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Identification
NameTiotropium
Accession NumberDB01409
TypeSmall Molecule
GroupsApproved
Description

Tiotropium is a long-acting, 24 hour, anticholinergic bronchodilator used in the management of chronic obstructive pulmonary disease (COPD). Tiotropium is a muscarinic receptor antagonist, on topical application it acts mainly on M3 muscarinic receptors located in the airways to produce smooth muscle relaxation, thus producing a bronchodilatory effect.

Structure
Thumb
SynonymsNot Available
External Identifiers
  • BA 679 BR
  • BA-679 BR
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Spirivacapsule18 ug/1oral; respiratory (inhalation)Boehringer Ingelheim Pharmaceuticals Inc.2005-10-11Not applicableUs
Spirivacapsule18 mcginhalationBoehringer Ingelheim (Canada) Ltd Ltee2002-11-21Not applicableCanada
Spirivacapsule18 ug/1oral; respiratory (inhalation)Physicians Total Care, Inc.2004-07-14Not applicableUs
Spirivacapsule18 ug/1oral; respiratory (inhalation)Lake Erie Medical & Surgical Supply DBA Quality Care Products LLC2005-10-11Not applicableUs
Spiriva Respimatsolution2.5 mcginhalationBoehringer Ingelheim (Canada) Ltd Ltee2014-12-19Not applicableCanada
Spiriva Respimatspray, metered1.562 ug/1respiratory (inhalation)Boehringer Ingelheim Pharmaceuticals, Inc.2015-09-15Not applicableUs
Spiriva Respimatspray, metered3.124 ug/1respiratory (inhalation)Boehringer Ingelheim Pharmaceuticals, Inc.2014-09-30Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Inspiolto RespimatBoehringer Ingelheim (Canada) Ltd Ltee
Stiolto RespimatBoehringer Ingelheim Pharmaceuticals Inc.
Salts
Name/CASStructureProperties
Tiotropium bromide
136310-93-5
Thumb
  • InChI Key: DQHNAVOVODVIMG-RGECMCKFNA-M
  • Monoisotopic Mass: 471.017362224
  • Average Mass: 472.416
DBSALT000348
Tiotropium bromide monohydrate
ThumbNot applicableDBSALT001524
Categories
UNII0EB439235F
CAS number186691-13-4
WeightAverage: 392.512
Monoisotopic: 392.099024577
Chemical FormulaC19H22NO4S2
InChI KeyLERNTVKEWCAPOY-DZZGSBJMSA-N
InChI
InChI=1S/C19H22NO4S2/c1-20(2)12-9-11(10-13(20)17-16(12)24-17)23-18(21)19(22,14-5-3-7-25-14)15-6-4-8-26-15/h3-8,11-13,16-17,22H,9-10H2,1-2H3/q+1/t11-,12-,13+,16-,17+
IUPAC Name
(1R,2R,4S,5S,7R)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-9-ium
SMILES
[H][C@]12O[C@@]1([H])[C@]1([H])C[C@@]([H])(C[C@@]2([H])[N+]1(C)C)OC(=O)C(O)(C1=CC=CS1)C1=CC=CS1
Taxonomy
ClassificationNot classified
Pharmacology
IndicationUsed in the management of chronic obstructive pulmonary disease (COPD).
PharmacodynamicsTiotropium is a long–acting, antimuscarinic agent, which is often referred to as an anticholinergic. It has similar affinity to the subtypes of muscarinic receptors, M1 to M5. In the airways, it exhibits pharmacological effects through inhibition of M3–receptors at the smooth muscle leading to bronchodilation. The competitive and reversible nature of antagonism was shown with human and animal origin receptors and isolated organ preparations. In preclinical in vitro as well as in vivo studies prevention of methacholine–induced bronchoconstriction effects were dose–dependent and lasted longer than 24 hours. The bronchodilation following inhalation of tiotropium is predominantly a site–specific effect.
Mechanism of actionTiotropium is a muscarinic receptor antagonist, often referred to as an antimuscarinic or anticholinergic agent. Although it does not display selectivity for specific muscarinic receptors, on topical application it acts mainly on M3 muscarinic receptors located in the airways to produce smooth muscle relaxation, thus producing a bronchodilatory effect.
