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Streptomycin information


Streptomycin
Clinical data
Other namesS/STR/STS[1]
AHFS/Drugs.comMonograph
License data
  • US DailyMed: Streptomycin
Routes of
administration
Intramuscular, intravenous
ATC code
  • A07AA04 (WHO) J01GA01 (WHO) A07AA54 (WHO) J04AM01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability84% to 88% IM (est.)[2] 0% by mouth
Elimination half-life5 to 6 hours
ExcretionKidney
Identifiers
IUPAC name
  • 5-(2,4-diguanidino-
    3,5,6-trihydroxy-cyclohexoxy)- 4-[4,5-dihydroxy-6-(hydroxymethyl)
    -3-methylamino-tetrahydropyran-2-yl] oxy-3-hydroxy-2-methyl
    -tetrahydrofuran-3-carbaldehyde
CAS Number
  • 57-92-1 checkY
PubChem CID
  • 19649
DrugBank
  • DB01082 checkY
ChemSpider
  • 18508 checkY
UNII
  • Y45QSO73OB
KEGG
  • D08531 checkY
  • as salt: D01350 checkY
ChEBI
  • CHEBI:17076 checkY
ChEMBL
  • ChEMBL1201194 ☒N
NIAID ChemDB
  • 07346
PDB ligand
  • SRY (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID4023597 Edit this at Wikidata
ECHA InfoCard100.000.323 Edit this at Wikidata
Chemical and physical data
FormulaC21H39N7O12
Molar mass581.580 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point12 °C (54 °F) [citation needed]
SMILES
  • CC1C(C(C(O1)OC2C(C(C(C(C2O)O)N=C(N)N)O)N=C(N)N)OC3C(C(C(C(O3)CO)O)O)NC)(C=O)O
InChI
  • InChI=1S/C21H39N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1 checkY
  • Key:UCSJYZPVAKXKNQ-HZYVHMACSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Streptomycin is an antibiotic medication used to treat a number of bacterial infections,[3] including tuberculosis, Mycobacterium avium complex, endocarditis, brucellosis, Burkholderia infection, plague, tularemia, and rat bite fever.[3] For active tuberculosis it is often given together with isoniazid, rifampicin, and pyrazinamide.[4] It is administered by injection into a vein or muscle.[3]

Common side effects include vertigo, vomiting, numbness of the face, fever, and rash.[3] Use during pregnancy may result in permanent deafness in the developing baby.[3] Use appears to be safe while breastfeeding.[4] It is not recommended in people with myasthenia gravis or other neuromuscular disorders.[4] Streptomycin is an aminoglycoside.[3] It works by blocking the ability of 30S ribosomal subunits to make proteins, which results in bacterial death.[3]

Albert Schatz first isolated streptomycin in 1943 from Streptomyces griseus.[5][6] It is on the World Health Organization's List of Essential Medicines.[7] The World Health Organization classifies it as critically important for human medicine.[8]

  1. ^ "Antibiotic abbreviations list". Retrieved June 22, 2023.
  2. ^ Cite error: The named reference Zhu2001 was invoked but never defined (see the help page).
  3. ^ a b c d e f g "Streptomycin Sulfate". The American Society of Health-System Pharmacists. Archived from the original on December 20, 2016. Retrieved December 8, 2016.
  4. ^ a b c World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 136, 144, 609. hdl:10665/44053. ISBN 9789241547659.
  5. ^ Torok E, Moran E, Cooke F (2009). Oxford Handbook of Infectious Diseases and Microbiology. OUP Oxford. p. Chapter 2. ISBN 9780191039621. Archived from the original on September 8, 2017.
  6. ^ Renneberg R, Demain AL (2008). Biotechnology for Beginners. Elsevier. p. 103. ISBN 9780123735812. Archived from the original on September 10, 2017.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528. License: CC BY-NC-SA 3.0 IGO.

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