U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H24N2O7.2ClH.5H2O
Molecular Weight 495.348
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SPECTINOMYCIN HYDROCHLORIDE

SMILES

O.O.O.O.O.Cl.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=DCHJOVNPPSBWHK-UXXUFHFZSA-N
InChI=1S/C14H24N2O7.2ClH.5H2O/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;2*1H;5*1H2/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
Screening for new compounds with antiherpes activity.
1984 Oct
Spectinomycin and cholestatic jaundice.
1985 Nov
[Decreased incidence of postgonococcal urethritis following minocycline treatment compared to penicillin/spectinomycin].
1986 Jun 1
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
Effectiveness of norfloxacin and ofloxacin for treatment of gonorrhoea and decrease of in vitro susceptibility to quinolones over time in Rwanda.
1993 Jun
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.
1993 Sep 24
In-vitro activities of aminoglycoside-aminocyclitols against mycobacteria.
1997 Jul
[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
[E-test quantitative determination for evaluating Neisseria gonorrhoeae resistance].
2010 Oct-Dec
Synergistic drug combinations for tuberculosis therapy identified by a novel high-throughput screen.
2011 Aug
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 HYDROCHLORIDE
USAN  
Official Name English
SPECTINOMYCIN HYDROCHLORIDE [USAN]
Common Name English
SPECTINOMYCIN HYDROCHLORIDE [USP IMPURITY]
Common Name English
SPECTINOMYCIN DIHYDROCHLORIDE PENTAHYDRATE
EP   GREEN BOOK   MI  
Common Name English
SPECTINOMYCIN HYDROCHLORIDE [VANDF]
Common Name English
NSC-757319
Code English
SPECTINOMYCIN DIHYDROCHLORIDE PENTAHYDRATE [EP MONOGRAPH]
Common Name English
SPECTINOMYCIN HYDROCHLORIDE PENTAHYDRATE
GREEN BOOK   WHO-DD  
Common Name English
SPECTINOMYCIN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
Decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-4H-pyrano[2,3-b][1,4]benzodioxin-4-one dihydrochloride pentahydrate
Systematic Name English
SPECTINOMYCIN HYDROCHLORIDE HYDRATE
Common Name English
ACTINOSPECTACIN DIHYDROCHLORIDE PENTAHYDRATE
Common Name English
SPECTINOMYCIN DIHYDROCHLORIDE PENTAHYDRATE [GREEN BOOK]
Common Name English
SPECTINOMYCIN DIHYDROCHLORIDE PENTAHYDRATE [MI]
Common Name English
SPECTINOMYCIN HYDROCHLORIDE PENTAHYDRATE [GREEN BOOK]
Common Name English
ESPECTINOMICINA DIHYDROCHLORIDE PENTAHYDRATE
Common Name English
SPECTINOMYCIN DIHYDROCHLORIDE PENTAHYDRATE [EP IMPURITY]
Common Name English
SPECTINOMYCIN HYDROCHLORIDE HYDRATE [JAN]
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 DIHYDROCHLORIDE PENTAHYDRATE
Common Name English
SPECTINOMYCIN HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
SPECTINOMYCIN HCL
Common Name English
SPECTINOMYCIN HYDROCHLORIDE [USP-RS]
Common Name English
SPECTINOMYCIN HCL PENTAHYDRATE
Common Name English
M-141
Code English
4H-PYRANO(2,3-B)(1,4)BENZODIOXIN-4-ONE, DECAHYDRO-4A,7,9-TRIHYDROXY-2-METHYL-6,8-BIS(METHYLAMINO)-, DIHYDROCHLORIDE, PENTAHYDRATE
Systematic Name English
U-18409AE
Code English
SPECTINOMYCINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
Spectinomycin hydrochloride pentahydrate [WHO-DD]
Common Name English
4H-PYRANO(2,3-B)(1,4)BENZODIOXIN-4-ONE, DECAHYDRO-4A,7,9-TRIHYDROXY-2-METHYL-6,8-BIS(METHYLAMINO)-, HYDROCHLORIDE, HYDRATE (1:2:5), (2R,4AR,5AR,6S,7S,8R,9S,9AR,10AS)-
Common Name English
U-18,409AE
Code English
Classification Tree Code System Code
NCI_THESAURUS C2363
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1618003
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
EVMPD
SUB12327MIG
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
SMS_ID
100000084957
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
DAILYMED
HWT06H303Z
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID90944843
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
MERCK INDEX
m10136
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY Merck Index
EVMPD
SUB04522MIG
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
CHEBI
9217
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
WIKIPEDIA
Spectinomycin hydrochloride
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
PUBCHEM
30971
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
CHEBI
9216
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
ChEMBL
CHEMBL1167
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
NSC
757319
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
RXCUI
267342
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY RxNorm
FDA UNII
HWT06H303Z
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
CAS
22189-32-8
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
DRUG BANK
DBSALT001630
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
NCI_THESAURUS
C47728
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SPECTINOMYCIN HYDROCHLORIDE
Created by admin on Fri Dec 15 15:04:37 GMT 2023 , Edited by admin on Fri Dec 15 15:04:37 GMT 2023
PRIMARY Description: A white or almost white, crystalline powder; odourless. Solubility: Freely soluble in water; practically insoluble in ethanol (~750 g/l) TS and ether R. Category: Antibacterial drug. Storage: Spectinomycin hydrochloride should be kept in a well-closed container. Definition: Spectinomycin hydrochloride contains not less than 600 .MU.g of C14H24N2O7 per mg, calculated with reference to the anhydrous substance. Manufacture: The method of manufacture is validated to demonstrate that the product, if tested, would comply with the following test. Histamine-like substances. Carry out the test as described under 3.6 Test for histamine-like substances (vasodepressor substances) using 1 mL per kg of body mass of a solution in saline TS containing 25 mg of the substance to be examined per mL.