(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

• ChemBase ID: 795
• Molecular Formular: C14H24N2O7
• Molecular Mass: 332.34956
• Monoisotopic Mass: 332.15835112
• SMILES: O1[C@H]2[C@H](O[C@@H]3O[C@@H](CC(=O)[C@]13O)C)[C@@H](O)[C@H](NC)[C@H](O)[C@@H]2NC
• Canonical SMILES: CN[C@H]1[C@H](O)[C@H]2O[C@@H]3O[C@H](C)CC(=O)[C@@]3(O[C@@H]2[C@H]([C@H]1O)NC)O
• 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
• InChIKey: UNFWWIHTNXNPBV-WXKVUWSESA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: spectinomycin
• Brand Name: Actinospectacin; Spectam; Togamycin; Trobicin
• Synonyms: Espectinomicina [INN-Spanish]; Actinospectacina [Italian]; Antibiotic 2233wp; SCM; Spectinomicina [Italian]; Spectinomycin Di HCl; Spectinomycin HCl/ Sulphate; Spectinomycine [INN-French]; Spectinomycinum [INN-Latin]; Spectinomycin

Database IDs

• CAS Number: 1695-77-8
• PubChem SID: 46505032; 160964258
• PubChem CID: 15541

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.576982
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -5.963829
• LogD (pH = 7.4): -3.421742
• Log P: -2.3693373
• Molar Refractivity: 75.4362 cm^3
• Polarizability: 31.587643 Å^3
• Polar Surface Area: 129.51 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.4
• LOG S: -0.35
• Solubility (Water): 1.50e+02 g/l

PROPERTIES

Physical Property

• Solubility: Easily soluble in cold water
• Hydrophobicity(logP): -2.3

DETAILS

DrugBank - DB00919

• Drug Groups: approved
• Description: An antibiotic produced by Streptomyces spectabilis. It is active against gram-negative bacteria and used for the treatment of gonorrhea.
• 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.
• Pharmacology: 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.
• Toxicity: Acute oral toxicity (LD₅₀): >5000 mg/kg [Rat]. Information on overdosage in humans is not available.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Rapidly and almost completely absorbed after intramuscular injection.
• 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.
• Protein Binding: Not significant
• External Links: Wikipedia; RxList; Drugs.com