Acepromazine

Title: Acepromazine
CAS Registry Number: 61-00-7
CAS Name: 1-[10-[3-(Dimethylamino)propyl]-10H-phenothiazin-2-yl]ethanone
Additional Names: 10-[3-(dimethylamino)propyl]phenothiazin-2-yl methyl ketone; 2-acetyl-10-(3-dimethylaminopropyl)phenothiazine; 3-acetyl-10-(3-dimethylaminopropyl)phenothiazine; 10-(3-dimethylaminopropyl)phenothiazine-3-ethylone; acetazine; acetopromazine; acetylpromazine
Manufacturers' Codes: 1522-CB
Molecular Formula: C19H22N2OS
Molecular Weight: 326.46
Percent Composition: C 69.90%, H 6.79%, N 8.58%, O 4.90%, S 9.82%
Literature References: Prepn: J. Schmitt et al., Bull. Soc. Chim. Fr. 1957, 938. Pharmacology and toxicology: W. Wirth et al., Arch. Int. Pharmacodyn. 123, 78 (1959). GLC determn in plasma: S. Ballard, T. Tobin, J. Toxicol. Environ. Health 7, 745 (1981). Clinical trial in cats: D. H. Dyson et al., Can. Vet. J. 33, 462 (1992); in horses: A. Hashem, H. Keller, J. Vet. Pharmacol. Ther. 16, 359 (1993). Brief review of clinical experience: N. Brock, Can. Vet. J. 35, 458-459 (1994).
Properties: Yellow-colored oil, bp0.5 220-240°.
Boiling point: bp0.5 220-240°
Derivative Type: Maleate
CAS Registry Number: 3598-37-6
Trademarks: Atravet (Wyeth-Ayerst); Calmivet (Stricker); Plegicil (Sanofi); PromAce (Fort Dodge); Sedalin (Chassot); Vetranquil (Sanofi)
Molecular Formula: C19H22N2OS.C4H4O4
Molecular Weight: 442.53
Percent Composition: C 62.42%, H 5.92%, N 6.33%, O 18.08%, S 7.25%
Properties: Yellow crystals from ethyl acetate, mp 135-136°. pKa 9.3. Sol in water, alcohol, chloroform. pH of aq solns: ~4.0. LD50 orally in rats: 400 mg/kg; i.v. in mice: 59 mg/kg (Wirth).
Melting point: mp 135-136°
pKa: pKa 9.3
Toxicity data: LD50 orally in rats: 400 mg/kg; i.v. in mice: 59 mg/kg (Wirth)
Therap-Cat-Vet: Tranquilizer.
Acequinocyl Acerin Acerola ACES Acesulfame

Acepromazine
Acepromazine.svg
Systematic (IUPAC) name
1-{10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethanone
Clinical data
AHFS/Drugs.com International Drug Names
Legal status not approved for use in cattle
Routes IV, IM, oral
Pharmacokinetic data
Bioavailability 6.6L/kg, high volume of distribution
Half-life 3 hours in horses
Excretion found in equine urine up to 96 hours after dosage
Identifiers
CAS number 61-00-7 YesY
ATC code N05AA04
PubChem CID 6077
DrugBank DB01614
ChemSpider 5852 YesY
UNII 54EJ303F0R YesY
KEGG D07065 YesY
ChEBI CHEBI:44932 YesY
ChEMBL CHEMBL39560 YesY
Chemical data
Formula C19H22N2OS 
Mol. mass 326.456 g/mol
 YesY (what is this?)  (verify)

Acepromazine or acetylpromazine (more commonly known as ACP, Ace, or by the trade names Atravet or Acezine 2, number depending on mg/ml dose) is a phenothiazine derivative antipsychotic drug. It was first used in humans in the 1950s,[1] but is now little used in humans (the closely related analogue, chlorpromazine, is still used as an antipsychotic in humans). Acepromazine is frequently used in animals as a sedative and antiemetic. Its principal value is in quietening and calming anxious animals. The standard pharmaceutical preparation, acepromazine maleate, is used in veterinary medicine in dogs, and cats. It is used widely in horses as a pre-anaesthetic sedative and has been shown to reduce anaesthesia related death. However, is contraindicated in stallions due to the risk of paraphimosis and persistent priapism. Its potential for cardiac effects, namely hypotension due to peripheral vasodilation, can be profound and as such is not recommended for use in geriatric or debilitated animals, especially dogs. In these cases it is most often substituted with midazolam or diazepam and left out of the preanesthetic medication altogether.