Chenodeoxycholic Acid Specifications
| Product Name | Chenodeoxycholic acid |
| Chemical Name | (R)-4-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid |
| Synonym | Chenodeoxycholic Acid;
Anthropodeoxycholic acid; Anthropodesoxycholic acid; CCRIS 2195; Chendol; chenic acid; Chenix; Chenodeoxycholic acid; Chenodesoxycholic acid; Chenodiol; Gallodesoxycholic acid; NSC 657949; Xenbilox |
| CAS Number | 474-25-9 |
| InChIKey | RUDATBOHQWOJDD-BSWAIDMHSA-N |
| Molecular Formula | C24H40O4 |
| Molecular Weight | 392.57 |
| Monoisotopic Mass | 392.29265975 |
| Melting Point | 165-167 °C (lit.) |
| Boiling Point | 437.26°C (rough estimate) |
| Density | 0.9985 (rough estimate) |
| Color | White to off-white |
| Solubility | PRACTICALLY INSOLUBLE |
| Storage Temperature | room temp |
| Application | Chenodeoxycholic acid has been used in a study to assess its effects as a long-term replacement therapy for cerebrotendinous xanthomatosis (CTX). It has also been used in a study to investigate its effects on the small-intestinal absorption of bile acids in patients with ileostomies. |
| Testing Report | Available |
Chenodeoxycholic Acid
Chenodeoxycholic acid, more commonly known as chenodiol, is a type of bile acid that is found naturally in the human body and is also used exogenously for the chenodeoxycholic acid benefits. The use of this bile acid is recommended for the treatment of various medical conditions and these recommendations are supported by scientific evidence. The chenodeoxycholic acid mechanism of action has been studied in detail, in multiple different studies, with the purpose of finding the uses, benefits, and side effects of chenodiol.
What Are Bile Acids?
Bile acids are, as the name aptly describes, steroidal acids that are found in the human bile and bile of other mammals. Bile is the digestive fluid that is synthesized by the liver and stored in the gallbladder. Most of the bile acids are synthesized in the liver and can combine with the amino acids; taurine and glycine, to produce bile salts.
The bile acids that are synthesized by the liver are referred to as primary bile acids and include colic acid and chenodeoxycholic acid. Before secreting these primary bile acids, they are converted into bile salts. It is these bile salts that are then released, and reach the small intestines. Once in the duodenal part of the small intestine, the amino acids that are conjugated with the bile acids are removed by the gut flora. They undergo further modifications which result in colic acid being converted to deoxycholic acids and chenodeoxycholic acid into lithocholic acids. Deoxycholic and lithocholic acids are secondary bile acids.
Since the bile acids are synthesized in the liver from cholesterol, they have a steroid ring structure as their base. This is one of the reasons why bile acids act like steroid hormones in the body and perform a key role in signal transduction. However, the main function of bile acids is to improve the digestion of fats and oils that are consumed, and they do so by surrounding the dietary fat, creating a micelle.
Micelle is formed when lipids in the diet are coated and carried in a sphere made of bile salts. It is worth mentioning that the micelles contain bile acids but are formed by bile salts that lie right on the water and lipid interface. Their location along with their hydroponic and hydrophilic nature allows the bile salts to form these micelles at the right concentration. It is important to note that the micelle formation is key to the breakdown of fat by the necessary enzymes.
Bile acids also have other important functions, one of which is reducing the gut flora, which is also crucial for the formation of secondary bile acids. Removal of cholesterol and facilitating the absorption of fat-soluble Vitamins are some of the other functions of bile acids. They play a key role in the human body and something as minor as a concentration change could alter the body physiology significantly.
What is Chenodeoxycholic Acid(CDCA) Powder?
Chenodeoxycholic Acid Powder(474-25-9) or Chenodiol Powder is an exogenous bile acid that can
be consumed to achieve the same benefits as those achieved from endogenous chenodiol. The powder is used therapeutically, primarily for the treatment of gallstones, which are just deposits of hardened bile in the gallbladder. Chenodiol can also be used in the treatment of other disorders such as issues of bile synthesis and metabolism. It is an FDA-approved medication that is commonly prescribed for liver disorders that, at their core, arise from issues with bile.
Where Does The Chenodeoxycholic Acid Powder Come From?
The chenodeoxycholic acid is produced by hepatic cells from cholesterol. The exogenous chenodiol powder however is isolated from the bile of a swan, Cygnus melanocoryphus.
