Details of the Drug

General Information of Drug (ID: DMNZBRY)

Drug Name
Capreomycin
Synonyms
Capreomycin Sulfate Standard; Capreomycin sulphate; Caprocin (Disulfate); Ogostal (Disulfate); (3S)-3,6-diamino-N-[[(2S,5S,8E,11S,15S)-15-amino-11-[(6R)-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; (3S)-3,6-diamino-N-[[(2S,5S,8E,11S,15S)-15-amino-11-[(6R)-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
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Pulmonary tuberculosis 1B10.Z Approved [2]
Mycobacterium infection 1B10-1B21 Phase 2 [3]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J04AB30: Capreomycin
J04AB: Antibiotics
J04A: DRUGS FOR TREATMENT OF TUBERCULOSIS
J04: ANTIMYCOBACTERIALS
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski):
4		 Molecular Weight 1321.4
Logarithm of the Partition Coefficient Not Available
Rotatable Bond Count 19
Hydrogen Bond Donor Count 27
Hydrogen Bond Acceptor Count 23
ADMET Property
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 26.606 micromolar/kg/day [4]
Chemical Identifiers
Formula
C50H88N28O15
IUPAC Name
(3S)-3,6-diamino-N-[[(2S,5S,8E,11S,15S)-15-amino-11-[(6R)-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;(3S)-3,6-diamino-N-[[(2S,5S,8E,11S,15S)-15-amino-11-[(6R)-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
Canonical 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)[C@H]2CCN=C(N2)N)CNC(=O)C[C@H](CCCN)N.C1CN=C(N[C@H]1[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)C[C@H](CCCN)N)CO)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
Cross-matching ID
PubChem CID
3000502
CAS Number
11003-38-6
UNII
232HYX66HC
DrugBank ID
DB00314
TTD ID
D0E7MV
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial 70S ribosomal RNA (Bact 70S rRNA) TTIA0J5 NOUNIPROTAC Binder [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Capreomycin
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Rabeprazole DMMZXIW Moderate Increased risk of hypomagnesemia by the combination of Capreomycin and Rabeprazole. Bacterial infection [1A00-1C4Z] [6]
Coadministration of a Drug Treating the Disease Different from Capreomycin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Decreased renal excretion of Capreomycin caused by Remdesivir mediated nephrotoxicity. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [7]
Dronedarone DMA8FS5 Major Increased risk of ventricular arrhythmias by the combination of Capreomycin and Dronedarone. Angina pectoris [BA40] [8]
Promazine DMZAL7W Moderate Increased risk of ventricular arrhythmias by the combination of Capreomycin and Promazine. Appearance/behaviour symptom [MB23] [7]
Etidronic acid DM1XHYJ Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Etidronic acid. Bone paget disease [FB85] [9]
Iodipamide DMXIQYS Major Increased risk of nephrotoxicity by the combination of Capreomycin and Iodipamide. Cholelithiasis [DC11] [10]
Oxaliplatin DMQNWRD Moderate Decreased renal excretion of Capreomycin caused by Oxaliplatin mediated nephrotoxicity. Colorectal cancer [2B91] [11]
Atracurium DM42HXN Moderate Additive neuromuscular blocking effects by the combination of Capreomycin and Atracurium. Corneal disease [9A76-9A78] [12]
Mivacurium DM473VD Moderate Additive neuromuscular blocking effects by the combination of Capreomycin and Mivacurium. Corneal disease [9A76-9A78] [12]
Pancuronium DMB0VY8 Moderate Additive neuromuscular blocking effects by the combination of Capreomycin and Pancuronium. Corneal disease [9A76-9A78] [12]
Tubocurarine DMBZIVP Moderate Additive neuromuscular blocking effects by the combination of Capreomycin and Tubocurarine. Corneal disease [9A76-9A78] [12]
Methoxyflurane DML0RAE Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Methoxyflurane. Corneal disease [9A76-9A78] [13]
Cidofovir DMA13GD Major Increased risk of nephrotoxicity by the combination of Capreomycin and Cidofovir. Cytomegaloviral disease [1D82] [14]
Ethacrynic acid DM60QMR Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Ethacrynic acid. Essential hypertension [BA00] [7]
Amphotericin B DMTAJQE Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Amphotericin B. Fungal infection [1F29-1F2F] [7]