Related Articles
AbsorptionBioavailability is 19.5% following administration by inhalation. Oral solutions of tiotropium have an absolute bioavailability of 2-3%.
Volume of distribution
  • 32 L/kg
Protein binding72% bound to plasma proteins.
Metabolism

The extent of biotransformation appears to be small. This is evident from a urinary excretion of 74% of unchanged substance after an intravenous dose to young healthy volunteers. Tiotropium, an ester, is nonenzymatically cleaved to the alcohol N–methylscopine and dithienylglycolic acid, neither of which bind to muscarinic receptors. In vitro experiments with human liver microsomes and human hepatocytes suggest that a fraction of the administered dose (74% of an intravenous dose is excreted unchanged in the urine, leaving 25% for metabolism) is metabolized by cytochrome P450–dependent oxidation and subsequent glutathione conjugation to a variety of Phase II metabolites. Via inhibition studies, it is evident that CYP450 2D6 and 3A4 are involved in the metabolic pathway that is responsible for the elimination of a small part of the administered dose.

Route of eliminationIntravenously administered tiotropium was mainly excreted unchanged in urine (74%). After dry powder inhalation, urinary excretion was 14% of the dose, the remainder being mainly non-absorbed drug in the gut which was eliminated via the feces.
Half life5-6 days
Clearance
  • 880 mL/min [young healthy volunteers receiving IV administration]
  • Renal cl=326 mL/min [COPD patients (<58 years)]
  • Renal cl=163 mL/min [COPD patients (>70 years)]
ToxicityNo mortality was observed at inhalation tiotropium doses up to 32.4 mg/kg in mice, 267.7 mg/kg in rats, and 0.6 mg/kg in dogs. These doses correspond to 7,300, 120,000, and 850 times the recommended human daily dose on a mg/m2 basis, respectively.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9173
Blood Brain Barrier+0.5208
Caco-2 permeable+0.5294
P-glycoprotein substrateSubstrate0.7153
P-glycoprotein inhibitor INon-inhibitor0.7514
P-glycoprotein inhibitor IINon-inhibitor0.9762
Renal organic cation transporterNon-inhibitor0.7256
CYP450 2C9 substrateNon-substrate0.6633
CYP450 2D6 substrateNon-substrate0.7533
CYP450 3A4 substrateSubstrate0.6615
CYP450 1A2 substrateNon-inhibitor0.7787
CYP450 2C9 inhibitorNon-inhibitor0.812
CYP450 2D6 inhibitorNon-inhibitor0.8368
CYP450 2C19 inhibitorNon-inhibitor0.7284
CYP450 3A4 inhibitorNon-inhibitor0.7752
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9289
Ames testNon AMES toxic0.6133
CarcinogenicityNon-carcinogens0.9221
BiodegradationNot ready biodegradable0.9319
Rat acute toxicity2.6249 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9957
hERG inhibition (predictor II)Non-inhibitor0.8947
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Solutioninhalation
Capsuleinhalation18 mcg
Capsuleoral; respiratory (inhalation)18 ug/1
Solutioninhalation2.5 mcg
Spray, meteredrespiratory (inhalation)1.562 ug/1
Spray, meteredrespiratory (inhalation)3.124 ug/1
Spray, meteredrespiratory (inhalation)
Prices
Unit descriptionCostUnit
Spiriva HandiHaler 30 18 mcg capsule Box223.07USD box
Spiriva HandiHaler 5 18 mcg capsule Box63.64USD box
Spiriva HandiHaler 6 18 mcg capsule Box41.99USD box
Spiriva 18 mcg cp-handihaler6.31USD inhaler
Spiriva 18 mcg Capsule2.2USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2066248 No1998-08-042010-09-08Canada
US5478578 No1992-12-262012-12-26Us
US5964416 No1996-10-042016-10-04Us
US6149054 No1996-12-162016-12-16Us
US6176442 No1996-05-312016-05-31Us
US6453795 No1996-12-052016-12-05Us
US6726124 No1996-10-042016-10-04Us
US6777423 No2001-09-242021-09-24Us
US6846413 No1998-08-282018-08-28Us
US6908928 No2001-09-242021-09-24Us
US6977042 No1998-08-282018-08-28Us
US6988496 No2000-02-232020-02-23Us
US7056916 No2003-12-072023-12-07Us
US7070800 No2002-01-222022-01-22Us
US7104470 No1996-10-042016-10-04Us
US7220742 No2005-05-122025-05-12Us
US7246615 No1996-05-312016-05-31Us
US7284474 No2004-08-262024-08-26Us
