1,4,7,10,13-pentaazacyclohexadeca-3,6,9,12,16-pentaen-5-yl)methyl)hexanimidic acid compound with sulfuric acid (1:1)
3,6-Diamino-N-{[(8Z)-15-amino-11-(2-amino-3,4,5,6-tetrahydro-4-pyrimidinyl)-8-[(carbamoylamino)methylene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-5-yl]methyl}hexanamide sulfate (1:1)
Hexanamide, 3,6-diamino-N-[[(8Z)-15-amino-8-[[(aminocarbonyl)amino]methylene]-11-(2-amino-3,4,5,6-tetrahydro-4-pyrimidinyl)-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadec-5-yl]methyl]-, sulfate (1:1) (salt)

Biological Activity

[Description]:

Capreomycin is a macrocyclic peptide antibiotic. Capreomycin can be used for anti-multidrug-resistant-tuberculosis research. Capreomycin can inhibit phenylalanine synthesis in in mycobacterial ribosomes translation[1][2]

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Mycobacterial[1]

[In Vivo]

Capreomycin (1.4, 7.2, and 14.5 mg/kg for inhale; 20 mg/kg for i.m.; 4 weeks) decreases the wet lung weight and lowers bacterial burden in the lungs of infected guinea pigs[2]. Animal Model: Male guinea pigs [836 ± 162.3 g; infected via the respiratory route with nebulized suspensions 2 × 105 CFU/mL of Mycobacterium tuberculosis (strain H37Rv)][2] Dosage: 1.4, 7.2, and 14.5 mg/kg for inhale; 20 mg/kg for i.m. Administration: Inhaling or i.m.; 4 weeks Result: Significantly decreased the wet lung weight at 14.5 mg/kg, and smaller than receiving 1.4 mg/kg group and controls. Significantly lowered bacterial burden in the lungs (3.52 ± 0.20 CFU/mL; P < 0.05) at 14.5 mg/kg than controls (4.58 ± 0.20 CFU/mL) and at 1.4 and 7.2 mg/kg (4.02 ± 0.32 and 4.01 ± 0.29 CFU/mL, respectively).

[References]

[1]. Maus CE, et al. Mutation of tlyA confers capreomycin resistance in Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2005 Feb;49(2):571-7.

[2]. Garcia-Contreras L, et al. Inhaled large porous particles of capreomycin for treatment of tuberculosis in a guinea pig model. Antimicrob Agents Chemother. 2007 Aug;51(8):2830-6.

Chemical & Physical Properties

[ Boiling Point ]:
1376.7ºC at 760 mmHg

[ Molecular Formula ]:
C₂₅H₄₆N₁₄O₁₂S

[ Molecular Weight ]:
766.784

[ Flash Point ]:
786.4ºC

[ Exact Mass ]:
766.314026

[ PSA ]:
480.83000

[ Vapour Pressure ]:
0mmHg at 25°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EX8920000

CHEMICAL NAME :: Capreomycin

CAS REGISTRY NUMBER :: 11003-38-6

LAST UPDATED :: 198910

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 1371 mg/kg/96D-I

TOXIC EFFECTS :: Vascular - BP elevation not characterized in autonomic section Nutritional and Gross Metabolic - changes in potassium Nutritional and Gross Metabolic - metabolic alkalosis

REFERENCE :: AJKDDP American Journal of Kidney Diseases. (Grune & Stratton, Inc., Journal Subscription Dept., POB 6280, Duluth, MN 55806) V.1- 1981- Volume(issue)/page/year: 7,245,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 514 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 25,353,1974

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 238 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 25,353,1974

Related Compounds

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