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Identification
NameAmlodipine
Accession NumberDB00381  (APRD00520)
TypeSmall Molecule
GroupsApproved
Description

Amlodipine is a long-acting 1,4-dihydropyridine calcium channel blocker. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, amlodipine prevents calcium-dependent myocyte contraction and vasoconstriction. A second proposed mechanism for the drug’s vasodilatory effects involves pH-dependent inhibition of calcium influx via inhibition of smooth muscle carbonic anhydrase. Some studies have shown that amlodipine also exerts inhibitory effects on voltage-gated N-type calcium channels. N-type calcium channels located in the central nervous system may be involved in nociceptive signaling and pain sensation. Amlodipine is used to treat hypertension and chronic stable angina.

Structure
Thumb
Synonyms
SynonymLanguageCode
(RS)-3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylateNot AvailableIUPAC
3-Ethyl 5-methylester, (±)-2-[(2-aminoethoxy)methyl]-4-(o-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylateNot AvailableWHO
3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(O-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylateNot AvailableNot Available
AmlodipineNot AvailableBAN, DCF
Amlodipine free baseNot AvailableNot Available
AmlodipinoSpanishINN
AmlodipinumLatinINN
Salts
Name/CAS Structure Properties
Amlodipine Besilate
Thumb Not applicable DBSALT001054
Amlodipine Besylate
Thumb Not applicable DBSALT001055
Amlodipine Maleate
Thumb Not applicable DBSALT001056
Brand names
NameCompany
AforbesMerck
AgenZentiva
AkenKendrick Farmaceutica
AmcardApex Pharma Ltd
AmdepinCadila Pharmaceuticals
AmdipinLaboratorios Lafrancol
AmlocardAWD (Germany)
AmlodNot Available
AmlodineSumitomo Pharmaceuticals
AmlodipinNot Available
Amlodipin-Mepha 5/10Mepha Pharma AG
Amlodipine 5PT KALBE FARMA Tbk
AmlodisEczacibasi (Turkey)
AmlongMicro Labs
AmlopinLek
AmlopineBerlin
AmlostinDiscovery Pharmaceuticals
AmlosunSun Pharmaceutical
AmlovasMacleods Pharmaceuticals Ltd
AmlovascDr. Reddy's Laboratories
AmlozekAdamed
AmvazReddy (Malaysia)
AsomexEmcure Pharmaceuticals
Atecard-AMAlembic Ltd
CamlodinSquare
CorovalSandoz (Argentina)
DailyvascXeno Pharmaceuticals
EmadineMerck
IstinNot Available
LamaStadmed Private Limited
LodipTIME Pharmaceuticals
LodopinMerck Pakistan
LopinEdruc Ltd
NelodThe Kemiko Pharmaceuticals Ltd
NopidinAd-din Pharmaceuticals Ltd
NordipNot Available
NorvascPfizer
PerivascNot Available
Pharex AmlodipinePHAREX HealthCorp
TenoxKrka
Brand mixtures
Brand NameIngredients
AmlobenzAmlodipine + Benazepril
AmturnideAmlodipine + Aliskiren
Azoramlodipine + olmesartan
Caduetamlodipine + atorvastatin
Coroval Bamlodipine + benazepril
Exforgeamlodipine + valsartan
Hiprillisinopril with amlodipine (5 mg each)
Lotrelamlodipine + benazepril
TekamloAmlodipine + Aliskiren
TribenzorOlmesartan + Amlodipine + Hydrochlorothiazide
TwynstaAmlodipine + Telmisartan
Categories
CAS number88150-42-9
WeightAverage: 408.876
Monoisotopic: 408.145199627
Chemical FormulaC20H25ClN2O5
InChI KeyHTIQEAQVCYTUBX-UHFFFAOYSA-N
InChI
InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3
IUPAC Name
3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
SMILES
CCOC(=O)C1=C(COCCN)NC(C)=C(C1C1=CC=CC=C1Cl)C(=O)OC
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPyridines and Derivatives
SubclassHydropyridines
Direct parentDihydropyridinecarboxylic Acids and Derivatives
