Florfenicol

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Florfenicol

Systematic (IUPAC) name
2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	veterinary prescription only
Routes	intramuscular, subcutaneous
Identifiers
CAS number	73231-34-2^N
ATCvet code	QJ01BA90 QJ51BA90
PubChem	CID 114811
ChemSpider	102776^Y
UNII	9J97307Y1H^Y
KEGG	D04194^Y
ChEMBL	CHEMBL1241590^N
Synonyms	2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(methylsulfonyl)phenyl)propan-2-yl)ethanamide
Chemical data
Formula	C₁₂H₁₄Cl₂F N O₄S
Mol. mass	358.21 g/mol
SMILES ClC(Cl)C(=O)N[C@@H]([C@H](O)c1ccc(cc1)S(=O)(=O)C)CF
InChI InChI=1S/C12H14Cl2FNO4S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)/t9-,10-/m1/s1^Y Key:AYIRNRDRBQJXIF-NXEZZACHSA-N^Y
N (what is this?) (verify)

Florfenicol (marketed by Schering-Plough Animal Health under the trade name Nuflor) is a fluorinated synthetic analog of thiamphenicol.^[1]

In the United States, florfenicol is currently indicated for the treatment of bovine respiratory disease (BRD) associated with Mannheimia (Pasteurella) haemolytica, Pasteurella multocida, and Haemophilus somnus, for treatment of bovine interdigital phlegmon (foot rot, acute interdigital necrobacillosis, infectious pododermatitis) associated with Fusobacterium necrophorum and Bacteroides melaninogenicus.

The use of florfenicol in horses, and likely in other equids, typically causes diarrhea. This has been anecdotally reported to progress to lethal cases of acute colitis. Therefore, use of this antimicrobial in the equine patient should be limited to cases in which other, safer, options are not available. ^[2]

Contamination

Florfenicol was among the drug contaminants in a brand of supermarket eggs in Taiwan and Iran.^[3]

External links

Nuflor website

References

↑ Syriopoulou VP, Harding AL, Goldmann DA, Smith AL (February 1981). "In vitro antibacterial activity of fluorinated analogs of chloramphenicol and thiamphenicol.". Antimicrob Agents Chemother. 19 (2): 294–7. PMC 181412. PMID 6957162.
↑ Robinson, N.E.; Sprayberry, K.A. (2009). Current therapy in equine medicine. Saunders Elesevier. p. 13. ISBN 978-1-4160-5475-7. Retrieved March 21, 2011.
↑ http://www.taipeitimes.com/News/taiwan/archives/2013/01/08/2003552041

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

M: BAC

bact (clas)

gr+f/gr+a (t)/gr-p (c)/gr-o

drug (J1p, w, n, m, vacc)

Sprayberry SprayberrySprayberry

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