| Size | Price | Stock | Qty |
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Dehydrocholic Acid (3,7,12-Trioxo-5β-cholanic acid 5β-Cholanic acid-3,5,12-trione) is a bile acid used in the production of chenodeoxycholic acid by bioconversion.
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Duodenal experiments showed that dehydrocholic acid is absorbed in the proximal small intestine. Administered dehydrocholic acid is rapidly excreted via bile as bile acids conjugated with glycine and taurine. Pharmacokinetic data are currently unavailable. Metabolism/Metabolites The primary site of metabolism is considered to be the liver. The major metabolite, accounting for 70% of all detectable metabolites, is dihydroxymonoketone bile acid (3α,7α-dihydroxy-12-keto-5β-cholanic acid). Approximately 20% of the metabolites are monohydroxydiketo acids (3α-hydroxy-7,12-keto-5β-cholanic acid), and approximately 10% are bile acids. Biological Half-Life Pharmacokinetic data are currently unavailable. |
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| Toxicity/Toxicokinetics |
Protein Binding
No pharmacokinetic data available. |
| Additional Infomation |
3,7,12-Trioxo-5β-cholanic acid is an oxo-5β-cholanic acid with three oxo-substituents attached to positions 3, 7, and 12 of its cholanic acid skeleton. It is a gastrointestinal drug. It is an oxo-5β-cholanic acid, 7-oxosteroid, 12-oxosteroid, and 3-oxo-5β-steroid. It is the conjugate acid of 3,7,12-trioxo-5β-cholan-24-acid. Dehydrocholic acid is a synthetic bile acid produced by the oxidation of cholic acid with chromic acid. It was once used to stimulate bile lipid secretion. Health Canada has discontinued the use of dehydrocholic acid in over-the-counter products. Dehydrocholic acid is a semi-synthetic bile acid made from cholic acid. It can be used as a choleretic, bile secretion stimulant, diuretic, and diagnostic aid.
Drug Indications There are currently no approved therapeutic indications. Mechanism of Action It is hypothesized that dehydrocholic acid (DHCA) induces bile secretion, which is associated with increased bile lipid secretion and decreased secretion of endogenous and/or exogenous bile components. Since bile produced by DHCA lacks micelle formation, it may reduce bile phospholipid secretion. One study showed that DHCA promotes direct exchange between bile and plasma due to increased permeability of tight junctions in the bile canaliculi. Pharmacodynamics In rats, infusion of DHCA reduced the secretion of all endogenous bile acids within 30–60 minutes post-infusion. Phospholipid secretion and cholesterol levels also decreased. Bile flow increased after administration of DHCA. |
| Molecular Formula |
C24H34O5
|
|---|---|
| Molecular Weight |
402.5238
|
| Exact Mass |
402.24
|
| CAS # |
81-23-2
|
| Related CAS # |
81-23-2 (acid);145-41-5 (sodium);
|
| PubChem CID |
6674
|
| Appearance |
White to off-white solid powder
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
581.5±50.0 °C at 760 mmHg
|
| Melting Point |
238-240 °C
|
| Flash Point |
319.5±26.6 °C
|
| Vapour Pressure |
0.0±3.5 mmHg at 25°C
|
| Index of Refraction |
1.535
|
| LogP |
1.77
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
29
|
| Complexity |
756
|
| Defined Atom Stereocenter Count |
8
|
| SMILES |
O=C1C[C@@H]2CC(CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCC(=O)O)[C@]1(C(C2)=O)C)=O
|
| InChi Key |
OHXPGWPVLFPUSM-KLRNGDHRSA-N
|
| InChi Code |
InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1
|
| Chemical Name |
(4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
|
| HS Tariff Code |
2934.99.9001
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| 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 (In Vitro) |
DMSO : ~25 mg/mL (~62.11 mM)
H2O : ~0.67 mg/mL (~1.66 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (6.21 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 (6.21 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4843 mL | 12.4217 mL | 24.8435 mL | |
| 5 mM | 0.4969 mL | 2.4843 mL | 4.9687 mL | |
| 10 mM | 0.2484 mL | 1.2422 mL | 2.4843 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.
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