US7309707 No2001-09-242021-09-24Us
US7396341 No2006-10-102026-10-10Us
US7491719 No2003-11-102023-11-10Us
US7642268 No2001-09-242021-09-24Us
US7694676 No2007-03-122027-03-12Us
US7727984 No2003-11-102023-11-10Us
US7786111 No2003-11-102023-11-10Us
US7802568 No1999-02-262019-02-26Us
US7837235 No2008-03-132028-03-13Us
US7896264 No2005-05-262025-05-26Us
US7988001 No2001-08-042021-08-04Us
US8022082 No2006-01-192026-01-19Us
US8034809 No2005-05-122025-05-12Us
US8044046 No2003-11-102023-11-10Us
US8733341 No2009-12-162029-12-16Us
US9027967 No2007-03-312027-03-31Us
USRE38912 No2001-10-112021-10-11Us
USRE39820 No1998-01-302018-01-30Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0156 mg/mLALOGPS
logP-0.55ALOGPS
logP-1.8ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)10.35ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.06 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.18 m3·mol-1ChemAxon
Polarizability39.52 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Rolf Banholzer, “Crystalline tiotropium bromide monohydrate, processes for the preparation thereof, and pharmaceutical compositions.” U.S. Patent US20020169321, issued November 14, 2002.

US20020169321
General ReferencesNot Available
External Links
ATC CodesR03AL06R03BB04R03BB54
AHFS Codes
  • 12:08.08
PDB EntriesNot Available
FDA labelDownload (401 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AclidiniumAclidinium may increase the anticholinergic activities of Tiotropium.
AmitriptylineAmitriptyline may increase the anticholinergic activities of Tiotropium.
AmoxapineAmoxapine may increase the anticholinergic activities of Tiotropium.
AtropineAtropine may increase the anticholinergic activities of Tiotropium.
AzelastineAzelastine may increase the anticholinergic activities of Tiotropium.
BenzatropineBenzatropine may increase the anticholinergic activities of Tiotropium.
Botulinum Toxin Type ATiotropium may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BTiotropium may increase the anticholinergic activities of Botulinum Toxin Type B.
BrompheniramineBrompheniramine may increase the anticholinergic activities of Tiotropium.
CarbinoxamineCarbinoxamine may increase the anticholinergic activities of Tiotropium.
CetirizineCetirizine may increase the anticholinergic activities of Tiotropium.
ChlorphenamineChlorphenamine may increase the anticholinergic activities of Tiotropium.
ChlorpromazineChlorpromazine may increase the anticholinergic activities of Tiotropium.
Cimetropium BromideTiotropium may increase the anticholinergic activities of Cimetropium Bromide.
ClemastineClemastine may increase the anticholinergic activities of Tiotropium.
ClomipramineClomipramine may increase the anticholinergic activities of Tiotropium.
ClozapineClozapine may increase the anticholinergic activities of Tiotropium.
CyclizineCyclizine may increase the anticholinergic activities of Tiotropium.
CyclobenzaprineCyclobenzaprine may increase the anticholinergic activities of Tiotropium.
CyclopentolateCyclopentolate may increase the anticholinergic activities of Tiotropium.
CyproheptadineCyproheptadine may increase the anticholinergic activities of Tiotropium.
DarifenacinDarifenacin may increase the anticholinergic activities of Tiotropium.
DesipramineDesipramine may increase the anticholinergic activities of Tiotropium.
DesloratadineDesloratadine may increase the anticholinergic activities of Tiotropium.
Dexchlorpheniramine maleateDexchlorpheniramine maleate may increase the anticholinergic activities of Tiotropium.
DicyclomineDicyclomine may increase the anticholinergic activities of Tiotropium.
DimenhydrinateDimenhydrinate may increase the anticholinergic activities of Tiotropium.
DiphenhydramineDiphenhydramine may increase the anticholinergic activities of Tiotropium.
DisopyramideDisopyramide may increase the anticholinergic activities of Tiotropium.
DoxepinDoxepin may increase the anticholinergic activities of Tiotropium.
DoxylamineDoxylamine may increase the anticholinergic activities of Tiotropium.
