Tìm theo
Diltiazem
Các tên gọi khác (6 ) :
  • (+)-cis-5-[2-(dimethylamino)Ethyl]-2,3-dihydro-3-hydroxy-2-(P-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one acetate ester
  • (2S-cis)-3-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
  • (2S,3S)-5-(2-(dimethylamino)Ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetate
  • Acetic acid (2S,3S)-5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester
  • Diltiazem
  • Diltiazemum
Thuốc tim mạch
Thuốc Gốc
Small Molecule
CAS: 42399-41-7
ATC: C08DB01
ĐG : Abbott Laboratories Ltd. , http://www.abbott.com
CTHH: C22H26N2O4S
PTK: 414.518
A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of the calcium ion in membrane functions. It is also teratogenic. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C22H26N2O4S
Phân tử khối
414.518
Monoisotopic mass
414.16132802
InChI
InChI=1S/C22H26N2O4S/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3/h5-12,20-21H,13-14H2,1-4H3/t20-,21+/m1/s1
InChI Key
InChIKey=HSUGRBWQSSZJOP-RTWAWAEBSA-N
IUPAC Name
(2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate
Traditional IUPAC Name
diltiazem
SMILES
COC1=CC=C(C=C1)[C@@H]1SC2=CC=CC=C2N(CCN(C)C)C(=O)[C@@H]1OC(C)=O
Độ tan chảy
187-188
Độ hòa tan
465 mg/L (at 25 °C)
logP
2.8
logS
-4.4
pKa (strongest acidic)
12.86
pKa (Strongest Basic)
8.18
PSA
59.08 Å2
Refractivity
114.37 m3·mol-1
Polarizability
43.65 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
4
H Bond Donor Count
0
Physiological Charge
1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
MDDR-Like Rule
true
caco2 Permeability
-4.38
Dược Lực Học : Diltiazem, a benzothiazepine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina. Diltiazem is a non-dihydropyridine (DHP)member of the calcium channel blocker class, along with Verapamil. Diltiazem is similar to other peripheral vasodilators. Diltiazem inhibits the influx of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.
Cơ Chế Tác Dụng : A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of the calcium ion in membrane functions. It is also teratogenic. [PubChem] Possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, diltiazem, like verapamil, inhibits the influx of extracellular calcium across both the myocardial and vascular smooth muscle cell membranes. The resultant inhibition of the contractile processes of the myocardial smooth muscle cells leads to dilation of the coronary and systemic arteries and improved oxygen delivery to the myocardial tissue.
Dược Động Học :
▧ Absorption :
Diltiazem is well absorbed from the gastrointestinal tract but undergoes substantial hepatic first-pass effect.
▧ Protein binding :
70%-80%
▧ Metabolism :
Diltiazem is metabolized by and acts as an inhibitor of the CYP3A4 enzyme.
▧ Half Life :
3.0 - 4.5 hours
Độc Tính : LD50=740mg/kg (orally in mice)
Chỉ Định : For the treatment of Hypertension
Tương Tác Thuốc :
  • Amiodarone Increased risk of cardiotoxicity and arrhythmias
  • Amlodipine Diltiazem 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.
  • Aprepitant This CYP3A4 inhibitor increases the effect and toxicity of aprepitant
  • Atazanavir Atazanavir may increase the therapeutic and adverse effects of diltiazem resulting in increased risk of AV block. Consider alternate therapy, a 50% dose reduction of diltiazem and monitor for changes in the therapeutic and adverse effects of diltiazem if atazanavir is initiated, discontinued or dose changed.
  • Atenolol Increased risk of bradycardia
  • Atorvastatin Diltiazem may increase the serum concentration of atorvastatin. Atorvastatin may increase the serum concentration of diltiazem. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if doses are changed.
  • Bromazepam Diltiazem may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or a reductin in the bromazepam dose. Monitor for changes in the therapeutic and adverse effects of bromazepam if diltiazem is initiated, discontinued or dose changed.
  • Buspirone The calcium channel blocker, diltiazem, increases the effect and toxicity of buspirone.
  • Carbamazepine Carbamazepine may decrease the serum concentration of diltiazem by increasing its metabolism. Diltiazem may increase the serum concentration of carbamazepine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if dosages are changed.
  • Cerivastatin Diltiazem may increase the serum concentration of cerivastatin. Cerivastatin may increase the serum concentration of diltiazem. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if doses are changed.
  • Cilostazol Diltiazem, a moderate CYP3A4 inhibitor, may increase the serum concentration of cilostazol by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of cilostazol if diltiazem is initiated, discontinued or dose changed.
