SPECTINOMYCIN

First approved in 1971

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H24N2O7
Molecular Weight	332.3496
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[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=UNFWWIHTNXNPBV-WXKVUWSESA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050347s060lbl.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11014183	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Acute gonorrheal urethritis 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050347s060lbl.pdf	Curative	Approved 8429	TROBICIN Approved Use TROBICIN 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 Date 4.7088001E10
Acute gonorrheal urethritis 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050347s060lbl.pdf	Curative	Approved 8429	TROBICIN Approved Use TROBICIN 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 Date 4.7088001E10
Acute gonorrheal urethritis 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050347s060lbl.pdf	Curative	Approved 8429	TROBICIN Approved Use TROBICIN 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 Date 4.7088001E10

C_max

Value	Dose	Co-administered	Analyte	Population
100 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050347s060lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050347s060lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.7 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050347s060lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050347s060lbl.pdf	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

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9215	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9215
ChemicalBook	CB8197632	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8197632
MolPort	MolPort-002-513-665	https://www.molport.com/shop/molecule-link/MolPort-002-513-665
ZINC	ZINC000053006806	http://zinc15.docking.org/substances/ZINC000053006806
eMolecules	1934872	https://www.emolecules.com/cgi-bin/more?vid=1934872
eMolecules	30151837	https://www.emolecules.com/cgi-bin/more?vid=30151837
eMolecules	30157345	https://www.emolecules.com/cgi-bin/more?vid=30157345

PubMed

Title	Date	PubMed
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.	1973 Sep	4202339
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Spectinomycin and cholestatic jaundice.	1985 Nov	2932048
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
Effectiveness of norfloxacin and ofloxacin for treatment of gonorrhoea and decrease of in vitro susceptibility to quinolones over time in Rwanda.	1993 Jun	8335312
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.	1993 Sep 24	8402886
In-vitro activities of aminoglycoside-aminocyclitols against mycobacteria.	1997 Jul	9249201
[Regeneration of cybrid Lycopersicon peruvianum x (Solanum rickii) plants with genetically transformed chloroplasts].	2005 Nov-Dec	16396314
[Stable transformation of Solanum rickii chloroplast DNA].	2005 Sep-Oct	16398139
[Biodegradation of pyridine by Shinella zoogloeoides BC026].	2008 Oct	19143398
Complete PHB mobilization in Escherichia coli enhances the stress tolerance: a potential biotechnological application.	2009 Aug 31	19719845
Experimental and computational validation of models of fluorescent and luminescent reporter genes in bacteria.	2010 Apr 29	20429918
Synergistic drug combinations for tuberculosis therapy identified by a novel high-throughput screen.	2011 Aug	21576426

Patents

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.

Name

Type

Language

SPECTINOMYCIN

Official Name

English

SPECTINOMYCIN [VANDF]

Common Name

English

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)-

Common Name

English

SPECTINOMYCIN [MI]

Common Name

English

SPECTINOMYCIN [GREEN BOOK]

Common Name

English

SPECTINOMYCIN [MART.]

Common Name

English

spectinomycin [INN]

Common Name

English

Spectinomycin [WHO-DD]

Common Name

English

CHX-3101

Code

English

ACTINOSPECTACIN

Common Name

English

ESPECTINOMICINA

Common Name

English

(2R-(2.ALPHA.,4A.BETA.,5A.BETA.,6.BETA.,7.BETA.,8.BETA.,9.ALPHA.,9A.ALPHA.,10A.BETA.))-DECAHYDRO-4A,7,9-TRIHYDROXY-2-METHYL-6,8-BIS(METHYLAMINO)-4H-PYRANO(2,3-B)(1,4)BENZODIOXIN-4-ONE

Common Name

English

ADSPEC

Brand Name

English

PROSPEC

Brand Name

English

4H-PYRANO(2,3-B)(1,4)BENZODIOXIN-4-ONE, DECAHYDRO-4A,7,9-TRIHYDROXY-2-METHYL-6,8-BIS(METHYLAMINO)-

Common Name

English

Classification Tree Code System Code

WHO-ESSENTIAL MEDICINES LIST

6.2.2