DronabinolTiotropium may increase the tachycardic activities of Dronabinol.
DroperidolDroperidol may increase the anticholinergic activities of Tiotropium.
EluxadolineTiotropium may increase the activities of Eluxadoline.
FesoterodineFesoterodine may increase the anticholinergic activities of Tiotropium.
FexofenadineFexofenadine may increase the anticholinergic activities of Tiotropium.
FlavoxateFlavoxate may increase the anticholinergic activities of Tiotropium.
FlupentixolFlupentixol may increase the anticholinergic activities of Tiotropium.
FluphenazineFluphenazine may increase the anticholinergic activities of Tiotropium.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Tiotropium is combined with Glucagon recombinant.
GlycopyrroniumGlycopyrrolate may increase the anticholinergic activities of Tiotropium.
HaloperidolHaloperidol may increase the anticholinergic activities of Tiotropium.
HomatropineHomatropine may increase the anticholinergic activities of Tiotropium.
HydroxyzineHydroxyzine may increase the anticholinergic activities of Tiotropium.
HyoscyamineHyoscyamine may increase the anticholinergic activities of Tiotropium.
ImipramineImipramine may increase the anticholinergic activities of Tiotropium.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Tiotropium.
IsocarboxazidIsocarboxazid may increase the anticholinergic activities of Tiotropium.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Tiotropium.
LevocabastineLevocabastine may increase the anticholinergic activities of Tiotropium.
LevocetirizineLevocetirizine may increase the anticholinergic activities of Tiotropium.
LoratadineLoratadine may increase the anticholinergic activities of Tiotropium.
LoxapineLoxapine may increase the anticholinergic activities of Tiotropium.
MaprotilineMaprotiline may increase the anticholinergic activities of Tiotropium.
MeclizineMeclizine may increase the anticholinergic activities of Tiotropium.
MepenzolateMepenzolate may increase the anticholinergic activities of Tiotropium.
MethotrimeprazineMethotrimeprazine may increase the anticholinergic activities of Tiotropium.
MethscopolamineMethscopolamine may increase the anticholinergic activities of Tiotropium.
MianserinMianserin may increase the anticholinergic activities of Tiotropium.
MirabegronThe risk or severity of adverse effects can be increased when Tiotropium is combined with Mirabegron.
MoclobemideMoclobemide may increase the anticholinergic activities of Tiotropium.
MorphineThe risk or severity of adverse effects can be increased when Tiotropium is combined with Morphine.
NortriptylineNortriptyline may increase the anticholinergic activities of Tiotropium.
OlanzapineOlanzapine may increase the anticholinergic activities of Tiotropium.
OlopatadineOlopatadine may increase the anticholinergic activities of Tiotropium.
OrphenadrineOrphenadrine may increase the anticholinergic activities of Tiotropium.
OxybutyninOxybutynin may increase the anticholinergic activities of Tiotropium.
PerphenazinePerphenazine may increase the anticholinergic activities of Tiotropium.
PhenelzinePhenelzine may increase the anticholinergic activities of Tiotropium.
PimozidePimozide may increase the anticholinergic activities of Tiotropium.
PizotifenPizotifen may increase the anticholinergic activities of Tiotropium.
Potassium ChlorideTiotropium may increase the ulcerogenic activities of Potassium Chloride.
PramlintidePramlintide may increase the anticholinergic activities of Tiotropium.
ProchlorperazineProchlorperazine may increase the anticholinergic activities of Tiotropium.
ProcyclidineProcyclidine may increase the anticholinergic activities of Tiotropium.
PromazinePromazine may increase the anticholinergic activities of Tiotropium.
PromethazinePromethazine may increase the anticholinergic activities of Tiotropium.
PropanthelinePropantheline may increase the anticholinergic activities of Tiotropium.
ProtriptylineProtriptyline may increase the anticholinergic activities of Tiotropium.
QuetiapineQuetiapine may increase the anticholinergic activities of Tiotropium.
RamosetronTiotropium may increase the activities of Ramosetron.
RisperidoneRisperidone may increase the anticholinergic activities of Tiotropium.
ScopolamineScopolamine may increase the anticholinergic activities of Tiotropium.
Scopolamine butylbromideScopolamine butylbromide may increase the anticholinergic activities of Tiotropium.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Tiotropium.
