Dihydrostreptomycin

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^Y
ChEMBL	CHEMBL1950576
ECHA InfoCard	100.004.445
Chemical and physical data
Formula	C₂₁H₄₁N₇O₁₂
Molar mass	583.59 g/mol
3D model (Jmol)	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 property.^[1] It's 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 non-functional proteins, which results in the bacterial cell's death.^[1]

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

References

1 2 "Dihydrostreptomycin (Code C61724) - NCI Thesaurus". Retrieved July 7, 2016.
↑ "Dihydrostreptomycin Sulfate - MeSH - NCBI". Retrieved July 7, 2016.
↑ Harrison, Wiley H. (1954). "Ototoxicity of dihydrostreptomycin.". Quarterly bulletin. Northwestern University (Evanston, Ill.). Medical School. 28 (3): 271–3. PMC 3803976. PMID 13186082.

External links

Dihydrostreptomycin | C21H41N7O12 - PubChem

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin Ribostamycin Kanamycin^# Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Plazomicin^† Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Oxytetracycline Penimepicycline Rolitetracycline Tetracycline

Glycylcyclines	Tigecycline

Fluorocyclines	Eravacycline^†

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Pleuromutilins	Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Clarithromycin Dirithromycin Erythromycin^# Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin^†

Lincosamides	Clindamycin^# Lincomycin Pirlimycin

Streptogramins	Pristinamycin Quinupristin/dalfopristin Virginiamycin

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

This article is issued from Wikipedia - version of the 8/1/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.

Dihydrostreptomycin

See also

References

External links