Tizanidine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Tizanidine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Tizanidine?

The molecule Tizanidine presents a molecular formula of C9H8ClN5S and its IUPAC name is 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine.

Tizanidine is a medication that is used to treat spasticity, or muscle stiffness and tightness, by temporarily relaxing muscle tone. It is a centrally acting α2-adrenergic agonist that was originally developed as a treatment for hypertension (high blood pressure). However, it was found to be more effective at treating spasticity. It exists as a generic medication and is sold under the brand names Zanaflex and Sirdalud..

Tizanidine is structurally similar to clonidine, another medication used to treat hypertension. However, tizanidine is more selective for the α2-adrenergic receptor subtype, which is responsible for its spasmolytic (anti-spasmodic) effect. Tizanidine is thought to work by reducing excitatory neurotransmitter release from neurons in the spinal cord. This results in a decrease in muscle tone and spasticity..

The most common side effects of tizanidine include dry mouth, drowsiness, dizziness, and weakness. Tizanidine can also cause low blood pressure and should be used with caution in patients with cardiovascular disease. It is important to let your doctor know if you are taking any other medications, as tizanidine can interact with a number of other drugs..

Tizanidine is generally well-tolerated and is an effective treatment for spasticity. If you are experiencing muscle stiffness and tightness, talk to your doctor about whether tizanidine may be right for you..

3D structure

Cartesian coordinates

Geometry of Tizanidine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Tizanidine XFYDIVBRZNQMJC-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Tizanidine

 

Molecule descriptors

 
IUPAC name5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine
InChI codeInChI=1S/C9H8ClN5S/c10-5-1-2-6-8(15-16-14-6)7(5)13-9-11-3-4-12-9/h1-2H,3-4H2,(H2,11,12,13)
InChI KeyXFYDIVBRZNQMJC-UHFFFAOYSA-N
SMILESClc1ccc2nsnc2c1N=C1NCCN1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (5-Chloro-benzo[1,2,5]thiadiazol-4-yl)-(4,5-dihydro-1H-imidazol-2-yl)-amine
  • 2,1,3-Benzothiadiazol-4-amine, 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-
  • 2,1,3-Benzothiadiazole, 5-chloro-4-(2-imidazolin-2-ylamino)-
  • 2,1,3-Benzothiadiazole-4-amine, 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-
  • 322T759
  • 4-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-8-thia-7,9-diazabicyclo(4.3.0)nona-2,4,6,9-tetraen-5-amine
  • 5-Chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole
  • 5-Chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-benzo[c][1,2,5]thiadiazol-4-amine
  • 5-chloro-4-(2-imidazolin-2-ylamino)benzo-2,1,3-thiadiazole
  • 5-chloro-4-(2-imidazolin-4-on-2-ylamino)-2,1,3-benzothiadiazole
  • 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine
  • 51322-75-9
  • 6AI06C00GW
  • A828535
  • AB00698468-04
  • AB00698468-06
  • AB00698468_07
  • BCP12884
  • BDBM50240671
  • BIDD:GT0580
  • BRN 0618691
  • C07452
  • CCG-266992
  • D08611
  • DB-051946
  • DB00697
  • DSSTox_CID_3679
  • DSSTox_GSID_23679
  • DSSTox_RID_77143
  • F20799
  • FT-0639985
  • GTPL7308
  • HMS2089B03
  • HMS3743M03
  • HMS3886K10
  • HY-B0194
  • L001084
  • MFCD00865192
  • MLS006011763
  • N-(5-Chloro-2,1,3-benzothiadiazol-4-yl)-N-(4,5-dihydro-1H-imidazol-2-yl)amine #
  • NCGC00160529-01
  • NCGC00160529-02
  • NCGC00160529-03
  • NCGC00160529-04
  • NCGC00160529-05
  • NCGC00160529-06
  • NCGC00160529-14
  • Q423538
  • SDCCGSBI-0633792.P001
  • SMR000857268
  • SR-01000765392
  • SR-01000765392-2
  • STK711168
  • Sirdalud
  • Ternelin
  • Tizanidina
  • Tizanidine
  • Tizanidine (INN)
  • Tizanidinum
  • Zanaflex
  • s5537
  • tizanidine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC19702309
  • CAS-51322-75-9
  • UNII-6AI06C00GW
  • AKOS005530682
  • BRD-K06335600-003-16-5
  • DTXSID9023679
  • CHEMBL1079
  • CHEBI:63629
  • Tox21_111876
  • Tox21_111876_1
  • SCHEMBL60334

Physico-Chemical properties

IUPAC name5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine
Molecular formulaC9H8ClN5S
Molecular weight253.711
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity72.57
LogP2.2
Topological polar surface area90.4

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.