Deoxycholic acid

Identification

Summary

Deoxycholic acid is a cytolytic agent injected subcutaneously to improve the appearance submental fat.

Brand Names
Belkyra, Kybella
Generic Name
Deoxycholic acid
DrugBank Accession Number
DB03619
Background

Deoxycholic acid is a a bile acid which emulsifies and solubilizes dietary fats in the intestine, and when injected subcutaneously, it disrupts cell membranes in adipocytes and destroys fat cells in that tissue. In April 2015, deoxycholic acid was approved by the FDA for the treatment submental fat to improve aesthetic appearance and reduce facial fullness or convexity. It is marketed under the brand name Kybella by Kythera Biopharma and is the first pharmacological agent available for submental fat reduction, allowing for a safer and less invasive alternative than surgical procedures.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 392.572
Monoisotopic: 392.292659768
Chemical Formula
C24H40O4
Synonyms
  • (3α,5β,12α)-3,12-dihydroxycholan-24-oic acid
  • 3alpha,12alpha-Dihydroxy-5beta-cholanic acid
  • 7α-deoxycholic acid
  • Deoxycholate
  • Deoxycholic acid
  • Desoxycholic acid
  • Desoxycholsäure
External IDs
  • ATX-101

Pharmacology

Indication

For improvement in appearance of moderate to severe fullness associated with submental fat in adults.

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Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

As a bile acid, deoxycholic acid emulsifies fat in the gut. Synthetically derived deoxycholic acid, when injected, stimulates a targeted breakdown of adipose cells by disrupting the cell membrane and causing adipocytolysis. This results in an inflammatory reaction and clearing of the adipose tissue remnants by macrophages. Deoxycholic acid's actions are reduced by albumin and tissue-associated proteins, therefore its effect is limited to protein-poor subcutaneous fat tissue. Protein-rich tissues like muscle and skin are unaffected by deoxycholic acid, contributing to its safety profile.

TargetActionsOrganism
USteroid Delta-isomeraseNot AvailablePseudomonas putida
UPpcANot AvailableGeobacter sulfurreducens
UElongation factor Tu GTP-binding domain-containing protein 1Not AvailableHumans
UCholoylglycine hydrolaseNot AvailableClostridium perfringens (strain 13 / Type A)
ULactaldehyde dehydrogenaseNot AvailableEscherichia coli (strain K12)
UAcriflavine resistance protein BNot AvailableEscherichia coli (strain K12)
UCytochrome c oxidase subunit 1Not AvailableRhodobacter sphaeroides
UCytochrome c oxidase subunit 2Not AvailableRhodobacter sphaeroides
UBile acid receptorNot AvailableHumans
UGlutathione S-transferase PNot AvailableHumans
UG-protein coupled bile acid receptor 1Not AvailableHumans
UGlutathione S-transferases (Cytosolic)
inhibitor
Humans
Absorption

Deoxycholic acid is rapidly absorbed after subcutaneous administration. After maximum recommended single treatment dose, 100mg, the post-treatment plasma levels returned to endogenous levels within 24 hours. With the proposed treatment guideline, no accumulation is expected.

Volume of distribution

Not Available

Protein binding

98%

Metabolism

Deoxycholic acid is not metabolized to any significant extent under normal conditions.

Route of elimination

The exogenous deoxycholic acid joins the endogenous bile acid pool in the enterohepatic circulation and is excreted unchanged in feces along with endogenous deoxycholic acid.

