Prajmaline

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Prajmaline
	File:Prajmaline.svg
Clinical data
ATC code	C01BA08 (WHO) ;
Identifiers
	IUPAC name (4α,16R,17R,21α)-4-propylajmalan-4-ium-17,21-diol;
CAS Number	35080-11-6 ;
PubChem CID	37042;
ChemSpider	16735977 ;
UNII	75934UD4GJ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C23H33N2O2+
Molar mass	369.520 g/mol
3D model (JSmol)	Interactive image;
	SMILES O[C@@H]6C4[C@@H]2C[C@]65c1ccccc1N(C)[C@H]5[C@@H]3C[C@H]4[C@H](CC)[C@@H](O)[N+]23CCC;
	InChI InChI=1S/C23H33N2O2/c1-4-10-25-17-11-14(13(5-2)22(25)27)19-18(25)12-23(21(19)26)15-8-6-7-9-16(15)24(3)20(17)23/h6-9,13-14,17-22,26-27H,4-5,10-12H2,1-3H3/q+1/t13-,14-,17-,18-,19?,20-,21+,22+,23+,25?/m0/s1 ; Key:UAUHEPXILIZYCU-UUEXUKNBSA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Prajmaline (Neo-gilurythmal)^[1] is a class Ia antiarrhythmic agent^[2] which has been available since the 1970s.^[3] Class Ia drugs increase the time one action potential lasts in the heart.^[4] Prajmaline is a semi-synthetic propyl derivative of ajmaline, with a higher bioavailability than its predecessor.^[5] It acts to stop arrhythmias of the heart through a frequency-dependent block of cardiac sodium channels.^[2]

Mechanism

Prajmaline causes a resting block in the heart.^[6] A resting block is the depression of a person's Vmax after a resting period. This effect is seen more in the atrium than the ventricle.^[6] The effects of some Class I antiarrhythmics are only seen in a patient who has a normal heart rate (~1 Hz).^[7] This is due to the effect of a phenomenon called reverse use dependence.^[7] The higher the heart rate, the less effect Prajmaline will have.

Uses

The drug Prajmaline has been used to treat a number of cardiac disorders. These include: coronary artery disease,^[8]^[9] angina,^[8]^[9] paroxysmal tachycardia and Wolff–Parkinson–White syndrome.^[1] Prajmaline has been indicated in the treatment of certain disorders where other antiarrhythmic drugs were not effective.^[1]

Administration

Prajmaline can be administered orally,^[9] parenterally^[8] or intravenously.^[8] Three days after the last dose, a limited effect has been observed. Therefore it has been suggested that treatment of arrhythmias with Prajmaline must be continuous to see acceptable results.^[1]

Pharmacokinetics

The main metabolites of Prajmaline are: 21-carboxyprajmaline and hydroxyprajmaline. Twenty percent of the drug is excreted in the urine unchanged.

Daily therapeutic dose is 40–80 mg. Distribution half-life is 10 minutes. Plasma protein binding is 60%. Oral bioavailability is 80%. Elimination half-life is 6 hours. Volume of distribution is 4-5 L/kg. ^[3]

Side Effects

There are no significant adverse side-effects of Prajmaline when taken alone and with a proper dosage.^[1]^[8]^[9] Patients who are taking other treatments for their symptoms (e.g. beta blockers and nifedipine) have developed minor transient conduction defects when given Prajmaline.^[8]

Overdose

An overdose of Prajmaline is possible. The range of symptoms seen during a Prajmaline overdose include: no symptoms, nausea/vomiting, bradycardia, tachycardia, hypotension, and death.^[3]

Other Potential Uses

Due to Prajmaline's sodium channel-blocking properties, it has been shown to protect rat white matter from anoxia (82 +/- 15%).^[10]^[11] The concentration used causes little suppression of the preanoxic response.^[10]^[11]

