ATIPAMEZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H16N2
Molecular Weight	212.2902
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1(CC2=CC=CC=C2C1)C3=CN=CN3

InChI

InChIKey=HSWPZIDYAHLZDD-UHFFFAOYSA-N

InChI=1S/C14H16N2/c1-2-14(13-9-15-10-16-13)7-11-5-3-4-6-12(11)8-14/h3-6,9-10H,2,7-8H2,1H3,(H,15,16)

HIDE SMILES / InChI

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=403065e1-4c1a-433c-bb1b-6a2951946297
Curator's Comment: description was created based on several sources, including: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm116099.pdf https://www.zoetisus.com/products/dogs/antisedan-_atipamezole_.aspx

Atipamezole is a synthetic α2-adrenergic antagonist. It competitively inhibits α2-adrenergic receptors. Atipamezole is indicated for the reversal of the sedative and analgesic effects of Dexdomitor and Domitor in dogs. Adverse reactions: occasional vomiting may occur. At times, a period of excitement or apprehensiveness may be seen in dogs treated with atipamezole. Other effects of atipamezole include hypersalivation, diarrhea, and tremors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-2 114 Target ID: CHEMBL2095158 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9402036 \| https://www.ncbi.nlm.nih.gov/pubmed/16389294	Antagonist 2849		1.6 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sedative and analgesic effects of Dexdomitor and Domitor 2 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm116099.pdf	Primary		Approved 8583	Antisedan Approved Use It is indicated for the reversal of the clinical effects of the sedative and analgesic agents. Launch Date 1996

C_max

Value	Dose	Analyte	Population
11 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	5 mg single, buccal dose: 5 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
15 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	10 mg single, buccal dose: 10 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
26 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	20 mg single, buccal dose: 20 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
38 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	40 mg single, buccal dose: 40 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
145 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
23 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	22.8 mg single, buccal dose: 22.8 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
0.095 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1975199/	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ATIPAMEZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.333 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1975199/	30 mg single, intravenous dose: 30 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ATIPAMEZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.191 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1975199/	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ATIPAMEZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
26 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	5 mg single, buccal dose: 5 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
44 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	10 mg single, buccal dose: 10 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
74 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	20 mg single, buccal dose: 20 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
112 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	40 mg single, buccal dose: 40 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
231 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
85 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	22.8 mg single, buccal dose: 22.8 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.655 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1975199/	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ATIPAMEZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.975 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1975199/	30 mg single, intravenous dose: 30 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ATIPAMEZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.806 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1975199/	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ATIPAMEZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	5 mg single, buccal dose: 5 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	10 mg single, buccal dose: 10 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	20 mg single, buccal dose: 20 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	40 mg single, buccal dose: 40 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	22.8 mg single, buccal dose: 22.8 mg route of administration: Buccal experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7586944/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ATIPAMEZOLE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
6.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31699808/	unknown, unknown		ATIPAMEZOLE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
67 ug/kg single, intravenous Highest studied dose Dose: 67 ug/kg Route: intravenous Route: single Dose: 67 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/1675577/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1675577/	Sources: https://pubmed.ncbi.nlm.nih.gov/1675577/

PubMed

Title	Date	PubMed
Seizures during medetomindine sedation and local anaesthesia in two dogs undergoing skin biopsy.	2009-05	19382926
Benzo(alpha)pyrene-induced up-regulation of CYP1A2 gene expression: role of adrenoceptor-linked signaling pathways.	2006-06-20	16510159
Anticataleptic properties of alpha2 adrenergic antagonists in the crossed leg position and bar tests: differential mediation by 5-HT1A receptor activation.	2005-02	15448976
Altered glucose homeostasis in alpha2A-adrenoceptor knockout mice.	2004-11-28	15556159
Alpha(2A) adrenoceptors contribute to feedback inhibition of capsaicin-induced hyperalgesia.	2004-07	15220790
Systemic administration of atipamezole, an alpha 2-antagonist, can reduce scopolamine-induced hyperactivity in rats.	1997-10	9832985
A comparative study of the reversal by different alpha 2-adrenoceptor antagonists of the central sympatho-inhibitory effect of clonidine.	1996-02	8821553
Rapid reversal of alpha 2-adrenoceptor agonist effects by atipamezole in human volunteers.	1991-02	1675577

Patents

Sample Use Guides

In Vivo Use Guide

The atipamezole dose for the reversal of Dexdomitor or Domitor is 3750 ug/m2 (intravenous) or 5000 ug/m2 (intramuscular).

Route of Administration: Other

In Vitro Use Guide

Affinity of atipamezole to a1- and a2-adrenoceptors in rat brain membranes is 13,300 and 1.6 nM respectively.

Name

Type

Language

ANTISEDAN

Preferred Name

English

ATIPAMEZOLE

Official Name

English

ATIPAMEZOLE [MART.]

Common Name

English

ATIPAMEZOLE [USAN]

Common Name

English

4-(2-ETHYL-2-INDANYL)IMIDAZOLE.

Common Name

English

ATIPAMEZOLE [MI]

Common Name

English

atipamezole [INN]

Common Name

English

1H-IMIDAZOLE, 4-(2-ETHYL-2,3-DIHYDRO-1H-INDEN-2-YL)-

Systematic Name

English

MPV-1248

Code

English

Classification Tree Code System Code

WHO-VATC

QV03AB90