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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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.
DrugInteraction
AbciximabThe risk or severity of adverse effects can be increased when Abciximab is combined with Deoxycholic acid.
AcenocoumarolThe risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Deoxycholic acid.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Deoxycholic acid.
AlteplaseThe risk or severity of bleeding and bruising can be increased when Alteplase is combined with Deoxycholic acid.
Aluminium phosphateAluminium phosphate can cause a decrease in the absorption of Deoxycholic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Food Interactions
No interactions found.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BelkyraSolution10 mg / mLSubcutaneousAbbvie2016-01-27Not applicableCanada flag
KybellaInjection, solution20 mg/2mLSubcutaneousKythera Biopharmaceuticals Inc.2015-06-08Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DebilineDeoxycholic acid (100 mg) + Pepsin (50 mg)TabletOralLab Nadeau LtÉe, Division Of Technilab Inc.1951-12-311999-09-28Canada flag
Debiline HDeoxycholic acid (100 mg / tab) + Homatropine methylbromide (2.5 mg / tab) + Pepsin (50 mg / tab)TabletOralLab Nadeau LtÉe, Division Of Technilab Inc.1951-12-311999-09-28Canada flag
Duchol EctDeoxycholic acid (30 mg) + Dehydrocholic acid (30 mg) + Pancrelipase (200 mg) + Pepsin (200 mg) + Sodium taurocholate (100 mg)Tablet, delayed releaseOralDuchesnay Inc.1977-12-312003-07-18Canada flag
ENZYPLEX TABLETDeoxycholic acid (30 mg) + Cyanocobalamin (5 mcg) + Dimethicone (25 mg) + Nicotinamide (10 mg) + Pancrelipase amylase (10000 u) + Pancrelipase lipase (240 u) + Pancrelipase protease (9000 u) + Calcium pantothenate (5 mg) + Pyridoxine (5 mg) + Riboflavin (5 mg) + Thiamine (10 mg)Tablet, coatedOralZUELLIG PHARMA PTE. LTD.1991-03-05Not applicableSingapore flag
MedicholDeoxycholic acid (30 mg) + Dehydrocholic acid (30 mg) + Pancrelipase (200 mg) + Pepsin (200 mg) + Sodium taurocholate (100 mg)TabletOralMedic Laboratory LtÉe1959-12-312007-10-22Canada flag

Categories

ATC Codes
D11AX24 — Deoxycholic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Bile acids, alcohols and derivatives
Direct Parent
Dihydroxy bile acids, alcohols and derivatives
Alternative Parents
3-alpha-hydroxysteroids / 12-hydroxysteroids / Secondary alcohols / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
12-hydroxysteroid / 3-alpha-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic alcohol / Dihydroxy bile acid, alcohol, or derivatives
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
bile acid, dihydroxy-5beta-cholanic acid (CHEBI:28834) / C24 bile acids, alcohols, and derivatives, Cholane and derivatives (C04483) / C24 bile acids, alcohols, and derivatives (LMST04010040)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
005990WHZZ
CAS number
83-44-3
InChI Key
KXGVEGMKQFWNSR-LLQZFEROSA-N
InChI
InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
IUPAC Name
(4R)-4-[(1R,3aS,3bR,5aR,7R,9aS,9bS,11S,11aR)-7,11-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C

References

Synthesis Reference

Filiberto Zadini, Giorgio Zadini, "Deoxycholic acid liposome-based dermatological topical preparation." U.S. Patent US20060222695, issued October 05, 2006.

