Acepromazine Description
Acepromazine is only found in individuals that have used or taken this drug. It is one of the phenothiazine derivative psychotropic drugs, used little in humans, however frequently in animals as a sedative and antiemetic.Acepromazine acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 – different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejacliation difficlities), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism – controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficlity/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects). Structure
Structure for HMDB15552 (Acepromazine)
Synonyms
Value Source 1-[10-(3-dimethylamino-PROPYL)-10H-phenothiazin-2-yl]-ethanoneChEBI 10-(3-Dimethylaminopropyl)phenothiazin-3-yl methyl ketoneChEBI 10-(3-Dimethylaminopropyl)phenothiazine-3-ethyloneChEBI AcetazineChEBI AcetopromazineChEBI AcetylpromazineChEBI CalmivetMeSH Sanofi brand OF acepromazine maleateMeSH Seid brand OF acepromazine maleateMeSH VetranquilMeSH Acepromazine maleateMeSH Maleate, acepromazineMeSH PlegicilMeSH Vétoquinol brand OF acepromazine maleateMeSH
Chemical Formlia
C19H22N2OS Average Molecliar Weight
326.456 Monoisotopic Molecliar Weight
326.145284026 IUPAC Name
1-{10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethan-1-one Traditional Name
Ace CAS Registry Number
61-00-7 SMILES
InChI Identifier
InChI Key
NOSIYYJFMPDDSA-UHFFFAOYSA-N Chemical Taxonomy Description
This compound belongs to the class of chemical entities known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring. Kingdom
Chemical entities Super Class
Organic compounds Class
Organoheterocyclic compounds Sub Class
Benzothiazines Direct Parent
Phenothiazines Alternative Parents
Substituents
Molecliar Framework
Aromatic heteropolycyclic compounds External Descriptors
Ontology Status
Expected but not Quantified Origin
Biofunction
Application
Cellliar locations
Physical Properties State
Liquid Experimental Properties
Property Value Reference Melting Point< 25 °CNot Available Boiling PointNot AvailableNot Available Water Solubility9.80e-03 g/LNot Available LogPNot AvailableNot Available
Predicted Properties
Property Value Source Water Solubility0.0098 mg/mLALOGPS logP4.32ALOGPS logP3.49ChemAxon logS-4.5ALOGPS pKa (Strongest Acidic)16.06ChemAxon pKa (Strongest Basic)8.5ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area23.55 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity99.35 m3·mol-1ChemAxon Polarizability37.17 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon
Spectra Spectra
Spectrum Type Description Splash Key LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-004i-0009000000-ba8f0be449800ec10cf1View in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-002r-9025000000-028fcf239ba77c5d26d0View in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-000i-9060000000-33b3210f75c9aa6899f3View in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0abi-9180000000-9b10f7d22435e199c283View in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4i-9670000000-0c65cbf1672ae4899236View in MoNA Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
Biological Properties Cellliar Locations
Biofluid Locations
Tissue Location
Not Available Pathways
Not Available Normal Concentrations
Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01614details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01614
details
Abnormal Concentrations
Not Available Associated Disorders and Diseases Disease References
None Associated OMIM IDs
None External Links DrugBank ID
DB01614 DrugBank Metabolite ID
Not Available Phenol Explorer Compound ID
Not Available Phenol Explorer Metabolite ID
Not Available FoodDB ID
Not Available KNApSAcK ID
Not Available Chemspider ID
5852 KEGG Compound ID
Not Available BioCyc ID
Not Available BiGG ID
Not Available Wikipedia Link
Acepromazine NuGOwiki Link
HMDB15552 Metagene Link
HMDB15552 METLIN ID
Not Available PubChem Compound
6077 PDB ID
PMZ ChEBI ID
44932
References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not AvailableEnzymes
- General function:
- Involved in G-protein coupled receptor protein signaling pathway
