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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

enzymes (4)transporters (1) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0015018

Secondary Accession Numbers

HMDB15018

Metabolite Identification

Common Name

Chlorothiazide

Description

Chlorothiazide is only found in individuals that have used or taken this drug. It is a thiazide diuretic with actions and uses similar to those of hydrochlorothiazide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p812)As a diuretic, chlorothiazide inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Thiazides like chlorothiazide also inhibit sodium ion transport across the renal tubular epithelium through binding to the thiazide sensitive sodium-chloride transporter. This results in an increase in potassium excretion via the sodium-potassium exchange mechanism. The antihypertensive mechanism of chlorothiazide is less well understood although it may be mediated through its action on carbonic anhydrases in the smooth muscle or through its action on the large-conductance calcium-activated potassium (KCa) channel, also found in the smooth muscle.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

880
  Mrv0541 02231215042D          

 17 18  0  0  0  0            999 V2000
    2.8075    1.0170    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6885   -0.6617    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.6330    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0927   -1.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2677   -1.3713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -1.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950    0.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885    1.0456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360   -0.2377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.0455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    0.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  9  1  0  0  0  0
  2 11  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  2  0  0  0  0
  3 10  1  0  0  0  0
  3 13  1  0  0  0  0
  8 12  1  0  0  0  0
  8 17  1  0  0  0  0
  9 17  2  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  2  0  0  0  0
 13 14  1  0  0  0  0
 13 16  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015018

> <DATABASE_NAME>
hmdb

> <SMILES>
NS(=O)(=O)C1=C(Cl)C=C2NC=NS(=O)(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H6ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-3H,(H,10,11)(H2,9,12,13)

> <INCHI_KEY>
JBMKAUGHUNFTOL-UHFFFAOYSA-N

> <FORMULA>
C7H6ClN3O4S2

> <MOLECULAR_WEIGHT>
295.723

> <EXACT_MASS>
294.948824782

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
24.546188424740766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-chloro-1,1-dioxo-4H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
-0.4421814846666665

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.11570362862818

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.103103082740821

> <JCHEM_PKA_STRONGEST_BASIC>
1.1482800428358007

> <JCHEM_POLAR_SURFACE_AREA>
118.69

> <JCHEM_REFRACTIVITY>
62.508200000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
microzide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 880                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       5.241   1.898   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      10.619  -1.235   0.000  0.00  0.00           S+0
HETATM    3  S   UNK     0       5.241  -1.182   0.000  0.00  0.00           S+0
HETATM    4  O   UNK     0      11.373  -2.577   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.833  -2.560   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       6.011  -2.515   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.471   0.152   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      10.619   1.952   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      12.014  -0.444   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       3.907  -1.952   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       9.242  -0.412   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.242   1.128   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -0.412   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908  -1.182   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908   1.898   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574   1.128   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.014   1.161   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2    4    5    9   11                                             
CONECT    3    6    7   10   13                                             
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8   12   17                                                       
CONECT    9    2   17                                                       
CONECT   10    3                                                            
CONECT   11    2   12   14                                                  
CONECT   12    8   11   15                                                  
CONECT   13    3   14   16                                                  
CONECT   14   11   13                                                       
CONECT   15   12   16                                                       
CONECT   16    1   13   15                                                  
CONECT   17    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-Chloro-1,1-dioxo-1,2-dihydro-1lambda6-benzo[1,2,4]thiadiazine-7-sulfonic acid amide	ChEBI
6-Chloro-7-sulfamoyl-2H-1,2,4-benzothiadiazine 1,1-dioxide	ChEBI
Chlorothiazidum	ChEBI
Clorotiazida	ChEBI
Diuril	Kegg
6-Chloro-1,1-dioxo-1,2-dihydro-1lambda6-benzo[1,2,4]thiadiazine-7-sulfonate amide	Generator
6-Chloro-1,1-dioxo-1,2-dihydro-1lambda6-benzo[1,2,4]thiadiazine-7-sulphonate amide	Generator
6-Chloro-1,1-dioxo-1,2-dihydro-1lambda6-benzo[1,2,4]thiadiazine-7-sulphonic acid amide	Generator
6-Chloro-7-sulphamoyl-2H-1,2,4-benzothiadiazine 1,1-dioxide	Generator
Chlorothiazid	HMDB
Chlorthiazide	HMDB
Chlortiazid	HMDB

