Identification

Name
Cholic Acid
Accession Number
DB02659  (EXPT00906)
Type
Small Molecule
Groups
Approved
Description

A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. [PubChem] Cholic acid, formulated as Cholbam capsules, is approved by the United States Food and Drug Administration as a treatment for children and adults with bile acid synthesis disorders due to single enzyme defects, and for peroxisomal disorders (such as Zellweger syndrome).

Structure
Thumb
Synonyms
Not Available
External IDs
E1000
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CholbamCapsule50 mg/1OralManchester Pharmaceuticals2015-03-31Not applicableUs
CholbamCapsule250 mg/1OralManchester Pharmaceuticals2015-03-31Not applicableUs
KolbamCapsule250 mgOralRetrophin Europe Ltd2015-11-20Not applicableEu
KolbamCapsule50 mgOralRetrophin Europe Ltd2015-11-20Not applicableEu
OrphacolCapsule250 mgOralLaboratoires Ctrs2013-09-12Not applicableEu
OrphacolCapsule50 mgOralLaboratoires Ctrs2013-09-12Not applicableEu
OrphacolCapsule250 mgOralLaboratoires Ctrs2013-09-12Not applicableEu
OrphacolCapsule50 mgOralLaboratoires Ctrs2013-09-12Not applicableEu
OrphacolCapsule250 mgOralLaboratoires Ctrs2013-09-12Not applicableEu
OrphacolCapsule50 mgOralLaboratoires Ctrs2013-09-12Not applicableEu
Categories
UNII
G1JO7801AE
CAS number
81-25-4
Weight
Average: 408.5714
Monoisotopic: 408.28757439
Chemical Formula
C24H40O5
InChI Key
BHQCQFFYRZLCQQ-OELDTZBJSA-N
InChI
InChI=1S/C24H40O5/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/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
IUPAC Name
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
SMILES
[H][C@@](C)(CCC(O)=O)[C@@]1([H])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

Pharmacology

Indication

Oral cholic acid is indicated for: treatment of bile acid synthesis disorders due to single enzyme defects; and as adjunctive treatment of peroxisomal disorders including Zellweger spectrum disorders in patients who exhibit manifestations of liver disease, steatorrhea or complications from decreased fat soluble vitamin absorption.

Structured Indications
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UFerrochelatase, mitochondrialNot AvailableHuman
UAlcohol dehydrogenase 1CNot AvailableHuman
UEstrogen-related receptor gammaNot AvailableHuman
UGastrotropinNot AvailableHuman
UCytochrome c oxidase subunit 4 isoform 1, mitochondrialNot AvailableHuman
UCytochrome c oxidase subunit 1Not AvailableHuman
UCytochrome c oxidase subunit 2Not AvailableHuman
UCytochrome c oxidase subunit 3Not AvailableHuman
UCytochrome c oxidase subunit 5A, mitochondrialNot AvailableHuman
UCytochrome c oxidase subunit 5B, mitochondrialNot AvailableHuman
UCytochrome c oxidase subunit 6CNot AvailableHuman
UCytochrome c oxidase subunit 7B, mitochondrialNot AvailableHuman
UCytochrome c oxidase subunit 7C, mitochondrialNot AvailableHuman
UCytochrome c oxidase subunit 8A, mitochondrialNot AvailableHuman
UCytochrome c oxidase subunit 6A2, mitochondrialNot AvailableHuman
UCytochrome c oxidase subunit 6B1Not AvailableHuman
UCytochrome c oxidase subunit 7A1, mitochondrialNot AvailableHuman
UPhospholipase A2Not AvailableHuman
ULiver carboxylesterase 1Not AvailableHuman
UFerrochelataseNot AvailableHuman
UCholoylglycine hydrolaseNot AvailableClostridium perfringens (strain 13 / Type A)
UBile acid receptorNot AvailableHuman
UG-protein coupled bile acid receptor 1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
27-Hydroxylase DeficiencyDisease
Cerebrotendinous Xanthomatosis (CTX)Disease
Bile Acid BiosynthesisMetabolic
Familial Hypercholanemia (FHCA)Disease
Congenital Bile Acid Synthesis Defect Type IIDisease
Zellweger SyndromeDisease
Congenital Bile Acid Synthesis Defect Type IIIDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcebutololThe serum concentration of Acebutolol can be decreased when it is combined with Cholic Acid.Approved
AcetaminophenThe serum concentration of Acetaminophen can be decreased when it is combined with Cholic Acid.Approved
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be decreased when it is combined with Cholic Acid.Approved
AldosteroneThe serum concentration of Aldosterone can be decreased when it is combined with Cholic Acid.Experimental
AlitretinoinThe serum concentration of Alitretinoin can be decreased when it is combined with Cholic Acid.Approved, Investigational
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Cholic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
AmbrisentanThe serum concentration of Ambrisentan can be decreased when it is combined with Cholic Acid.Approved, Investigational
AmitriptylineThe serum concentration of Amitriptyline can be decreased when it is combined with Cholic Acid.Approved
ApixabanThe serum concentration of Apixaban can be decreased when it is combined with Cholic Acid.Approved
Arsenic trioxideThe serum concentration of Arsenic trioxide can be decreased when it is combined with Cholic Acid.Approved, Investigational
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Cholic Acid.Approved, Investigational
AtenololThe serum concentration of Atenolol can be decreased when it is combined with Cholic Acid.Approved
AxitinibThe serum concentration of Axitinib can be decreased when it is combined with Cholic Acid.Approved, Investigational
BelinostatThe serum concentration of Belinostat can be decreased when it is combined with Cholic Acid.Approved, Investigational
