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Details

Stereochemistry ACHIRAL
Molecular Formula C19H22N2OS.C4H4O4
Molecular Weight 442.528
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ACEPROMAZINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CN(C)CCCN1C2=CC=CC=C2SC3=CC=C(C=C13)C(C)=O

InChI

InChIKey=FQRHOOHLUYHMGG-BTJKTKAUSA-N
InChI=1S/C19H22N2OS.C4H4O4/c1-14(22)15-9-10-19-17(13-15)21(12-6-11-20(2)3)16-7-4-5-8-18(16)23-19;5-3(6)1-2-4(7)8/h4-5,7-10,13H,6,11-12H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI
Molecular Formula C19H22N2OS
Molecular Weight 326.456
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Acepromazine a potent neuroleptic agent with a low order of toxicity, is of particular value in the tranquilization of dogs, cats and horses. Its rapid action and lack of hypnotic effect are added advantages. Acepromazine is a commonly used tranquilizer/sedative in dogs, cats, horses, and other animals. Veterinarians typically prescribe acepromazine to quiet agitated animals or use it as a part of an anesthetic protocol. It is important to note that when used alone, acepromazine is not an effective pain reliever and does little if anything to relieve a pet’s anxiety or fear. Acepromazine can also be used to treat motion sickness and nausea associated with car or plane rides. The mechanism by which acepromazine decreases a pet’s alertness is not fully understood. It is thought to block dopamine receptors in the brain or inhibit the activity of dopamine in other ways.

CNS Activity

Originator

Schmitt, J. et al.
3
Sources: Schmitt, J. et al.: Bull. Soc. Chim. Fr. (BSCFAS) 1957, 938, 1474.
Curator's Comment: reference retrieved from https://pharmaceutical-substances.thieme.com/ps/search-results?query=&sort=&searchValuesMode=session&page=1&docUri=KD-01-0015 | www.drugfuture.com/chemdata/acepromazine.html

Approval Year

2011
587
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
ACEPROMAZINE MALEATE

Approved Use

Actions: Acepromazine maleate has a depressant effect on the central nervous system and therefore, causes sedation, muscular relaxation and a reduction in spontaneous activity. It acts rapidly, exerting a prompt and pronounced calming effect. Indications: Dogs and Cats: Acepromazine Maleate Injection can be used as an aid in controlling intractable animals during examination, treatment, grooming, x-ray and minor surgical procedures; to alleviate itching as a result of skin irritation; as an antiemetic to control vomiting associated with motion sickness. Acepromazine Maleate Injection is particularly useful as a preanesthetic agent (1) to enhance and prolong the effects of barbiturates, thus reducing the requirements for general anesthesia; (2) as an adjunct to surgery under local anesthesia. Horses: Acepromazine Maleate Injection can be used as an aid in controlling fractious animals during examination, treatment, loading and transportation. Particularly useful when used in conjunction with local anesthesia for firing, castration, neurectomy, removal of skin tumors, ocular surgery and applying casts.
Primary
Not Provided
511
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.95 h
OTHER
https://pubmed.ncbi.nlm.nih.gov/25059809/
950 mg single, oral
dose: 950 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACEPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
2057

