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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H39N7O12
Molecular Weight 581.5741
Optical Activity UNSPECIFIED
Defined Stereocenters 15 / 15
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STREPTOMYCIN

SMILES

[H][C@]2(O[C@@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]1NC)[C@H](O[C@@]3([H])[C@H](O)[C@@H](O)[C@H](NC(N)=N)[C@@H](O)[C@@H]3NC(N)=N)O[C@@H](C)[C@]2(O)C=O

InChI

InChIKey=UCSJYZPVAKXKNQ-HZYVHMACSA-N
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

HIDE SMILES / InChI

Molecular Formula C21H39N7O12
Molecular Weight 581.5741
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 15 / 15
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Streptomycin is a water-soluble aminoglycoside derived from Streptomyces griseus. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses. Aminoglycosides like Streptomycin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically Streptomycin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes. Streptomycin is indicated for the treatment of tuberculosis. May also be used in combination with other drugs to treat tularemia (Francisella tularensis), plague (Yersia pestis), severe M. avium complex, brucellosis, and enterococcal endocarditis (e.g. E. faecalis, E. faecium).

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
5.36 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
STREPTOMYCIN SULFATE
Curative
STREPTOMYCIN SULFATE
Curative
STREPTOMYCIN SULFATE
Curative
STREPTOMYCIN SULFATE

Cmax

ValueDoseCo-administeredAnalytePopulation
42.6 μg/mL
18 mg/kg single, intramuscular
STREPTOMYCIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
264 μg × h/mL
18 mg/kg single, intramuscular
STREPTOMYCIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.67 h
18 mg/kg single, intramuscular
STREPTOMYCIN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
Intramuscular Route Only Adults: The preferred site is the upper outer quadrant of the buttock, (i.e., gluteus maximus), or themid-lateral thigh. Children: It is recommended that intramuscular injections be given preferably in the mid-lateral muscles of the thigh. In infants and small children the periphery of the upper outer quadrant of the gluteal region should be used only when necessary, such as in burn patients, in order to minimize the possibility of damage to the sciatic nerve. 1. TUBERCULOSIS: Children daily - 20-40 mg/kg Adults daily - 15 mg/kg Streptomycin is usually administered daily as a single intramuscular injection. A total dose of not more than 120 g over the course of therapy should be given unless there are no other therapeutic options. 2. TULAREMIA: One to 2 g daily in divided doses for 7 to 14 days until the patient is afebrile for 5 to 7 days. 3. PLAGUE: Two grams of Streptomycin daily in two divided doses should be administered intramuscularly. A minimum of 10 days of therapy is recommended. 4. BACTERIAL ENDOCARDITIS: a. Streptococcal endocarditis; in penicillin-sensitive alpha and non-hemolytic streptococcal endocarditis (penicillin MIC<0.1 mcg/mL), Streptomycin may be used for 2-week treatment concomitantly with penicillin. The Streptomycin regimen is 1 g b.i.d. for the first week, and 500 mg b.i.d. for the second week. If the patient is over 60 years of age, the dosage should be 500 mg b.i.d. for the entire 2- week period. b. Enterococcal endocarditis: Streptomycin in doses of 1 g b.i.d. for 2 weeks and 500 mg b.i.d. for an additional 4 weeks is given in combination with penicillin. Ototoxicity may require termination of the Streptomycin prior to completion of the 6-week course of treatment. 5. CONCOMITANT USE WITH OTHER AGENTS: For concomitant use with other agents to which the infecting organism is also sensitive: Streptomycin is considered a secondline agent for the treatment of gram-negative bacillary bactermia, meningitis, and pneumonia; brucellosis; granuloma inguinale; chancroid, and urinary tract infection. For adults: 1 to 2 grams in divided doses every six to twelve hours for moderate to severe infections. Doses should generally not exceed 2 grams per day. For children: 20 to 40 mg/kg/day (8 to 20 mg/lb/day) in divided doses every 6 to 12 hours. (Particular care should be taken to avoid excessive dosage in children).
Route of Administration: Intramuscular
In Vitro Use Guide
At 5 and 50 ug/ml, streptomycin inhibited the tubercle bacilli strongly and killed some; at the lowest tested concentration of 0.5 ug/ml, it inhibited them weakly.
Substance Class Chemical
Record UNII
Y45QSO73OB
Record Status Validated (UNII)
Record Version