How Does Chenodeoxycholic Acid Powder Work?
Chenodioxycholic acid powder is primarily used for the treatment of gallstones, which are divided into two categories based on their contents and their appearance on radiography. Chenodiol is only able to effectively treat gallstones that are composed of cholesterol and appear radiolucent. Gallstones that are radiopaque or if they are radiolucent but composed of bile pigment, are not treated by CDCA powder.
Chenodiol treats gallstones by dissolving the cholesterol in them which is the result of biliary cholesterol desaturation by the CDCA powder. The chenodeoxycholic acid powder mechanism of action is simple, as it inhibits the synthesis of cholesterol and colic acid in the liver. Over time, it replaces cholic acid and its derivatives in the body. The saturation of cholesterol hence decreases, forcing the cholesterol stones to dissolve for balancing cholesterol concentration.
When taken orally, chenodiol makes its way to the intestines, where it is absorbed and sent to the liver for conjugation with taurine and glycine residues. Once conjugated, meaning that bile salts have been synthesized, CDCA bile salts are released into the bile. CDCA bile salts remain in the enterohepatic circulation meaning that serum levels or urine levels of CDCA are going to remain significantly unchanged.
What Is Chenodeoxycholic Acid Used For?
Chenodeoxycolic acid powder is used for:
- Treatment of radiolucent cholesterol gallstones, cannot be operated on due to the presence of other conditions which make surgery a difficult choice.
- Treatment of cerebrotendineous xanthomatosis
- Improved bowel function and management of constipation
- Treatment of inborn errors or biliary tree
- Management of hyperlipidemia
What Is The Importance Of Chenodeoxycholic Acid In Digestion?
Chenodeoxycholic acid is especially beneficial in facilitating lipid digestion by forming micelles around the fatty acids that have been absorbed from the intestine. The purpose of forming a micelle around lipids is to make them water-soluble so that they can be brought up to the intestinal surface for optimal absorption. Micelles are formed by bile salts and contain bile acids such as chenodeoxycholic acids, hence, making the latter an important ingredient for the facilitation of lipid digestion in the human body.
What Are The Benefits & Effects of Chenodeoxycholic Acid Powder?
Chenodeoxycholic acid powder is approved by FDA for use in the management of gallstones and certain other disorders. There are quite a few benefits of chenodiol which have been reported by users and proven by concrete scientific data. These benefits should be considered when prescribing CDCA powder to ensure that the benefits outweigh the risks.
Gallstones management is the primary role of Chenodiol, however, it only manages and treats a specific type of gallstone. If the gallstone isn’t radiolucent and contains cholesterol, the use of CDCA powder will not be enough for its dissolution. A study performed with the purpose of comparing the different treatment options for cholesterol gallstones found the use of chenodiol along with lithotripsy to be the treatment of choice. Chenodiol is especially recommended when surgical excision of the gall bladder is not a viable option.
Chenodeoxycholic acid powder benefits also include the treatment of metabolic disorders such as cerebrotendinous xanthomas. This disorder includes a genetic mutation in the gene that encodes the enzyme required for the conversion of cholesterol to bile acids in the liver. Absence of this enzyme results in a net decrease in bile acid synthesis and a significant increase in cholesterol which accumulates in different regions of the body, hence, forming xanthomas. Treating with exogenous bile acids such as chenodiol helps reduce cholesterol concentration in the body and improves the symptoms of this genetic disorder.
Chenodeoxycholic acid, along with its epimer, ursodeoxycholic acid, is believed to have antioxidant and anti-inflammatory properties, although these benefits are seen more with ursodiol. Chenodiol is also useful in the treatment of inborn errors of metabolism and other acute liver diseases.
How to Take Chenodeoxycholic Acid Powder？
(1)Before taking chenodiol powder
Before starting to take chenodeoxycholic powder, it is highly recommended to inform the prescribing doctor of all the current and past medications and health conditions to ensure that there are no possible interactions that could result in fatal consequences. For example, CDCA powder has several side effects that are related directly to the functioning of the liver which is why using it in liver disease is contraindicated. It is also important to notify the doctor of any allergies to the contents of the chenodiol tablet or powder, to ensure a reduced risk of side effects.
(2)Chenodeoxycholic acid powder dosage
Chenodiol powder should be taken orally, either with food or without. The exact chenodeoxycholic acid powder dosage is dependent on the weight of the person, the medical condition it is being used for, and the response to therapy. What the last part means is that the initial dose and the maintaining dose of the chenodeoxycholic acid powder may differ significantly based on how well or adversely the body reacts to it. Generally, for an adult, the dosage is between 13 mg and 16 mg per kilogram of weight.
Chenodiol powder is primarily used for the treatment of gallstones, and as they can take a long time for complete breakdown and excretion, the powder can be used for up to two years. However, after 2 years, the use of chenodeoxycholic acid should be stopped as the bile acid has potent hepatotoxic side effects. Moreover, the symptoms of gallstones or other biliary disorders may take up to a year to disappear with CDCA powder use.
(3)What happens if I miss a dose or overdose?
In case a dose of the chenodiol powder is missed, it is best to leave that be and take the next dose at the usual time. Double dosing can lead to overdose and is not recommended. While there aren’t many reported overdoses with chenodiol powder, there are a few that warrant a warning. If overdose is expected and the affected individual has trouble breathing, immediate medical help should be sought out.
(4)What should I avoid while taking chenodiol?
The use of chenodeoxycholic acid powder is contraindicated in certain conditions, such as:
- Hepatitis
- Cirrhosis
- Liver disease
- Pancreatic disease
- Obstruction in the gut
- Hemolytic anemia or other disorders or hemolysis
- Regular use of Alcohol
- Alcohol Abuse
- Pregnancy
The use of chenodiol during pregnancy can be severely teratogenic to the fetus and it is absolutely contraindicated. During breastfeeding, however, it is not known if the bile acid CDCA enters the breast milk and hence, is relatively contraindicated. Consulting a doctor before starting to take chenodeoxycholic acid powder while breastfeeding is highly advised.
What Other Drugs Will Interact with Chenodeoxycholic Acid?
The reported chenodeoxycholic acid side effects are mainly due to the effect of the bile acids directly, and rarely due to the interaction of the powder with other medications. That does not, however, mean that chenodeoxycholic acid powder will not interact with other medications. If chenodiol is taken with specific herbal products or medications, the effect of the powder will change significantly. The risk of developing adverse effects will also increase with these interactions.
Specific drugs that haven’t the ability to interact with chenodeoxycholic acid powder are:
- Cholestyramine
- Colestipol
- Birth control pills or hormone replacement therapy
- Antacids that contain aluminum as their main ingredients such as Almacone, Gelusil, Maalox, Mag-al Plus, Mylanta, Rulox, and others
- Blood thinners such as warfarin, Coumadin, Jantoven.
Cholestyramine and colestipol are both bile acid sequestrants that act in the stomach by trapping bile acids, hence, inhibiting their function. Taking bile acid sequestrants with bile acid would make the latter redundant and no benefits would be seen. Instead, the medical condition for which chenodeoxycholic acid is prescribed will get worse.
It is important to not take chenodiol with other forms of bile acids as that may increase the risk of side effects. It is highly recommended to check with the doctor and inform them of any other vitamins or drugs one may be taking, before starting chenodiol as some medications may need to be stopped before starting chenodeoxycholic acid. Not just that, mentioning medications that have been recently used and then discontinued may also be beneficial as some drugs can stay in the system for a long time.
What Are The Differences Between Ursodeoxycholic Acid Powder And Chenodeoxycholic Acid Powder?
Chenodeoxycholic acid powder and Ursodeoxycholic acid powder are two of the major exogenous bile acids that are prescribed and used for the management of gallstones.
Ursodeoxycholic acid powder
Ursodeoxycholic acid powder or ursodiol is a secondary bile acid in the human body, that is synthesized from the modification of bile salts by the gut flora. Unlike chenodeoxycholic acid which is primary bile acid and synthesized in the liver, ursodiol is synthesized in the small intestines. The exogenous ursodeoxycholic acid powder is produced from cholic acid which is extracted from the bovine bile.
Comparison of benefits and function
Ursodiol and Chenodiol are used for gallstone dissolution, however, the other uses of the two are not as similar. Ursodiol is also used for the management of primary biliary cholangitis and primary sclerosing cholangitis. Due to its higher safety profile, ursodiol is the bile acid of choice for the treatment of intrahepatic cholestasis of pregnancy.