Chemical Formula

C₇H₆ClN₃O₄S₂

Average Molecular Weight

295.723

Monoisotopic Molecular Weight

294.948824782

IUPAC Name

6-chloro-1,1-dioxo-4H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide

Traditional Name

microzide

CAS Registry Number

58-94-6

SMILES

NS(=O)(=O)C1=C(Cl)C=C2NC=NS(=O)(=O)C2=C1

InChI Identifier

InChI=1S/C7H6ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-3H,(H,10,11)(H2,9,12,13)

InChI Key

JBMKAUGHUNFTOL-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thiadiazines

Sub Class

Benzothiadiazines

Direct Parent

1,2,4-benzothiadiazine-1,1-dioxides

Alternative Parents

Substituents

1,2,4-benzothiadiazine-1,1-dioxide
Aryl chloride
Aryl halide
Organosulfonic acid amide
Benzenoid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Propargyl-type 1,3-dipolar organic compound
Formamidine
Amidine
Organic 1,3-dipolar compound
Azacycle
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organosulfur compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzothiadiazine (CHEBI:3640 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015018)
Membrane (HMDB: HMDB0015018)

Source

Exogenous

Exogenous (HMDB: HMDB0015018)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Chlorothiazide Action Pathway (PathBank: SMP0000078)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	350 °C	Not Available
Boiling Point	608.77 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.4 g/L	Not Available
LogP	-0.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	161.037	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000969

