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11-deoxy Prostaglandin F1α

Alias: 11-deoxy PGF1α
Cat No.:V103007 Purity: ≥98%
11-Deoxyprostaglandin F1α (11-deoxyPGF1α) is an analog of prostaglandin F1α that has adverse effects on the intestine of guinea pigs and induces uterine contractions in SD rats.
11-deoxy Prostaglandin F1α
11-deoxy Prostaglandin F1α Chemical Structure CAS No.: 37785-98-1
Product category: Prostaglandin Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
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Product Description
11-deoxy Prostaglandin F1α (11-deoxy PGF1α) is an analog of prostaglandin F1α, which has adverse effects on the guinea pig intestine and causes uterine contraction in SD rats. 11-deoxy Prostaglandin F1α can act as a vasoconstrictor and bronchial constrictor.
11-deoxy Prostaglandin F1alpha (11-deoxy PGF1alpha) is a synthetic analog of the naturally occurring prostaglandin PGF1alpha, characterized by the removal of the 11-hydroxy group. This structural modification alters its pharmacological profile compared to the parent compound. 11-deoxy PGF1alpha exhibits vasopressor (blood pressure-increasing) and bronchoconstrictor activities. It is also known to cause uterine contractions and has been shown to inhibit gastric acid secretion in whole animal studies. It is intended for research use only.
Biological Activity I Assay Protocols (From Reference)
Targets
The biological targets of 11-deoxy Prostaglandin F1alpha are the prostaglandin F receptor (FP receptor) and potentially other prostaglandin receptors (EP, DP, IP, TP) depending on the tissue. Prostaglandin F2alpha (PGF2alpha) and its analogs bind to FP receptors to mediate smooth muscle contraction, vasoconstriction, and bronchoconstriction. The removal of the 11-hydroxy group alters the binding affinity and selectivity compared to PGF1alpha.
ln Vitro
In whole animal studies, 11-deoxy PGF1alpha at a dose of 32 mg/kg inhibited gastric acid secretion by 35%. It is also known to cause rat uterine contractions at a dose 0.3 times that of PGF1alpha, indicating it is approximately three times more potent than the parent compound in this assay. The compound exhibits activity as a vasopressor (blood pressure-elevating) and a bronchoconstrictor. 11-deoxy PGF1alpha (0-10 mg/kg, intravenous) stimulates uterine contractions in pregnant rats.
ln Vivo
11-deoxy PGF1α (0-10 mg/kg, intravenous, single dose) stimulates uterine contractions in pregnant Sprague-Dawley rats and slightly affects fertility in hamsters [1].
11-deoxy PGF1alpha exhibits activity as a vasopressor and bronchoconstrictor, and causes uterine contractions. At a dose of 32 mg/kg, it inhibited gastric acid secretion by 35% in whole animal studies. It causes rat uterine contractions at a dose 0.3 times that of PGF1alpha, meaning it is approximately three times more potent than the parent compound in this assay. 11-deoxy PGF1alpha (0-10 mg/kg, IV) stimulates uterine contractions in pregnant Sprague-Dawley rats.
Enzyme Assay
Not applicable. 11-deoxy Prostaglandin F1alpha is a prostaglandin analog, and its activity is typically measured in functional tissue assays rather than cell-free receptor binding. However, a typical FP receptor binding assay: Membrane preparations from cells expressing the FP receptor are incubated with 0.5-2 nM [3H]-PGF2alpha and varying concentrations of unlabeled 11-deoxy PGF1alpha (0.1-10,000 nM) in binding buffer (50 mM Tris-HCl pH 7.4, 10 mM MgCl2) at 25degC for 60 minutes. Bound radioactivity is separated by filtration, and IC50 is calculated.
Cell Assay
Standard cell-based assays for prostaglandin activity: FP receptor-expressing cells (e.g., Swiss 3T3 fibroblasts or HEK293 cells stably expressing FP receptor) are loaded with a calcium-sensitive dye (Fluo-4 AM) and treated with varying concentrations of 11-deoxy PGF1alpha (0.01 nM to 10 uM). Intracellular calcium mobilization is measured in a fluorescence plate reader. For IP1 or cAMP accumulation (if activating other prostaglandin receptors), cells are treated with compound for 30 minutes and cAMP is measured by HTRF or ELISA.
Animal Protocol
Animal/Disease Models: pregnant Sprague-Dawley rats[1]
Doses: 0-10 mg/kg
Route of Administration: i.v., single dose
Experimental Results: Stimulated uterine contraction 3 times active as PGF1α.
For gastric acid secretion studies: Rats are fasted for 24 hours. Under anesthesia, the stomach is cannulated. 11-deoxy PGF1alpha is administered intravenously or intraperitoneally at doses ranging from 1-100 mg/kg. Gastric juice is collected for 1-2 hours, and the volume and acidity (titratable acid) are measured. For uterine contraction studies: Pregnant rats are anesthetized, and uterine horns are exposed. 11-deoxy PGF1alpha (0-10 mg/kg, IV) is administered, and uterine contractions are recorded using an isometric force transducer.
ADME/Pharmacokinetics
No PK data was found for 11-deoxy Prostaglandin F1alpha. Prostaglandin analogs typically have very short half-lives in circulation (measured in minutes), as they are rapidly metabolized by 15-hydroxyprostaglandin dehydrogenase (15-PGDH) and beta-oxidation. The compound is rapidly cleared from the bloodstream following intravenous administration.
Toxicity/Toxicokinetics
No specific toxicity data was found. 11-deoxy PGF1alpha is a prostaglandin analog and, like other prostaglandins, may produce dose-dependent side effects including bronchoconstriction (wheezing, difficulty breathing), vasoconstriction (hypertension), and gastrointestinal effects (nausea, diarrhea, abdominal cramps). At high doses, uterine contractions could pose risks in pregnant animals. Standard lab safety practices apply.
References