Alternative parentsChlorobenzenes; Aryl Chlorides; Dicarboxylic Acids and Derivatives; Carboxylic Acid Esters; Enolates; Enamines; Ethers; Polyamines; Organochlorides; Monoalkylamines
Substituentschlorobenzene; dicarboxylic acid derivative; aryl halide; aryl chloride; benzene; carboxylic acid ester; carboxylic acid derivative; polyamine; enolate; ether; enamine; organohalogen; organochloride; amine; primary amine; primary aliphatic amine; organonitrogen compound
Classification descriptionThis compound belongs to the dihydropyridinecarboxylic acids and derivatives. These are compounds containing a dihydropyridine moiety bearing a carboxylic acid group.
Pharmacology
IndicationFor the treatment of hypertension and chronic stable angina.
PharmacodynamicsAmlodipine belongs to the dihydropyridine (DHP) class of calcium channel blockers (CCBs), the most widely used class of CCBs. There are at least five different types of calcium channels in Homo sapiens: L-, N-, P/Q-, R- and T-type. It was widely accepted that DHP CCBs target L-type calcium channels, the major channel in muscle cells that mediate contraction; however, some studies have indicated that amlodipine also binds to and inhibits N-type calcium channels (see references in Targets section). Similar to other DHP CCBs, amlodipine binds directly to inactive L-type calcium channels stabilizing their inactive conformation. Since arterial smooth muscle depolarizations are longer in duration than cardiac muscle depolarizations, inactive channels are more prevalent in smooth muscle cells. Alternative splicing of the alpha-1 subunit of the channel gives amlodipine additional arterial selectivity. At therapeutic sub-toxic concentrations, amlodipine has little effect on cardiac myocytes and conduction cells.
Mechanism of actionAmlodipine decreases arterial smooth muscle contractility and subsequent vasoconstriction by inhibiting the influx of calcium ions through L-type calcium channels. Calcium ions entering the cell through these channels bind to calmodulin. Calcium-bound calmodulin then binds to and activates myosin light chain kinase (MLCK). Activated MLCK catalyzes the phosphorylation of the regulatory light chain subunit of myosin, a key step in muscle contraction. Signal amplification is achieved by calcium-induced calcium release from the sarcoplasmic reticulum through ryanodine receptors. Inhibition of the initial influx of calcium decreases the contractile activity of arterial smooth muscle cells and results in vasodilation. The vasodilatory effects of amlodipine result in an overall decrease in blood pressure. Amlodipine is a long-acting CCB that may be used to treat mild to moderate essential hypertension and exertion-related angina (chronic stable angina). Another possible mechanism is that amlodipine inhibits vascular smooth muscle carbonic anhydrase I activity causing cellular pH increases which may be involved in regulating intracelluar calcium influx through calcium channels.
AbsorptionAmlodipine is slowly and almost completely absorbed from the gastrointestinal tract. Peak plasma concentrations are reached 6-12 hour following oral administration. Its estimated bioavailability is 64-90%. Absorption is not affected by food.
Volume of distributionNot Available
Protein binding97.5%
Metabolism

Hepatic. Metabolized extensively (90%) to inactive metabolites via the cytochrome P450 3A4 isozyme.

