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Dihydrostreptomycin

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Dihydrostreptomycin
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	S01AA15 (WHO) QA07AA90 (WHO) QJ01GA90 (WHO) QJ51GA90 (WHO)
Identifiers
IUPAC name 2-[(1S,2R,3R,4S,5R,6R)-5-(Diaminomethylideneamino)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)- 4,5-dihydroxy-6-(hydroxymethyl)-3-methylaminooxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)- 5-methyloxolan-2-yl]oxy-3,4,6-trihydroxycyclohexyl]guanidine
CAS Number	128-46-1
PubChem CID	439369
ChemSpider	388489
UNII	P2I6R8W6UA
ChEMBL	ChEMBL1950576
CompTox Dashboard (EPA)	DTXSID0022937
ECHA InfoCard	100.004.445
Chemical and physical data
Formula	C₂₁H₄₁N₇O₁₂
Molar mass	583.596 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)NC(=N)N)O)NC(=N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(CO)O
InChI InChI=1S/C21H41N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1 Key:ASXBYYWOLISCLQ-HZYVHMACSA-N
(verify)

Dihydrostreptomycin is a derivative of streptomycin that has a bactericidal properties.^[1] It is a semisynthetic aminoglycoside antibiotic used in the treatment of tuberculosis.^[2]

It acts by irreversibly binding the S12 protein in the bacterial 30S ribosomal subunit, after being actively transported across the cell membrane, which interferes with the initiation complex between the mRNA and the bacterial ribosome. This leads to the synthesis of defective, nonfunctional proteins, which results in the bacterial cell's death.^[1]

It causes ototoxicity,^[3] which is why it is no longer used in humans.^{[citation needed]}

References[edit]

^ ^a ^b "Dihydrostreptomycin (Code C61724) - NCI Thesaurus". Retrieved July 7, 2016.

^ "Dihydrostreptomycin Sulfate - MeSH - NCBI". Retrieved July 7, 2016.

^ Harrison WH (1954). "Ototoxicity of dihydrostreptomycin". Quarterly Bulletin. Northwestern University. 28 (3): 271–3. PMC 3803976. PMID 13186082.

External links[edit]

Dihydrostreptomycin | C21H41N7O12 - PubChem

Antibacterials that inhibit protein synthesis (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)

Streptomycin^#
Dihydrostreptomycin

Neomycin^#
- Framycetin
- Paromomycin^#
- Ribostamycin

Kanamycin
- Amikacin^#
- Arbekacin
- Bekanamycin
- Dibekacin

-micin (Micromonospora)

Gentamicin^#
- Netilmicin
- Sisomicin
- Micronomicin
- Plazomicin^#
- Isepamicin

other

Butirosin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines

Glycylcyclines

Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols

Pleuromutilins

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Boromycin Carbomycin Carrimycin Clarithromycin^# Dirithromycin Erythromycin^# Flurithromycin Gamithromycin Josamycin Kitasamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Solithromycin Spiramycin Telithromycin Tildipirosin Tilmicosin Troleandomycin Tulathromycin Tylosin Tylvalosin
Ketolides	Telithromycin^‡ Cethromycin Solithromycin^†
Lincosamides	Clindamycin^# Lincomycin Pirlimycin
Streptogramins	Pristinamycin (IA, IIA, IIB) NXL103 (Flopristin, Linopristin) Quinupristin/dalfopristin (Dalfopristin, Quinupristin) Streptogramin A Streptogramin B Virginiamycin (S1)

EF-G

Steroid antibacterials

Fusidic acid

^#WHO-EM

^‡Withdrawn from market

Clinical trials:

^†Phase III
^§Never to phase III

This systemic antibiotic-related article is a stub. You can help Wikipedia by expanding it.

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