  • Cisapride Diltiazem, a moderate CYP3A4 inhibitor, may increase the serum concentration of cisapride by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of cisapride if diltiazem is initiated, discontinued or dose changed.
  • Cyclosporine Diltiazem may increase the effect and toxicity of cyclosporine.
  • Dihydroquinidine barbiturate Increases the effect and toxicity of quinidine
  • Dronedarone Diltiazem is a moderate CYP3A4 inhibitor and will increase dronedarone levels 1.4-1.7 fold. Decrease doses of non-dihyropyridinic calcium-channel blocker.
  • Eltrombopag Affects hepatic CYP1A2 metabolism, increases Eltrombopag level or affect.
  • Lovastatin Diltiazem may increase the serum concentration of lovastatin. Lovastatin may increase the serum concentration of diltiazem. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if doses are changed.
  • Mesoridazine Increased risk of cardiotoxicity and arrhythmias
  • Metoprolol Increased risk of bradycardia
  • Midazolam The calcium channel blocker, diltiazem, may increase the effect and toxicity of the benzodiazepine, midazolam.
  • Moricizine Increased effect/toxicity of moricizine
  • Pindolol Increased risk of bradycardia
  • Propranolol Increased risk of bradycardia
  • Quinidine Diltiazem may increase the serum concentration of quinidine. Monitor for changes in the therapeutic and adverse effects of quinidine if diltiazem is initiated, discontinued or dose changed.
  • Quinidine barbiturate Increases the effect and toxicity of quinidine
  • Quinupristin This combination presents an increased risk of toxicity
  • Ranolazine Diltiazem may increase the serum concentration of ranolazine. Consider alternate therapy or limit ranolazine dose to 500 mg twice daily and monitor for changes in the therapeutic and adverse effects if diltiazem is initiated, discontinued or dose changed.
  • Rifampicin Rifampin decreases levels of diltiazem
  • Ritonavir Ritonavir increases diltiazem levels
  • Saxagliptin Diltiazem is a moderate inhibitor of CYP3A4 and increases AUC of saxagliptin by 109%. Exposure of the active metabolite decreased by 34%. However, these changes in pharmacokinetics are not clinical significant.
  • Silodosin Moderate inhibitors of CYP3A4 may increase levels of silodosin. Monitor concomitant therapy closely.
  • Simvastatin Diltiazem may increase the serum concentration of simvastatin. Simvastatin may increase the serum concentration of diltiazem. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if doses are changed.
  • Sirolimus Increases the effect and toxicity of sirolimus
  • Tacrolimus Diltiazem may increase the serum concentration of tacrolimus by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of tacrolimus if diltiazem therapy is initiated, discontinued or dose changed.
  • Tamsulosin Diltiazem, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Diltiazem is initiated, discontinued, or dose changed.
  • Telithromycin Telithromycin may reduce clearance of Diltiazem. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Diltiazem if Telithromycin is initiated, discontinued or dose changed.
  • Terfenadine Increased risk of cardiotoxicity and arrhythmias
  • Thiopental The CYP3A4 inducer, Thiopental, may increase the metabolism and clearance of Diltiazem, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Diltiazem if Thiopental is initiated, discontinued or dose changed.
  • Thioridazine Increased risk of cardiotoxicity and arrhythmias
  • Timolol Additive effects of decreased heart rate and contractility may occur. Increased risk of heart block.
  • Tipranavir Tipranavir, co-administered with Ritonavir, may alter the concentration of Diltiazem. Monitor for efficacy and adverse/toxic effects of Diltiazem.
  • Tolterodine Diltiazem may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
  • Tolvaptan Diltiazem is a moderate inhibitor of CYP3A4 and will considerably increase tolvaptan serum concentrations
  • Tramadol Diltiazem may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
  • Trazodone The CYP3A4 inhibitor, Diltizem, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Diltiazem is initiated, discontinued or dose changed.
  • Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
  • Triazolam The calcium channel blocker, diltiazem, may increase the effect and toxicity of the benzodiazepine, triazolam.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of diltiazem by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of diltiazem if voriconazole is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Capsule, extended release - Oral
Liquid - Intravenous
Solution - Intravenous
Tablet - Oral
Tablet, extended release - Oral
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Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00343
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=39186
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505667
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06958
ChemSpider
http://www.chemspider.com/Chemical-Structure.35850.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50004704
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/54868-4970-0
PharmGKB
http://www.pharmgkb.org/drug/PA449334
Wikipedia
http://en.wikipedia.org/wiki/Diltiazem
RxList
http://www.rxlist.com/cgi/generic/diltiaz.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/car1068.shtml
Drugs.com
http://www.drugs.com/diltiazem.html
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