BetamethasoneThe serum concentration of Betamethasone can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
BoceprevirThe serum concentration of Boceprevir can be decreased when it is combined with Cholic Acid.Withdrawn
BosentanBosentan may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Cholic Acid.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be decreased when it is combined with Cholic Acid.Approved
BromocriptineThe serum concentration of Bromocriptine can be decreased when it is combined with Cholic Acid.Approved, Investigational
CabazitaxelThe serum concentration of Cabazitaxel can be decreased when it is combined with Cholic Acid.Approved
CaffeineThe serum concentration of Caffeine can be decreased when it is combined with Cholic Acid.Approved
CamptothecinThe serum concentration of Camptothecin can be decreased when it is combined with Cholic Acid.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be decreased when it is combined with Cholic Acid.Approved
CarbamazepineThe serum concentration of Carbamazepine can be decreased when it is combined with Cholic Acid.Approved, Investigational
CarfilzomibThe serum concentration of Carfilzomib can be decreased when it is combined with Cholic Acid.Approved
CeritinibThe serum concentration of Ceritinib can be decreased when it is combined with Cholic Acid.Approved
CerivastatinThe serum concentration of Cerivastatin can be decreased when it is combined with Cholic Acid.Withdrawn
ChlorpromazineChlorpromazine may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved, Vet Approved
CholestyramineCholestyramine can cause a decrease in the absorption of Cholic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CimetidineCimetidine may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
CiprofloxacinThe serum concentration of Ciprofloxacin can be decreased when it is combined with Cholic Acid.Approved, Investigational
CisplatinThe serum concentration of Cisplatin can be decreased when it is combined with Cholic Acid.Approved
CitalopramThe serum concentration of Citalopram can be decreased when it is combined with Cholic Acid.Approved
ClarithromycinThe serum concentration of Clarithromycin can be decreased when it is combined with Cholic Acid.Approved
ClobazamThe serum concentration of Clobazam can be decreased when it is combined with Cholic Acid.Approved, Illicit
ClofazimineClofazimine may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved, Investigational
ClomifeneThe serum concentration of Clomifene can be decreased when it is combined with Cholic Acid.Approved, Investigational
ClonidineThe serum concentration of Clonidine can be decreased when it is combined with Cholic Acid.Approved
ClopidogrelThe serum concentration of Clopidogrel can be decreased when it is combined with Cholic Acid.Approved, Nutraceutical
ClozapineThe serum concentration of Clozapine can be decreased when it is combined with Cholic Acid.Approved
CobimetinibThe serum concentration of Cobimetinib can be decreased when it is combined with Cholic Acid.Approved
ColchicineThe serum concentration of Colchicine can be decreased when it is combined with Cholic Acid.Approved
ColesevelamColesevelam can cause a decrease in the absorption of Cholic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of Cholic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Conjugated estrogensThe serum concentration of Conjugated estrogens can be decreased when it is combined with Cholic Acid.Approved
CopanlisibThe serum concentration of Copanlisib can be decreased when it is combined with Cholic Acid.Approved
CrizotinibThe serum concentration of Crizotinib can be decreased when it is combined with Cholic Acid.Approved
CyclosporineCyclosporine may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be decreased when it is combined with Cholic Acid.Approved
DabrafenibThe serum concentration of Dabrafenib can be decreased when it is combined with Cholic Acid.Approved
DactinomycinThe serum concentration of Dactinomycin can be decreased when it is combined with Cholic Acid.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be decreased when it is combined with Cholic Acid.Approved
DasatinibThe serum concentration of Dasatinib can be decreased when it is combined with Cholic Acid.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Cholic Acid.Approved
DebrisoquinThe serum concentration of Debrisoquin can be decreased when it is combined with Cholic Acid.Approved
DexamethasoneThe serum concentration of Dexamethasone can be decreased when it is combined with Cholic Acid.Approved, Investigational, Vet Approved
DiazepamThe serum concentration of Diazepam can be decreased when it is combined with Cholic Acid.Approved, Illicit, Vet Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Cholic Acid.Approved
DigitoxinThe serum concentration of Digitoxin can be decreased when it is combined with Cholic Acid.Approved
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Cholic Acid.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be decreased when it is combined with Cholic Acid.Illicit
DiltiazemThe serum concentration of Diltiazem can be decreased when it is combined with Cholic Acid.Approved
DipyridamoleThe serum concentration of Dipyridamole can be decreased when it is combined with Cholic Acid.Approved