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 Janicki, K., J. Orski, and J. Kakol. "Antiarrhythmic Effects of Prajmaline (Neo-Gilurythmal) in Stable Angina Pectoris." Przegl Lek 52.10 (1995): 485-91. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/8834838>.
↑ ^2.0 ^2.1 Weirich, J., and H. Antoni. "Differential Analysis of the Frequency-Dependent Effects of Class 1 Antiarrhythmic Drugs According to Periodical Ligand Binding." Journal of Cardiovascular Pharmacology 15.6 (1990): 998-1009. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/1694924>.
↑ ^3.0 ^3.1 ^3.2 Koppel, Claus, Ursula Oberdisse, and Gerhard Heinemeyer. "Clinical Course and Outcome in Class IC Antiarrhythmic Overdose." Clinical Toxicology 28.4 (1990): 433-44. Web. 6 Feb. 2011. <http://informahealthcare.com/doi/pdf/10.3109/15563659009038586>.
↑ Milne, J. R., K. J. Hellestrand, R. S. Bexton, P. J. Burnett, N. Debbas, and A. Camm. "Class 1 Antiarrhythmic Drugs — Characteristic Electrocardiographic Differences When Assessed by Atrial and Ventricular Pacing." European Heart Journal 5 (1984): 99-107. Web. 6 Feb. 2011. <http://eurheartj.oxfordjournals.org/content/5/2/99.full.pdf>.
↑ Hinse, C., and J. Stöckigt. "The Structure of the Ring-opened N Beta-propyl-ajmaline (Neo-Gilurytmal) at Physiological PH Is Obviously Responsible for Its Better Absorption and Bioavailability When Compared with Ajmaline (Gilurytmal)." Pharmazie 55.7 (2000): 531-32. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/10944783>.
↑ ^6.0 ^6.1 Langenfeld, H., J. Weirich, C. Köhler, and K. Kochsiek. "Comparative Analysis of the Action of Class I Antiarrhythmic Drugs (Lidocaine, Quinidine, and Prajmaline) in Rabbit Atrial and Ventricular Myocardium." Journal of Cardiovascular Pharmacology 15.2 (1990): 338-45. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/1689432>.
↑ ^7.0 ^7.1 Langenfeld, H., C. Köhler, J. Weirich, M. Kirstein, and K. Kochsiek. "Reverse Use Dependence of Antiarrhythmic Class Ia, Ib, and Ic: Effects of Drugs on the Action Potential Duration?" Pacing and Clinical Electrophysiology 2nd ser. 15.11 (1992): 2097-102. Web. 6 Feb. 2011. <http://onlinelibrary.wiley.com/doi/10.1111/j.1540-8159.1992.tb03028.x/pdf>.
↑ ^8.0 ^8.1 ^8.2 ^8.3 ^8.4 ^8.5 Sowton, E., I. D. Sullivan, and J. C. P. Crick. "Acute Haemodynamic Effects of Ajmaline and Prajmaline in Patients with Coronary Heart Disease." European Journal of Clinical Pharmacology 26.2 (1984): 147-50. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/6723753>.
↑ ^9.0 ^9.1 ^9.2 ^9.3 Handler, C. E., A. Kritikos, I. D. Sullivan, A. Charalambakis, and E. Sowton. "Effects of Oral Prajmaline Bitartrate on Exercise Test Responses in Patients with Coronary Artery Disease." European Journal of Clinical Pharmacology 28.4 (1985): 371-74. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/4029242>.
↑ ^10.0 ^10.1 Stys, PK. "Protective Effects of Antiarrhythmic Agents against Anoxic Injury in CNS White Matter." Journal of Cerebral Blood Flow & Metabolism 15.3 (1995): 425-32. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/7714000>.
↑ ^11.0 ^11.1 Malek, S., J. Adorante, and P. Stys. "Differential Effects of Na-K-ATPase Pump Inhibition, Chemical Anoxia, and Glycolytic Blockade on Membrane Potential of Rat Optic Nerve." Brain Research 1037.1-2 (2005): 171-79.

Template:Antiarrhythmic agents

[Jan-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 Janicki, K., J. Orski, and J. Kakol. "Antiarrhythmic Effects of Prajmaline (Neo-Gilurythmal) in Stable Angina Pectoris." Przegl Lek 52.10 (1995): 485-91. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/8834838>.

[Weir-2] 2.0 ^2.1 Weirich, J., and H. Antoni. "Differential Analysis of the Frequency-Dependent Effects of Class 1 Antiarrhythmic Drugs According to Periodical Ligand Binding." Journal of Cardiovascular Pharmacology 15.6 (1990): 998-1009. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/1694924>.

[Kopp-3] 3.0 ^3.1 ^3.2 Koppel, Claus, Ursula Oberdisse, and Gerhard Heinemeyer. "Clinical Course and Outcome in Class IC Antiarrhythmic Overdose." Clinical Toxicology 28.4 (1990): 433-44. Web. 6 Feb. 2011. <http://informahealthcare.com/doi/pdf/10.3109/15563659009038586>.

