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
Structure for Fluprostenol (DB11519)
- 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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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAceclofenac The therapeutic efficacy of Fluprostenol can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Fluprostenol can be decreased when used in combination with Acemetacin. Acetylsalicylic acid The therapeutic efficacy of Fluprostenol can be decreased when used in combination with Acetylsalicylic acid. Alclofenac The therapeutic efficacy of Fluprostenol can be decreased when used in combination with Alclofenac. Aminophenazone The therapeutic efficacy of Fluprostenol can be decreased when used in combination with Aminophenazone. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Fluprostenol sodium 6H4ZY4O7NA 55028-71-2 MUVLUMTZYKYXRV-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
- 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]
- 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]
- 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]
- Cooper MJ: Fluprostenol in mares: clinical trials for the treatment of infertility. Vet Rec. 1976 Jun 26;98(26):523-5. [Article]
- Rossdale Pd, Jeffcott LB, Allen WR: Foaling induced by a synthetic prostaglandin analogue (fluprostenol). Vet Rec. 1976 Jul 10;99(2):26-8. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- External Links
- ChemSpider
- 4470630
- BindingDB
- 50206025
- ChEBI
- 60782
- ChEMBL
- CHEMBL1201379
- ZINC
- ZINC000004474587
Clinical Trials
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
Property Value Source Water Solubility 0.0164 mg/mL ALOGPS logP 3.39 ALOGPS logP 2.92 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 4.36 Chemaxon pKa (Strongest Basic) -2.9 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 107.22 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 113.92 m3·mol-1 Chemaxon Polarizability 45.1 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 191.14685 predictedDeepCCS 1.0 (2019) [M-H]- 191.14685 predictedDeepCCS 1.0 (2019) [M+H]+ 192.80005 predictedDeepCCS 1.0 (2019) [M+H]+ 192.80005 predictedDeepCCS 1.0 (2019) [M+Na]+ 198.9569 predictedDeepCCS 1.0 (2019) [M+Na]+ 198.9569 predictedDeepCCS 1.0 (2019)
Drug created at February 26, 2016 17:32 / Updated at February 21, 2021 18:53