DocetaxelThe serum concentration of Docetaxel can be decreased when it is combined with Cholic Acid.Approved, Investigational
DomperidoneThe serum concentration of Domperidone can be decreased when it is combined with Cholic Acid.Approved, Investigational, Vet Approved
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Cholic Acid.Approved, Investigational
EdoxabanThe serum concentration of Edoxaban can be decreased when it is combined with Cholic Acid.Approved
ElbasvirThe serum concentration of Elbasvir can be decreased when it is combined with Cholic Acid.Approved
EletriptanThe serum concentration of Eletriptan can be decreased when it is combined with Cholic Acid.Approved, Investigational
EltrombopagThe serum concentration of Cholic Acid can be increased when it is combined with Eltrombopag.Approved
EnasidenibThe serum concentration of Enasidenib can be decreased when it is combined with Cholic Acid.Approved
EpinastineThe serum concentration of Epinastine can be decreased when it is combined with Cholic Acid.Approved, Investigational
ErlotinibThe serum concentration of Erlotinib can be decreased when it is combined with Cholic Acid.Approved, Investigational
ErythromycinThe serum concentration of Erythromycin can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Cholic Acid.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
EstroneThe serum concentration of Estrone can be decreased when it is combined with Cholic Acid.Approved
Ethinyl EstradiolEthinyl Estradiol may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
EtoposideThe serum concentration of Etoposide can be decreased when it is combined with Cholic Acid.Approved
EzetimibeThe serum concentration of Ezetimibe can be decreased when it is combined with Cholic Acid.Approved
FesoterodineThe serum concentration of Fesoterodine can be decreased when it is combined with Cholic Acid.Approved
FexofenadineThe serum concentration of Fexofenadine can be decreased when it is combined with Cholic Acid.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be decreased when it is combined with Cholic Acid.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be decreased when it is combined with Cholic Acid.Approved
Fusidic AcidFusidic Acid may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
GefitinibThe serum concentration of Gefitinib can be decreased when it is combined with Cholic Acid.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be decreased when it is combined with Cholic Acid.Approved
GlecaprevirThe serum concentration of Glecaprevir can be decreased when it is combined with Cholic Acid.Approved
GlyburideGlyburide may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
Glycochenodeoxycholic AcidGlycochenodeoxycholic Acid may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Experimental
GrazoprevirThe serum concentration of Grazoprevir can be decreased when it is combined with Cholic Acid.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be decreased when it is combined with Cholic Acid.Withdrawn
HaloperidolThe serum concentration of Haloperidol can be decreased when it is combined with Cholic Acid.Approved
HydrocortisoneThe serum concentration of Hydrocortisone can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
IbuprofenThe serum concentration of Ibuprofen can be decreased when it is combined with Cholic Acid.Approved
IdelalisibThe serum concentration of Idelalisib can be decreased when it is combined with Cholic Acid.Approved
ImatinibThe serum concentration of Imatinib can be decreased when it is combined with Cholic Acid.Approved
ImipramineThe serum concentration of Imipramine can be decreased when it is combined with Cholic Acid.Approved
IndacaterolThe serum concentration of Indacaterol can be decreased when it is combined with Cholic Acid.Approved
IndinavirThe serum concentration of Indinavir can be decreased when it is combined with Cholic Acid.Approved
IndomethacinThe serum concentration of Indomethacin can be decreased when it is combined with Cholic Acid.Approved, Investigational
Inotuzumab ozogamicinThe serum concentration of Inotuzumab ozogamicin can be decreased when it is combined with Cholic Acid.Approved
IrinotecanThe serum concentration of Irinotecan can be decreased when it is combined with Cholic Acid.Approved, Investigational
IvermectinThe serum concentration of Ivermectin can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
KetazolamThe serum concentration of Ketazolam can be decreased when it is combined with Cholic Acid.Approved
KetoconazoleKetoconazole may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be decreased when it is combined with Cholic Acid.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Cholic Acid.Approved, Investigational
LansoprazoleThe serum concentration of Lansoprazole can be decreased when it is combined with Cholic Acid.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Cholic Acid.Approved
LenalidomideThe serum concentration of Lenalidomide can be decreased when it is combined with Cholic Acid.Approved
LenvatinibThe serum concentration of Lenvatinib can be decreased when it is combined with Cholic Acid.Approved
LevetiracetamThe serum concentration of Levetiracetam can be decreased when it is combined with Cholic Acid.Approved, Investigational
LevofloxacinThe serum concentration of Levofloxacin can be decreased when it is combined with Cholic Acid.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be decreased when it is combined with Cholic Acid.Approved