Major Differences
The major difference between chenodeoxycholic acid powder and ursodeoxycholic acid powder is that the latter is not hepatotoxic and can be used freely whereas the former is hepatotoxic and can cause potentially fatal liver disease. Chenodiol is a primary bile acid and Ursodiol is a secondary bile acid along with being an epimer of chenodiol.
Recent studies that were performed with the purpose of comparing ursodiol and chenodiol found that UDCA was more effective at reducing the size of gallstones at the 3-month mark and 6-month mark. However, after 12 months the efficiency of both chenodiol and ursodiol was balanced out and there were no significant differences between the two. Moreover, it was found that Ursodiol could effectively target and treat large and small gallstones at both, high doses and low doses. Chenodiol, on the other hand, was only effective at reducing the size of small gallstones at higher doses.
According to a different study, chenodiol at lower doses was associated with an increased incidence of cholecystectomy.
What Are The Possible Side Effects Of Chenodeoxycholic Acid?
When chenodeoxycholic acid is prescribed, it is recommended to follow up with the patient frequently. Each follow-up visit should include a blood test with the main focus being on liver enzymes. This is because of the hepatotoxic nature of chenodeoxycholic acid. The potential side effects of chenodeoxycholic acid can be divided into five categories, based on the organ system that is mostly affected by the side effects:
Hematologic side effects
A few cases of hematologic side effects have been reported, with all of the affected individuals reporting a significant decrease in white blood cell concentration. The concentration never dropped below 3000 and despite this decrease, the medication was well tolerated. The decision to discontinue the CDCA powder was not made for any of these patients as this side effect did not raise any major health concerns.
Hepatic side effects
Chenodeoxycholic acid powder is hepatotoxic which is why its use is contraindicated in liver diseases. Moreover, the hepatotoxicity of CDCA powder can be severe enough that regular monitoring of liver enzymes is crucial when the medication is started. These side effects are not commonly seen if proper precautions such as monitoring of liver function are taken. The use of chenodiol powder without focusing on the liver function tests can cause life-threatening liver failure and disease.
The symptoms of liver disease that may present themselves with hepatotoxicity of chenodiol are:
- Yellowing of eyes
- Yellow skin
- Dark-colored urine
- Unusual fatigue and lethargy
- Severe abdominal pain
- Nausea and vomiting that does not resolve
Gastrointestinal side effects
These side effects may manifest at any point during the treatment plan however, they are most commonly observed when the treatment is first started. This is quite a casual side effect as most medications when initially used, can cause mild gastrointestinal irritation. Approximately 30 percent to 40 percent of people taking chenodiol report diarrhea that is well tolerated and not severe. Only up to 15 percent of those suffering from dose-dependent diarrhea required a dose reduction. Some reported improvement in symptoms after adjunct use of anti-diarrheal agents.
Rarely, discontinuation of chenodiol is required when the diarrhea is severe and is accompanied by debilitating abdominal cramps. Before discontinuing the medication, it is important to differentiate between the diarrheal cramps from the colicky, abdominal pain that may be present with gallstones. Confusing the latter with the former and discontinuing CDCA powder could be detrimental to overall health.
Some of the rarer gastrointestinal side effects include,
- Nausea and vomiting
- Cramps
- Heartburn
- Constipation
- Dyspepsia
- Generalized abdominal pain
- Flatulence
- Anorexia
Cholesterol Concentration
An approximate 10 percent increase in the concentration of cholesterol and bad fats, LDL, may be seen with the use of chenodeoxycholic acid powder. A few females taking the bile acid also reported a mild increase in their triglycerides levels, along with total cholesterol and LDL levels. No change in HDL or the good fats has been reported.
Gallbladder removal or cholecystectomy rates
Individuals with gallstones and a history of biliary pain frequently required a cholecystectomy procedure as a treatment for their gallstones. Moreover, these patients also were unable to tolerate high dose chenodeoxycholic acid powder and were given low doses instead. Inability to tolerate high dose CDCA powder has, thus, been associated with increased cholecystectomy rates.
What Measures Are Being Taken To Ensure The Safe And Effective Use Of Chenodeoxycholic Acid?
Healthcare personnel and general practitioners conduct follow-up visits to actively lookout for any potential side effects of chenodeoxycholic acid powder to ensure its safety and the overall efficacy of the powder.
Where Can I Get More Information On Chenodeoxycholic Acid Powder Sold?
For more information on chenodeoxycholic acid powder sales in bulk, you can use online resources such as the websites of different chenodeoxycholic acid powder manufacturers or factory.