Route of eliminationAmlodipine is extensively (about 90%) converted to inactive metabolites via hepatic metabolism with 10% of the parent compound and 60% of the metabolites excreted in the urine.
Half life30-50 hours
ClearanceNot Available
ToxicityGross overdosage could result in excessive peripheral vasodilatation and possibly reflex tachycardia. Marked and probably prolonged systemic hypotension up to an including shock with fatal outcome have been reported.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Natriuretic peptides A
Gene symbol: NPPA
UniProt: P01160
rs5065 Not AvailableAA alleleThose with the rs5065(AA) allele had more favorable cardiovascular disease outcomes if given amlodipine than if treated with chlorthalidone (diuretic)18212314
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9479
Blood Brain Barrier - 0.7744
Caco-2 permeable - 0.5468
P-glycoprotein substrate Substrate 0.9102
P-glycoprotein inhibitor I Inhibitor 0.8564
P-glycoprotein inhibitor II Non-inhibitor 0.8473
Renal organic cation transporter Non-inhibitor 0.803
CYP450 2C9 substrate Non-substrate 0.8627
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Substrate 0.6967
CYP450 1A2 substrate Inhibitor 0.538
CYP450 2C9 substrate Inhibitor 0.514
CYP450 2D6 substrate Non-inhibitor 0.7626
CYP450 2C19 substrate Inhibitor 0.5871
CYP450 3A4 substrate Inhibitor 0.8608
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6642
Ames test Non AMES toxic 0.7605
Carcinogenicity Non-carcinogens 0.8568
Biodegradation Not ready biodegradable 0.9791
Rat acute toxicity 2.5396 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8302
hERG inhibition (predictor II) Inhibitor 0.8411
Pharmacoeconomics
Manufacturers
  • Synthon pharmaceuticals inc
  • Actavis totowa llc
  • Alkem laboratories ltd
  • Amneal pharmaceuticals ny llc
  • Apotex inc
  • Aurobindo pharma ltd
  • Caraco pharmaceutical laboratories ltd
  • Dr reddys laboratories ltd
  • Gedeon richter usa inc
  • Genpharm inc
  • Glenmark generics ltd
  • Invagen pharmaceuticals inc
  • Lek pharmaceuticals dd
  • Lupin ltd
  • Matrix laboratories ltd
  • Mutual pharmacal co
  • Mylan laboratories inc
  • Orchid healthcare
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
  • Teva pharmaceuticals usa inc
  • Torrent pharmaceuticals ltd
  • Upsher smith laboratories inc
  • Vintage pharmaceuticals llc
  • Watson laboratories inc
  • Wockhardt ltd
  • World gen llc
  • Zydus pharmaceuticals usa inc
  • Pfizer inc
  • Dr reddys laboratories inc
Packagers
Dosage forms
FormRouteStrength
TabletOral10 mg
TabletOral2.5 mg
TabletOral5 mg
Prices
Unit descriptionCostUnit
Amlodipine besylate powder9.99USDg
Lotrel 10-40 mg capsule5.21USDcapsule
Lotrel 10-20 mg capsule4.8USDcapsule
Lotrel 5-40 mg capsule4.37USDcapsule
Lotrel 5-20 mg capsule4.13USDcapsule
Lotrel 5-10 mg capsule3.91USDcapsule
Lotrel 2.5-10 mg capsule3.83USDcapsule
Norvasc 10 mg tablet3.16USDtablet
Amlodipine besylate 10 mg tablet2.42USDtablet
Norvasc 2.5 mg tablet2.36USDtablet
Norvasc 5 mg tablet2.36USDtablet
Norvasc 10 mg Tablet2.14USDtablet
Amlodipine besylate 2.5 mg tablet1.76USDtablet
Amlodipine besylate 5 mg tablet1.76USDtablet
Norvasc 5 mg Tablet1.44USDtablet
Amlodipine 10 mg Tablet1.03USDtablet
Apo-Amlodipine 10 mg Tablet1.03USDtablet
Co Amlodipine 10 mg Tablet1.03USDtablet
Gd-Amlodipine 10 mg Tablet1.03USDtablet
Jamp-Amlodipine 10 mg Tablet1.03USDtablet
Mylan-Amlodipine 10 mg Tablet1.03USDtablet
Novo-Amlodipine 10 mg Tablet1.03USDtablet
Phl-Amlodipine 10 mg Tablet1.03USDtablet
Pms-Amlodipine 10 mg Tablet1.03USDtablet
Ran-Amlodipine 10 mg Tablet1.03USDtablet
Ratio-Amlodipine 10 mg Tablet1.03USDtablet
Sandoz Amlodipine 10 mg Tablet1.03USDtablet
Amlodipine 5 mg Tablet0.7USDtablet
Apo-Amlodipine 5 mg Tablet0.7USDtablet
Co Amlodipine 5 mg Tablet0.7USDtablet
Gd-Amlodipine 5 mg Tablet0.7USDtablet
Jamp-Amlodipine 5 mg Tablet0.7USDtablet
Mylan-Amlodipine 5 mg Tablet0.7USDtablet
Novo-Amlodipine 5 mg Tablet0.7USDtablet
Phl-Amlodipine 5 mg Tablet0.7USDtablet
Pms-Amlodipine 5 mg Tablet0.7USDtablet
Ran-Amlodipine 5 mg Tablet0.7USDtablet
Ratio-Amlodipine 5 mg Tablet0.7USDtablet
Sandoz Amlodipine 5 mg Tablet0.7USDtablet
Phl-Amlodipine 2.5 mg Tablet0.35USDtablet
Pms-Amlodipine 2.5 mg Tablet0.35USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States68283392002-11-202022-11-20
Canada21702781999-08-032014-08-10
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point178-179 °CNot Available
water solubility75.3 mg/LNot Available
logP3.00AUSTIN,RP ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0074ALOGPS
logP2.22ALOGPS
logP1.64ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.88 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity108.64 m3·mol-1ChemAxon
Polarizability42.29 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra1D NMR2D NMR
References
Synthesis Reference