LinagliptinThe serum concentration of Linagliptin can be decreased when it is combined with Cholic Acid.Approved
LoperamideThe serum concentration of Loperamide can be decreased when it is combined with Cholic Acid.Approved
LosartanThe serum concentration of Losartan can be decreased when it is combined with Cholic Acid.Approved
MannitolThe serum concentration of Mannitol can be decreased when it is combined with Cholic Acid.Approved, Investigational
MethotrexateThe serum concentration of Methotrexate can be decreased when it is combined with Cholic Acid.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
MetoprololThe serum concentration of Metoprolol can be decreased when it is combined with Cholic Acid.Approved, Investigational
MidazolamThe serum concentration of Midazolam can be decreased when it is combined with Cholic Acid.Approved, Illicit
MirabegronThe serum concentration of Mirabegron can be decreased when it is combined with Cholic Acid.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be decreased when it is combined with Cholic Acid.Approved, Investigational
MorphineThe serum concentration of Morphine can be decreased when it is combined with Cholic Acid.Approved, Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Cholic Acid.Approved, Investigational
NadololThe serum concentration of Nadolol can be decreased when it is combined with Cholic Acid.Approved
NaloxoneThe serum concentration of Naloxone can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
NelfinavirThe serum concentration of Nelfinavir can be decreased when it is combined with Cholic Acid.Approved
NicardipineThe serum concentration of Nicardipine can be decreased when it is combined with Cholic Acid.Approved
NifedipineThe serum concentration of Nifedipine can be decreased when it is combined with Cholic Acid.Approved
NilotinibThe serum concentration of Nilotinib can be decreased when it is combined with Cholic Acid.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be decreased when it is combined with Cholic Acid.Approved
NizatidineThe serum concentration of Nizatidine can be decreased when it is combined with Cholic Acid.Approved
NovobiocinNovobiocin may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved, Vet Approved
OdanacatibThe serum concentration of Odanacatib can be decreased when it is combined with Cholic Acid.Investigational
OlanzapineThe serum concentration of Olanzapine can be decreased when it is combined with Cholic Acid.Approved, Investigational
OmbitasvirThe serum concentration of Ombitasvir can be decreased when it is combined with Cholic Acid.Approved
OsimertinibThe serum concentration of Osimertinib can be decreased when it is combined with Cholic Acid.Approved
PaclitaxelPaclitaxel may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved, Vet Approved
PanobinostatThe serum concentration of Panobinostat can be decreased when it is combined with Cholic Acid.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be decreased when it is combined with Cholic Acid.Approved
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with Cholic Acid.Approved
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
PibrentasvirThe serum concentration of Pibrentasvir can be decreased when it is combined with Cholic Acid.Approved
PitavastatinThe serum concentration of Pitavastatin can be decreased when it is combined with Cholic Acid.Approved
PomalidomideThe serum concentration of Pomalidomide can be decreased when it is combined with Cholic Acid.Approved
PonatinibPonatinib may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
PravastatinThe serum concentration of Pravastatin can be decreased when it is combined with Cholic Acid.Approved
PrazosinThe serum concentration of Prazosin can be decreased when it is combined with Cholic Acid.Approved
PrednisoloneThe serum concentration of Prednisolone can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
ProgesteroneProgesterone may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved, Vet Approved
PropranololThe serum concentration of Propranolol can be decreased when it is combined with Cholic Acid.Approved, Investigational
QuetiapineThe serum concentration of Quetiapine can be decreased when it is combined with Cholic Acid.Approved
QuinidineQuinidine may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
QuinineThe serum concentration of Quinine can be decreased when it is combined with Cholic Acid.Approved
RanitidineThe serum concentration of Ranitidine can be decreased when it is combined with Cholic Acid.Approved
ReserpineReserpine may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
RifampicinRifampicin may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
RisperidoneThe serum concentration of Risperidone can be decreased when it is combined with Cholic Acid.Approved, Investigational
RitonavirThe serum concentration of Ritonavir can be decreased when it is combined with Cholic Acid.Approved, Investigational
RivaroxabanThe serum concentration of Rivaroxaban can be decreased when it is combined with Cholic Acid.Approved
RomidepsinThe serum concentration of Romidepsin can be decreased when it is combined with Cholic Acid.Approved, Investigational
Salicylic acidThe serum concentration of Salicylic acid can be decreased when it is combined with Cholic Acid.Approved, Vet Approved