SolifenacinSolifenacin may increase the anticholinergic activities of Tiotropium.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Tiotropium.
TacrineThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Tacrine.
ThioridazineThioridazine may increase the anticholinergic activities of Tiotropium.
ThiothixeneThiothixene may increase the anticholinergic activities of Tiotropium.
TolterodineTolterodine may increase the anticholinergic activities of Tiotropium.
TopiramateThe risk or severity of adverse effects can be increased when Tiotropium is combined with Topiramate.
TranylcypromineTranylcypromine may increase the anticholinergic activities of Tiotropium.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Tiotropium.
TrifluoperazineTrifluoperazine may increase the anticholinergic activities of Tiotropium.
TrihexyphenidylTrihexyphenidyl may increase the anticholinergic activities of Tiotropium.
TrimethobenzamideTrimethobenzamide may increase the anticholinergic activities of Tiotropium.
TrimipramineTrimipramine may increase the anticholinergic activities of Tiotropium.
TriprolidineTriprolidine may increase the anticholinergic activities of Tiotropium.
TrospiumTrospium may increase the anticholinergic activities of Tiotropium.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Tiotropium.
ZuclopenthixolZuclopenthixol may increase the anticholinergic activities of Tiotropium.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Hansel TT, Barnes PJ: Tiotropium bromide: a novel once-daily anticholinergic bronchodilator for the treatment of COPD. Drugs Today (Barc). 2002 Sep;38(9):585-600. [PubMed:12582447 ]
  3. Barnes PJ: Tiotropium bromide. Expert Opin Investig Drugs. 2001 Apr;10(4):733-40. [PubMed:11281822 ]
  4. Barnes PJ, Belvisi MG, Mak JC, Haddad EB, O'Connor B: Tiotropium bromide (Ba 679 BR), a novel long-acting muscarinic antagonist for the treatment of obstructive airways disease. Life Sci. 1995;56(11-12):853-9. [PubMed:10188785 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
References
  1. Hansel TT, Barnes PJ: Tiotropium bromide: a novel once-daily anticholinergic bronchodilator for the treatment of COPD. Drugs Today (Barc). 2002 Sep;38(9):585-600. [PubMed:12582447 ]
  2. Barnes PJ: Tiotropium bromide. Expert Opin Investig Drugs. 2001 Apr;10(4):733-40. [PubMed:11281822 ]
  3. Barnes PJ, Belvisi MG, Mak JC, Haddad EB, O'Connor B: Tiotropium bromide (Ba 679 BR), a novel long-acting muscarinic antagonist for the treatment of obstructive airways disease. Life Sci. 1995;56(11-12):853-9. [PubMed:10188785 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Hansel TT, Barnes PJ: Tiotropium bromide: a novel once-daily anticholinergic bronchodilator for the treatment of COPD. Drugs Today (Barc). 2002 Sep;38(9):585-600. [PubMed:12582447 ]
  2. Barnes PJ, Belvisi MG, Mak JC, Haddad EB, O'Connor B: Tiotropium bromide (Ba 679 BR), a novel long-acting muscarinic antagonist for the treatment of obstructive airways disease. Life Sci. 1995;56(11-12):853-9. [PubMed:10188785 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular Weight:
62751.08 Da
References
  1. Nakamura T, Nakanishi T, Haruta T, Shirasaka Y, Keogh JP, Tamai I: Transport of ipratropium, an anti-chronic obstructive pulmonary disease drug, is mediated by organic cation/carnitine transporters in human bronchial epithelial cells: implications for carrier-mediated pulmonary absorption. Mol Pharm. 2010 Feb 1;7(1):187-95. doi: 10.1021/mp900206j. [PubMed:20020740 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET).
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Molecular Weight:
62154.48 Da
References
  1. Nakamura T, Nakanishi T, Haruta T, Shirasaka Y, Keogh JP, Tamai I: Transport of ipratropium, an anti-chronic obstructive pulmonary disease drug, is mediated by organic cation/carnitine transporters in human bronchial epithelial cells: implications for carrier-mediated pulmonary absorption. Mol Pharm. 2010 Feb 1;7(1):187-95. doi: 10.1021/mp900206j. [PubMed:20020740 ]
Comments
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Drug created on July 17, 2007 06:36 / Updated on July 23, 2016 01:55