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Details

Stereochemistry ACHIRAL
Molecular Formula C19H22N2OS.C4H4O4
Molecular Weight 442.5299
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ACEPROMAZINE MALEATE

SMILES

CC(=O)c1ccc2c(c1)N(CCCN(C)C)c3ccccc3S2.C(\[H])(=C(\[H])/C(=O)O)/C(=O)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 C4H4O4
Molecular Weight 116.0723
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C19H22N2OS
Molecular Weight 326.4576
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Originator

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Weight gain in post-seized rats is facilitated by adding aspirin, glucose, or glucose-taurine-acetaminophen to food mush.
2001 Aug
Effects of acetylpromazine or morphine on urine production in halothane-anesthetized dogs.
2001 Dec
Recovery from carotid artery catheterization performed under various anesthetics in male, Sprague-Dawley rats.
2001 Jul
Prospective survey of tick paralysis in dogs.
2001 Jun
Cardiopulmonary effects of three different anaesthesia protocols in cats.
2001 Nov
Prolonged general anesthesia in MR studies of rats.
2001 Nov
[Sent home while still sleeping].
2001 Oct 1
Synergistic induction of severe hypothermia (poikilothermia) by limbic seizures, acepromazine and physical restraint: role of noradrenergic alpha-1 receptors.
2001 Oct-Nov
Survey on small animal anaesthesia.
2001 Sep
Effects of medetomidine and buprenorphine administered for sedation in dogs.
2001 Sep
Human exposure to pet prescription medications.
2002 Aug
Intraocular pressure and tear production in five herbivorous wildlife species.
2002 Aug 31
Effects of medetomidine-midazolam, acepromazine-butorphanol, and midazolam-butorphanol on induction dose of thiopental and propofol and on cardiopulmonary changes in dogs.
2002 Dec
[Priapism in the stallion].
2002 Dec 15
Effect of acepromazine and butorphanol on isoflurane minimum alveolar concentration in goats.
2002 Feb
Mask induction of anaesthesia with isoflurane or sevoflurane in premedicated cats.
2002 Jan
Comparison between meloxicam and carprofen for postoperative analgesia after feline ovariohysterectomy.
2002 Jul
Evaluation of the perioperative stress response in dogs administered medetomidine or acepromazine as part of the preanesthetic medication.
2002 Jul
Cerebral blood volume measurements by rapid contrast infusion and T2*-weighted echo planar MRI.
2002 Jun
Structure of TAR RNA complexed with a Tat-TAR interaction nanomolar inhibitor that was identified by computational screening.
2002 Jun
Development of a mouse model to determine the systemic activity of potential flea-control compounds.
2002 Mar 20
Effects of preoperative administration of ketoprofen on anesthetic requirements and signs of postoperative pain in dogs undergoing elective ovariohysterectomy.
2002 Nov 1
Reduced resident time and pharmacodynamic effects of acepromazine after subclinical multiple dosage in exercised thoroughbreds.
2002 Oct
Effects of two preanesthetic regimens for ophthalmic surgery on intraocular pressure and cardiovascular measurements in dogs.
2002 Spring
Hematology and serum chemistry of the island spotted skunk on Santa Cruz Island.
2003 Apr
Effects of acepromazine on capture stress in roe deer (Capreolus capreolus).
2003 Apr
Effects of dopamine antagonists on alfentanil-induced locomotor activity in horses.
2003 Jul
Progressive changes in ophthalmic blood velocities in Beagles with primary open angle glaucoma.
2003 Mar
Changes in intraocular pressure and pupil size following intramuscular administration of hydromorphone hydrochloride and acepromazine in clinically normal dogs.
2003 Mar
Temporal changes in ventricular function assessed echocardiographically in conscious and anesthetized mice.
2003 Nov
Analysis of phenothiazine and its derivatives using LC/electrochemistry/MS and LC/electrochemistry/fluorescence.
2003 Sep 15
Relationships between a proprietary index, bispectral index, and hemodynamic variables as a means for evaluating depth of anesthesia in dogs anesthetized with sevoflurane.
2004 Aug
Investigation of the effect of acepromazine on intravenous glucose tolerance tests in dogs.
2004 Aug
Determinants of cardiac electrophysiological properties in mice.
2004 Aug
Standing sedation and pain management for ophthalmic patients.
2004 Aug
The neuromatrix and the epileptic brain: behavioral and learning preservation in limbic epileptic rats treated with ketamine but not acepromazine.
2004 Feb
Evaluation of intraperitoneal and incisional lidocaine or bupivacaine for analgesia following ovariohysterectomy in the dog.
2004 Jan
Elevated nociceptive thresholds in rats with multifocal brain damage induced with single subcutaneous injections of lithium and pilocarpine.
2004 Jun
Sonographic features of drug-induced splenic congestion.
2004 May-Jun
Effect of meloxicam and carprofen on renal function when administered to healthy dogs prior to anesthesia and painful stimulation.
2004 Oct
Neuroleptanalgesia in wild Asian elephants (Elephas maximus maximus).
2004 Oct
Effects of doxapram HCl on laryngeal function of normal dogs and dogs with naturally occurring laryngeal paralysis.
2004 Oct
Intentional overdose of Large Animal Immobilon.
2004 Oct
Does the A-line ARX-lndex provide a reasonable assessment of anaesthetic depth in dogs undergoing routine surgery?
2004 Sep
Effects of ovariohysterectomy on canine blood neutrophil respiratory burst: a chemiluminescence study.
2004 Sep-Oct
Effects of chronic baroreceptor unloading on blood pressure in the dog.
2005 Apr
Laparoscopic nonanatomic hepatic resection employing the LigaSure device.
2005 Jan-Mar
Effects of acepromazine on pulmonary gas exchange and circulation during sedation and dissociative anaesthesia in horses.
2005 Mar
Results of 24-hour ambulatory electrocardiography in dogs undergoing ovariohysterectomy following premedication with medetomidine or acepromazine.
2005 Mar 1
Analgesic efficacy of preoperative administration of meloxicam or butorphanol in onychectomized cats.
2005 Mar 15
Patents

Patents

Sample Use Guides

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
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 Fri Jun 25 20:53:51 UTC 2021
Edited
by admin
on Fri Jun 25 20:53:51 UTC 2021
Record UNII
37862HP2OM
Record Status Validated (UNII)
Record Version
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Name Type Language
ACEPROMAZINE MALEATE
GREEN BOOK   MART.   MI   USAN   USP   USP-RS   WHO-DD  
USAN  
Official Name English
ACEPROMAZINE MALEATE [MI]
Common Name English
ACEPROMAZINE MALEATE [GREEN BOOK]
Common Name English
ACEPROMAZINE MALEATE [WHO-DD]
Common Name English
NSC-264522
Code 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 Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL39560
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY
EVMPD
SUB21524
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY
NCI_THESAURUS
C76652
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY
EPA CompTox
3598-37-6
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY
USP_CATALOG
1001502
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY USP-RS
FDA UNII
37862HP2OM
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY
ECHA (EC/EINECS)
222-748-9
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY
PUBCHEM
6420038
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY
MERCK INDEX
M1303
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY Merck Index
DRUG BANK
DBSALT001612
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY
CAS
3598-37-6
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY
RXCUI
1114057
Created by admin on Fri Jun 25 20:53:51 UTC 2021 , Edited by admin on Fri Jun 25 20:53:51 UTC 2021
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY