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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:11 UTC
HMDB IDHMDB0014702
Secondary Accession Numbers
  • HMDB14702
Metabolite Identification
Common NameBenzthiazide
DescriptionBenzthiazide is used to treat hypertension and edema. Like other thiazides, benzthiazide promotes water loss from the body (diuretics). They inhibit Na+/Cl- reabsorption from the distal convoluted tubules in the kidneys. Thiazides also cause loss of potassium and an increase in serum uric acid. Thiazides are often used to treat hypertension, but their hypotensive effects are not necessarily due to their diuretic activity. Thiazides have been shown to prevent hypertension-related morbidity and mortality although the mechanism is not fully understood. Thiazides cause vasodilation by activating calcium-activated potassium channels (large conductance) in vascular smooth muscles and inhibiting various carbonic anhydrases in vascular tissue.
Structure
Data?1582753211
Synonyms
ValueSource
3-((Benzylthio)methyl)-6-chloro-7-sulfamoyl-2H-benzo-1,2,4-thiadiazine 1,1-dioxideChEBI
3-Benzylthiomethyl-6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxideChEBI
3-Benzylthiomethyl-6-chloro-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxideChEBI
6-Chloro-1,1-dioxo-3-(phenylmethylsulfanylmethyl)-4H-benzo[e][1,2,4]thiadiazine-7-sulfonamideChEBI
6-Chloro-7-sulfamoyl-3-benzylthiomethyl-2H-1,2,4-benzothiadiazine 1,1-dioxideChEBI
BenzothiazideChEBI
BenzotiazidaChEBI
BenzthiazidumChEBI
ExnaKegg
3-((Benzylthio)methyl)-6-chloro-7-sulphamoyl-2H-benzo-1,2,4-thiadiazine 1,1-dioxideGenerator
3-Benzylthiomethyl-6-chloro-2H-1,2,4-benzothiadiazine-7-sulphonamide 1,1-dioxideGenerator
3-Benzylthiomethyl-6-chloro-7-sulphamoyl-1,2,4-benzothiadiazine 1,1-dioxideGenerator
6-Chloro-1,1-dioxo-3-(phenylmethylsulphanylmethyl)-4H-benzo[e][1,2,4]thiadiazine-7-sulphonamideGenerator
6-Chloro-7-sulphamoyl-3-benzylthiomethyl-2H-1,2,4-benzothiadiazine 1,1-dioxideGenerator
Chemical FormulaC15H14ClN3O4S3
Average Molecular Weight431.937
Monoisotopic Molecular Weight430.983495728
IUPAC Name3-[(benzylsulfanyl)methyl]-6-chloro-1,1-dioxo-4H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide
Traditional Nameregulon
CAS Registry Number91-33-8
SMILES
NS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C1
InChI Identifier
InChI=1S/C15H14ClN3O4S3/c16-11-6-12-14(7-13(11)25(17,20)21)26(22,23)19-15(18-12)9-24-8-10-4-2-1-3-5-10/h1-7H,8-9H2,(H,18,19)(H2,17,20,21)
InChI KeyNDTSRXAMMQDVSW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2,4-benzothiadiazine-1,1-dioxides. These are aromatic heterocyclic compounds containing a 1,2,4-benzothiadiazine ring system with two S=O bonds at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiadiazines
Sub ClassBenzothiadiazines
Direct Parent1,2,4-benzothiadiazine-1,1-dioxides
Alternative Parents
Substituents
  • 1,2,4-benzothiadiazine-1,1-dioxide
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Organosulfonic acid amide
  • Imidolactam
  • Benzenoid
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Amidine
  • Azacycle
  • Dialkylthioether
  • Thioether
  • Sulfenyl compound
  • Organic oxide
  • Organosulfur compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point231.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 g/LNot Available
LogP1.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available186.734http://allccs.zhulab.cn/database/detail?ID=AllCCS00000947
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP10(2.26) g/LALOGPS
logP10(1.84) g/LChemAxon
logS10(-4.5) g/LALOGPS
pKa (Strongest Acidic)8.77ChemAxon
pKa (Strongest Basic)1.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area118.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity104.14 m³·mol⁻¹ChemAxon
Polarizability41.5 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzthiazideNS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C15555.8Standard polar33892256
BenzthiazideNS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C13217.4Standard non polar33892256
BenzthiazideNS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C14386.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzthiazide,1TMS,isomer #1C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O3753.7Semi standard non polar33892256
Benzthiazide,1TMS,isomer #1C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O3694.3Standard non polar33892256
Benzthiazide,1TMS,isomer #1C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O5348.8Standard polar33892256
Benzthiazide,1TMS,isomer #2C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C213665.9Semi standard non polar33892256
Benzthiazide,1TMS,isomer #2C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C213891.5Standard non polar33892256
Benzthiazide,1TMS,isomer #2C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C215703.4Standard polar33892256
Benzthiazide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O3594.3Semi standard non polar33892256
Benzthiazide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O3900.3Standard non polar33892256
Benzthiazide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O5234.4Standard polar33892256
Benzthiazide,2TMS,isomer #2C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O3625.0Semi standard non polar33892256
