3-[(1S,4S)-bicyclo[2.2.1]hept-5-en-2-yl]-6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide

• ChemBase ID: 126826
• Molecular Formular: C14H16ClN3O4S2
• Molecular Mass: 389.87754
• Monoisotopic Mass: 389.02707569
• SMILES: O=S(=O)(c1c(Cl)cc2c(c1)S(=O)(=O)NC(N2)C1[C@@H]2C=C[C@@H](C2)C1)N
• Canonical SMILES: Clc1cc2NC(NS(=O)(=O)c2cc1S(=O)(=O)N)C1C[C@@H]2C[C@H]1C=C2
• InChI: InChI=1S/C14H16ClN3O4S2/c15-10-5-11-13(6-12(10)23(16,19)20)24(21,22)18-14(17-11)9-4-7-1-2-8(9)3-7/h1-2,5-9,14,17-18H,3-4H2,(H2,16,19,20)/t7-,8+,9?,14?/m0/s1
• InChIKey: BOCUKUHCLICSIY-QJWLJZLASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1S,4S)-bicyclo[2.2.1]hept-5-en-2-yl]-6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide
• IUPAC Traditional name: cyclothiazide
• Synonyms: Cyclothiazide; 6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-2H-1,2-4-benzothiadiazine-7-sulfonamide 1,1-dioxide; Cyclothiazide

Database IDs

• CAS Number: 2259-96-3
• EC Number: 218-859-7
• MDL Number: MFCD00210192
• PubChem SID: 24278350; 162221153
• PubChem CID: 5388988; 2910
• ATC CODE: C03AA09
• CHEMBL: 61593
• Chemspider ID: 4535011
• DrugBank ID: DB00606
• KEGG ID: D01256
• Unique Ingredient Identifier: P71U09G5BW
• Wikipedia Title: Cyclothiazide

CALCULATED PROPERTIES

• Acid pKa: 9.0615
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.94380784
• LogD (pH = 7.4): 0.93555397
• Log P: 0.9439139
• Molar Refractivity: 92.6485 cm^3
• Polarizability: 36.39785 Å^3
• Polar Surface Area: 118.36 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: DK9610000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Legal Status: Rx-only
• Gene Information: human ... CA1(759), CA4(762), GRIA1(2890), GRIA2(2891), GRIA3(2892), GRIA4(2893)rat ... Gria1(50592)

DETAILS

Sigma Aldrich - C9847

Biochem/physiol Actions
Blocks the rapid desensitization of the AMPA glutamate receptors and markedly prolongs the decay time of the evoked excitatory post-synaptic current.