More Research About Chenodeoxycholic Acid
Chenodeoxycholic acid is currently being studied for other potential uses of the compound, apart from its biliary-specific uses. An Australian biotechnology company is currently studying chenodiol in combination with a lipid-lowering drug, bezafibrate for the treatment of Hepatitis C.
Frequently Asked Questions
(1)Why is chenodeoxycholic acid (chenodiol) only for select people?
Chenodiol is a potent bile acid that can help treat gallstones. However, it is also hepatotoxic and can cause severe liver disease. This is why it is not recommended for those with liver disease as the symptoms of the disease may be exaggerated by the bile acid.
(2)Can I take Chenodal (chenodiol) if I’m pregnant?
The use of chenodiol is not recommended during pregnancy due to the teratogenic potential of the medication.
(3)How long should I take Chenodal (chenodeoxycholic acid)?
Chenodal can be taken for up to two years at a time, and it can take the chenodeoxycholic acid CDCA powder up to a year to alleviate the symptoms and treat the condition. After using CDCA powder for two years, it is important to take a break.
(4)Why am I asked to see my provider periodically for tests?
Your provider is testing your liver enzymes and cholesterol levels to ensure that everything is within normal range, and chenodiol hasn’t had any negative effect on your overall health. Due to the extremely hepatotoxic nature of the CDCA powder and its ability to cause liver disease rather rapidly, your chenodeoxycholic acid supplier will ask you periodically for tests. Cholesterol levels have also been found to increase with the use of chenodiol, which is another test that your provider will request from you.
(5)What medications should I avoid while taking Chenodal (chenodiol)?
When taking Chenodiol, you should steer clear of bile acid sequestrants such as cholestyramine and colestipol as they would interact with CDCA powder and make its use redundant. It is not recommended to take anticoagulants such as warfarin and coumadin, birth control pills with estrogen in them, or antacids and other medications containing aluminum. If you are taking any vitamins supplement, herbal supplements, and herbal teas, or have just stopped taking a medication, you should inform your doctor to ensure none of your current or recent medications interact with chenodiol.
Reference
- Russell DW (2003). “The enzymes, regulation, and genetics of bile acid synthesis”. Annu. Rev. Biochem. 72: 137– doi:10.1146/annurev.biochem.72.121801.161712. PMID 12543708.
- Bhagavan, N.V.; Ha, Chung-Eun (2015). “Gastrointestinal Digestion and Absorption”. Essentials of Medical Biochemistry. pp. 137– doi:10.1016/B978-0-12-416687-5.00011-7. ISBN 9780124166875.
- Dawson, PA; Karpen, SJ (June 2015). “Intestinal transport and metabolism of bile acids”. Journal of Lipid Research. 56 (6): 1085– doi:10.1194/jlr.R054114. PMC 4442867. PMID 25210150.
- Carey MC (December 1975). “Editorial: Cheno and urso: what the goose and the bear have in common”. N. Engl. J. Med. 293 (24): 1255– doi:10.1056/NEJM197512112932412. PMID 1186807.
- Berginer VM, Salen G, Shefer S (December 1984). “Long-term treatment of cerebrotendinous xanthomatosis with chenodeoxycholic acid”. N. Engl. J. Med. 311 (26): 1649– doi:10.1056/NEJM198412273112601. PMID 6504105.
- Rao, AS; Wong, BS; Camilleri, M; Odunsi-Shiyanbade, ST; McKinzie, S; Ryks, M; Burton, D; Carlson, P; Lamsam, J; Singh, R; Zinsmeister, AR (November 2010). “Chenodeoxycholate in females with irritable bowel syndrome-constipation: a pharmacodynamic and pharmacogenetic analysis”. Gastroenterology. 139 (5): 1549–58, 1558.e1. doi:10.1053/j.gastro.2010.07.052. PMC 3189402. PMID 20691689.
- Thistle JL, Hofmann AF (September 1973). “Efficacy and specificity of chenodeoxycholic acid therapy for dissolving gallstones”. N. Engl. J. Med. 289 (13): 655– doi:10.1056/NEJM197309272891303. PMID 4580472.
- Hofmann, AF (September 1989). “Medical dissolution of gallstones by oral bile acid therapy”. American Journal of Surgery. 158 (3): 198– doi:10.1016/0002-9610(89)90252-3. PMID 2672842.