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	0.41	ALOGPS
logP	-0.44	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	1.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	118.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	62.51 m³·mol⁻¹	ChemAxon
Polarizability	24.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	152.684	30932474
DeepCCS	[M-H]-	150.326	30932474
DeepCCS	[M-2H]-	183.485	30932474
DeepCCS	[M+Na]+	158.777	30932474
AllCCS	[M+H]+	160.0	32859911
AllCCS	[M+H-H2O]+	156.5	32859911
AllCCS	[M+NH4]+	163.3	32859911
AllCCS	[M+Na]+	164.2	32859911
AllCCS	[M-H]-	149.0	32859911
AllCCS	[M+Na-2H]-	149.0	32859911
AllCCS	[M+HCOO]-	149.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.34 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9014 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.97 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	52.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1121.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	329.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	76.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	60.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	270.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	352.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	627.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	747.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	165.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	978.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	239.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	577.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	336.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	359.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorothiazide	NS(=O)(=O)C1=C(Cl)C=C2NC=NS(=O)(=O)C2=C1	4042.4	Standard polar	33892256
Chlorothiazide	NS(=O)(=O)C1=C(Cl)C=C2NC=NS(=O)(=O)C2=C1	2686.6	Standard non polar	33892256
Chlorothiazide	NS(=O)(=O)C1=C(Cl)C=C2NC=NS(=O)(=O)C2=C1	3254.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chlorothiazide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	2806.1	Semi standard non polar	33892256
Chlorothiazide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	2738.9	Standard non polar	33892256
Chlorothiazide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	4170.7	Standard polar	33892256
Chlorothiazide,1TMS,isomer #2	C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	2765.1	Semi standard non polar	33892256
Chlorothiazide,1TMS,isomer #2	C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	2977.5	Standard non polar	33892256
Chlorothiazide,1TMS,isomer #2	C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	4277.9	Standard polar	33892256
Chlorothiazide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	2697.6	Semi standard non polar	33892256
Chlorothiazide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	2907.5	Standard non polar	33892256
Chlorothiazide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	4114.0	Standard polar	33892256
Chlorothiazide,2TMS,isomer #2	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=NS2(=O)=O	2763.8	Semi standard non polar	33892256
Chlorothiazide,2TMS,isomer #2	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=NS2(=O)=O	2971.6	Standard non polar	33892256
Chlorothiazide,2TMS,isomer #2	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=NS2(=O)=O	3751.4	Standard polar	33892256
Chlorothiazide,3TMS,isomer #1	C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C21	2712.9	Semi standard non polar	33892256
Chlorothiazide,3TMS,isomer #1	C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C21	3299.3	Standard non polar	33892256
Chlorothiazide,3TMS,isomer #1	C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C21	3829.4	Standard polar	33892256
Chlorothiazide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	3064.3	Semi standard non polar	33892256
Chlorothiazide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	2995.4	Standard non polar	33892256
Chlorothiazide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	4224.8	Standard polar	33892256
Chlorothiazide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	3051.4	Semi standard non polar	33892256
Chlorothiazide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	3229.7	Standard non polar	33892256
Chlorothiazide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	4460.4	Standard polar	33892256
Chlorothiazide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	3205.8	Semi standard non polar	33892256
Chlorothiazide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	3398.8	Standard non polar	33892256
Chlorothiazide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O	4127.4	Standard polar	33892256
Chlorothiazide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=NS2(=O)=O	3226.1	Semi standard non polar	33892256
Chlorothiazide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=NS2(=O)=O	3416.2	Standard non polar	33892256
Chlorothiazide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=NS2(=O)=O	3853.5	Standard polar	33892256
Chlorothiazide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=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=C21	3436.7	Semi standard non polar	33892256
Chlorothiazide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=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=C21	4034.0	Standard non polar	33892256
Chlorothiazide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=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=C21	3936.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorothiazide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fvi-3390000000-4907b28333e017912f33	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorothiazide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF	splash10-0006-0090000000-e74dd6446e0284a7f0aa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF	splash10-0006-0090000000-baf93e639a13c39dc1d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF	splash10-01ox-0090000000-473477518be3f6c8ddcd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF	splash10-03di-0290000000-0e599c26917ade291ca0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF	splash10-03di-0890000000-ad270ef1247ce9a114ad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF	splash10-004i-0920000000-3c4bb920bb8316022718	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF	splash10-004i-2900000000-eca13dbca70054de3470	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF	splash10-02vr-9700000000-9261e1bf4e212aee7d84	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF	splash10-0i09-9100000000-491baf01fc6ef9ca39e1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF	splash10-0002-0090000000-388cb4ff11dc0a41ad99	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF	splash10-002b-0090000000-5645eee512f78cd689a7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF	splash10-0udi-0390000000-a39ffe78224ed4cacc13	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF	splash10-0pbl-0920000000-eb979e3c4ecd1f12fb71	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF	splash10-059f-2900000000-4c2eb27958fba0102431	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF	splash10-05tk-5900000000-b42b446bc2b9f6216af1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF	splash10-00kk-9400000000-b4b975e3c1fabe09f4a7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF	splash10-03di-9100000000-f8f80586b12a43c2a667	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF	splash10-03di-9000000000-9d41a0f061f998097c17	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorothiazide 60V, Negative-QTOF	splash10-03di-0190000000-b4aa6830cd5272c0d44b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorothiazide 10V, Positive-QTOF	splash10-0002-0090000000-6500ac39cf672b42f75d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorothiazide 20V, Positive-QTOF	splash10-014i-0090000000-80ebd93be346579a63b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorothiazide 40V, Positive-QTOF	splash10-0uxr-0790000000-2156a2679d57dbda9635	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorothiazide 10V, Negative-QTOF	splash10-0006-0090000000-d2924827db1564ab2598	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorothiazide 20V, Negative-QTOF	splash10-0006-1090000000-5218745f5848fdcbeb08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorothiazide 40V, Negative-QTOF	splash10-004i-9020000000-8cc5eabcbcc35fa29dbc	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Chlorothiazide Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00880	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00880	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00880

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2619

KEGG Compound ID

C07461

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorothiazide

METLIN ID

Not Available

PubChem Compound

2720

PDB ID

Not Available

ChEBI ID

3640

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1309071

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Carbonic anhydrase 1

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

Puscas I, Coltau M, Baican M, Domuta G, Hecht A: Vasodilatory effect of diuretics is dependent on inhibition of vascular smooth muscle carbonic anhydrase by a direct mechanism of action. Drugs Exp Clin Res. 1999;25(6):271-9. [PubMed:10713865 ]
Puscas I, Coltau M, Baican M, Pasca R, Domuta G: The inhibitory effect of diuretics on carbonic anhydrases. Res Commun Mol Pathol Pharmacol. 1999;105(3):213-36. [PubMed:10954127 ]