US20060222695
General References
  1. Wollina U, Goldman A: ATX-101 for reduction of submental fat. Expert Opin Pharmacother. 2015 Apr;16(5):755-62. doi: 10.1517/14656566.2015.1019465. Epub 2015 Feb 27. [Article]
  2. Walker P, Lee D: A phase 1 pharmacokinetic study of ATX-101: serum lipids and adipokines following synthetic deoxycholic acid injections. J Cosmet Dermatol. 2015 Mar;14(1):33-9. doi: 10.1111/jocd.12122. Epub 2015 Feb 14. [Article]
  3. FDA Approved Drug Products: KYBELLA (deoxycholic acid) injection [Link]
Human Metabolome Database
HMDB0000626
KEGG Compound
C04483
PubChem Compound
222528
PubChem Substance
46506360
ChemSpider
193196
BindingDB
50375599
RxNav
3194
ChEBI
28834
ChEMBL
CHEMBL406393
ZINC
ZINC000003914810
PDBe Ligand
DXC
Drugs.com
Drugs.com Drug Page
Wikipedia
Deoxycholic_acid
PDB Entries
1e3v / 1fm4 / 1os6 / 2bjf / 2opx / 2w1b / 3dtu / 3r9v / 3rv5 / 3sel
show 26 more
FDA label
Download (3.18 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAdiposity2
4CompletedTreatmentBody Fat Disorder1
4CompletedTreatmentBrassiere Strap Fat (BSF)1
4CompletedTreatmentContour1
4CompletedTreatmentFacial Rhytides, Skin Folds, Loss of Volume and Skin Quality1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solution10 MG/ML
Injection, solution10 mg/1ml
SolutionSubcutaneous10 mg / mL
Injection, solutionParenteral10 mg/ml
Injection, solutionSubcutaneous10.00 mg/mL
SolutionSubcutaneous10 mg
Tablet, delayed releaseOral
Tablet, coatedOral
Injection, solutionSubcutaneous20 mg/2mL
TabletOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8546367No2013-10-012028-02-21US flag
US7622130No2009-11-242027-12-10US flag
US7754230No2010-07-132027-12-10US flag
US8298556No2012-10-302025-08-03US flag
US8846066No2014-09-302025-02-08US flag
US8367649No2013-02-052030-03-02US flag
US8461140No2013-06-112028-02-21US flag
US8883770No2014-11-112028-02-21US flag
US8653058No2014-02-182030-03-02US flag
US8101593No2012-01-242030-03-02US flag
US8242294No2012-08-142028-05-16US flag
US9522155No2016-12-202028-02-21US flag
US9636349No2017-05-022028-02-21US flag
US9949986No2018-04-242028-02-21US flag
US10500214No2019-12-102030-03-02US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)177 °CPhysProp
water solubility43.6 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.50RODA,A ET AL. (1990)
logS-3.95ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0173 mg/mLALOGPS
logP3.3ALOGPS
logP3.79Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.65Chemaxon
pKa (Strongest Basic)-0.35Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area77.76 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity109.2 m3·mol-1Chemaxon
Polarizability46.3 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9766
Blood Brain Barrier+0.9288
Caco-2 permeable+0.73
P-glycoprotein substrateSubstrate0.6648
P-glycoprotein inhibitor INon-inhibitor0.8737
P-glycoprotein inhibitor IIInhibitor0.5368
Renal organic cation transporterNon-inhibitor0.8537
CYP450 2C9 substrateNon-substrate0.7818
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9456
CYP450 2D6 inhibitorNon-inhibitor0.9781
CYP450 2C19 inhibitorNon-inhibitor0.9707
CYP450 3A4 inhibitorNon-inhibitor0.8405
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9563
Ames testNon AMES toxic0.8794
CarcinogenicityNon-carcinogens0.9329
BiodegradationNot ready biodegradable0.992
Rat acute toxicity2.5624 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9622
hERG inhibition (predictor II)Non-inhibitor0.7246
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00os-0119000000-ff101495d4bc6a37fc83
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-0006-0009000000-8b9c4803e9cb1d194c2e
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0006-0009000000-cccabd9d13ac783b6e31
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0007-2009000000-d7c20760d2074c07af22
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0006-0009000000-269a5d1ed75b71c78ecb
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, NegativeLC-MS/MSsplash10-0007-0009000000-72f1acf9f31f344daaa1
LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , NegativeLC-MS/MSsplash10-000x-0008000900-ebb0e6a61bd8f06a21f7
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-0002-0009000000-8078ef73008efc65c713
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0009000000-269a5d1ed75b71c78ecb
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0007-0009000000-827a9ce119d7f2f1cb5c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-054o-0019000000-d1e04345957f21884170
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-bb2fb14c04379a690ba8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-6215bb0a35a15ca7f67c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-3179000000-2adf531a499498cfd00f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fh3-0039000000-10aa809d47cf5ed659bb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-066r-4930000000-b701e89eb982f6536d7d
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.1984715
predicted
DarkChem Lite v0.1.0
[M-H]-193.4198624
predicted
DarkChem Standard v0.1.0
[M-H]-209.2866715
predicted
DarkChem Lite v0.1.0
[M-H]-206.5020715
predicted
DarkChem Lite v0.1.0
[M-H]-200.64854
predicted
DeepCCS 1.0 (2019)
[M+H]+201.6679715
predicted
DarkChem Lite v0.1.0
[M+H]+209.8921715
predicted
DarkChem Lite v0.1.0