DrugSyn.org

US4572909
General Reference
  1. Nayler WG, Gu XH: The unique binding properties of amlodipine: a long-acting calcium antagonist. J Hum Hypertens. 1991 Aug;5 Suppl 1:55-9. Pubmed
  2. van Zwieten PA: Amlodipine: an overview of its pharmacodynamic and pharmacokinetic properties. Clin Cardiol. 1994 Sep;17(9 Suppl 3):III3-6. Pubmed
External Links
ResourceLink
KEGG CompoundC06825
PubChem Compound2162
PubChem Substance46507214
ChemSpider2077
ChEBI2668
ChEMBLCHEMBL1491
Therapeutic Targets DatabaseDAP000139
PharmGKBPA448388
Drug Product Database878936
RxListhttp://www.rxlist.com/cgi/generic/amlod2.htm
Drugs.comhttp://www.drugs.com/amlodipine.html
PDRhealthhttp://www.pdrhealth.com/drugs/rx/rx-mono.aspx?contentFileName=nor1306.html&contentName=Norvasc&contentId=538
WikipediaAmlodipine
ATC CodesC08CA01
AHFS Codes
  • 24:28.08
PDB Entries
FDA labelshow(91.4 KB)
MSDSshow(74.5 KB)
Interactions
Drug Interactions
Drug
DiltiazemDiltiazem may increase the serum concentration of amlodipine. Concomitant therapy will result in additive hypotensive effects. Monitor for changes in the hypotensive effect of amlodipine if diltiazem is initiated, discontinued or dose changed.
QuinupristinThis combination presents an increased risk of toxicity
TacrineThe metabolism of Tacrine, a CYP1A2 substrate, may be reduced by Amlopidine, a CYP1A2 inhibitors. Monitor the efficacy and toxicity of Tacrine if Amlopidine is initiated, discontinued or if the dose is changed.
TelaprevirTelaprevir inhibits the metabolism of amlodipine and concomitant therapy is contraindicated.
TelithromycinTelithromycin may reduce clearance of Amlopidine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Amlopidine if Telithromycin is initiated, discontinued or dose changed.
ThiopentalThe CYP3A4 inducer, Thiopental, may increase the metabolism and clearance of Amlodipine, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Amlodipine if Thiopental is initiated, discontinued or dose changed.
TipranavirTipranavir may decrease the metabolism and clearance of the calcium channel blocker, Amlopidine. Monitor for changes in Amlopidine therapeutic and toxic effects if Tipranavir is initiated, discontinued or dose changed.
TizanidineAmlopidine may decrease the metabolism and clearance of Tizanidine. Consider alternate therapy or use caution during co-administration.
TreprostinilAdditive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
VoriconazoleVoriconazole may increase the serum concentration of amlodipine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of amlodipine if voriconazole is initiated, discontinued or dose changed.
Food Interactions
  • Avoid natural licorice.
  • Grapefruit down regulates post-translational expression of CYP3A4, the major metabolizing enzyme of amlodipine. Grapefruit, in all forms (e.g. whole fruit, juice and rind), can significantly increase serum levels of amlodipine and may cause toxicity. Avoid grapefruit products while on this medication.
  • Take without regard to meals.