Dexlansoprazole DM1DBV5 Moderate Increased risk of hypomagnesemia by the combination of Capreomycin and Dexlansoprazole. Gastro-oesophageal reflux disease [DA22] [6]
Omeprazole DM471KJ Moderate Increased risk of hypomagnesemia by the combination of Capreomycin and Omeprazole. Gastro-oesophageal reflux disease [DA22] [6]
Furosemide DMMQ8ZG Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Furosemide. Heart failure [BD10-BD1Z] [7]
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [7]
Balsalazide DM7I1T9 Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Balsalazide. Indeterminate colitis [DD72] [15]
Ibandronate DM0QZBN Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Ibandronate. Low bone mass disorder [FB83] [16]
Arsenic trioxide DM61TA4 Major Increased risk of ventricular arrhythmias by the combination of Capreomycin and Arsenic trioxide. Mature B-cell lymphoma [2A85] [17]
Clofarabine DMCVJ86 Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Clofarabine. Mature B-cell lymphoma [2A85] [18]
Exjade DMHPRWG Major Increased risk of nephrotoxicity by the combination of Capreomycin and Exjade. Mineral absorption/transport disorder [5C64] [19]
Zoledronate DMIXC7G Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Zoledronate. Mineral excesses [5B91] [16]
Droperidol DM0DXA8 Major Increased risk of ventricular arrhythmias by the combination of Capreomycin and Droperidol. Nausea/vomiting [MD90] [20]
Levomethadyl Acetate DM06HG5 Major Increased risk of ventricular arrhythmias by the combination of Capreomycin and Levomethadyl Acetate. Opioid use disorder [6C43] [21]
Carboplatin DMG281S Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Carboplatin. Ovarian cancer [2C73] [7]
Esomeprazole DM7BN0X Moderate Increased risk of hypomagnesemia by the combination of Capreomycin and Esomeprazole. Peptic ulcer [DA61] [6]
Pemetrexed DMMX2E6 Moderate Decreased renal excretion of Capreomycin caused by Pemetrexed mediated nephrotoxicity. Pleural mesothelioma [2C26] [22]
Fluphenazine DMIT8LX Moderate Increased risk of ventricular arrhythmias by the combination of Capreomycin and Fluphenazine. Psychotic disorder [6A20-6A25] [7]
Everolimus DM8X2EH Major Increased risk of nephrotoxicity by the combination of Capreomycin and Everolimus. Renal cell carcinoma [2C90] [23]
Temsirolimus DMS104F Major Increased risk of nephrotoxicity by the combination of Capreomycin and Temsirolimus. Renal cell carcinoma [2C90] [23]
Colistimethate DMZ9BMU Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Colistimethate. Respiratory infection [CA07-CA4Z] [7]
Sulfasalazine DMICA9H Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Sulfasalazine. Rheumatoid arthritis [FA20] [15]
Thioridazine DM35M8J Moderate Increased risk of ventricular arrhythmias by the combination of Capreomycin and Thioridazine. Schizophrenia [6A20] [7]
Paliperidone DM7NPJS Moderate Increased risk of ventricular arrhythmias by the combination of Capreomycin and Paliperidone. Schizophrenia [6A20] [7]
Haloperidol DM96SE0 Moderate Increased risk of ventricular arrhythmias by the combination of Capreomycin and Haloperidol. Schizophrenia [6A20] [7]
Chlorpromazine DMBGZI3 Moderate Increased risk of ventricular arrhythmias by the combination of Capreomycin and Chlorpromazine. Schizophrenia [6A20] [7]
Trifluoperazine DMKBYWI Moderate Increased risk of ventricular arrhythmias by the combination of Capreomycin and Trifluoperazine. Schizophrenia [6A20] [7]
Risperidone DMN6DXL Moderate Increased risk of ventricular arrhythmias by the combination of Capreomycin and Risperidone. Schizophrenia [6A20] [7]
Amisulpride DMSJVAM Moderate Increased risk of ventricular arrhythmias by the combination of Capreomycin and Amisulpride. Schizophrenia [6A20] [7]
Pimozide DMW83TP Major Increased risk of ventricular arrhythmias by the combination of Capreomycin and Pimozide. Schizophrenia [6A20] [24]
Bacitracin DM5OHYE Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Bacitracin. Skin and skin-structure infection [1F28-1G0Z] [7]
Cisplatin DMRHGI9 Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Cisplatin. Solid tumour/cancer [2A00-2F9Z] [7]