- Specific function:
- This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
- Gene Name:
- DRD2
- Uniprot ID:
- P14416
- Molecular weight:
- 50618.9
References
- Oades RD, Rao ML, Bender S, Sartory G, Muller BW: Neuropsychological and conditioned blocking performance in patients with schizophrenia: assessment of the contribution of neuroleptic dose, serum levels and dopamine D2-receptor occupancy. Behav Pharmacol. 2000 Jun;11(3-4):317-30. [PubMed:11103886 ]
- Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
- Wu S, Xing Q, Gao R, Li X, Gu N, Feng G, He L: Response to chlorpromazine treatment may be associated with polymorphisms of the DRD2 gene in Chinese schizophrenic patients. Neurosci Lett. 2005 Mar 7;376(1):1-4. Epub 2004 Dec 2. [PubMed:15694263 ]
- Wu SN, Gao R, Xing QH, Li HF, Shen YF, Gu NF, Feng GY, He L: Association of DRD2 polymorphisms and chlorpromazine-induced extrapyramidal syndrome in Chinese schizophrenic patients. Acta Pharmacol Sin. 2006 Aug;27(8):966-70. [PubMed:16867246 ]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
- Seeman P: Dopamine D2 receptors as treatment targets in schizophrenia. Clin Schizophr Relat Psychoses. 2010 Apr;4(1):56-73. doi: 10.3371/CSRP.4.1.5. [PubMed:20643630 ]
- General function:
- Involved in G-protein coupled receptor protein signaling pathway
- Specific function:
- This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
- Gene Name:
- HTR1A
- Uniprot ID:
- P08908
- Molecular weight:
- 46106.3
References
- Cosi C, Koek W: Agonist, antagonist, and inverse agonist properties of antipsychotics at human recombinant 5-HT(1A) receptors expressed in HeLa cells. Eur J Pharmacol. 2001 Dec 14;433(1):55-62. [PubMed:11755134 ]
- Newman-Tancredi A, Gavaudan S, Conte C, Chaput C, Touzard M, Verriele L, Audinot V, Millan MJ: Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study. Eur J Pharmacol. 1998 Aug 21;355(2-3):245-56. [PubMed:9760039 ]
- General function:
- Involved in G-protein coupled receptor protein signaling pathway
- Specific function:
- This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
- Gene Name:
- HTR2A
- Uniprot ID:
- P28223
- Molecular weight:
- 52602.6
References
- Kusumi I, Takahashi Y, Suzuki K, Kameda K, Koyama T: Differential effects of subchronic treatments with atypical antipsychotic drugs on dopamine D2 and serotonin 5-HT2A receptors in the rat brain. J Neural Transm (Vienna). 2000;107(3):295-302. [PubMed:10821438 ]
- Yamada J, Sugimoto Y, Horisaka K: Serotonin2 (5-HT2) receptor agonist 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) inhibits chlorpromazine- and haloperidol-induced hypothermia in mice. Biol Pharm Bull. 1995 Nov;18(11):1580-3. [PubMed:8593484 ]
- General function:
- Involved in G-protein coupled receptor protein signaling pathway
- Specific function:
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
- Gene Name:
- ADRA1A
- Uniprot ID:
- P35348
- Molecular weight:
- 51486.0
References
- Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [PubMed:15695070 ]
- General function:
- Involved in G-protein coupled receptor protein signaling pathway
- Specific function:
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
- Gene Name:
- ADRA1B
- Uniprot ID:
- P35368
- Molecular weight:
- 56835.4
References
- Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [PubMed:15695070 ]
- General function:
- Involved in G-protein coupled receptor protein signaling pathway
- Specific function:
- This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
- Gene Name:
- DRD1
- Uniprot ID:
- P21728
- Molecular weight:
- 49292.8
References
- Kanba S, Suzuki E, Nomura S, Nakaki T, Yagi G, Asai M, Richelson E: Affinity of neuroleptics for D1 receptor of human brain striatum. J Psychiatry Neurosci. 1994 Jul;19(4):265-9. [PubMed:7918347 ]
Transporters
- General function:
- Involved in ion transmembrane transporter activity
- Specific function:
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
- Gene Name:
- SLC22A1
- Uniprot ID:
- O15245
- Molecular weight:
- 61187.4
References
- Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755 ]