Tiamulin

Tiamulin
Systematic (IUPAC) name

(4R,5S,6S,8R,9aR,10R)-5-Hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propanocyclopenta[8]annulen-8-yl {[2-(diethylamino)ethyl]sulfanyl}acetate
Clinical data
Routes of administration	Oral
Legal status	Veterinary use only
Identifiers
CAS Number	55297-95-5^Y
ATCvet code	QJ01XQ01(WHO)
PubChem	CID 656958
ChemSpider	571196
UNII	E38WZ4U54R^N
ChEBI	CHEBI:44137
ChEMBL	CHEMBL498466^N
Chemical data
Formula	C₂₈H₄₇NO₄S
Molar mass	493.742 g/mol
SMILES CCN(CC)CCSCC(=O)O[C@@H]1C[C@@]([C@H]([C@@H]([C@@]23CC[C@H]([C@@]1([C@@H]2C(=O)CC3)C)C)C)O)(C)C=C
InChI InChI=1S/C28H47NO4S/c1-8-26(6)17-22(33-23(31)18-34-16-15-29(9-2)10-3)27(7)19(4)11-13-28(20(5)25(26)32)14-12-21(30)24(27)28/h8,19-20,22,24-25,32H,1,9-18H2,2-7H3/t19-,20+,22-,24+,25+,26-,27+,28+/m1/s1 Key:UURAUHCOJAIIRQ-QGLSALSOSA-N
^NY (what is this?) (verify)

Tiamulin is a pleuromutilin antibiotic drug that is used in veterinary medicine particularly for pigs and poultry.^[1]^[2]

Tiamulin is a diterpene antimicrobial with a pleuromutilin chemical structure similar to that of valnemulin.^[3]

References

↑ HACCP: Tiamulin in Veterinary Medicine - Overview
↑ Long, K. S.; Hansen, L. H.; Jakobsen, L.; Vester, B. (April 2006). "Interaction of Pleuromutilin Derivatives with the Ribosomal Peptidyl Transferase Center" (PDF). Antimicrobial Agents and Chemotherapy 50 (4): 1458–1462. doi:10.1128/AAC.50.4.1458-1462.2006. PMC 1426994. PMID 16569865.
↑ EMEA: Tiamulin Summary Report

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 Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

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

Glycylcyclines	Tigecycline

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

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