| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| 5mg |
|
||
| 10mg |
|
||
| 25mg |
|
||
| 50mg |
|
||
| 100mg | |||
| Other Sizes |
| Targets |
Carboprost targets the prostaglandin F2α (FP) receptor in the uterus. As a synthetic analogue of prostaglandin F2α, it binds to and activates the FP receptor, which is a G protein-coupled receptor. Activation of the FP receptor leads to increased intracellular calcium levels and smooth muscle contraction. This uterotonic effect is the basis for its clinical use in managing postpartum hemorrhage and inducing abortion. The 15-methyl substitution provides metabolic stability, prolonging its duration of action compared to the natural prostaglandin.
|
|---|---|
| ln Vitro |
Carboprost exhibits potent in vitro activity as a uterotonic agent. It stimulates contraction of uterine smooth muscle in isolated tissue preparations. The compound's activity is mediated through activation of the prostaglandin F2α receptor, leading to increased intracellular calcium and muscle contraction. In vitro studies have demonstrated its ability to induce myometrial contractions in a dose-dependent manner. However, detailed in vitro activity data, including EC50 values, are typically found in proprietary pharmacological studies.
|
| ln Vivo |
Serum progesterone was lowered to 12% of pretreatment values within 24 hours of administering carboprost methyl ester (15(S)-15-methylprostaglandin F2α; 15M-PGF2α, 12.5 mg/monkey); however, progesterone returned to normal range within 48 hours. [1].
Carboprost has well-established in vivo activity as a uterotonic agent. It is used clinically to treat postpartum uterine hemorrhage due to atony and to induce second-trimester abortion. The compound is administered by intramuscular injection. Its in vivo effects include increased uterine tone and rhythmic contractions, which help to control bleeding after delivery. The 15-methyl substitution provides metabolic stability, ensuring a longer duration of action compared to natural prostaglandin F2α. |
| Enzyme Assay |
In vitro receptor binding experiments for Carboprost typically involve measuring its affinity for the prostaglandin F2α (FP) receptor. Radioligand binding assays are performed using membrane preparations from cells expressing the FP receptor. The compound's binding affinity (Ki) and selectivity for the FP receptor over other prostaglandin receptors are determined. Functional assays measuring receptor activation, such as calcium flux or inositol phosphate accumulation, are also performed to assess its agonist activity.
|
| Cell Assay |
In vitro cellular assays for Carboprost typically involve studying its effects on cells expressing the prostaglandin F2α receptor. Cells are treated with the compound, and receptor activation is measured by monitoring downstream signaling pathways, such as calcium mobilization or cAMP inhibition. The compound's effects on cell proliferation and viability are also assessed. Cytotoxicity assays are performed to ensure that the observed effects are not due to cell death.
|
| Animal Protocol |
In vivo animal experiments for Carboprost have been conducted in various animal models to evaluate its uterotonic effects and pharmacokinetic properties. Studies typically involve administering the compound to pregnant or non-pregnant animals and measuring uterine contractility, blood loss, and other parameters. The compound's efficacy in inducing abortion and managing postpartum hemorrhage has been demonstrated in preclinical studies. However, detailed in vivo protocols are typically found in proprietary pharmacological studies.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of Carboprost have been characterized in humans. The compound is administered by intramuscular injection. It is rapidly absorbed and distributed. The 15-methyl substitution provides metabolic stability, prolonging its half-life compared to natural prostaglandin F2α. The compound is metabolized in the liver and excreted in the urine. Its pharmacokinetic profile supports its clinical use as a single or repeat dose for managing postpartum hemorrhage.
|
| Toxicity/Toxicokinetics |
Toxicological data for Carboprost indicate that it is generally well-tolerated when used clinically. Common adverse effects include nausea, vomiting, diarrhea, fever, and flushing. More serious adverse effects can include uterine hyperstimulation, bronchospasm, and hypertension. The compound is contraindicated in patients with certain medical conditions. Comprehensive toxicology studies have been conducted as part of its clinical development and regulatory approval process.
|
| References | |
| Additional Infomation |
Carboprost is a derivative of prostaglandin F2α, with its 15-hydrogen atom replaced by a methyl group (S configuration). It is an abortifacient effective in early and mid-pregnancy. It has a dual effect of inducing labor and causing abortion. Its function is related to prostaglandin F2α. It is the conjugate acid of carboprost (1-). Carboprost is a prostaglandin analog. Carboprost is a (15S)-15 methyl analog of the naturally occurring, labor-inducing prostaglandin F2α (PGF2α). Carboprost mimics endogenous PGF2α, activating the G protein-coupled receptor—prostaglandin F receptor—on smooth muscle cells, thereby causing smooth muscle contraction. When injected intramuscularly into pregnant women, it can induce uterine muscle contraction, thereby initiating corpus luteum dissolution and ultimately leading to delivery. In addition, carboprost acts on vascular smooth muscle and gastrointestinal sphincters, causing elevated blood pressure and vomiting or diarrhea, respectively. This product is a nonsteroidal abortifacient effective in early and mid-pregnancy. See also: Carboprost tromethamine (salt form).
Carboprost is an FDA-approved active pharmaceutical ingredient (API) that has been in clinical use for several decades. It is marketed as the tromethamine salt under the trade name Hemabate for the treatment of postpartum uterine hemorrhage due to atony. It is also used for inducing second-trimester abortion. The compound is classified as a nonsteroidal abortifacient agent and is also known as 15(S)-15-methyl Prostaglandin F2α. It is available as a sterile solution for intramuscular injection. |
| Molecular Formula |
C21H36O5
|
|---|---|
| Molecular Weight |
368.50754
|
| Exact Mass |
368.256
|
| CAS # |
35700-23-3
|
| PubChem CID |
5281075
|
| Appearance |
White to off-white ointment
|
| Density |
1.1±0.1 g/cm3
|
| Boiling Point |
536.6±50.0 °C at 760 mmHg
|
| Melting Point |
79-82ºC
|
| Flash Point |
292.4±26.6 °C
|
| Vapour Pressure |
0.0±3.2 mmHg at 25°C
|
| Index of Refraction |
1.565
|
| LogP |
2.49
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
12
|
| Heavy Atom Count |
26
|
| Complexity |
473
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
CCCCC[C@@](C)(/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@H](C[C@H]1O)O)O
|
| InChi Key |
DLJKPYFALUEJCK-IIELGFQLSA-N
|
| InChi Code |
InChI=1S/C21H36O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,19-,21+/m1/s1
|
| Chemical Name |
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]hept-5-enoic acid
|
| 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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~271.36 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.78 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.78 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.78 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7136 mL | 13.5682 mL | 27.1363 mL | |
| 5 mM | 0.5427 mL | 2.7136 mL | 5.4273 mL | |
| 10 mM | 0.2714 mL | 1.3568 mL | 2.7136 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.
Calculation results
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.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
