Identification
- Generic Name
- Glycocholic acid
- DrugBank Accession Number
- DB02691
- Background
The glycine conjugate of cholic acid. It acts as a detergent to solubilize fats for absorption and is itself absorbed.
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
Structure for Glycocholic acid (DB02691)
- Weight
- Average: 464.624
Monoisotopic: 464.301761656 - Chemical Formula
- C26H42NO6
- Synonyms
- N-choloylglycine
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
Target Actions Organism UGastrotropin Not Available Humans - 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 softwareAbciximab The risk or severity of adverse effects can be increased when Abciximab is combined with Glycocholic acid. Acenocoumarol The risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Glycocholic acid. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Glycocholic acid. Alteplase The risk or severity of bleeding and bruising can be increased when Alteplase is combined with Glycocholic acid. Aluminium phosphate Aluminium phosphate can cause a decrease in the absorption of Glycocholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy. - Food Interactions
- Not Available
Categories
- Drug Categories
- Amino Acids
- Amino Acids, Peptides, and Proteins
- Bile Acids and Salts
- Cholagogues and Choleretics
- Cholanes
- Cholic Acids
- Compounds used in a research, industrial, or household setting
- Detergents
- Fused-Ring Compounds
- Gastrointestinal Agents
- Household Products
- N-substituted Glycines
- Steroids
- Surface-Active Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as glycinated bile acids and derivatives. These are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Bile acids, alcohols and derivatives
- Direct Parent
- Glycinated bile acids and derivatives
- Alternative Parents
- Trihydroxy bile acids, alcohols and derivatives / 12-hydroxysteroids / 3-alpha-hydroxysteroids / 7-hydroxysteroids / N-acyl-alpha amino acids / N-acyl amines / Secondary carboxylic acid amides / Secondary alcohols / Cyclic alcohols and derivatives / Polyols show 8 more
- Substituents
- 12-hydroxysteroid / 3-alpha-hydroxysteroid / 3-hydroxysteroid / 7-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-amino acid or derivatives / Carbonyl group / Carboxamide group / Carboxylic acid show 23 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- N-acylglycinate (CHEBI:29746)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- G59NX3I3RT
- CAS number
- 475-31-0
- InChI Key
- RFDAIACWWDREDC-FRVQLJSFSA-M
- InChI
- InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/p-1/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1
- IUPAC Name
- 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetate
- SMILES
- [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCC([O-])=O
References
- General References
- Not Available
- External Links
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Inborn Error of Bile Acid Conjugation / Inborn Error of Bile Acid Metabolism / Inborn Errors of Bile Acid Synthesis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 166.5 °C PhysProp water solubility 3.3 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 1.65 RODA,A ET AL. (1990) logS -5.15 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.0214 mg/mL ALOGPS logP 2.07 ALOGPS logP 1.38 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 3.77 Chemaxon pKa (Strongest Basic) -0.14 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 129.92 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 134.43 m3·mol-1 Chemaxon Polarizability 52.37 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9543 Blood Brain Barrier + 0.8437 Caco-2 permeable - 0.8855 P-glycoprotein substrate Substrate 0.7178 P-glycoprotein inhibitor I Non-inhibitor 0.767 P-glycoprotein inhibitor II Non-inhibitor 0.5333 Renal organic cation transporter Non-inhibitor 0.8654 CYP450 2C9 substrate Non-substrate 0.7788 CYP450 2D6 substrate Non-substrate 0.773 CYP450 3A4 substrate Substrate 0.7391 CYP450 1A2 substrate Non-inhibitor 0.9382 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8426 Ames test Non AMES toxic 0.9154 Carcinogenicity Non-carcinogens 0.9478 Biodegradation Not ready biodegradable 0.9798 Rat acute toxicity 2.5186 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9826 hERG inhibition (predictor II) Non-inhibitor 0.7952
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 211.87187 predictedDeepCCS 1.0 (2019) [M+H]+ 213.5956 predictedDeepCCS 1.0 (2019) [M+Na]+ 219.92456 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transporter activity
- Specific Function
- Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile ac...
- Gene Name
- FABP6
- Uniprot ID
- P51161
- Uniprot Name
- Gastrotropin
- Molecular Weight
- 14371.245 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:45