Daltroban
Basic information
- CAS
79094-20-5- Standard SMILES
O=C(O)Cc1ccc(CCNS(=O)(=O)c2ccc(Cl)cc2)cc1- InChIKey
IULOBWFWYDMECP-UHFFFAOYSA-N- Molecular formula
- C16H16ClNO4S
- Average molar mass
- 353.8 g/mol
- Monoisotopic mass
- 353.04885667
Overview
Daltroban is a small molecule drug. Daltroban has a monoisotopic molecular weight of 353.05 Da.
Names & identifiers
- Preferred name
- Daltroban
- IUPAC
- 2-[4-[2-[(4-chlorophenyl)sulfonylamino]ethyl]phenyl]acetic acid
- English name
- Daltroban
- Molecular formula
- C16H16ClNO4S
- Molecular weight
- 353.82
Names & synonyms
DALTROBAN79094-20-5BM-13505DaltrobanumSKF-96148SKF 961482-[4-[2-[(4-chlorophenyl)sulfonylamino]ethyl]phenyl]acetic acidBM 13.505SK&F 96148DTXSID6046501S25VDY08ZCSKF96148
Show more names
Daltroban USP/EP/BPDatelliptiumChlorideDaltroban >98% (HPLC)Daltroban, 10 mM in DMSO4-[2-(4-Chlorobenzene-sulfonamido)ethyl]benzeneacetic acid4-[2-[(4-CHLOROPHENYLSULFONYL)AMINO]ETHYL]BENZENEACETIC ACID2-[4-[2-(4-chlorophenyl)sulfonylaminoethyl]phenyl]acetic acid
BM13505DTXCID40265012-(4-(2-((4-chlorophenyl)sulfonylamino)ethyl)phenyl)acetic acid4-(2-(4-Chlorophenylsulfonylamino)ethyl)phenylacetic acid4-(2-(4-Chlorobenzenesulfonylamino)ethyl)benzeneacetic acidRefChem:585160635-983-0BM 13505
Database identifiers
- CAS
79094-20-5- PubChem CID
- 54343
- DTXSID
DTXSID6046501- ChEMBL
CHEMBL71685- UNII
- S25VDY08ZC
- EC Number
- 635-983-0
- Nikkaji
- J153.943D
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 91.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 7
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 475
Physicochemical properties
- Melting point
- 132.5 · 132.5-137.4 °C(lit.)
- Boiling point
- 555.3 · 555.3±60.0 °C(Predicted)
- Density
- 1.378 · 1.378±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 22 mg/mL, · DMSO: 22 mg/mL, soluble
- pka
- 4.33 · 4.33±0.10(Predicted)
- form
- A solid
- color
- white
- InChI
- InChI=1S/C16H16ClNO4S/c17-14-5-7-15(8-6-14)23(21,22)18-10-9-12-1-3-13(4-2-12)11-16(19)20/h1-8,18H,9-11H2,(H,19,20)
- InChIKey
- IULOBWFWYDMECP-UHFFFAOYSA-N
- SMILES
- C1(CC(O)=O)=CC=C(CCNS(C2=CC=C(Cl)C=C2)(=O)=O)C=C1
- CAS DataBase Reference
- 79094 · 79094-20-5(CAS DataBase Reference)
- FDA UNII
- 25 VDY08ZC · S25VDY08ZC
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36/37
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
Applications
DescriptionDaltroban (BM 13505, SKF 96148), a specific thromboxane A2 receptor antagonist, was studied as an antithrombotic agent. Daltroban increases intracellular calcium in vascular smooth muscle cells. Daltroban shows a protective effect in reperfusion injury. The drug was licensed to Smith Kline Beecham and underwent phase III clinical trials in the UK and Germany as an antithrombotic agent but did not enter clinical trials in the USA. Besides, вaltroban was investigated in patients with an ischemic heart disorder. However, the development of daltroban has been discontinued.
UsesImmunosuppressant.
UsesDaltroban can be used as a2 receptor to target adipose-derived stem cell for treating ischemic diseases.
UsesDaltroban (BM-13505) is a selective and specific thromboxane A2 (TXA2) receptor antagonist that increases intracellular calcium ions in vascular smooth muscle cells and protects against reperfusion injury after myocardial ischaemia but not in coronary artery endothelial cells. Daltroban may also be useful in the treatment of patients with COPD-related pulmonary hypertension.
Upstream & downstream products
Upstream raw materials
Related reactions
4 records
Compound notes
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