florfenicol

ID: ALA1241590

Cas Number: 73231-34-2

PubChem CID: 114811

Product Number: F111293, Order Now?

Max Phase: Phase

Molecular Formula: C12H14Cl2FNO4S

Molecular Weight: 358.22

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Nuflor | NSC-759287 | SCH 25298 | SCH-25298 | Florfenicol|73231-34-2|Nuflor|(-)-Florfenicol|Sch-25298|76639-94-6|Sch 25298|Nuflor gold|Aquafen|2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide|DTXSID9045500|UNII-9J97307Y1H|CHEBI:87185|9J97307Y1H|NSC-759287|2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide|D-threo-2,2-Dichloro-N-(alpha-(fluoromethyl)-beta-hydroxy-p-(methylsulfonyl)phenethyl)acetamide|florphenicol|AShow More⌵

Canonical SMILES:  CS(=O)(=O)c1ccc([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)cc1

Standard 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

Standard InChI Key:  AYIRNRDRBQJXIF-NXEZZACHSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  1  0  0  0  0  0999 V2000
  -12.7223    3.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0078    3.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2933    3.5543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5789    3.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8644    3.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1499    3.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4368    3.9668    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  -12.7223    2.7293    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  -12.0078    4.7918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5789    4.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8644    5.2043    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8644    2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4354    3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7210    3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7210    4.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4355    5.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1499    4.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0065    5.2043    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2921    4.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5899    5.7876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4232    5.7876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  2  0
  4 10  1  6
 10 11  1  0
  5 12  1  1
  6 13  1  0
  6 17  2  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
 18 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1241590

   Florfenicol

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 358.22

Molecular Weight (Monoisotopic): 357.0005

AlogP: 1.38

#Rotatable Bonds: 6

Polar Surface Area: 83.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.49

CX Basic pKa: ┄

CX LogP: 0.67

CX LogD: 0.64

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.75

Np Likeness Score: -0.43

References

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2. Pasmans F, Baert K, Martel A, Bousquet-Melou A, Lanckriet R, De Boever S, Van Immerseel F, Eeckhaut V, de Backer P, Haesebrouck F..  (2008)  Induction of the carrier state in pigeons infected with Salmonella enterica subspecies enterica serovar typhimurium PT99 by treatment with florfenicol: a matter of pharmacokinetics.,  52  (3): [PMID:18180355] [10.1128/aac.00575-07]

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Source

Source(6):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• AstraZeneca Deposited Data
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6