Ibutilide fumarate

Names

[ Name ]:
Ibutilide fumarate

[Synonym ]:
N-(4-{4-[Ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide (2E)-but-2-enedioate (2:1)
(±)-N-(4-(4-(Ethylheptylamino)-1-hydroxybutyl)phenyl)methanesulfonamide (E)-2-butenedioate (2:1) (Salt)
Bis[N-ethyl-N-(4-hydroxy-4-{4-[(methylsulfonyl)amino]phenyl}butyl)heptan-1-aminium] (2E)-but-2-enedioate
N-(4-{4-[Ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide (2E)-2-butenedioate (2:1)
Methanesulfonamide, N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]-, (2E)-2-butenedioate (2:1) (salt)
Bis[N-ethyl-N-(4-hydroxy-4-{4-[(methylsulfonyl)amino]phenyl}butyl)heptan-1-aminium]-(2E)-but-2-endioat
(±)-4'-(4-(Ethylheptylamino)-1-hydroxybutyl)methanesulfoanilide (E)-2-Butenedioate (2:1)
N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide (2E)-but-2-enedioate (2:1) (salt)
Bis[N-ethyl-N-(4-hydroxy-4-{4-[(methylsulfonyl)amino]phenyl}butyl)-1-heptanaminium] (2E)-2-butenedioate
Ibutilide hemifumarate salt
Ibutilide fumarate
UNII:9L5X4M5L6I
(2E)-But-2-endisäure--N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methansulfonamid(1:2)
acide (2E)-but-2-ènedioïque - N-(4-{4-[éthyl(heptyl)amino]-1-hydroxybutyl}phényl)méthanesulfonamide (1:2)
Corvert
Ibutilide (fumarate)

Biological Activity

[Description]:

Ibutilide Fumarate is a Class III antiarrhythmic agent that is indicated for acute cardioconversion of atrial fibrillation and atrial flutter of a recent onset to sinus rhythm.Target: Calcium ChannelIbutilide is the first 'pure' class III antiarrhythmic drug to become available. Its predominant action is prolongation of the myocardial action potential duration. Intravenous ibutilide 0.01 to 0.025 mg/kg or 1 to 2 mg successfully converted atrial flutter or fibrillation to sinus rhythm in 33 to 49% of patients in 2 placebo-controlled trials involving 439 patients with sustained arrhythmia [1]. Ibutilide appears to be an effective alternative method for rapid conversion of recent-onset AF or AFl. The drug may be particularly useful in patients who have undergone recent cardiac surgery or those who are not ideal candidates for DCC [2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Research Areas >> Cardiovascular Disease

[References]

[1]. Foster, R.H., M.I. Wilde, and A. Markham, Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs, 1997. 54(2): p. 312-30.

[2]. Howard, P.A., Ibutilide: an antiarrhythmic agent for the treatment of atrial fibrillation or flutter. Ann Pharmacother, 1999. 33(1): p. 38-47.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
522.4ºC at 760 mmHg

[ Melting Point ]:
112-117?C

[ Molecular Formula ]:
C₂₂H₃₈N₂O₅S

[ Molecular Weight ]:
442.61

[ Flash Point ]:
269.7ºC

[ PSA ]:
230.64000

[ LogP ]:
10.34740

[ Vapour Pressure ]:
9.71E-12mmHg at 25°C

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: PB0475700

CAS REGISTRY NUMBER :: 122647-32-9

LAST UPDATED :: 199712

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C40-H72-N4-O6-S2.C4-H4-O4

MOLECULAR WEIGHT :: 885.36

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 49,406,1994

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 94200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 49,406,1994 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 400 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 54,157,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 400 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 54,157,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 200 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 54,157,1996

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ RIDADR ]:
NONH for all modes of transport

Articles

Efficacy and safety of ibutilide for chemical cardioversion of atrial fibrillation and atrial flutter in cancer patients.

Am. J. Med. Sci. 347(4) , 277-81, (2014)

Atrial fibrillation and atrial flutter (AF/AFL) are the most common arrhythmias encountered in clinical practice. Rate versus rhythm control remains a difficult decision, especially in the acute setti...

Brugada syndrome masked by ibutilide treatment in a patient with atrial flutter.

Cardiology 122(2) , 89-92, (2012)

We present a case of Brugada syndrome in a young patient whose typical ECG pattern was 'masked' after ibutilide was administered for atrial flutter cardioversion. Ibutilide, a class III antiarrhythmic...

Effects of ibutilide on canine cardiac pacing threshold and on induction rates of atrial fibrillation.

Cell Biochem. Biophys. 64(3) , 197-203, (2012)

This study aims to observe the effects of ibutilide on canine cardiac pacing threshold and on induction rates of atrial fibrillation. Eighteen mongrel dogs were anesthetized and administrated with ibu...