SaquinavirThe serum concentration of Saquinavir can be decreased when it is combined with Cholic Acid.Approved, Investigational
SelexipagThe serum concentration of Selexipag can be decreased when it is combined with Cholic Acid.Approved
SevelamerSevelamer can cause a decrease in the absorption of Cholic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SilodosinThe serum concentration of Silodosin can be decreased when it is combined with Cholic Acid.Approved
SimeprevirSimeprevir may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
SitagliptinThe serum concentration of Sitagliptin can be decreased when it is combined with Cholic Acid.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Cholic Acid.Approved
SorafenibThe serum concentration of Sorafenib can be decreased when it is combined with Cholic Acid.Approved, Investigational
SparfloxacinThe serum concentration of Sparfloxacin can be decreased when it is combined with Cholic Acid.Approved
SphingosineThe serum concentration of Sphingosine can be decreased when it is combined with Cholic Acid.Experimental
SucralfateSucralfate can cause a decrease in the absorption of Cholic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
TacrolimusThe serum concentration of Tacrolimus can be decreased when it is combined with Cholic Acid.Approved, Investigational
TamoxifenTamoxifen may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be decreased when it is combined with Cholic Acid.Experimental
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be decreased when it is combined with Cholic Acid.Approved
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Cholic Acid.Withdrawn
TemsirolimusThe serum concentration of Temsirolimus can be decreased when it is combined with Cholic Acid.Approved
TeriflunomideThe serum concentration of Cholic Acid can be increased when it is combined with Teriflunomide.Approved
TicagrelorThe serum concentration of Ticagrelor can be decreased when it is combined with Cholic Acid.Approved
TimololThe serum concentration of Timolol can be decreased when it is combined with Cholic Acid.Approved
TolvaptanThe serum concentration of Tolvaptan can be decreased when it is combined with Cholic Acid.Approved
TopotecanThe serum concentration of Topotecan can be decreased when it is combined with Cholic Acid.Approved, Investigational
ToremifeneThe serum concentration of Toremifene can be decreased when it is combined with Cholic Acid.Approved, Investigational
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be decreased when it is combined with Cholic Acid.Approved
TroglitazoneTroglitazone may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Withdrawn
UlipristalThe serum concentration of Ulipristal can be decreased when it is combined with Cholic Acid.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be decreased when it is combined with Cholic Acid.Approved
Ursodeoxycholic acidUrsodeoxycholic acid may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved, Investigational
VecuroniumThe serum concentration of Vecuronium can be decreased when it is combined with Cholic Acid.Approved
VelpatasvirThe serum concentration of Velpatasvir can be decreased when it is combined with Cholic Acid.Approved
VenetoclaxThe serum concentration of Venetoclax can be decreased when it is combined with Cholic Acid.Approved
VenlafaxineThe serum concentration of Venlafaxine can be decreased when it is combined with Cholic Acid.Approved
VerapamilVerapamil may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
VinblastineVinblastine may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
VincristineThe serum concentration of Vincristine can be decreased when it is combined with Cholic Acid.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be decreased when it is combined with Cholic Acid.Approved
VoxilaprevirThe serum concentration of Voxilaprevir can be decreased when it is combined with Cholic Acid.Approved
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Cholic Acid.Approved
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
Human Metabolome Database
HMDB00619
KEGG Drug
D10699
KEGG Compound
C00695
PubChem Compound
221493
PubChem Substance
46507063
ChemSpider
192176
BindingDB
21680
ChEBI
16359
ChEMBL
CHEMBL205596
PharmGKB
PA166160055
HET
CHD
Drugs.com
Drugs.com Drug Page
ATC Codes
A05AA03 — Cholic acid
AHFS Codes
  • 56:92
PDB Entries
1ee2 / 1hrk / 1on5 / 1s9q / 1tw4 / 1v54 / 1v55 / 2azy / 2dqy / 2dyr
show 64 more
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentHepatic Steatosis1
3CompletedTreatmentAdrenoleukodystrophy / Cerebrohepatorenal syndrome / Cholestasis / Infantile Refsum's Disease / Peroxisomal Disorders1
3CompletedTreatmentBile Acid Synthesis Defect1
3CompletedTreatmentInborn Errors of Bile Acid Synthesis1
Not AvailableTerminatedTreatmentAdrenoleukodystrophy / Bifunctional Enzyme Deficiency / Cerebrohepatorenal syndrome / Infantile Refsum's Disease1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral250 mg/1
CapsuleOral50 mg/1
CapsuleOral250 mg
CapsuleOral50 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)198 °CPhysProp
water solubility175 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.02RODA,A ET AL. (1990)
logS-3.37ADME Research, USCD
pKa4.98 (at 20 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility0.0738 mg/mLALOGPS
logP2.26ALOGPS