Enzyme Details

2. Carbonic anhydrase 2

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

Weiner ID, Verlander JW: Renal and hepatic expression of the ammonium transporter proteins, Rh B Glycoprotein and Rh C Glycoprotein. Acta Physiol Scand. 2003 Dec;179(4):331-8. [PubMed:14656370 ]
Puscas I, Coltau M, Baican M, Pasca R, Domuta G: The inhibitory effect of diuretics on carbonic anhydrases. Res Commun Mol Pathol Pharmacol. 1999;105(3):213-36. [PubMed:10954127 ]
Verlander JW, Miller RT, Frank AE, Royaux IE, Kim YH, Weiner ID: Localization of the ammonium transporter proteins RhBG and RhCG in mouse kidney. Am J Physiol Renal Physiol. 2003 Feb;284(2):F323-37. Epub 2002 Oct 8. [PubMed:12388412 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Solute carrier family 12 member 3

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

Thakker RV: Molecular pathology of renal chloride channels in Dent's disease and Bartter's syndrome. Exp Nephrol. 2000 Nov-Dec;8(6):351-60. [PubMed:11014932 ]
Schmidt H, Kabesch M, Schwarz HP, Kiess W: Clinical, biochemical and molecular genetic data in five children with Gitelman's syndrome. Horm Metab Res. 2001 Jun;33(6):354-7. [PubMed:11456284 ]
Wilson FH, Kahle KT, Sabath E, Lalioti MD, Rapson AK, Hoover RS, Hebert SC, Gamba G, Lifton RP: Molecular pathogenesis of inherited hypertension with hyperkalemia: the Na-Cl cotransporter is inhibited by wild-type but not mutant WNK4. Proc Natl Acad Sci U S A. 2003 Jan 21;100(2):680-4. Epub 2003 Jan 6. [PubMed:12515852 ]
Maki N, Komatsuda A, Wakui H, Ohtani H, Kigawa A, Aiba N, Hamai K, Motegi M, Yamaguchi A, Imai H, Sawada K: Four novel mutations in the thiazide-sensitive Na-Cl co-transporter gene in Japanese patients with Gitelman's syndrome. Nephrol Dial Transplant. 2004 Jul;19(7):1761-6. Epub 2004 Apr 6. [PubMed:15069170 ]
Reinalter SC, Jeck N, Peters M, Seyberth HW: Pharmacotyping of hypokalaemic salt-losing tubular disorders. Acta Physiol Scand. 2004 Aug;181(4):513-21. [PubMed:15283765 ]

Enzyme Details

4. Carbonic anhydrase 4

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

Puscas I, Coltau M, Baican M, Domuta G, Hecht A: Vasodilatory effect of diuretics is dependent on inhibition of vascular smooth muscle carbonic anhydrase by a direct mechanism of action. Drugs Exp Clin Res. 1999;25(6):271-9. [PubMed:10713865 ]
Puscas I, Coltau M, Baican M, Pasca R, Domuta G: The inhibitory effect of diuretics on carbonic anhydrases. Res Commun Mol Pathol Pharmacol. 1999;105(3):213-36. [PubMed:10954127 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Uwai Y, Saito H, Hashimoto Y, Inui KI: Interaction and transport of thiazide diuretics, loop diuretics, and acetazolamide via rat renal organic anion transporter rOAT1. J Pharmacol Exp Ther. 2000 Oct;295(1):261-5. [PubMed:10991988 ]

Showing metabocard for Chlorothiazide (HMDB0015018)

MOL for HMDB0015018 (Chlorothiazide)

3D MOL for HMDB0015018 (Chlorothiazide)

3D SDF for HMDB0015018 (Chlorothiazide)

3D-SDF for HMDB0015018 (Chlorothiazide)

PDB for HMDB0015018 (Chlorothiazide)

3D PDB for HMDB0015018 (Chlorothiazide)

SMILES for HMDB0015018 (Chlorothiazide)

INCHI for HMDB0015018 (Chlorothiazide)

Structure for HMDB0015018 (Chlorothiazide)

3D Structure for HMDB0015018 (Chlorothiazide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

Transporters

References