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Identification
- Summary
Spectinomycin is an aminocyclitol antibiotic used to treat susceptible strains of Neisseria gonorrhoeae.
- Generic Name
- Spectinomycin
- DrugBank Accession Number
- DB00919
- Background
An antibiotic produced by Streptomyces spectabilis. It is active against gram-negative bacteria and used for the treatment of gonorrhea.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
Structure for Spectinomycin (DB00919)
- Weight
- Average: 332.3496
Monoisotopic: 332.158351132 - Chemical Formula
- C14H24N2O7
- Synonyms
- Actinospectacina
- Espectinomicina
- SCM
- Spectinomicina
- Spectinomycin
- Spectinomycine
- Spectinomycinum
- External IDs
- Antibiotic 2233wp
- CHX-3101
Pharmacology
- Indication
For use 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.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Spectinomycin is an aminocyclitol antibiotic produced by a species of soil microorganism designated as Streptomyces spectabilis. 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.
- Mechanism of action
Spectinomycin is an inhibitor of protein synthesis in the bacterial cell; the site of action is the 30S ribosomal subunit. It is bactericidal in its action.
Target Actions Organism A30S ribosomal protein S12 inhibitorEscherichia coli (strain K12) - Absorption
Rapidly and almost completely absorbed after intramuscular injection.
- Volume of distribution
Not Available
- Protein binding
Not significant
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
1 to 3 hours in patients with normal renal function and 10 to 30 hours in patients with impaired renal function with a creatinine clearance < 20 mL per minute.
- Clearance
Not Available
- Adverse Effects
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Acute oral toxicity (LD50): >5000 mg/kg [Rat]. Information on overdosage in humans is not available.
- Pathways
Pathway Category Spectinomycin Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Spectinomycin is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Spectinomycin is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Spectinomycin is combined with Articaine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Spectinomycin. Benzocaine The risk or severity of methemoglobinemia can be increased when Spectinomycin is combined with Benzocaine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Spectinomycin dihydrochloride pentahydrate Not Available Not Available Not applicable Spectinomycin hydrochloride HL7KC2YV22 22193-75-5 BIPVCOUVVAMJMZ-MTTMTQIXSA-N Spectinomycin hydrochloride pentahydrate HWT06H303Z 22189-32-8 DCHJOVNPPSBWHK-UXXUFHFZSA-N Spectinomycin sulfate BZ0H4TLF9X 23312-56-3 XGBFWQUQYQIFLB-MTTMTQIXSA-N Spectinomycin sulfate tetrahydrate YS91P54918 64058-48-6 OBZDRKHRQYPQDZ-SACNDDTHSA-N - International/Other Brands
- Actinospectacin / Spectam / Togamycin
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Trobicin Solution 400 mg/1mL Intramuscular Pharmacia and Upjohn Company LLC 1971-07-01 2006-05-31 US 
Trobicin Inj 400mg/ml Powder, for solution 400 mg / mL Intramuscular Upjohn 1972-12-31 1997-08-28 Canada 
Categories
- ATC Codes
- J01XX04 — Spectinomycin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1,4-dioxanes. These are organic compounds containing 1,4-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 4.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Dioxanes
- Sub Class
- 1,4-dioxanes
- Direct Parent
- 1,4-dioxanes
- Alternative Parents
- Oxanes / Secondary alcohols / Ketones / Hemiacetals / Cyclic alcohols and derivatives / 1,2-aminoalcohols / Polyols / Oxacyclic compounds / Dialkylamines / Acetals show 3 more
- Substituents
- 1,2-aminoalcohol / Acetal / Alcohol / Aliphatic heteropolycyclic compound / Amine / Carbonyl group / Cyclic alcohol / Hemiacetal / Hydrocarbon derivative / Ketone show 13 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- cyclic ketone, organic heterotricyclic compound, secondary amino compound, cyclic hemiketal, cyclic acetal (CHEBI:9215) / Actinamines (C02078)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 93AKI1U6QF
- CAS number
- 1695-77-8
- InChI Key
- UNFWWIHTNXNPBV-WXKVUWSESA-N
- InChI
- InChI=1S/C14H24N2O7/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/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1
- IUPAC Name
- (1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.0^{3,8}]tetradecan-7-one
- SMILES
- [H][C@@]12O[C@H](C)CC(=O)[C@]1(O)O[C@]1([H])[C@@H](NC)[C@@H](O)[C@@H](NC)[C@H](O)[C@@]1([H])O2
References
- Synthesis Reference
David R. White, "Intermediate compounds in the preparation of spectinomycin." U.S. Patent US4344882, issued August, 1966.
