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

Identification

Generic Name
Fluprostenol
DrugBank Accession Number
DB11519
Background

Not Available

Type
Small Molecule
Groups
Vet approved
Structure
Weight
Average: 458.474
Monoisotopic: 458.191623143
Chemical Formula
C23H29F3O6
Synonyms
  • Fluprostenol
  • Fluprostenolum
  • Travoprost acid
  • Travoprost free acid
External IDs
  • AL-5848
  • EINECS 255-029-3
  • ICI 81,008

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AceclofenacThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Acetylsalicylic acid.
AlclofenacThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Alclofenac.
AminophenazoneThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Aminophenazone.
AntipyrineThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Antipyrine.
AntrafenineThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Antrafenine.
BalsalazideThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Balsalazide.
BenorilateThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Benorilate.
BenoxaprofenThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Benoxaprofen.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Fluprostenol sodium6H4ZY4O7NA55028-71-2MUVLUMTZYKYXRV-KXXGZHCCSA-M

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Eicosanoids
Direct Parent
Prostaglandins and related compounds
Alternative Parents
Long-chain fatty acids / Trifluoromethylbenzenes / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Halogenated fatty acids / Hydroxy fatty acids / Unsaturated fatty acids / Cyclopentanols / Cyclic alcohols and derivatives
show 7 more
Substituents
Alcohol / Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic alcohol
show 20 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
prostaglandins Falpha, hydroxy monocarboxylic acid, (trifluoromethyl)benzenes (CHEBI:60782)
Affected organisms
Not Available

Chemical Identifiers

UNII
358S7VUE5N
CAS number
40666-16-8
InChI Key
WWSWYXNVCBLWNZ-QIZQQNKQSA-N
InChI
InChI=1S/C23H29F3O6/c24-23(25,26)15-6-5-7-17(12-15)32-14-16(27)10-11-19-18(20(28)13-21(19)29)8-3-1-2-4-9-22(30)31/h1,3,5-7,10-12,16,18-21,27-29H,2,4,8-9,13-14H2,(H,30,31)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m1/s1
IUPAC Name
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoic acid
SMILES
[H]\C(CCCC(O)=O)=C(/[H])C[C@@]1([H])[C@@]([H])(O)C[C@@]([H])(O)[C@]1([H])C(\[H])=C(/[H])[C@@]([H])(O)COC1=CC=CC(=C1)C(F)(F)F

References

General References
  1. Copeland DD, Schultz RH, Canady JD: Use of fluprostenol to manage the equine estrous cycle. Vet Med Small Anim Clin. 1981 Sep;76(9):1329-31. [Article]
  2. Williams LM, Hollingsworth M, Dukes M, Morris ID: Fluprostenol-induced softening of the cervix of the pregnant rat. J Endocrinol. 1983 May;97(2):283-90. [Article]
  3. Ousey JC, Dudan FE, Rossdale PD, Silver M: Effects of fluprostenol administration in mares during late pregnancy. Equine Vet J. 1984 Jul;16(4):264-9. [Article]
  4. Cooper MJ: Fluprostenol in mares: clinical trials for the treatment of infertility. Vet Rec. 1976 Jun 26;98(26):523-5. [Article]
  5. Rossdale Pd, Jeffcott LB, Allen WR: Foaling induced by a synthetic prostaglandin analogue (fluprostenol). Vet Rec. 1976 Jul 10;99(2):26-8. [Article]
  6. Schultz RH, Copeland DD, Canady JD: Treatment of infertility in the mare with fluprostenol. Vet Med Small Anim Clin. 1981 Jun;76(6):885-8. [Article]
  7. Rossdale PD, Pashen RL, Jeffcott LB: The use of synthetic prostaglandin analogue (fluprostenol) to induce foaling. J Reprod Fertil Suppl. 1979;(27):521-9. [Article]
  8. Thieme H, Schimmat C, Munzer G, Boxberger M, Fromm M, Pfeiffer N, Rosenthal R: Endothelin antagonism: effects of FP receptor agonists prostaglandin F2alpha and fluprostenol on trabecular meshwork contractility. Invest Ophthalmol Vis Sci. 2006 Mar;47(3):938-45. [Article]
  9. Carrasco MP, Phaneuf S, Asboth G, Lopez Bernal A: Fluprostenol activates phospholipase C and Ca2+ mobilization in human myometrial cells. J Clin Endocrinol Metab. 1996 Jun;81(6):2104-10. [Article]
  10. Chapman DI, Moss MS, Tomlinson PW, Harrison MP, Simmons PJ: The disposition and metabolism of the synthetic prostaglandin fluprostenol (ICI 81,008) in the horse. Xenobiotica. 1980 Sep;10(9):715-23. [Article]
  11. Katsuyama M, Fan C, Yabe-Nishimura C: NADPH oxidase is involved in prostaglandin F2alpha-induced hypertrophy of vascular smooth muscle cells: induction of NOX1 by PGF2alpha. J Biol Chem. 2002 Apr 19;277(16):13438-42. Epub 2002 Feb 6. [Article]
  12. McCue BA, Cason MM, Curtis MA, Faulkner RD, Dahlin DC: Determination of travoprost and travoprost free acid in human plasma by electrospray HPLC/MS/MS. J Pharm Biomed Anal. 2002 Apr 15;28(2):199-208. [Article]
  13. Dodson KS, Watson J: Effects of cloprostenol (ICI 80996) and fluprostenol (ICI 81008) on progesterone production by human luteal tissue superfused in vitro. Prostaglandins Med. 1979 Mar;2(3):239-40. [Article]
ChemSpider
4470630
BindingDB
50206025
ChEBI
60782
ChEMBL
CHEMBL1201379
ZINC
ZINC000004474587

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0164 mg/mLALOGPS
logP3.39ALOGPS
logP2.92ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity113.92 m3·mol-1ChemAxon
Polarizability45.1 Å3ChemAxon
Number of Rings2ChemAxon
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 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

Drug created at February 26, 2016 17:32 / Updated at February 21, 2021 18:53