Pipecuronium DM5F84A Moderate Additive neuromuscular blocking effects by the combination of Capreomycin and Pipecuronium. Tonus and reflex abnormality [MB47] [12]
Doxacurium DMKE7L9 Moderate Additive neuromuscular blocking effects by the combination of Capreomycin and Doxacurium. Tonus and reflex abnormality [MB47] [12]
Vecuronium DMP0UK2 Moderate Additive neuromuscular blocking effects by the combination of Capreomycin and Vecuronium. Tonus and reflex abnormality [MB47] [12]
Cisatracurium DMUZPJ5 Moderate Additive neuromuscular blocking effects by the combination of Capreomycin and Cisatracurium. Tonus and reflex abnormality [MB47] [12]
Rocuronium DMY9BMK Moderate Additive neuromuscular blocking effects by the combination of Capreomycin and Rocuronium. Tonus and reflex abnormality [MB47] [12]
Sirolimus DMGW1ID Major Increased risk of nephrotoxicity by the combination of Capreomycin and Sirolimus. Transplant rejection [NE84] [23]
Tacrolimus DMZ7XNQ Major Increased risk of nephrotoxicity by the combination of Capreomycin and Tacrolimus. Transplant rejection [NE84] [23]
Olsalazine DMZW9HA Moderate Increased risk of nephrotoxicity by the combination of Capreomycin and Olsalazine. Ulcerative colitis [DD71] [15]
Amiodarone DMUTEX3 Major Increased risk of ventricular arrhythmias by the combination of Capreomycin and Amiodarone. Ventricular tachyarrhythmia [BC71] [25]
⏷ Show the Full List of 53 DDI Information of This Drug

References

1 Novel agents in the management of Mycobacterium tuberculosis disease. Curr Med Chem. 2007;14(18):2000-8.
2 Capreomycin FDA Label
3 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 Interaction between the ribosomal subunits: 16S rRNA suppressors of the lethal DeltaA1916 mutation in the 23S rRNA of Escherichia coli. Mol Genet Genomics. 2007 Sep;278(3):307-15.
6 FDA. U.S. Food and Drug Administration "FDA Drug Safety Communication: Low magnesium levels can be associated with long-term use of proton pump inhibitor drugs (PPIs).".
7 Cerner Multum, Inc. "Australian Product Information.".
8 Product Information. Multaq (dronedarone). sanofi-aventis , Bridgewater, NJ.
9 Chang JT, Green L, Beitz J "Renal failure with the use of zoledronic acid." N Engl J Med 349 (2003): 1676-9 discussion 1676-9. [PMID: 14573746]
10 Wong GT, Lee EY, Irwin MG. Contrast induced nephropathy in vascular surgery.?Br J Anaesth. 2016;117 Suppl 2:ii63-ii73. [PMID: 27566809]
11 Product Information. Eloxatin (oxaliplatin). Sanofi Winthrop Pharmaceuticals, New York, NY.
12 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
13 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
14 Product Information. Vistide (cidofovir). Gilead Sciences, Foster City, CA.
15 Novis BH, Korzets Z, Chen P, Bernheim J "Nephrotic syndrome after treatment with 5-aminosalicylic acid." Br Med J (Clin Res Ed) 296 (1988): 1442. [PMID: 3132281]
16 Banerjee D, Asif A, Striker L, Preston RA, Bourgoignie JJ, Roth D "Short-term, high-dose pamidronate-induced acute tubular necrosis: The postulated mechanisms of bisphosphonate nephrotoxicity." Am J Kidney Dis 41 (2003): E18. [PMID: 12778436]
17 Ohnishi K, Yoshida H, Shigeno K, et al. "Prolongation of the QT interval and ventricular tachycardia in patients treated with arsenic trioxide for acute promyelocytic leukemia." Ann Intern Med 133 (2000): 881-5. [PMID: 11103058]
18 Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
19 Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
20 Canadian Pharmacists Association.
21 Cohen J "Long-term efficacy and safety of terazosin alone and in combination with other antihypertensive agents." Am Heart J 122 (1991): 919-25. [PMID: 1678923]
22 Product Information. Alimta (pemetrexed). Lilly, Eli and Company, Indianapolis, IN.
23 Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
24 Product Information. Orap Tablets (pimozide). Gate Pharmaceuticals, Sellersville, PA.
25 Antonelli D, Atar S, Freedberg NA, Rosenfeld T "Torsade de pointes in patients on chronic amiodarone treatment: contributing factors and drug interactions." Isr Med Assoc J 7 (2005): 163-5. [PMID: 15792261]