logP2.48ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.79 m3·mol-1ChemAxon
Polarizability46.93 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-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0fk9-5796000000-2876080f3fa17fb96370
Mass Spectrum (Electron Ionization)MSsplash10-0596-9642000000-e425981b8a0ac72ea6ee
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-0009000000-85abf6e916e1cc1c46b6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-0009000000-476dc71e401cc2327292
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00nb-2109000000-0181c85f78bb9e29ea53
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-0009700000-63a8d2c748b3bc631c17
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052r-1009200000-ba378537551be8134141
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9006000000-caef890bd53da215442e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0000900000-806d3b03c76019afbf7d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0000900000-4edb603ca5534669120e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0000900000-4a76e64b2f0411d0b701
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0001900000-41aa3a7cb25fcf549046
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0057900000-790a3808fa512d5d1687
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0010900000-e6bedfc253363160a37e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0030900000-da4a7bfccbaf1e42171c
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0020900000-772055897702843a1d50
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0021900000-0405fe63d70d3a88bf6f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0aou-3844900000-cb3c2aba1b9a29785616
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-0007-0019000000-fb9a5b5952cf65eb7988
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-0001900000-9583bd9c6c0d2b069b68
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-1027900000-31f3cf065ad48561c0a2
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0000900000-b0504ee652d51a711f3a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0000900000-18dd8b6be45775ec83c2
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0007-0019000000-285d3d0d87f5471b419a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0007-0019000000-0fcb0f6819b05ab63c12
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0000900000-b0504ee652d51a711f3a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0000900000-18dd8b6be45775ec83c2
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0007-0019000000-285d3d0d87f5471b419a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0007-0019000000-0fcb0f6819b05ab63c12
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl 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
Trihydroxy bile acids, alcohols and derivatives
Alternative Parents
7-hydroxysteroids / 3-alpha-hydroxysteroids / 12-hydroxysteroids / Secondary alcohols / Cyclic alcohols and derivatives / Polyols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Trihydroxy bile acid, alcohol, or derivatives / 3-hydroxysteroid / 12-hydroxysteroid / 7-hydroxysteroid / 3-alpha-hydroxysteroid / Hydroxysteroid / Cyclic alcohol / Secondary alcohol / Carboxylic acid derivative / Carboxylic acid
show 9 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
bile acid, trihydroxy-5beta-cholanic acid (CHEBI:16359) / C24 bile acids, alcohols, and derivatives, Cholane and derivatives (C00695) / C24 bile acids, alcohols, and derivatives (LMST04010001)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Iron-responsive element binding
Specific Function
Catalyzes the ferrous insertion into protoporphyrin IX.
Gene Name
FECH
Uniprot ID
P22830
Uniprot Name
Ferrochelatase, mitochondrial
Molecular Weight
47861.77 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
  3. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
ADH1C
Uniprot ID
P00326
Uniprot Name
Alcohol dehydrogenase 1C
Molecular Weight
39867.27 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Orphan receptor that acts as transcription activator in the absence of bound ligand. Binds specifically to an estrogen response element and activates reporter genes controlled by estrogen response ...
Gene Name
ESRRG
Uniprot ID
P62508
Uniprot Name
Estrogen-related receptor gamma
Molecular Weight
51305.485 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. [PubMed:10592235]
Kind
Protein
Organism
Human
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
  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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
Specific Function
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name
COX4I1
Uniprot ID
P13073
Uniprot Name
Cytochrome c oxidase subunit 4 isoform 1, mitochondrial
Molecular Weight
19576.6 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. [PubMed:10592235]
Kind
Protein
Organism
Human
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
MT-CO1
Uniprot ID
P00395
Uniprot Name
Cytochrome c oxidase subunit 1
Molecular Weight
57040.91 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
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. Subunit 2 transfers the ...
Gene Name
MT-CO2
Uniprot ID
P00403
Uniprot Name
Cytochrome c oxidase subunit 2
Molecular Weight
25564.73 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
Specific Function
Subunits I, II and III form the functional core of the enzyme complex.