BSEP
550

CYP1A2
2153

bCYP1A
3
dog P-gp
3
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C19
2141
 no
CYP2C9
2497
 no
CYP3A4
2633
 no
BSEP
554
 weak [IC50 111.6 uM]
CYP1A2
2333
 yes [IC50 1.585 uM]
CYP2D6
2546
 yes [IC50 2.5119 uM]
bCYP1A
3
 yes [Ki 10.6 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
dog P-gp
3
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Effects of chronic baroreceptor unloading on blood pressure in the dog.
2005-04
Laparoscopic nonanatomic hepatic resection employing the LigaSure device.
2005-03-29
Analgesic efficacy of preoperative administration of meloxicam or butorphanol in onychectomized cats.
2005-03-15
Results of 24-hour ambulatory electrocardiography in dogs undergoing ovariohysterectomy following premedication with medetomidine or acepromazine.
2005-03-01
Effects of acepromazine on pulmonary gas exchange and circulation during sedation and dissociative anaesthesia in horses.
2005-03
Muscle metabolic changes associated with long-term inhalation anaesthesia in the horse analysed by muscle biopsy and microdialysis techniques.
2005-03
Therapeutic effects of Holmium-166 chitosan complex in rat brain tumor model.
2005-02-28
Overdose during chemical restraint in a black rhinoceros (Diceros bicornis).
2005-01
Gamma scintigraphic evaluation of a miniaturized AERx pulmonary delivery system for aerosol delivery to anesthetized animals using a positive pressure ventilation system.
2005
Effect of meloxicam and carprofen on renal function when administered to healthy dogs prior to anesthesia and painful stimulation.
2004-10
Neuroleptanalgesia in wild Asian elephants (Elephas maximus maximus).
2004-10
Effects of doxapram HCl on laryngeal function of normal dogs and dogs with naturally occurring laryngeal paralysis.
2004-10
Intentional overdose of Large Animal Immobilon.
2004-10
Effects of ovariohysterectomy on canine blood neutrophil respiratory burst: a chemiluminescence study.
2004-09-15
Does the A-line ARX-lndex provide a reasonable assessment of anaesthetic depth in dogs undergoing routine surgery?
2004-09
Relationships between a proprietary index, bispectral index, and hemodynamic variables as a means for evaluating depth of anesthesia in dogs anesthetized with sevoflurane.
2004-08
Investigation of the effect of acepromazine on intravenous glucose tolerance tests in dogs.
2004-08
Determinants of cardiac electrophysiological properties in mice.
2004-08
Standing sedation and pain management for ophthalmic patients.
2004-08
Effects of propofol on the electrocardiogram and systolic blood pressure of healthy cats pre-medicated with acepromazine.
2004-07
Comparison of preoperative carprofen and postoperative butorphanol as postsurgical analgesics in cats undergoing ovariohysterectomy.
2004-07
Intense (18)F-FDG uptake in brown fat can be reduced pharmacologically.
2004-07
Sonographic features of drug-induced splenic congestion.
2004-06-18
NF-kappaB p50 facilitates neutrophil accumulation during LPS-induced pulmonary inflammation.
2004-06-09
Elevated nociceptive thresholds in rats with multifocal brain damage induced with single subcutaneous injections of lithium and pilocarpine.
2004-06
An animal model for ultrasound lung imaging.
2004-05
Normal spatial and contextual learning for ketamine-treated rats in the pilocarpine epilepsy model.
2004-05
Middle-latency auditory-evoked potential in acepromazine-sedated dogs.
2004-04-03
The effect of four anesthetic protocols on splenic size in dogs.
2004-04
Effects of various anesthetic agents on laryngeal motion during laryngoscopy in normal dogs.
2004-03-19
Ganglion cell contributions to the rat full-field electroretinogram.
2004-02-15
Development of a rapid screening test for veterinary sedatives and the beta-blocker carazolol in porcine kidney by ELISA.
2004-02
The neuromatrix and the epileptic brain: behavioral and learning preservation in limbic epileptic rats treated with ketamine but not acepromazine.
2004-02
Systemic lidocaine infusion as an analgesic for intraocular surgery in dogs: a pilot study.
2004-01
Evaluation of intraperitoneal and incisional lidocaine or bupivacaine for analgesia following ovariohysterectomy in the dog.
2004-01
Effects of acepromazine on the incidence of vomiting associated with opioid administration in dogs.
2004-01
Orthologous gene-expression profiling in multi-species models: search for candidate genes.
2004
Temporal changes in ventricular function assessed echocardiographically in conscious and anesthetized mice.
2003-11
Effects of midazolam-butorphanol, acepromazine-butorphanol and medetomidine on an induction dose of propofol and their compatibility in dogs.
2003-10
A comparison of preoperative tramadol and morphine for the control of early postoperative pain in canine ovariohysterectomy.
2003-10
Analysis of phenothiazine and its derivatives using LC/electrochemistry/MS and LC/electrochemistry/fluorescence.
2003-09-15
Effects of dopamine antagonists on alfentanil-induced locomotor activity in horses.
2003-07
Changes in the EEG during castration in horses and ponies anaesthetized with halothane.
2003-07
The sedative and behavioral effects of nalbuphine in dogs.
2003-07
A comparison of the analgesic effects of butorphanol with those of meloxicam after elective ovariohysterectomy in dogs.
2003-07
Hypotensive effect of push-pull gravitational stress occurs after autonomic blockade.
2003-07
Effects of acepromazine on renal function in anesthetized dogs.
2003-05
Hematology and serum chemistry of the island spotted skunk on Santa Cruz Island.
2003-04
Effects of acepromazine on capture stress in roe deer (Capreolus capreolus).
2003-04
Application of pulsed Doppler ultrasound for the evaluation of small intestinal motility in dogs.
2001-04
Patents

