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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H24N2O7.H2O4S
Molecular Weight 430.428
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SPECTINOMYCIN SULFATE

SMILES

OS(O)(=O)=O.[H][C@@]12O[C@H](C)CC(=O)[C@]1(O)O[C@]3([H])[C@@H](NC)[C@@H](O)[C@@H](NC)[C@H](O)[C@@]3([H])O2

InChI

InChIKey=XGBFWQUQYQIFLB-MTTMTQIXSA-N
InChI=1S/C14H24N2O7.H2O4S/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14;1-5(2,3)4/h5,7-13,15-16,18-20H,4H2,1-3H3;(H2,1,2,3,4)/t5-,7-,8+,9+,10+,11-,12-,13+,14+;/m1./s1

HIDE SMILES / InChI

Description

Spectinomycin is an antibiotic produced by Streptomyces spectabilis. It is active against gram-negative bacteria and used for the treatment of acute gonorrheal urethritis and proctitis in the male and acute gonorrheal cervicitis and proctitis in the female when due to susceptible strains of Neisseria gonorrhoeae. In vitro studies have shown spectinomycin to be active against most strains of Neisseria gonorrhoeae (minimum inhibitory concentration <7.5 to 20 mcg/mL). Footprint studies indicate that spectinomycin exerts regional effects on ribosomal structure. Spectinomycin hydrochloride is an inhibitor of protein synthesis in the bacterial cell; the site of action is the 30S ribosomal subunit. The antibiotic is not significantly bound to plasma protein. Spectinomycin was discovered 1961. It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system. This antibiotic is no longer available in the United States. Pfizer has discontinued distribution of spectinomycin (Trobicin) in the U.S. The drug continues to be distributed outside the U.S.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TROBICIN
Curative
TROBICIN
Curative
TROBICIN

Cmax

ValueDoseCo-administeredAnalytePopulation
100 μg/mL
2 g single, intramuscular
SPECTINOMYCIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
460 μg × h/mL
2 g single, intramuscular
SPECTINOMYCIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.7 h
2 g single, intramuscular
SPECTINOMYCIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
2 g single, intramuscular
SPECTINOMYCIN plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
Adults (Men and Women)—Inject 5 mL intramuscularly for a 2-gram dose. This is also the recommended dose for patients being treated after failure of previous antibiotic therapy
Route of Administration: Intramuscular
In Vitro Use Guide
Antibiotic susceptibility surveillance testing was performed on clinical isolates of Neisseria gonorrhoeae collected in September 1989 in the Philippines. Spectinomycin resistance was rare (10 of 117), but the MIC90 was 32 micrograms/ml.