Deacetyldiltiazem (CHEM035475)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:47:51 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035475
Identification
Common NameDeacetyldiltiazem
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DiltiazemHMDB
Deacetyldiltiazem, (cis)-isomerMeSH, HMDB
DesacetyldiltiazemMeSH, HMDB
Deacetyldiltiazem hydrochloride, (cis-(+-))-isomerMeSH, HMDB
Deacetyldiltiazem hydrochloride, (cis)-isomerMeSH, HMDB
Deacetyldiltiazem hydrochloride, (trans)-isomerMeSH, HMDB
DeacetyldiltiazemMeSH
Chemical FormulaC20H24N2O3S
Average Molecular Mass372.481 g/mol
Monoisotopic Mass372.151 g/mol
CAS Registry Number42399-40-6
IUPAC Name(2S,3S)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one
Traditional Namedesacetyldiltiazem
SMILESCOC1=CC=C(C=C1)[C@@H]1SC2=CC=CC=C2N(CCN(C)C)C(=O)[C@@H]1O
InChI IdentifierInChI=1S/C20H24N2O3S/c1-21(2)12-13-22-16-6-4-5-7-17(16)26-19(18(23)20(22)24)14-8-10-15(25-3)11-9-14/h4-11,18-19,23H,12-13H2,1-3H3/t18-,19+/m1/s1
InChI KeyNZHUXMZTSSZXSB-MOPGFXCFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzothiazepines. These are organic compounds containing a benzene fused to a thiazepine ring (a seven-membered ring with a nitrogen atom and a sulfur atom replacing two carbon atoms).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazepines
Sub ClassNot Available
Direct ParentBenzothiazepines
Alternative Parents
Substituents
  • Benzothiazepine
  • Phenol ether
  • Methoxybenzene
  • Anisole
  • Aryl thioether
  • Phenoxy compound
  • Alkyl aryl ether
  • Alkylarylthioether
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Thioether
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.31ALOGPS
logP2.29ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)12.33ChemAxon
pKa (Strongest Basic)8.18ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.01 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity105.21 m³·mol⁻¹ChemAxon
Polarizability39.29 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-6968000000-31d69e76cb441c8eb468Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9222300000-7e8a04693a2f019c8e3eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0309000000-4f78253225444d766ea1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-1900000000-1318fea4679c168e8d97Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-056s-0900000000-497dbcafd358c5226427Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0ufr-0900000000-007ed6981e6a7674cea3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00b9-0907000000-69fc05ea7be6f47f006bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-74bf9165b0dca218f517Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0900000000-13b286bd59bfa08ca3f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-0900000000-b831c8e8da4a17767b72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2109000000-4f4d8b04f6fb38782b6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-5933000000-444752d9e318a3bdc1f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-7900000000-727d8d2bd166506d75c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-f7c98d8fc7f115cdcf72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ht9-0439000000-399a4eb4aff7fe5b62f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-1930000000-637a90a35ba5c3d96664Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-7527d5f0c7e68d3bff36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-0198000000-ea4b553a352be3090135Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0536-0691000000-10d11ae35e2a14440fabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-5a8213501fca1b97c1f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-7209000000-9bcca83a828848518636Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5931000000-c443a5ed8d50f8d8e7e5Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002873
FooDB IDFDB023076
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID2271
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID82743
ChEBI IDNot Available
PubChem Compound ID91638
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
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2. Vivian EM, Goebig ML: Slowing the progression of renal disease in diabetic patients. Ann Pharmacother. 2001 Apr;35(4):452-63.
3. Gashti CN, Bakris GL: The role of calcium antagonists in chronic kidney disease. Curr Opin Nephrol Hypertens. 2004 Mar;13(2):155-61.
4. Shamim W, Bakhai A, Yousufuddin M, Coats AJ: Increased urinary cortisol and androgen metabolites in a young female with hypertension: partial glucocorticoid resistance syndrome. Cardiology. 2000;93(1-2):131-2.
5. Mousa O, Brater DC, Sunblad KJ, Hall SD: The interaction of diltiazem with simvastatin. Clin Pharmacol Ther. 2000 Mar;67(3):267-74.