Patents

US4508715A
3

Sample Use Guides

In Vivo Use Guide
Acepromazine Maleate Injection may be given intravenously, intramuscularly or subcutaneously. The following schedule may be used as a guide to IV, IM or SC injections:Dogs: 0.25-0.5 mg/lb of body weight.Cats: 0.5-1 mg/lb of body weight.Horses: 2-4 mg/100 lb of body weight.0.25 - 3 mg per kg body weight by oral administration.
Route of Administration: Other
In Vitro Use Guide
The crude extract of Chlamydia pneumoniae induced the differentiation of monocytes into macrophages in 45 ± 5% of the cells. Acepromazine significantly reduced the mean percentage of differentiated cells: with 10−5 M ACP, 18 ± % (p < 0.005) of the cells differentiated into macrophages and with 10−4 M the mean percentage of differentiated cells was equivalent to the control values: 5 ± 1% (p < 0.001). Viability of the differentiated and nondifferentiated THP-1 was = 98%.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:51:11 GMT 2025
Edited
by admin
on Mon Mar 31 17:51:11 GMT 2025
Record UNII
37862HP2OM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-264522
Preferred Name English
ACEPROMAZINE MALEATE
GREEN BOOK   MART.   MI   USAN   USP   USP-RS   WHO-DD  
USAN  
Official Name English
Acepromazine maleate [WHO-DD]
Common Name English
ACEPROMAZINE MALEATE [MI]
Common Name English
ACEPROMAZINE MALEATE [GREEN BOOK]
Common Name English
10-[3-(Dimethylamino)propyl]phenothiazin-2-yl methyl ketone maleate (1:1)
Systematic Name English
ACEPROMAZINE MALEATE [USAN]
Common Name English
ETHANONE, 1-(10-(3-(DIMETHYLAMINO)PROPYL)-10H-PHENOTHIAZIN-2-YL)-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
ACEPROMAZINE MALEATE [USP MONOGRAPH]
Common Name English
ACEPROMAZINE MALEATE [USP-RS]
Common Name English
ACEPROMAZINE MALEATE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66883
Created by admin on Mon Mar 31 17:51:11 GMT 2025 , Edited by admin on Mon Mar 31 17:51:11 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL39560
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PRIMARY
EVMPD
SUB21524
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PRIMARY
SMS_ID
100000088299
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PRIMARY
RS_ITEM_NUM
1001502
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PRIMARY
NCI_THESAURUS
C76652
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PRIMARY
EPA CompTox
DTXSID6047783
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PRIMARY
FDA UNII
37862HP2OM
Created by admin on Mon Mar 31 17:51:11 GMT 2025 , Edited by admin on Mon Mar 31 17:51:11 GMT 2025
PRIMARY
ECHA (EC/EINECS)
222-748-9
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PRIMARY
PUBCHEM
6420038
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PRIMARY
DAILYMED
37862HP2OM
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PRIMARY
MERCK INDEX
m1303
Created by admin on Mon Mar 31 17:51:11 GMT 2025 , Edited by admin on Mon Mar 31 17:51:11 GMT 2025
PRIMARY Merck Index
NSC
264522
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PRIMARY
DRUG BANK
DBSALT001612
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PRIMARY
CAS
3598-37-6
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PRIMARY
RXCUI
1114057
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PRIMARY RxNorm
Related Record Type Details
Structure of ACEPROMAZINE
PARENT -> SALT/SOLVATE
Structure of Maleic Acid
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ACEPROMAZINE
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