Benzthiazide,2TMS,isomer #2C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O3870.5Standard non polar33892256
Benzthiazide,2TMS,isomer #2C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O4992.0Standard polar33892256
Benzthiazide,3TMS,isomer #1C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C213584.3Semi standard non polar33892256
Benzthiazide,3TMS,isomer #1C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C214222.7Standard non polar33892256
Benzthiazide,3TMS,isomer #1C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C215008.7Standard polar33892256
Benzthiazide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O3967.3Semi standard non polar33892256
Benzthiazide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O3970.4Standard non polar33892256
Benzthiazide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O5323.3Standard polar33892256
Benzthiazide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C213956.3Semi standard non polar33892256
Benzthiazide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C214157.2Standard non polar33892256
Benzthiazide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C215684.8Standard polar33892256
Benzthiazide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O4107.0Semi standard non polar33892256
Benzthiazide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O4422.2Standard non polar33892256
Benzthiazide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O5195.8Standard polar33892256
Benzthiazide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O4072.4Semi standard non polar33892256
Benzthiazide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O4384.7Standard non polar33892256
Benzthiazide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O4936.3Standard polar33892256
Benzthiazide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C214247.2Semi standard non polar33892256
Benzthiazide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C215017.0Standard non polar33892256
Benzthiazide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C214951.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzthiazide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9242000000-15561d025e3aa0c753082017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzthiazide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-06r6-9624000000-532194fb14045a87f8de2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 10V, Positive-QTOFsplash10-001l-6202900000-2a70b9803c4b86c5dd1f2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 20V, Positive-QTOFsplash10-00ko-9567100000-99dca328e8d7361a3afc2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 40V, Positive-QTOFsplash10-01vo-9551000000-d1e207308294a5deee082016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 10V, Negative-QTOFsplash10-0iki-2069300000-96a7d5e7dc1269a420442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 20V, Negative-QTOFsplash10-004r-9128100000-4954efc1704bdde450092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 40V, Negative-QTOFsplash10-004i-9010000000-d24b3facbec316c46e122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 10V, Negative-QTOFsplash10-0a4i-0009000000-ef28da9b71b01c96fb7a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 20V, Negative-QTOFsplash10-0a4i-0009000000-8007d10d85565090d5492021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 40V, Negative-QTOFsplash10-0fb9-9520000000-542b3b8a75568a776f6a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 10V, Positive-QTOFsplash10-001i-0001900000-e655f017360118b76da12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 20V, Positive-QTOFsplash10-001i-3101900000-f89180b83227d57566b22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzthiazide 40V, Positive-QTOFsplash10-0006-9000000000-688382bcfe309825184b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00562 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00562 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00562
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2253
KEGG Compound IDC07759
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzthiazide
METLIN IDNot Available
PubChem Compound2343
PDB IDNot Available
ChEBI ID3047
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular weight:
28870.0
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 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular weight:
29245.895
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide.
Gene Name:
CA12
Uniprot ID:
O43570
Molecular weight:
39450.615
References
  1. Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [PubMed:19119014 ]
General function:
Involved in transport
Specific function:
Electrically silent transporter system. Mediates sodium and chloride reabsorption
Gene Name:
SLC12A3
Uniprot ID:
P55017
Molecular weight:
113124.0
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 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:
CA4
Uniprot ID:
P22748
Molecular weight:
35032.075
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 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.
Gene Name:
CA9
Uniprot ID:
Q16790
Molecular weight:
49697.36
References
  1. Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [PubMed:19119014 ]