[M+H]+209.2271715
predicted
DarkChem Lite v0.1.0
[M+H]+205.9119715
predicted
DarkChem Lite v0.1.0
[M+H]+202.46455
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.5818715
predicted
DarkChem Lite v0.1.0
[M+Na]+207.2345715
predicted
DarkChem Lite v0.1.0
[M+Na]+207.3657715
predicted
DarkChem Lite v0.1.0
[M+Na]+205.5353715
predicted
DarkChem Lite v0.1.0
[M+Na]+208.64919
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Steroid Delta-isomerase
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Steroid delta-isomerase activity
Specific Function
Not Available
Gene Name
ksi
Uniprot ID
P07445
Uniprot Name
Steroid Delta-isomerase
Molecular Weight
14535.48 Da
References
  1. 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]
Kind
Protein
Organism
Geobacter sulfurreducens
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
ppcA
Uniprot ID
Q8GGK7
Uniprot Name
Cytochrome C
Molecular Weight
9747.54 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ribosome binding
Specific Function
Involved in the biogenesis of the 60S ribosomal subunit and translational activation of ribosomes. Together with SBDS, triggers the GTP-dependent release of EIF6 from 60S pre-ribosomes in the cytop...
Gene Name
EFTUD1
Uniprot ID
Q7Z2Z2
Uniprot Name
Elongation factor Tu GTP-binding domain-containing protein 1
Molecular Weight
125428.745 Da
References
  1. 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]
Kind
Protein
Organism
Clostridium perfringens (strain 13 / Type A)
Pharmacological action
Unknown
General Function
Choloylglycine hydrolase activity
Specific Function
The enzyme catalyzes the degradation of conjugated bile acids in the mammalian gut.
Gene Name
cbh
Uniprot ID
P54965
Uniprot Name
Choloylglycine hydrolase
Molecular Weight
37185.0 Da
References
  1. 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]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Succinate-semialdehyde dehydrogenase [nad(p)+] activity
Specific Function
Acts on lactaldehyde as well as other aldehydes.
Gene Name
aldA
Uniprot ID
P25553
Uniprot Name
Lactaldehyde dehydrogenase
Molecular Weight
52272.37 Da
References
  1. 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]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
AcrA-AcrB-AcrZ-TolC is a drug efflux protein complex with broad substrate specificity that uses the proton motive force to export substrates.Involved in contact-dependent growth inhibition (CDI), a...
Gene Name
acrB
Uniprot ID
P31224
Uniprot Name
Multidrug efflux pump subunit AcrB
Molecular Weight
113572.75 Da
References
  1. 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]
Kind
Protein
Organism
Rhodobacter sphaeroides
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Cytochrome c oxidase is the component of the respiratory chain that catalyzes the reduction of oxygen to water. Subunits 1-3 form the functional core of the enzyme complex. Co I is the catalytic su...
Gene Name
ctaD
Uniprot ID
P33517
Uniprot Name
Cytochrome c oxidase subunit 1
Molecular Weight
63146.395 Da
References
  1. 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]
Kind
Protein
Organism
Rhodobacter sphaeroides
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
Specific Function
Subunits I and II form the functional core of the enzyme complex. Electrons originating in cytochrome c are transferred via heme a and Cu(A) to the binuclear center formed by heme a3 and Cu(B).
Gene Name
ctaC
Uniprot ID
Q03736
Uniprot Name
Cytochrome c oxidase subunit 2
Molecular Weight
32930.42 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxyla...
Gene Name
NR1H4
Uniprot ID
Q96RI1
Uniprot Name
Bile acid receptor
Molecular Weight
55913.915 Da
References
  1. Fujino T, Une M, Imanaka T, Inoue K, Nishimaki-Mogami T: Structure-activity relationship of bile acids and bile acid analogs in regard to FXR activation. J Lipid Res. 2004 Jan;45(1):132-8. Epub 2003 Sep 16. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
S-nitrosoglutathione binding
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name
GSTP1
Uniprot ID
P09211
Uniprot Name
Glutathione S-transferase P
Molecular Weight
23355.625 Da
References
  1. Nobuoka A, Takayama T, Miyanishi K, Sato T, Takanashi K, Hayashi T, Kukitsu T, Sato Y, Takahashi M, Okamoto T, Matsunaga T, Kato J, Oda M, Azuma T, Niitsu Y: Glutathione-S-transferase P1-1 protects aberrant crypt foci from apoptosis induced by deoxycholic acid. Gastroenterology. 2004 Aug;127(2):428-43. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
G-protein coupled bile acid receptor activity
Specific Function
Receptor for bile acid. Bile acid-binding induces its internalization, activation of extracellular signal-regulated kinase and intracellular cAMP production. May be involved in the suppression of m...
Gene Name
GPBAR1
Uniprot ID
Q8TDU6
Uniprot Name
G-protein coupled bile acid receptor 1
Molecular Weight
35247.795 Da
References
  1. Yoneno K, Hisamatsu T, Shimamura K, Kamada N, Ichikawa R, Kitazume MT, Mori M, Uo M, Namikawa Y, Matsuoka K, Sato T, Koganei K, Sugita A, Kanai T, Hibi T: TGR5 signalling inhibits the production of pro-inflammatory cytokines by in vitro differentiated inflammatory and intestinal macrophages in Crohn's disease. Immunology. 2013 May;139(1):19-29. doi: 10.1111/imm.12045. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.