Targets

1. Voltage-dependent L-type calcium channel subunit alpha-1C

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Voltage-dependent L-type calcium channel subunit alpha-1C Q13936 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Striessnig, J. (2004). Ca 2+ channel blockers. In S. Offermanns, & W. Rosenthal (Eds.). Encyclopedic reference of molecular pharmacology (pp. 201-207). Berlin, Germany: Springer.

2. Voltage-dependent calcium channel subunit alpha-2/delta-1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Voltage-dependent calcium channel subunit alpha-2/delta-1 P54289 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Striessnig, J. (2004). Ca 2+ channel blockers. In S. Offermanns, & W. Rosenthal (Eds.). Encyclopedic reference of molecular pharmacology (pp. 201-207). Berlin, Germany: Springer.

3. Voltage-dependent L-type calcium channel subunit beta-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Voltage-dependent L-type calcium channel subunit beta-2 Q08289 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Striessnig, J. (2004). Ca 2+ channel blockers. In S. Offermanns, & W. Rosenthal (Eds.). Encyclopedic reference of molecular pharmacology (pp. 201-207). Berlin, Germany: Springer.

4. Voltage-dependent L-type calcium channel subunit alpha-1D

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Voltage-dependent L-type calcium channel subunit alpha-1D Q01668 Details

References:

  1. Sinnegger-Brauns MJ, Huber IG, Koschak A, Wild C, Obermair GJ, Einzinger U, Hoda JC, Sartori SB, Striessnig J: Expression and 1,4-dihydropyridine-binding properties of brain L-type calcium channel isoforms. Mol Pharmacol. 2009 Feb;75(2):407-14. Epub 2008 Nov 24. Pubmed

5. Voltage-dependent L-type calcium channel subunit alpha-1S

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Voltage-dependent L-type calcium channel subunit alpha-1S Q13698 Details

References:

  1. Peterson BZ, Catterall WA: Allosteric interactions required for high-affinity binding of dihydropyridine antagonists to Ca(V)1.1 Channels are modulated by calcium in the pore. Mol Pharmacol. 2006 Aug;70(2):667-75. Epub 2006 May 4. Pubmed

6. Voltage-dependent N-type calcium channel subunit alpha-1B

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Voltage-dependent N-type calcium channel subunit alpha-1B Q00975 Details

References:

