Budiodarone information

Budiodarone
Clinical data
ATC code	None;
Legal status
Legal status	US: Investigational New Drug;
Identifiers
	IUPAC name [(2S)-butan-2-yl] 2-[3-[4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetate;
CAS Number	335148-45-3;
PubChem CID	9833332;
ChemSpider	8009056;
UNII	F5Y53150C8;
ChEMBL	ChEMBL2105631;
Chemical and physical data
Formula	C27H31I2NO5
Molar mass	703.356 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Ic1cc(cc(I)c1OCCN(CC)CC)C(=O)c2c3ccccc3oc2CC(=O)O[C@@H](C)CC;
	InChI InChI=1S/C27H31I2NO5/c1-5-17(4)34-24(31)16-23-25(19-10-8-9-11-22(19)35-23)26(32)18-14-20(28)27(21(29)15-18)33-13-12-30(6-2)7-3/h8-11,14-15,17H,5-7,12-13,16H2,1-4H3/t17-/m0/s1; Key:ZXOSVKYCXLTVGS-KRWDZBQOSA-N;

Budiodarone (ATI-2042) is an antiarrhythmic agent and chemical analog of amiodarone that is currently being studied in clinical trials. Amiodarone is considered the most effective antiarrhythmic drug available,^[1]^[2]^[3] but its adverse side effects, including hepatic, pulmonary and thyroid toxicity as well as multiple drug interactions,^[4] are discouraging its use. Budiodarone only differs in structure from amiodarone through the presence of a sec-butyl acetate side chain at position 2 of the benzofuran moiety.^[5] This side chain allows for budiodarone to have a shorter half-life in the body than amiodarone (7 hours versus 35–68 days) which allows it to have a faster onset of action and metabolism while still maintaining similar electrophysiological activity.^[4] The faster metabolism of budiodarone allows for fewer adverse side effects than amiodarone principally due to decreased levels of toxicity in the body.

^ Roy D, Talajic M, Dorian P, Connolly S, Eisenberg MJ, Green M, Kus T, Lambert J, Dubuc M, Gagné P, Nattel S, Thibault B (March 2000). "Amiodarone to prevent recurrence of atrial fibrillation. Canadian Trial of Atrial Fibrillation Investigators". The New England Journal of Medicine. 342 (13): 913–20. doi:10.1056/NEJM200003303421302. PMID 10738049.
^ Singh BN, Singh SN, Reda DJ, Tang XC, Lopez B, Harris CL, Fletcher RD, Sharma SC, Atwood JE, Jacobson AK, Lewis HD, Raisch DW, Ezekowitz MD (May 2005). "Amiodarone versus sotalol for atrial fibrillation". The New England Journal of Medicine. 352 (18): 1861–72. doi:10.1056/NEJMoa041705. PMID 15872201.
^ Kochiadakis GE, Igoumenidis NE, Marketou ME, Kaleboubas MD, Simantirakis EN, Vardas PE (September 2000). "Low dose amiodarone and sotalol in the treatment of recurrent, symptomatic atrial fibrillation: a comparative, placebo controlled study". Heart (British Cardiac Society). 84 (3): 251–7. doi:10.1136/heart.84.3.251. PMC 1760955. PMID 10956284.
^ ^a ^b Morey TE, Seubert CN, Raatikainen MJ, Martynyuk AE, Druzgala P, Milner P, Gonzalez MD, Dennis DM (April 2001). "Structure-activity relationships and electrophysiological effects of short-acting amiodarone homologs in guinea pig isolated heart". The Journal of Pharmacology and Experimental Therapeutics. 297 (1): 260–6. PMID 11259553.
^ Mason PK, DiMarco JP (2009). "Advances in Arrhythmia and Electrophysiology". Circulation. 2: 588–597. CiteSeerX 10.1.1.991.2904.

[pmid10738049-1] Roy D, Talajic M, Dorian P, Connolly S, Eisenberg MJ, Green M, Kus T, Lambert J, Dubuc M, Gagné P, Nattel S, Thibault B (March 2000). "Amiodarone to prevent recurrence of atrial fibrillation. Canadian Trial of Atrial Fibrillation Investigators". The New England Journal of Medicine. 342 (13): 913–20. doi:10.1056/NEJM200003303421302. PMID 10738049.

[pmid15872201-2] Singh BN, Singh SN, Reda DJ, Tang XC, Lopez B, Harris CL, Fletcher RD, Sharma SC, Atwood JE, Jacobson AK, Lewis HD, Raisch DW, Ezekowitz MD (May 2005). "Amiodarone versus sotalol for atrial fibrillation". The New England Journal of Medicine. 352 (18): 1861–72. doi:10.1056/NEJMoa041705. PMID 15872201.

[pmid10956284-3] Kochiadakis GE, Igoumenidis NE, Marketou ME, Kaleboubas MD, Simantirakis EN, Vardas PE (September 2000). "Low dose amiodarone and sotalol in the treatment of recurrent, symptomatic atrial fibrillation: a comparative, placebo controlled study". Heart (British Cardiac Society). 84 (3): 251–7. doi:10.1136/heart.84.3.251. PMC 1760955. PMID 10956284.

[Morey-4] Morey TE, Seubert CN, Raatikainen MJ, Martynyuk AE, Druzgala P, Milner P, Gonzalez MD, Dennis DM (April 2001). "Structure-activity relationships and electrophysiological effects of short-acting amiodarone homologs in guinea pig isolated heart". The Journal of Pharmacology and Experimental Therapeutics. 297 (1): 260–6. PMID 11259553.

[5] Mason PK, DiMarco JP (2009). "Advances in Arrhythmia and Electrophysiology". Circulation. 2: 588–597. CiteSeerX 10.1.1.991.2904.

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Clinical data

ATC code	None
Legal status
Legal status	US: Investigational New Drug
Identifiers
IUPAC name [(2S)-butan-2-yl] 2-[3-[4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetate
CAS Number	335148-45-3
PubChem CID	9833332
ChemSpider	8009056
UNII	F5Y53150C8
ChEMBL	ChEMBL2105631
Chemical and physical data
Formula	C₂₇H₃₁I₂NO₅
Molar mass	703.356 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Ic1cc(cc(I)c1OCCN(CC)CC)C(=O)c2c3ccccc3oc2CC(=O)O[C@@H](C)CC
InChI InChI=1S/C27H31I2NO5/c1-5-17(4)34-24(31)16-23-25(19-10-8-9-11-22(19)35-23)26(32)18-14-20(28)27(21(29)15-18)33-13-12-30(6-2)7-3/h8-11,14-15,17H,5-7,12-13,16H2,1-4H3/t17-/m0/s1 Key:ZXOSVKYCXLTVGS-KRWDZBQOSA-N