Basic information
- CAS
1094-08-2- Standard SMILES
CCN(CC)C(C)CN1c2ccccc2Sc2ccccc21- InChIKey
CDOZDBSBBXSXLB-UHFFFAOYSA-N- Molecular formula
- C19H24N2S
- Average molar mass
- 312.5 g/mol
- Monoisotopic mass
- 312.16601995
Overview
Profenamine is a member of the class of phenothiazines that is phenothiazine in which the hydrogen attached to the nitrogen is substituted by a 2-(diethylamino)propyl group. An antimuscarinic, it is used as the hydrochloride for the symptomatic treatment of Parkinson's disease. It has a role as an adrenergic antagonist, a histamine antagonist, an antiparkinson drug, a muscarinic antagonist and an antidyskinesia agent. It is a member of phenothiazines and a tertiary amino compound.
Names & identifiers
- Preferred name
- (+-)-Ethopropazine
- IUPAC
- N,N-diethyl-1-phenothiazin-10-ylpropan-2-amine
- English name
- ETHOPROPAZINE
- Molecular formula
- C19H24N2S
- Molecular weight
- 312.47226
Names & synonyms
ethopropazineProfenamineEthopromazine522-00-9ProfenaminumProfenamina2-Diethylamino-1-propyl-N-dibenzoparathiazineN,N-Diethyl-alpha-methyl-10H-phenothiazine-10-ethanamineW-483RP-3356SC-25387WI4P02YN1
Show more names
ParkinparkTomilsc2538rp3356RP 3356RodipalRocipel
(+-)-Ethopropazine10-[2-(Diethylamino)propyl]phenothiazine10-[2-(Diethylamino)-1-Propyl]phenothiazine10H-Phenothiazine-10-ethanamine, N,N-diethyl-alpha-methyl-10-[2-(Diethylamino)-2-methylethyl]phenothiazinePHENOTHIAZINE, 10-(2-(DIETHYLAMINO)PROPYL)-diethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amineN,N-Diethyl-1-(10H-phenothiazin-10-yl)-2-propanamine
Database identifiers
- CAS
1094-08-2、522-00-9- PubChem CID
- 3290
- DTXSID
DTXSID2023018- ChEMBL
CHEMBL1206- ChEBI
CHEBI:313639
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 31.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 322
Experimental & physicochemical properties
LogP
5.2
4.77
Solubility5.24e-03 g/L
Human DrugsPharmaceuticals
Melting Point
166-168
64.5 °C
Physical DescriptionSolid
Collision Cross Section174.37 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 53 · 53-55°
- Density
- 1.107 · 1.1070 (rough estimate)
- refractive index
- 1.58 · 1.5800 (estimate)
- storage temp.
- -20 °C · -20°C
- FDA UNII
- 7 WI4P02YN1 · 7WI4P02YN1
- ATC code
- 4 AA05 · N04AA05
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Protein Binding93%
Pharmacodynamics
Profenamine, a phenothiazine and antidyskinetic, is used in the treatment of Parkinson's disease. By improving muscle control and reducing stiffness, this drug permits more normal movements of the body as the disease symptoms are reduced. It is also used to control severe reactions to certain medicines such as reserpine, phenothiazines, chlorprothixene, thiothixene, loxapine, and haloperidol. Unlike other NMDA antagonists, profenamine — because of its anticholinergic action — is largely devoid of neurotoxic side effects. Profenamine also has a slight antihistaminic and local anesthetic effect.
Mechanism of Action
Profenamine's anti-Parkinson action can be attributed to its anticholinergic properties. Profenamine partially blocks central (striatal) cholinergic receptors, thereby helping to balance cholinergic and dopaminergic activity in the basal ganglia; salivation may be decreased, and smooth muscle may be relaxed. Drug-induced extrapyramidal symptoms and those due to parkinsonism may be relieved, but tardive dyskinesia is not alleviated and may be aggravated by anticholinergic effects. Profenamine's local anesthetic effect is due to its antagonism of the NMDA glutamate receptor. Glutamate is recognized as an important transmitter in nociceptive pathways, and the N-methyl-D-aspartate (NMDA) subtype of the glutamate receptor, in particular, has been implicated in the mediation of neuropathic pain. Excessive release of glutamate at NMDA receptors on dorsal horn neurons of the spinal cord results in hyperactivation and hypersensitivity of these receptors (perceived as hyperalgesia), thought to be an integral feature of neuropathic pain.
Biological Half-Life1 to 2 hours
MeSH Pharmacological Classification
Drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. Classical antihistaminics block the histamine H1 receptors only.
Related reactions
1 records
Compound notes
Loading…