SPECTINOMYCIN MONOHYDROCHLORIDE

First approved in 1971

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H24N2O7.ClH
Molecular Weight	368.811
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of SPECTINOMYCIN MONOHYDROCHLORIDE

Structure Search

SMILES

Cl.CN[C@@H]1[C@H](O)[C@H](NC)[C@H]2O[C@]3(O)[C@@H](O[C@H](C)CC3=O)O[C@@H]2[C@H]1O

InChI

InChIKey=BIPVCOUVVAMJMZ-MTTMTQIXSA-N

InChI=1S/C14H24N2O7.ClH/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;1H/t5-,7-,8+,9+,10+,11-,12-,13+,14+;/m1./s1

HIDE SMILES / InChI

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	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 180 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11014183	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Acute gonorrheal urethritis 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050347s060lbl.pdf	Curative	Approved 8583	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 1971
Acute gonorrheal urethritis 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050347s060lbl.pdf	Curative	Approved 8583	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 1971
Acute gonorrheal urethritis 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050347s060lbl.pdf	Curative	Approved 8583	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 1971

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
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
MolPort	MolPort-002-513-665	https://www.molport.com/shop/molecule-link/MolPort-002-513-665
ZINC	ZINC000053006806	http://zinc15.docking.org/substances/ZINC000053006806

PubMed

Title	Date	PubMed
Spectinamides: a new class of semisynthetic antituberculosis agents that overcome native drug efflux.	2014-02	24464186
Synergistic drug combinations for tuberculosis therapy identified by a novel high-throughput screen.	2011-08	21576426
[E-test quantitative determination for evaluating Neisseria gonorrhoeae resistance].	2011-04-20	21500474
Experimental and computational validation of models of fluorescent and luminescent reporter genes in bacteria.	2010-04-29	20429918
Complete PHB mobilization in Escherichia coli enhances the stress tolerance: a potential biotechnological application.	2009-08-31	19719845
[Somatic hybrids among transgenic Solanum tuberosum and transplastomic Solanum rickii].	2009-01-15	19140429
[Biodegradation of pyridine by Shinella zoogloeoides BC026].	2008-10	19143398
Antimicrobial and toxicological evaluation of the leaves of Baissea axillaries Hua used in the management of HIV/AIDS patients.	2006-06-21	16790064
[Stable transformation of Solanum rickii chloroplast DNA].	2006-01-10	16398139
[Regeneration of cybrid Lycopersicon peruvianum x (Solanum rickii) plants with genetically transformed chloroplasts].	2006-01-07	16396314
In-vitro activities of aminoglycoside-aminocyclitols against mycobacteria.	1997-07	9249201
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.	1993-09-24	8402886
Effectiveness of norfloxacin and ofloxacin for treatment of gonorrhoea and decrease of in vitro susceptibility to quinolones over time in Rwanda.	1993-06	8335312
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992-09	1416885
Comparison of in vitro antimicrobial susceptibilities of Mycobacterium avium-M. intracellulare strains from patients with acquired immunodeficiency syndrome (AIDS), patients without AIDS, and animal sources.	1990-07	2386370
[Decreased incidence of postgonococcal urethritis following minocycline treatment compared to penicillin/spectinomycin].	1986-06-01	2943086
Spectinomycin and cholestatic jaundice.	1985-11	2932048
Screening for new compounds with antiherpes activity.	1984-10	6517562
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.	1973-09	4202339

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 11:28:35 GMT 2025` Edited by `admin` on `Wed Apr 02 11:28:35 GMT 2025`
Record UNII	HL7KC2YV22
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SPECTINOMYCIN MONOHYDROCHLORIDE

Common Name

English

NSC-132679

Preferred Name

English

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

Systematic Name

English

Code System Code Type Description

FDA UNII

HL7KC2YV22