[4] Milne, J. R., K. J. Hellestrand, R. S. Bexton, P. J. Burnett, N. Debbas, and A. Camm. "Class 1 Antiarrhythmic Drugs — Characteristic Electrocardiographic Differences When Assessed by Atrial and Ventricular Pacing." European Heart Journal 5 (1984): 99-107. Web. 6 Feb. 2011. <http://eurheartj.oxfordjournals.org/content/5/2/99.full.pdf>.

[5] Hinse, C., and J. Stöckigt. "The Structure of the Ring-opened N Beta-propyl-ajmaline (Neo-Gilurytmal) at Physiological PH Is Obviously Responsible for Its Better Absorption and Bioavailability When Compared with Ajmaline (Gilurytmal)." Pharmazie 55.7 (2000): 531-32. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/10944783>.

[Lang-6] 6.0 ^6.1 Langenfeld, H., J. Weirich, C. Köhler, and K. Kochsiek. "Comparative Analysis of the Action of Class I Antiarrhythmic Drugs (Lidocaine, Quinidine, and Prajmaline) in Rabbit Atrial and Ventricular Myocardium." Journal of Cardiovascular Pharmacology 15.2 (1990): 338-45. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/1689432>.

[Langen-7] 7.0 ^7.1 Langenfeld, H., C. Köhler, J. Weirich, M. Kirstein, and K. Kochsiek. "Reverse Use Dependence of Antiarrhythmic Class Ia, Ib, and Ic: Effects of Drugs on the Action Potential Duration?" Pacing and Clinical Electrophysiology 2nd ser. 15.11 (1992): 2097-102. Web. 6 Feb. 2011. <http://onlinelibrary.wiley.com/doi/10.1111/j.1540-8159.1992.tb03028.x/pdf>.

[Sow-8] 8.0 ^8.1 ^8.2 ^8.3 ^8.4 ^8.5 Sowton, E., I. D. Sullivan, and J. C. P. Crick. "Acute Haemodynamic Effects of Ajmaline and Prajmaline in Patients with Coronary Heart Disease." European Journal of Clinical Pharmacology 26.2 (1984): 147-50. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/6723753>.

[Hand-9] 9.0 ^9.1 ^9.2 ^9.3 Handler, C. E., A. Kritikos, I. D. Sullivan, A. Charalambakis, and E. Sowton. "Effects of Oral Prajmaline Bitartrate on Exercise Test Responses in Patients with Coronary Artery Disease." European Journal of Clinical Pharmacology 28.4 (1985): 371-74. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/4029242>.

[Stys-10] 10.0 ^10.1 Stys, PK. "Protective Effects of Antiarrhythmic Agents against Anoxic Injury in CNS White Matter." Journal of Cerebral Blood Flow & Metabolism 15.3 (1995): 425-32. PubMed. Web. 6 Feb. 2011. <http://www.ncbi.nlm.nih.gov/pubmed/7714000>.

[Malek-11] 11.0 ^11.1 Malek, S., J. Adorante, and P. Stys. "Differential Effects of Na-K-ATPase Pump Inhibition, Chemical Anoxia, and Glycolytic Blockade on Membrane Potential of Rat Optic Nerve." Brain Research 1037.1-2 (2005): 171-79.

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Clinical data
File:Prajmaline.svg
ATC code	C01BA08 (WHO)
Identifiers
IUPAC name (4α,16R,17R,21α)-4-propylajmalan-4-ium-17,21-diol
CAS Number	35080-11-6^N
PubChem CID	37042
ChemSpider	16735977^Y
UNII	75934UD4GJ
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₃H₃₃N₂O₂⁺
Molar mass	369.520 g/mol
3D model (JSmol)	Interactive image
SMILES O[C@@H]6C4[C@@H]2C[C@]65c1ccccc1N(C)[C@H]5[C@@H]3C[C@H]4[C@H](CC)[C@@H](O)[N+]23CCC
InChI InChI=1S/C23H33N2O2/c1-4-10-25-17-11-14(13(5-2)22(25)27)19-18(25)12-23(21(19)26)15-8-6-7-9-16(15)24(3)20(17)23/h6-9,13-14,17-22,26-27H,4-5,10-12H2,1-3H3/q+1/t13-,14-,17-,18-,19?,20-,21+,22+,23+,25?/m0/s1^Y Key:UAUHEPXILIZYCU-UUEXUKNBSA-N^Y
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