(3S)-3,6-diamino-N-{[(2S,5S,8E,11S,15S)-15-amino-11-[(4R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-5-yl]methyl}hexanamide; (3S)-3,6-diamino-N-{[(2S,5S,8E,11S,15S)-15-amino-11-[(4R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-methyl-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-5-yl]methyl}hexanamide

• ChemBase ID: 199
• Molecular Formular: C50H88N28O15
• Molecular Mass: 1321.41232
• Monoisotopic Mass: 1320.69839426
• SMILES: O=C1NC[C@H](N)C(=O)N[C@H](C(=O)N[C@@H](CNC(=O)C[C@@H](N)CCCN)C(=O)N/C(=C/NC(=O)N)/C(=O)N[C@H]1[C@@H]1NC(=NCC1)N)CO.O=C1NC[C@H](N)C(=O)N[C@H](C(=O)N[C@@H](CNC(=O)C[C@@H](N)CCCN)C(=O)N/C(=C/NC(=O)N)/C(=O)N[C@H]1[C@@H]1NC(=NCC1)N)C
• Canonical SMILES: NCCC[C@@H](CC(=O)NC[C@@H]1NC(=O)[C@H](CO)NC(=O)[C@@H](N)CNC(=O)[C@@H](NC(=O)/C(=C\NC(=O)N)/NC1=O)[C@H]1CCN=C(N1)N)N.NCCC[C@@H](CC(=O)NC[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](N)CNC(=O)[C@@H](NC(=O)/C(=C\NC(=O)N)/NC1=O)[C@H]1CCN=C(N1)N)N
• InChI: InChI=1S/C25H44N14O8.C25H44N14O7/c26-4-1-2-11(27)6-17(41)32-8-14-20(43)35-15(9-34-25(30)47)21(44)39-18(13-3-5-31-24(29)38-13)23(46)33-7-12(28)19(42)37-16(10-40)22(45)36-14;1-11-19(41)36-15(9-32-17(40)7-12(27)3-2-5-26)21(43)37-16(10-34-25(30)46)22(44)39-18(14-4-6-31-24(29)38-14)23(45)33-8-13(28)20(42)35-11/h9,11-14,16,18,40H,1-8,10,26-28H2,(H,32,41)(H,33,46)(H,35,43)(H,36,45)(H,37,42)(H,39,44)(H3,29,31,38)(H3,30,34,47);10-15,18H,2-9,26-28H2,1H3,(H,32,40)(H,33,45)(H,35,42)(H,36,41)(H,37,43)(H,39,44)(H3,29,31,38)(H3,30,34,46)/b15-9+;16-10+/t11-,12-,13+,14-,16-,18-;11-,12-,13-,14+,15-,18-/m00/s1
• InChIKey: VCOPTHOUUNAYKQ-WBTCAYNUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3,6-diamino-N-{[(2S,5S,8E,11S,15S)-15-amino-11-[(4R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-5-yl]methyl}hexanamide; (3S)-3,6-diamino-N-{[(2S,5S,8E,11S,15S)-15-amino-11-[(4R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-methyl-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-5-yl]methyl}hexanamide
• IUPAC Traditional name: (3S)-3,6-diamino-N-{[(2S,5S,8E,11S,15S)-15-amino-11-[(4R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-5-yl]methyl}hexanamide; (3S)-3,6-diamino-N-{[(2S,5S,8E,11S,15S)-15-amino-11-[(4R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-methyl-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-5-yl]methyl}hexanamide
• Brand Name: Ogostal; Caprocin
• Synonyms: Capreomycin sulphate; Capreomycin; Capastat; Capastat sulfate; Capreomycin sulfate; Capreomycin

Database IDs

• CAS Number: 11003-38-6
• PubChem SID: 46508514; 160963662
• PubChem CID: 3000502

CALCULATED PROPERTIES

• Acid pKa: 10.622467
• H Acceptors: 14
• H Donor: 14
• LogD (pH = 5.5): -20.15656
• LogD (pH = 7.4): -17.134743
• Log P: -11.191733
• Molar Refractivity: 162.2049 cm^3
• Polarizability: 63.26125 Å^3
• Polar Surface Area: 378.42 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Soluble in water as disulfate salt.
• Hydrophobicity(logP): -9.609

DETAILS

DrugBank - DB00314

• Drug Groups: approved
• Description: Cyclic peptide antibiotic similar to viomycin. It is produced by Streptomyces capreolus. [PubChem]
• Indication: Used in the treatment of tuberculosis in combination with other drugs.
• Pharmacology: Capreomycin is a member of the aminoglycoside family of antibiotics. These antibiotics have the ability to kill a wide variety of bacteria, including bacteria responsible for causing tuberculosis (TB).
• Toxicity: Hypokalemia, hypocalcemia, hypomagnesemia, and an electrolyte disturbance resembling Bartter's syndrome have been reported to occur in patients with capreomycin toxicity. The subcutaneous median lethal dose (LD₅₀) in mice was 514 mg/kg.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Not absorbed in significant quantities from the gastrointestinal tract and must be administered parenterally.
• Elimination: When a 1–g dose of capreomycin was given intramuscularly to normal volunteers, 52% was excreted in the urine within 12 hours.
• External Links: Wikipedia; Drugs.com