Streptomycin

Streptomycin
Clinical data


AHFS/Drugs.com	Monograph
Pregnancy category	US: D (Evidence of risk)
Routes of administration	intramuscular, intravenous
ATC code	A07AA04 (WHO) J01GA01 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	84% to 88% IM (est.) 0% by mouth
Biological half-life	5 to 6 hours
Excretion	kidney
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^Y
PubChem CID	19649
DrugBank	DB01082^Y
ChemSpider	18508^Y
UNII	Y45QSO73OB
KEGG	D08531^Y
ChEBI	CHEBI:17076^Y
ChEMBL	CHEMBL1201194^N
NIAID ChemDB	07346
ECHA InfoCard	100.000.323
Chemical and physical data
Formula	C₂₁H₃₉N₇O₁₂
Molar mass	581.574 g/mol
3D model (Jmol)	Interactive image
Melting point	12 °C (54 °F)
SMILES C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](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^Y Key:UCSJYZPVAKXKNQ-HZYVHMACSA-N^Y
^NY (what is this?)

84% to 88% IM (est.)

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

Common side effects include feeling like the world is spinning, vomiting, numbness of the face, fever, and rash. Use during pregnancy may result in permanent deafness in the baby. Use appears to be safe while breastfeeding. It is not recommended in people with myasthenia gravis. Streptomycin is in the aminoglycoside class of medication. It works by blocking the ability of 30S ribosomal subunits to make proteins which results in bacterial death.

Streptomycin was discovered in 1943 from Streptomyces griseus. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is between 0.38 and 4.39 USD per day. In the United States a course of treatment costs more than 200 USD.