  1. Furukawa T, Nukada T, Suzuki K, Fujita Y, Mori Y, Nishimura M, Yamanaka M: Voltage and pH dependent block of cloned N-type Ca2+ channels by amlodipine. Br J Pharmacol. 1997 Jul;121(6):1136-40. Pubmed
  2. Furukawa T, Yamakawa T, Midera T, Sagawa T, Mori Y, Nukada T: Selectivities of dihydropyridine derivatives in blocking Ca(2+) channel subtypes expressed in Xenopus oocytes. J Pharmacol Exp Ther. 1999 Nov;291(2):464-73. Pubmed
  3. Miyashita Y, Furukawa T, Kamegaya E, Yoshii M, Nukada T: A region of N-type Ca(2+) channel critical for blockade by the dihydropyridine amlodipine. Eur J Pharmacol. 2010 Apr 25;632(1-3):14-22. Epub 2010 Jan 22. Pubmed
  4. Murakami M, Nakagawasai O, Fujii S, Kameyama K, Murakami S, Hozumi S, Esashi A, Taniguchi R, Yanagisawa T, Tan-no K, Tadano T, Kitamura K, Kisara K: Antinociceptive action of amlodipine blocking N-type Ca2+ channels at the primary afferent neurons in mice. Eur J Pharmacol. 2001 May 11;419(2-3):175-81. Pubmed
  5. Ogihara T, Kano T, Kakinuma C: Evaluation of the inhibitory effect of dihydropyridines on N-type calcium channel by virtual three-dimensional pharmacophore modeling. Arzneimittelforschung. 2009;59(6):283-8. Pubmed
  6. Qu YL, Sugiyama K, Ohnuki T, Hattori K, Watanabe K, Nagatomo T: Comparison of binding affinities of omega-conotoxin and amlodipine to N-type Ca2+ channels in rat brain. Zhongguo Yao Li Xue Bao. 1998 Mar;19(2):97-100. Pubmed

7. Voltage-dependent calcium channel subunit alpha-2/delta-3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Voltage-dependent calcium channel subunit alpha-2/delta-3 Q8IZS8 Details

References:

  1. Furukawa T, Nukada T, Suzuki K, Fujita Y, Mori Y, Nishimura M, Yamanaka M: Voltage and pH dependent block of cloned N-type Ca2+ channels by amlodipine. Br J Pharmacol. 1997 Jul;121(6):1136-40. Pubmed
  2. Furukawa T, Yamakawa T, Midera T, Sagawa T, Mori Y, Nukada T: Selectivities of dihydropyridine derivatives in blocking Ca(2+) channel subtypes expressed in Xenopus oocytes. J Pharmacol Exp Ther. 1999 Nov;291(2):464-73. Pubmed
  3. Miyashita Y, Furukawa T, Kamegaya E, Yoshii M, Nukada T: A region of N-type Ca(2+) channel critical for blockade by the dihydropyridine amlodipine. Eur J Pharmacol. 2010 Apr 25;632(1-3):14-22. Epub 2010 Jan 22. Pubmed
  4. Murakami M, Nakagawasai O, Fujii S, Kameyama K, Murakami S, Hozumi S, Esashi A, Taniguchi R, Yanagisawa T, Tan-no K, Tadano T, Kitamura K, Kisara K: Antinociceptive action of amlodipine blocking N-type Ca2+ channels at the primary afferent neurons in mice. Eur J Pharmacol. 2001 May 11;419(2-3):175-81. Pubmed
  5. Ogihara T, Kano T, Kakinuma C: Evaluation of the inhibitory effect of dihydropyridines on N-type calcium channel by virtual three-dimensional pharmacophore modeling. Arzneimittelforschung. 2009;59(6):283-8. Pubmed
  6. Qu YL, Sugiyama K, Ohnuki T, Hattori K, Watanabe K, Nagatomo T: Comparison of binding affinities of omega-conotoxin and amlodipine to N-type Ca2+ channels in rat brain. Zhongguo Yao Li Xue Bao. 1998 Mar;19(2):97-100. Pubmed

8. Voltage-gated calcium channel beta 1 subunit splice variant CavB1d

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Voltage-gated calcium channel beta 1 subunit splice variant CavB1d Q6TME4 Details

References:

