This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Sarafloxacin
Accession Number
DB11491
Type
Small Molecule
Groups
Vet approved, Withdrawn
Description

Sarafloxacin (INN) is a quinolone antibiotic drug, which was removed from clinical use by its manufacturer Abbott Laboratories from April 30, 2001. It was never approved for use in the US or Canada.

Structure
Thumb
Synonyms
Not Available
External IDs
ABBOTT-57135
Product Ingredients
IngredientUNIICASInChI Key
Sarafloxacin hydrochlorideI36JP4Q9DF91296-87-6KNWODGJQLCISLC-UHFFFAOYSA-N
Categories
UNII
RC3WJ907XY
CAS number
98105-99-8
Weight
Average: 385.3641
Monoisotopic: 385.123797835
Chemical Formula
C20H17F2N3O3
InChI Key
XBHBWNFJWIASRO-UHFFFAOYSA-N
InChI
InChI=1S/C20H17F2N3O3/c21-12-1-3-13(4-2-12)25-11-15(20(27)28)19(26)14-9-16(22)18(10-17(14)25)24-7-5-23-6-8-24/h1-4,9-11,23H,5-8H2,(H,27,28)
IUPAC Name
6-fluoro-1-(4-fluorophenyl)-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
SMILES
OC(=O)C1=CN(C2=CC=C(F)C=C2)C2=CC(N3CCNCC3)=C(F)C=C2C1=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Sarafloxacin.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Sarafloxacin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Sarafloxacin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Sarafloxacin.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Sarafloxacin.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Sarafloxacin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Sarafloxacin.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with Sarafloxacin.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Sarafloxacin.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Sarafloxacin.
Food Interactions
Not Available

References

General References
  1. Authors unspecified: Evaluation of certain veterinary drug residues in food. Fiftieth report of the joint FAO/WHO Expert Committee on Food Additives. World Health Organ Tech Rep Ser. 1999;888:i-vii, 1-95. [PubMed:10416362]
  2. Gingerich WH, Stehly GR, Clark KJ, Hayton WL: Crop grouping: a proposal for public aquaculture. Vet Hum Toxicol. 1998;40 Suppl 2:24-31. [PubMed:9823579]
External Links
Human Metabolome Database
HMDB0039526
PubChem Compound
56208
PubChem Substance
347827981
ChemSpider
50727
ChEBI
94493
ChEMBL
CHEMBL37858
Wikipedia
Sarafloxacin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.105 mg/mLALOGPS
logP0.29ALOGPS
logP0.56ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)5.74ChemAxon
pKa (Strongest Basic)8.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.88 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity99.9 m3·mol-1ChemAxon
Polarizability37.15 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0009000000-d47328df5ce72c290c73
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0009000000-be757d6bc548f7ae632e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0079-0298000000-56c1868d9a505a5ac940
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0009000000-41d7e30d2cdfe003d56b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000f-0019000000-353fd43b65bf2b9df386
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000b-0098000000-96ca0f6085a81c7621e2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0192000000-88be2a87a02807977dc2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4j-0490000000-6e43540b7935c936fc98
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a6r-0590000000-cb1034859aef55b5a527
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-056r-2970000000-c8e1f01af7fe477cadbc
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a7i-4940000000-9463f2c28615a52c711d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a7i-6920000000-a41dfb757e7cae46b5ad

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Phenylquinolines
Direct Parent
Phenylquinolines
Alternative Parents
Quinoline carboxylic acids / Fluoroquinolones / N-arylpiperazines / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Fluorobenzenes
show 13 more
Substituents
Phenylquinoline / Quinoline-3-carboxylic acid / Fluoroquinolone / N-arylpiperazine / Aminoquinoline / Haloquinoline / Dihydroquinolone / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
Curator comments
This drug is a fluoroquinolone, and these agents are known to inhibit CYP1A2.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Shahzadi A, Javed I, Aslam B, Muhammad F, Asi MR, Ashraf MY, Zia-ur-Rahman: Therapeutic effects of ciprofloxacin on the pharmacokinetics of carbamazepine in healthy adult male volunteers. Pak J Pharm Sci. 2011 Jan;24(1):63-8. [PubMed:21190921]
  2. Zhang L, Wei MJ, Zhao CY, Qi HM: Determination of the inhibitory potential of 6 fluoroquinolones on CYP1A2 and CYP2C9 in human liver microsomes. Acta Pharmacol Sin. 2008 Dec;29(12):1507-14. doi: 10.1111/j.1745-7254.2008.00908.x. [PubMed:19026171]

Drug created on February 26, 2016 09:18 / Updated on November 02, 2018 08:54