US4344882- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015055
- KEGG Compound
- C02078
- PubChem Compound
- 15541
- PubChem Substance
- 46505032
- ChemSpider
- 14785
- 270
- ChEBI
- 9215
- ChEMBL
- CHEMBL1167
- ZINC
- ZINC000053006806
- Therapeutic Targets Database
- DAP000403
- PharmGKB
- PA164781342
- PDBe Ligand
- SCM
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Spectinomycin
- PDB Entries
- 1fjg / 4v56 / 4v57 / 6xxq / 6xz0 / 7n2v / 7p7q / 7p7r / 7p7s / 7p7t … show 5 more
- MSDS
- Download (24.8 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data0 Terminated Treatment Osteomyelitis 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Pharmacia and upjohn co
- Packagers
- Pfizer Inc.
- Pharmacia Inc.
- Dosage Forms
Form Route Strength Powder Oral Solution Oral Solution Intramuscular 400 mg/1mL Injection, powder, for solution Intramuscular 2 g Powder, for solution Intramuscular 400 mg / mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Easily soluble in cold water Not Available logP -2.3 Not Available pKa 6.95 MERCK INDEX (1996); pKa1 - Predicted Properties
Property Value Source Water Solubility 150.0 mg/mL ALOGPS logP -1.4 ALOGPS logP -2.2 Chemaxon logS -0.35 ALOGPS pKa (Strongest Acidic) 8.53 Chemaxon pKa (Strongest Basic) 9.23 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 129.51 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 75.44 m3·mol-1 Chemaxon Polarizability 33.39 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.7118 Blood Brain Barrier - 0.9892 Caco-2 permeable - 0.6803 P-glycoprotein substrate Non-substrate 0.526 P-glycoprotein inhibitor I Non-inhibitor 0.6468 P-glycoprotein inhibitor II Non-inhibitor 0.9228 Renal organic cation transporter Non-inhibitor 0.9646 CYP450 2C9 substrate Non-substrate 0.7711 CYP450 2D6 substrate Non-substrate 0.8496 CYP450 3A4 substrate Non-substrate 0.5056 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9182 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8434 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9254 Ames test Non AMES toxic 0.7167 Carcinogenicity Non-carcinogens 0.9602 Biodegradation Not ready biodegradable 0.983 Rat acute toxicity 1.8538 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.996 hERG inhibition (predictor II) Non-inhibitor 0.9493
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.6814832 predictedDarkChem Lite v0.1.0 [M-H]- 184.5385832 predictedDarkChem Lite v0.1.0 [M-H]- 187.0207832 predictedDarkChem Lite v0.1.0 [M-H]- 170.14143 predictedDeepCCS 1.0 (2019) [M+H]+ 183.8582832 predictedDarkChem Lite v0.1.0 [M+H]+ 185.5225832 predictedDarkChem Lite v0.1.0 [M+H]+ 187.3950832 predictedDarkChem Lite v0.1.0 [M+H]+ 172.35603 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.6401832 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.6845832 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.09645 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Trna binding
- Specific Function
- With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Lo...
- Gene Name
- rpsL
- Uniprot ID
- P0A7S3
- Uniprot Name
- 30S ribosomal protein S12
- Molecular Weight
- 13736.995 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Yamagata H, Dombou M, Sato T, Mizushima S, Uchida H: Deletion mapping and heterogenote analysis of a mutation responsible for osmosis-sensitive growth, spectinomycin resistance, and alteration of cytoplasmic membrane in Escherichia coli. J Bacteriol. 1980 Aug;143(2):661-7. [Article]
- Gordeev VK, Turkov MI: [Functioning of amino acid operons in Escherichia coli strains with an altered transcription and translation apparatus. II. The effect of mutations in genes coding ribosomal protein S5 and translation elongation factor G on the functioning of the ilv operon]. Genetika. 1983;19(2):217-20. [Article]
- Eisenstein BI, Beachey EH, Ofek I: Influence of sublethal concentrations of antibiotics on the expression of the mannose-specific ligand of Escherichia coli. Infect Immun. 1980 Apr;28(1):154-9. [Article]
- Carter AP, Clemons WM, Brodersen DE, Morgan-Warren RJ, Wimberly BT, Ramakrishnan V: Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics. Nature. 2000 Sep 21;407(6802):340-8. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 07, 2024 17:45