Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H24N2O7.2ClH.5H2O |
Molecular Weight | 495.348 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.O.O.Cl.Cl.[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=DCHJOVNPPSBWHK-UXXUFHFZSA-N
InChI=1S/C14H24N2O7.2ClH.5H2O/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;;;;;;;/h5,7-13,15-16,18-20H,4H2,1-3H3;2*1H;5*1H2/t5-,7-,8+,9+,10+,11-,12-,13+,14+;;;;;;;/m1......./s1
Molecular Formula | C14H24N2O7 |
Molecular Weight | 332.3496 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.jwatch.org/ac200604260000004/2006/04/26/spectinomycin-discontinued-treatment-gonorrhea
Curator's Comment: description was created based on several sources, including
http://www.jwatch.org/ac200604260000004/2006/04/26/spectinomycin-discontinued-treatment-gonorrhea
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
Sources: Applied microbiology (1961), 9, 524-8.
Curator's Comment: https://books.google.es/books?id=5Fv0BwAAQBAJ&pg=PA47&lpg=PA47&dq=spectinomycin+was+discovered+1961&source=bl&ots=tz5daI3o3n&sig=HdeWzppPEz7i1UZ7Y_zxMM7qsFo&hl=ru&sa=X&ved=0ahUKEwjX1YWN9NDPAhXE0hoKHc8mB5cQ6AEIJDAB#v=onepage&q=spectinomycin%20was%20discovered%201961&f=false
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11014183 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | TROBICIN Approved UseTROBICIN Sterile Powder is indicated in 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. Men and women with known recent exposure to gonorrhea should be treated as those known to have gonorrhea. Launch Date4.7088001E10 |
|||
Curative | TROBICIN Approved UseTROBICIN Sterile Powder is indicated in 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. Men and women with known recent exposure to gonorrhea should be treated as those known to have gonorrhea. Launch Date4.7088001E10 |
|||
Curative | TROBICIN Approved UseTROBICIN Sterile Powder is indicated in 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. Men and women with known recent exposure to gonorrhea should be treated as those known to have gonorrhea. Launch Date4.7088001E10 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
100 μg/mL |
2 g single, intramuscular dose: 2 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
SPECTINOMYCIN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
460 μg × h/mL |
2 g single, intramuscular dose: 2 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
SPECTINOMYCIN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.7 h |
2 g single, intramuscular dose: 2 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
SPECTINOMYCIN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
100% |
2 g single, intramuscular dose: 2 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
SPECTINOMYCIN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains. | 1973 Sep |
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Screening for new compounds with antiherpes activity. | 1984 Oct |
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Spectinomycin and cholestatic jaundice. | 1985 Nov |
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Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs. | 1992 Sep |
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Effectiveness of norfloxacin and ofloxacin for treatment of gonorrhoea and decrease of in vitro susceptibility to quinolones over time in Rwanda. | 1993 Jun |
|
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. | 1993 Sep 24 |
|
In-vitro activities of aminoglycoside-aminocyclitols against mycobacteria. | 1997 Jul |
|
[Somatic hybrids among transgenic Solanum tuberosum and transplastomic Solanum rickii]. | 2008 Jul-Aug |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1605592
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:04:36 UTC 2023
by
admin
on
Fri Dec 15 15:04:36 UTC 2023
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Record UNII |
HWT06H303Z
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C2363
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1618003
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SUB12327MIG
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100000084957
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HWT06H303Z
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DTXSID90944843
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m10136
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SUB04522MIG
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9217
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Spectinomycin hydrochloride
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30971
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9216
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CHEMBL1167
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757319
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267342
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HWT06H303Z
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22189-32-8
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DBSALT001630
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C47728
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SPECTINOMYCIN HYDROCHLORIDE
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PRIMARY | Description: A white or almost white, crystalline powder; odourless. Solubility: Freely soluble in water; practically insoluble in ethanol (~750 g/l) TS and ether R. Category: Antibacterial drug. Storage: Spectinomycin hydrochloride should be kept in a well-closed container. Definition: Spectinomycin hydrochloride contains not less than 600 .MU.g of C14H24N2O7 per mg, calculated with reference to the anhydrous substance. Manufacture: The method of manufacture is validated to demonstrate that the product, if tested, would comply with the following test. Histamine-like substances. Carry out the test as described under 3.6 Test for histamine-like substances (vasodepressor substances) using 1 mL per kg of body mass of a solution in saline TS containing 25 mg of the substance to be examined per mL. |
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |