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Capreomycin (sulfate)

CAT: 0804-HY-17566-01Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-17566-01Size:500 mg
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Description
Capreomycin sulfate is a macrocyclic peptide antibiotic that inhibits phenylalanine synthesis in mycobacterial ribosomal translation. Capreomycin sulfate has anti-amyloidogenic and pro-fibrinolytic activities, reducing amyloid-induced cytotoxicity by inhibiting the occurrence of amyloid fibrillation. Capreomycin sulfate can be used in the study of multidrug-resistant tuberculosis, type 2 diabetes, Alzheimer's disease and Parkinson's disease[1][2][3][4][5].
CAS Number
1405-37-4
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Antibiotic; Bacterial
Type
Natural Products
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Infection; Metabolic Disease; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/Capreomycin-sulfate.html
Purity
99.52
Solubility
H2O : 100 mg/mL (ultrasonic)
Smiles
OS(O)(=O)=O.[R]C[C@H](N1)C(N[C@@H](CNC(CC(N)CCCN)=O)C(N/C(C(N[C@H](C(NC[C@H](N)C1=O)=O)[C@@H]2NC(NCC2)=N)=O)=C\NC(N)=O)=O)=O.OS(O)(=O)=O.[R=OH1A].[R=H1B]
Molecular Weight
638.61
Precautions
H302, H315, H319, H335
References & Citations
[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.|[3]Siddiqi M K, et al. Capreomycin inhibits the initiation of amyloid fibrillation and suppresses amyloid induced cell toxicity[J]. Biochimica et Biophysica Acta (BBA) -Proteins and Proteomics, 2018, 1866 (4) : 549-557.|[4]Reisfeld B, et al. A physiologically based pharmacokinetic model for capreomycin[J]. Antimicrobial agents and chemotherapy, 2012, 56 (2) : 926-934.|[5]Le Conte P, et al. Pharmacokinetics, toxicity, and efficacy of liposomal capreomycin in disseminated Mycobacterium avium beige mouse model[J]. Antimicrobial agents and chemotherapy, 1994, 38 (12) : 2695-2701.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, sealed storage, away from moisture)
Scientific Category
Natural Products
Clinical Information
Launched
Isoform
Aminoglycoside

Chemical Information

Capreomycin Sulfate

Capreomycin Sulfate is a calcium salt form of capreomycin, a cyclic polypeptide isolated from Streptomyces capreolus with antitubercular activity. Capreomycin acts by blocking bacterial ribosomal translocation.

CAS Number1405-37-4
PubChem CID71457947
IUPAC Name3,6-diamino-N-[[(2S,5S,8Z,11S,15S)-15-amino-11-(2-amino-1,4,5,6-tetrahydropyrimidin-6-yl)-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide;3,6-diamino-N-[[(2S,5S,8Z,11S,15S)-15-amino-11-(2-amino-1,4,5,6-tetrahydropyrimidin-6-yl)-8-[(carbamoylamino)methylidene]-2-methyl-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide;sulfuric acid
Molecular FormulaC50H92N28O23S2
Molecular Weight1517.6
Topological Polar Surface Area903
Hydrogen Bond Donor Count31
Hydrogen Bond Acceptor Count31
Rotatable Bond Count19
Heavy Atom Count103
Formal Charge0
Complexity2550
SMILES
C[C@H]1C(=O)N[C@H](C(=O)N/C(=C\NC(=O)N)/C(=O)N[C@H](C(=O)NC[C@@H](C(=O)N1)N)C2CCN=C(N2)N)CNC(=O)CC(CCCN)N.C1CN=C(NC1[C@H]2C(=O)NC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N/C(=C\NC(=O)N)/C(=O)N2)CNC(=O)CC(CCCN)N)CO)N)N.OS(=O)(=O)O.OS(=O)(=O)O
InChI
InChI=1S/C25H44N14O8.C25H44N14O7.2H2O4S/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;2*1-5(2,3)4/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);2*(H2,1,2,3,4)/b15-9-;16-10-;;/t11?,12-,13?,14-,16-,18-;11-,12?,13-,14?,15-,18-;;/m00../s1
InChIKey
TUATYNXRYJTQTQ-BVRBKCERSA-N
Chemical Structure
2D Structure
2D structure of Capreomycin Sulfate
CAS: 1405-37-4
CID: 71457947
Formula: C50H92N28O23S2
MW: 1517.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1517.6
Hydrogen Bond Donor Count31
Hydrogen Bond Acceptor Count31
Rotatable Bond Count19
Exact Mass1516.6331536
Monoisotopic Mass1516.6331536
Topological Polar Surface Area903 Ų
Heavy Atom Count103
Formal Charge0
Complexity2550
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count4
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count4
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
B1689-5.1Capreomycin Sulfate
90021020Capreomycin sulfate (Capastat sulfate)
27428602Capastat sulfate (Capreomycin sulfate)
2486GR005Capreomycin sulfate for biochemistry
A16425-5000Capreomycin Sulfate 5g
A16425-100Capreomycin Sulfate 100mg
A16425-1000Capreomycin Sulfate 1g
A16425-500Capreomycin Sulfate 500mg

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