Gene Name
MT-CO3
Uniprot ID
P00414
Uniprot Name
Cytochrome c oxidase subunit 3
Molecular Weight
29950.6 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
This is the heme A-containing chain of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name
COX5A
Uniprot ID
P20674
Uniprot Name
Cytochrome c oxidase subunit 5A, mitochondrial
Molecular Weight
16761.985 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name
COX5B
Uniprot ID
P10606
Uniprot Name
Cytochrome c oxidase subunit 5B, mitochondrial
Molecular Weight
13695.57 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
Specific Function
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name
COX6C
Uniprot ID
P09669
Uniprot Name
Cytochrome c oxidase subunit 6C
Molecular Weight
8781.36 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
Specific Function
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport. Plays a role in proper central nervous system (CNS) de...
Gene Name
COX7B
Uniprot ID
P24311
Uniprot Name
Cytochrome c oxidase subunit 7B, mitochondrial
Molecular Weight
9160.485 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
Specific Function
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name
COX7C
Uniprot ID
P15954
Uniprot Name
Cytochrome c oxidase subunit 7C, mitochondrial
Molecular Weight
7245.45 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
Specific Function
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name
COX8A
Uniprot ID
P10176
Uniprot Name
Cytochrome c oxidase subunit 8A, mitochondrial
Molecular Weight
7579.0 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
Specific Function
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name
COX6A2
Uniprot ID
Q02221
Uniprot Name
Cytochrome c oxidase subunit 6A2, mitochondrial
Molecular Weight
10815.32 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
Specific Function
Connects the two COX monomers into the physiological dimeric form.
Gene Name
COX6B1
Uniprot ID
P14854
Uniprot Name
Cytochrome c oxidase subunit 6B1
Molecular Weight
10192.345 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
Specific Function
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name
COX7A1
Uniprot ID
P24310
Uniprot Name
Cytochrome c oxidase subunit 7A1, mitochondrial
Molecular Weight
9117.44 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. [PubMed:10592235]
Details
18. Phospholipase A2
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides, this releases glycerophospholipids and arachidonic acid that serve as the precursors of signal molecules.
Gene Name
PLA2G1B
Uniprot ID
P04054
Uniprot Name
Phospholipase A2
Molecular Weight
16359.535 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ferrochelatase activity
Specific Function
Catalyzes the ferrous insertion into protoporphyrin IX.
Gene Name
DKFZp686P18130
Uniprot ID
Q7KZA3
Uniprot Name
Ferrochelatase
Molecular Weight
47131.925 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. [PubMed:10592235]
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. [PubMed:10592235]
Details
22. Bile acid receptor
Kind
Protein
Organism
Human
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. [PubMed:13130122]
Kind
Protein
Organism
Human
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. Ishizawa M, Matsunawa M, Adachi R, Uno S, Ikeda K, Masuno H, Shimizu M, Iwasaki K, Yamada S, Makishima M: Lithocholic acid derivatives act as selective vitamin D receptor modulators without inducing hypercalcemia. J Lipid Res. 2008 Apr;49(4):763-72. doi: 10.1194/jlr.M700293-JLR200. Epub 2008 Jan 7. [PubMed:18180267]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phospholipid binding
Specific Function
Plays a role in lipoprotein-mediated cholesterol uptake in hepatocytes (PubMed:25732850). Binds cholesterol (PubMed:25732850). Binds free fatty acids and their coenzyme A derivatives, bilirubin, an...
Gene Name
FABP1
Uniprot ID
P07148
Uniprot Name
Fatty acid-binding protein, liver
Molecular Weight
14208.34 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. [PubMed:10592235]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Hartmann G, Cheung AK, Piquette-Miller M: Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia. J Pharmacol Exp Ther. 2002 Oct;303(1):273-81. [PubMed:12235261]
  2. Green RM, Hoda F, Ward KL: Molecular cloning and characterization of the murine bile salt export pump. Gene. 2000 Jan 4;241(1):117-23. [PubMed:10607905]
  3. Mita S, Suzuki H, Akita H, Stieger B, Meier PJ, Hofmann AF, Sugiyama Y: Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G159-67. Epub 2004 Aug 5. [PubMed:15297262]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [PubMed:11438506]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Hartmann G, Cheung AK, Piquette-Miller M: Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia. J Pharmacol Exp Ther. 2002 Oct;303(1):273-81. [PubMed:12235261]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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. Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [PubMed:11438506]