  1. Furukawa T, Nukada T, Suzuki K, Fujita Y, Mori Y, Nishimura M, Yamanaka M: Voltage and pH dependent block of cloned N-type Ca2+ channels by amlodipine. Br J Pharmacol. 1997 Jul;121(6):1136-40. Pubmed
  2. Furukawa T, Yamakawa T, Midera T, Sagawa T, Mori Y, Nukada T: Selectivities of dihydropyridine derivatives in blocking Ca(2+) channel subtypes expressed in Xenopus oocytes. J Pharmacol Exp Ther. 1999 Nov;291(2):464-73. Pubmed
  3. Miyashita Y, Furukawa T, Kamegaya E, Yoshii M, Nukada T: A region of N-type Ca(2+) channel critical for blockade by the dihydropyridine amlodipine. Eur J Pharmacol. 2010 Apr 25;632(1-3):14-22. Epub 2010 Jan 22. Pubmed
  4. Murakami M, Nakagawasai O, Fujii S, Kameyama K, Murakami S, Hozumi S, Esashi A, Taniguchi R, Yanagisawa T, Tan-no K, Tadano T, Kitamura K, Kisara K: Antinociceptive action of amlodipine blocking N-type Ca2+ channels at the primary afferent neurons in mice. Eur J Pharmacol. 2001 May 11;419(2-3):175-81. Pubmed
  5. Ogihara T, Kano T, Kakinuma C: Evaluation of the inhibitory effect of dihydropyridines on N-type calcium channel by virtual three-dimensional pharmacophore modeling. Arzneimittelforschung. 2009;59(6):283-8. Pubmed
  6. Qu YL, Sugiyama K, Ohnuki T, Hattori K, Watanabe K, Nagatomo T: Comparison of binding affinities of omega-conotoxin and amlodipine to N-type Ca2+ channels in rat brain. Zhongguo Yao Li Xue Bao. 1998 Mar;19(2):97-100. Pubmed

9. Carbonic anhydrase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 1 P00915 Details

References:

  1. Puscas I, Gilau L, Coltau M, Pasca R, Domuta G, Baican M, Hecht A: Hypotensive effect of calcium channel blockers is parallel with carbonic anhydrase I inhibition. Clin Pharmacol Ther. 2000 Oct;68(4):443-9. Pubmed
  2. Puscas L, Gilau L, Coltau M, Pasca R, Domuta G, Baican M, Hecht A: Calcium channel blockers reduce blood pressure in part by inhibiting vascular smooth muscle carbonic anhydrase I. Cardiovasc Drugs Ther. 2000 Oct;14(5):523-8. Pubmed
  3. Puscas I, Coltau M, Baican M, Pasca R, Domuta G, Hecht A: Vasoconstrictive drugs increase carbonic anhydrase I in vascular smooth muscle while vasodilating drugs reduce the activity of this isozyme by a direct mechanism of action. Drugs Exp Clin Res. 2001;27(2):53-60. Pubmed

10. Sphingomyelin phosphodiesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sphingomyelin phosphodiesterase P17405 Details

References:

  1. Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Muhle C, Terfloth L, Groemer TW, Spitzer GM, Liedl KR, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase. PLoS One. 2011;6(8):e23852. doi: 10.1371/journal.pone.0023852. Epub 2011 Aug 31. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Katoh M, Nakajima M, Shimada N, Yamazaki H, Yokoi T: Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):843-52. Pubmed
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. 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. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

3. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

4. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Katoh M, Nakajima M, Shimada N, Yamazaki H, Yokoi T: Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):843-52. Pubmed
  2. 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. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. Katoh M, Nakajima M, Shimada N, Yamazaki H, Yokoi T: Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):843-52. Pubmed
  2. 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. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Katoh M, Nakajima M, Shimada N, Yamazaki H, Yokoi T: Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):843-52. Pubmed
  2. 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. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 2A6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2A6 P11509 Details

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. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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. Epub 2009 Nov 24. Pubmed

9. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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. Epub 2009 Nov 24. Pubmed

10. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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. Epub 2009 Nov 24. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Katoh M, Nakajima M, Yamazaki H, Yokoi T: Inhibitory potencies of 1,4-dihydropyridine calcium antagonists to P-glycoprotein-mediated transport: comparison with the effects on CYP3A4. Pharm Res. 2000 Oct;17(10):1189-97. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on March 15, 2014 15:38