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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

SMILES

Cl.[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=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

Description
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.

Originator

Sources: Applied microbiology (1961), 9, 524-8. 
Curator's Comment: https://books.google.es/books?id=5Fv0BwAAQBAJ&pg=PA47&lpg=PA47&dq=spectinomycin+was+discovered+1961&source=bl&ots=tz5daI3o3n&sig=HdeWzppPEz7i1UZ7Y_zxMM7qsFo&hl=ru&sa=X&ved=0ahUKEwjX1YWN9NDPAhXE0hoKHc8mB5cQ6AEIJDAB#v=onepage&q=spectinomycin%20was%20discovered%201961&f=false

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Curative
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
Curative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
100 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
460 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.7 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
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
PubMed

PubMed

TitleDatePubMed
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.
1973 Sep
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 Jul
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
[Regeneration of cybrid Lycopersicon peruvianum x (Solanum rickii) plants with genetically transformed chloroplasts].
2005 Nov-Dec
[Stable transformation of Solanum rickii chloroplast DNA].
2005 Sep-Oct
Antimicrobial and toxicological evaluation of the leaves of Baissea axillaries Hua used in the management of HIV/AIDS patients.
2006 Jun 21
[Somatic hybrids among transgenic Solanum tuberosum and transplastomic Solanum rickii].
2008 Jul-Aug
[Biodegradation of pyridine by Shinella zoogloeoides BC026].
2008 Oct
Complete PHB mobilization in Escherichia coli enhances the stress tolerance: a potential biotechnological application.
2009 Aug 31
Experimental and computational validation of models of fluorescent and luminescent reporter genes in bacteria.
2010 Apr 29
Spectinamides: a new class of semisynthetic antituberculosis agents that overcome native drug efflux.
2014 Feb
Patents

Sample Use Guides

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 MONOHYDROCHLORIDE
Common Name English
NSC-132679
Code 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
Created by admin on Sat Dec 16 18:32:47 GMT 2023 , Edited by admin on Sat Dec 16 18:32:47 GMT 2023
PRIMARY
CAS
22193-75-5
Created by admin on Sat Dec 16 18:32:47 GMT 2023 , Edited by admin on Sat Dec 16 18:32:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID30944847
Created by admin on Sat Dec 16 18:32:47 GMT 2023 , Edited by admin on Sat Dec 16 18:32:47 GMT 2023
PRIMARY
PUBCHEM
64769
Created by admin on Sat Dec 16 18:32:47 GMT 2023 , Edited by admin on Sat Dec 16 18:32:47 GMT 2023
PRIMARY
NSC
132679
Created by admin on Sat Dec 16 18:32:47 GMT 2023 , Edited by admin on Sat Dec 16 18:32:47 GMT 2023
PRIMARY