  2. Kullak-Ublick GA, Hagenbuch B, Stieger B, Schteingart CD, Hofmann AF, Wolkoff AW, Meier PJ: Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver. Gastroenterology. 1995 Oct;109(4):1274-82. [PubMed:7557095]
  3. 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. [PubMed:8045503]
  4. Kanai N, Lu R, Bao Y, Wolkoff AW, Schuster VL: Transient expression of oatp organic anion transporter in mammalian cells: identification of candidate substrates. Am J Physiol. 1996 Feb;270(2 Pt 2):F319-25. [PubMed:8779893]
  5. 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. [PubMed:12842829]
  6. Jacquemin E, Hagenbuch B, Stieger B, Wolkoff AW, Meier PJ: Expression cloning of a rat liver Na(+)-independent organic anion transporter. Proc Natl Acad Sci U S A. 1994 Jan 4;91(1):133-7. [PubMed:8278353]
  7. Kouzuki H, Suzuki H, Ito K, Ohashi R, Sugiyama Y: Contribution of organic anion transporting polypeptide to uptake of its possible substrates into rat hepatocytes. J Pharmacol Exp Ther. 1999 Feb;288(2):627-34. [PubMed:9918568]
  8. Eckhardt U, Schroeder A, Stieger B, Hochli M, Landmann L, Tynes R, Meier PJ, Hagenbuch B: Polyspecific substrate uptake by the hepatic organic anion transporter Oatp1 in stably transfected CHO cells. Am J Physiol. 1999 Apr;276(4 Pt 1):G1037-42. [PubMed:10198348]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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. Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [PubMed:11438506]
  2. 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. [PubMed:9458785]
  3. 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. [PubMed:10101301]
  4. 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. [PubMed:12092825]
  5. Walters HC, Craddock AL, Fusegawa H, Willingham MC, Dawson PA: Expression, transport properties, and chromosomal location of organic anion transporter subtype 3. Am J Physiol Gastrointest Liver Physiol. 2000 Dec;279(6):G1188-200. [PubMed:11093941]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [PubMed:11438506]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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
  1. Hartmann G, Cheung AK, Piquette-Miller M: Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia. J Pharmacol Exp Ther. 2002 Oct;303(1):273-81. [PubMed:12235261]
  2. Konig J, Cui Y, Nies AT, Keppler D: A novel human organic anion transporting polypeptide localized to the basolateral hepatocyte membrane. Am J Physiol Gastrointest Liver Physiol. 2000 Jan;278(1):G156-64. [PubMed:10644574]
  3. Cui Y, Konig J, Leier I, Buchholz U, Keppler D: Hepatic uptake of bilirubin and its conjugates by the human organic anion transporter SLC21A6. J Biol Chem. 2001 Mar 30;276(13):9626-30. Epub 2000 Dec 27. [PubMed:11134001]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocyte...
Gene Name
ABCC3
Uniprot ID
O15438
Uniprot Name
Canalicular multispecific organic anion transporter 2
Molecular Weight
169341.14 Da
References
  1. Hirohashi T, Suzuki H, Takikawa H, Sugiyama Y: ATP-dependent transport of bile salts by rat multidrug resistance-associated protein 3 (Mrp3). J Biol Chem. 2000 Jan 28;275(4):2905-10. [PubMed:10644759]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Rius M, Nies AT, Hummel-Eisenbeiss J, Jedlitschky G, Keppler D: Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. Hepatology. 2003 Aug;38(2):374-84. [PubMed:12883481]
  2. Bai J, Lai L, Yeo HC, Goh BC, Tan TM: Multidrug resistance protein 4 (MRP4/ABCC4) mediates efflux of bimane-glutathione. Int J Biochem Cell Biol. 2004 Feb;36(2):247-57. [PubMed:14643890]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Hagenbuch B, Stieger B, Foguet M, Lubbert H, Meier PJ: Functional expression cloning and characterization of the hepatocyte Na+/bile acid cotransport system. Proc Natl Acad Sci U S A. 1991 Dec 1;88(23):10629-33. [PubMed:1961729]
  2. Schroeder A, Eckhardt U, Stieger B, Tynes R, Schteingart CD, Hofmann AF, Meier PJ, Hagenbuch B: Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells. Am J Physiol. 1998 Feb;274(2 Pt 1):G370-5. [PubMed:9486191]
  3. 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. [PubMed:12842829]
  4. Mita S, Suzuki H, Akita H, Stieger B, Meier PJ, Hofmann AF, Sugiyama Y: Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G159-67. Epub 2004 Aug 5. [PubMed:15297262]
  5. Platte HD, Honscha W, Schuh K, Petzinger E: Functional characterization of the hepatic sodium-dependent taurocholate transporter stably transfected into an immortalized liver-derived cell line and V79 fibroblasts. Eur J Cell Biol. 1996 May;70(1):54-60. [PubMed:8738419]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [PubMed:11306713]
  2. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [PubMed:10224140]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
References
  1. Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. [PubMed:9650585]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
  1. Cui Y, Konig J, Leier I, Buchholz U, Keppler D: Hepatic uptake of bilirubin and its conjugates by the human organic anion transporter SLC21A6. J Biol Chem. 2001 Mar 30;276(13):9626-30. Epub 2000 Dec 27. [PubMed:11134001]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:13