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Spectinomycin

Spectinomycin structure

CAS No:
1695-77-8
Formula:
C14H24N2O7
Chemical Name:
Spectinomycin
Synonyms:
4H-Pyrano[2,3-b][1,4]benzodioxin-4-one,decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-,(2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-;4H-Pyrano[2,3-b][1,4]benzodioxin-4-one,decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-;4H-Pyrano[2,3-b][1,4]benzodioxin-4-one,decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-,[2R-(2α,4aβ,5aβ,6β,7β,8β,9α,9aα,10aβ)]-;(2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-Decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-4H-pyrano[2,3-b][1,4]benzodioxin-4-one;Actinospectacin;Trobicin;Spectinomycin;Espectinomicina;M 141;U 18409E;Spectam;Togamycin;Antibiotic 2233wp;Spectacin;1404-65-5;11002-81-6;23559-31-1;856611-91-1
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

ChEBI: An organic heterotricyclic antibiotic that is active against gram-negative bacteria and used (as its dihydrochloride pentahydrate) to treat gonorrhea. It is produced by the bacterium Streptomyces spectabilis.

Solid

Spectinomycin is a pyranobenzodioxin and antibiotic that is active against gram-negative bacteria and used (as its dihydrochloride pentahydrate) to treat gonorrhea. It is produced by the bacterium Streptomyces spectabilis. It has a role as an antimicrobial agent, a bacterial metabolite and an antibacterial drug. It is a cyclic hemiketal, a cyclic acetal, a cyclic ketone, a secondary amino compound, a pyranobenzodioxin and a secondary alcohol. It is a conjugate base of a spectinomycin(2+) and a spectinomycin(1+).|An antibiotic produced by Streptomyces spectabilis. It is active against gram-negative bacteria and used for the treatment of gonorrhea.|Spectinomycin is an aminocyclitol aminoglycoside antibiotic derived from Streptomyces spectabilis with bacteriostatic activity. Spectinomycin binds to the bacterial 30S ribosomal subunit. As a result, this agent interferes with the initiation of protein synthesis and with proper protein elongation. This eventually leads to bacterial cell death.

Spectinomycin Basic Attributes

Molecular Weight：

332.35

Exact Mass：

332.35

EC Number：

216-911-3

UNII：

93AKI1U6QF

DSSTox ID：

DTXSID9023592|DTXSID9045429

NCI Thesaurus Code：

C61951

ATC Code：

J - Antiinfectives for systemic use

HScode：

3003209000

Characteristics

PSA：

130

XLogP3：

-2.3

Density：

1.43±0.1 g/cm3(Predicted)

Melting Point：

185 °C (decomp)

Boiling Point：

583.1±50.0 °C(Predicted)

Water Solubility：

Easily soluble in cold water

Specific rotation：

D25 -20° (water)

Dissociation Constants：

6.95

Collision Cross Section：

176.2 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|183.5 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]

Safety Information

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Danger|H317 (98.21%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 57 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H315 (96.08%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 54 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Acute oral toxicity (LD50): >5000 mg/kg [Rat]. Information on overdosage in humans is not available.

Protein Binding：

Not significant

Drug Information

Drug 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.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Absorption：

Rapidly and almost completely absorbed after intramuscular injection.

Biological 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.

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.

MeSH Entry Terms：

Actinospectacin

Spectinomycin Use and Manufacturing

Uses

Gonorrhea in penicillin-allergic patients or due to penicillin-resistant strains (single-dose treatment)

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Food Additive Classes：

Veterinary Drug -> ANTIMICROBIAL_AGENT;

Computed Properties

Molecular Weight:332.35
XLogP3:-3.1
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:2
Exact Mass:332.15835111
Monoisotopic Mass:332.15835111
Topological Polar Surface Area:130
Heavy Atom Count:23
Complexity:478
Defined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is an aminoglycoside antibiotic produced by Streptomyces spectabilis. It has high antibacterial activity against Neisseria gonorrhoeae, and also has good antibacterial activity against Neisseria gonorrhoeae that produces beta-lactamase; it has moderate antibacterial activity against many Enterobacteriaceae. Providencia and Pseudomonas aeruginosa are usually resistant to this product; strains resistant to this product are often still sensitive to streptomycin, gentamicin, tobramycin, etc. This product has a good effect on Ureaplasma urealyticum, and is inactive against Chlamydia trachomatis and Treponema pallidum. The mechanism of action of this product is to bind to the 30S subunit of the bacterial ribosome and inhibit the synthesis of bacterial proteins.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Spectinomycin Hydrochloride for Injection
Ingredients	Main ingredient: Spectinomycin.
Indication	According to literature reports, the combined use of this product with lithium carbonate may cause toxic effects of lithium carbonate in some patients.
Specifications	2 grams (2 million units) (calculated as spectinomycin)

Spectinomycin Hydrochloride for Injection
Ingredients	Spectinomycin.
Indication	According to literature reports, the combined use of this product with lithium carbonate may cause toxic effects of lithium carbonate in some patients.
Specifications	2g (2 million units)
Manufacturer	Anhu Welman Pharmaceut Icai Cd.ltd

Spectinomycin Hydrochloride for Injection
Ingredients	The main ingredient of this product is spectinomycin
Indication	According to literature reports, the combined use of this product with lithium carbonate may cause toxic effects of lithium carbonate in some patients.
Specifications	2g (2 million units) (calculated as C14H24N2O7)
Manufacturer	Shandong Lukang Pharmaceutical Co., Ltd.

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