Components:
References
  1. Zakharyan RA, Sampayo-Reyes A, Healy SM, Tsaprailis G, Board PG, Liebler DC, Aposhian HV: Human monomethylarsonic acid (MMA(V)) reductase is a member of the glutathione-S-transferase superfamily. Chem Res Toxicol. 2001 Aug;14(8):1051-7. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Schuetz EG, Strom S, Yasuda K, Lecureur V, Assem M, Brimer C, Lamba J, Kim RB, Ramachandran V, Komoroski BJ, Venkataramanan R, Cai H, Sinal CJ, Gonzalez FJ, Schuetz JD: Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450. J Biol Chem. 2001 Oct 19;276(42):39411-8. doi: 10.1074/jbc.M106340200. Epub 2001 Aug 16. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. Kullak-Ublick GA, Hagenbuch B, Stieger B, Wolkoff AW, Meier PJ: Functional characterization of the basolateral rat liver organic anion transporting polypeptide. Hepatology. 1994 Aug;20(2):411-6. [Article]
  2. Hata S, Wang P, Eftychiou N, Ananthanarayanan M, Batta A, Salen G, Pang KS, Wolkoff AW: Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. Am J Physiol Gastrointest Liver Physiol. 2003 Nov;285(5):G829-39. Epub 2003 Jul 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Bile acid:sodium symporter activity
Specific Function
Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism.
Gene Name
SLC10A2
Uniprot ID
Q12908
Uniprot Name
Ileal sodium/bile acid cotransporter
Molecular Weight
37713.405 Da
References
  1. Craddock AL, Love MW, Daniel RW, Kirby LC, Walters HC, Wong MH, Dawson PA: Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. Am J Physiol. 1998 Jan;274(1 Pt 1):G157-69. [Article]
  2. Saeki T, Matoba K, Furukawa H, Kirifuji K, Kanamoto R, Iwami K: Characterization, cDNA cloning, and functional expression of mouse ileal sodium-dependent bile acid transporter. J Biochem. 1999 Apr;125(4):846-51. [Article]
  3. Saeki T, Takahashi N, Kanamoto R, Iwami K: Characterization of cloned mouse Na+/taurocholate cotransporting polypeptide by transient expression in COS-7 cells. Biosci Biotechnol Biochem. 2002 May;66(5):1116-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Virus receptor activity
Specific Function
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
Gene Name
SLC10A1
Uniprot ID
Q14973
Uniprot Name
Sodium/bile acid cotransporter
Molecular Weight
38118.64 Da
References
  1. Hata S, Wang P, Eftychiou N, Ananthanarayanan M, Batta A, Salen G, Pang KS, Wolkoff AW: Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. Am J Physiol Gastrointest Liver Physiol. 2003 Nov;285(5):G829-39. Epub 2003 Jul 3. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 31, 2022 19:25