6. Abadin JA, Duran JA, Perez de Leon JA: Probable diltiazem-induced acute interstitial nephritis. Ann Pharmacother. 1998 Jun;32(6):656-8.
7. Mies S, Massarollo PC, Figueira ER, Leitao RM, Raia S: Lower incidence of liver graft rejection in patients on diltiazem plus cyclosporine therapy. Transplant Proc. 1998 Jun;30(4):1437-8.
8. Kawano Y, Makino Y, Okuda N, Takishita S, Omae T: Effects of diltiazem retard on ambulatory blood pressure and heart rate variability in patients with essential hypertension. Blood Press Monit. 2000 Jun;5(3):181-5.
9. Zhao XJ, Jones DR, Wang YH, Grimm SW, Hall SD: Reversible and irreversible inhibition of CYP3A enzymes by tamoxifen and metabolites. Xenobiotica. 2002 Oct;32(10):863-78.
10. Zucker ML, Budd SE, Dollar LE, Chernoff SB, Altman R: Effect of diltiazem and low-dose aspirin on platelet aggregation and ATP release induced by paired agonists. Thromb Haemost. 1993 Aug 2;70(2):332-5.
11. Zhang XL, Xu B, Feng Y: Effects of diltiazem on down-regulation of lymphocyte beta-adrenoceptors in patients with chronic congestive heart failure. Acta Pharmacol Sin. 2000 Oct;21(10):927-30.
12. Fukuoka Y, Tachibana T, Yasui A: Anaphylatoxin C3a induces rapid protein phosphorylation in guinea pig platelets. Immunopharmacology. 1994 Sep-Oct;28(2):95-104.
13. Dimmitt DC, Bhargava VO, Arumugham T, Eller M, Weir SJ: Relative bioavailability of Cardizem CD and Tiazac controlled-release diltiazem dosage forms after single and multiple dosing in healthy volunteers. Am J Ther. 1998 May;5(3):173-9.
14. Sperschneider H, Wagner C, Korn A, Christians U: [Effect of diltiazem on concentration of cyclosporin metabolites in Sandimmune and Neoral treated kidney transplant patients]. Med Klin (Munich). 1997 Oct 15;92(10):589-96.
15. Morimoto Y, Kemmotsu O, Gando S, Shibano T, Shikama H: The effect of calcium channel blockers on cerebral oxygenation during tracheal extubation. Anesth Analg. 2000 Aug;91(2):347-52.
16. Mayhew BS, Jones DR, Hall SD: An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation. Drug Metab Dispos. 2000 Sep;28(9):1031-7.
17. Odawara A, Kikkawa K, Katoh M, Toryu H, Shimazaki T, Sasaki Y: Inhibitory effects of TA-993, a new 1,5-benzothiazepine derivative, on platelet aggregation. Circ Res. 1996 Apr;78(4):643-9.
18. Jones TE, Morris RG: Pharmacokinetic interaction between tacrolimus and diltiazem: dose-response relationship in kidney and liver transplant recipients. Clin Pharmacokinet. 2002;41(5):381-8.
19. Tateishi T, Ohashi K, Fujimura A, Ebihara A: The influence of diltiazem versus cimetidine on propranolol metabolism. J Clin Pharmacol. 1992 Dec;32(12):1099-104.
20. Roth M, Eickelberg O, Kohler E, Erne P, Block LH: Ca2+ channel blockers modulate metabolism of collagens within the extracellular matrix. Proc Natl Acad Sci U S A. 1996 May 28;93(11):5478-82.
21. Du Souich P, Lery N, Lery L, Varin F, Boucher S, Vezina M, Pilon D, Spenard J, Caille G: Influence of food on the bioavailability of diltiazem and two of its metabolites following the administration of conventional tablets and slow-release capsules. Biopharm Drug Dispos. 1990 Mar;11(2):137-47.
22. Shibata N, Morita K, Ono T, Nishikawa S, Kinoshita M, Kawakita S, Takada K, Muranishi S, Shimakawa H: Effects of diltiazem on rheological properties of human blood. J Pharmacobiodyn. 1988 Mar;11(3):175-80.