[1]. Uterine stimulant action of some omega-chain modified (+)-11-deoxyprostaglandins. Prostaglandins. 1981 Jul;22(1):53-64.

[2]. Structure-activity relationships in a series of 11-deoxy prostaglandins. Prostaglandins. 1976 Mar;11(3):573-87.

Additional Infomation
11-Deoxyprostaglandin F1alpha is a prostaglandin. The references provided refer to the (9α,13E,15S)-isomer.
11-deoxy Prostaglandin F1alpha (11-deoxy PGF1alpha) is a research-grade prostaglandin analog with molecular formula C20H36O4 and molecular weight 340.50. Purity reported as ≥95%. It is a synthetic analog of PGF1alpha used as a research tool for studying prostaglandin biology, smooth muscle contraction, and gastric physiology. For research use only, not for human therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H36O4
Molecular Weight
340.50
Exact Mass
340.261
CAS #
37785-98-1
PubChem CID
5283069
Appearance
Typically exists as solids at room temperature
Density
1.1±0.1 g/cm3
Boiling Point
507.2±40.0 °C at 760 mmHg
Flash Point
274.6±23.8 °C
Vapour Pressure
0.0±3.0 mmHg at 25°C
Index of Refraction
1.538
LogP
4.21
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
13
Heavy Atom Count
24
Complexity
367
Defined Atom Stereocenter Count
4
SMILES
CCCCC[C@@H](/C=C/[C@H]1CC[C@@H]([C@@H]1CCCCCCC(=O)O)O)O
InChi Key
HYBPXYQCXNOTFK-DUSCRHDRSA-N
InChi Code
InChI=1S/C20H36O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12,14,16-19,21-22H,2-11,13,15H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+,19-/m0/s1
Chemical Name
7-[(1R,2S,5R)-2-hydroxy-5-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]heptanoic acid
Synonyms
11-deoxy PGF1α
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9369 mL 14.6843 mL 29.3686 mL
5 mM 0.5874 mL 2.9369 mL 5.8737 mL
10 mM 0.2937 mL 1.4684 mL 2.9369 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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