Metoprolol

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Metoprolol
Systematic (IUPAC) name
1-[4-(2-methoxyethyl)phenoxy]
-3-propan-2-ylamino-propan-2-ol
Identifiers
CAS number 37350-58-6
ATC code C07AB02
PubChem 4171
DrugBank APRD00208
ChemSpider 4027
Chemical data
Formula C15H25NO3 
Mol. mass 267.364 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability 12%
Metabolism Hepatic
Half life 3-7 hours
Excretion Renal
Therapeutic considerations
Licence data

US
Pregnancy cat.

C(AU) C(US)
Legal status

℞ Prescription only
Routes oral iv
"Minax" redirects here. For Ultima game character, see Minax (Ultima).

Metoprolol is a selective β1 receptor blocker used in treatment of several diseases of the cardiovascular system, especially hypertension. It is marketed under the brand name Lopressor or Lopresor, respectively, by Novartis, and Toprol-XL (in the USA); Selokeen (in Nederlands); as Minax by Alphapharm (in Australia), Metrol by Arrow Pharmaceuticals (in Australia), as Betaloc by AstraZeneca, as Neobloc by Unipharm (in Israel) and as Corvitol by Berlin-Chemie AG. A number of generic products are available as well. The active substance metoprolol is employed either as metoprolol succinate or metoprolol tartrate (whereas 100 mg metoprolol tartrate corresponds to 95 mg metoprolol succinate), respectively as prolonged-release or conventional-release formulation.

Contents

Physical properties

Metoprolol is very low melting. Its melting point is around 45 degrees Celsius (as determined by Differential scanning calorimetry). For this reason metoprolol is always manufactured in salt form, as drugs with melting points below 100 degrees Celsius are difficult to work with in a manufacturing environment. The free base exists as a waxy white solid, where the tartrate salt is finer crystalline material.

Pharmacology

  • Selective
  • Moderately Lipophilic
  • Without intrinsic sympathomimetic activity (ISA)
  • With weak membrane stabilizing activity
  • Short half-life, therefore must be taken at least twice daily or as a Slow-release preparation.
  • Decreases Heart Rate, Contractility and Cardiac Output, therefore decreasing blood pressure

Indications

Due to its selectivity in blocking the beta1 receptors in the heart, metoprolol is also prescribed for off-label use in performance anxiety, social anxiety disorder, and other anxiety disorders.

Toprol XL 50mg
Toprol XL 50mg

Side effects

Transient effects include dizziness, lightheadedness, drowsiness, tiredness, diarrhea, unusual dreams, ataxia, trouble sleeping, and vision problems. It may also reduce blood flow to the hands and feet, causing them to feel numb and cold; smoking may worsen this effect.[3]

Serious side effects that are not to be tolerated for any length of time include symptoms of a very slow heartbeat (less than 50 bpm) (e.g. persistent dizziness, fainting, unusual fatigue), bluish discoloration of the fingers and toes, numbness/tingling/swelling of the hands or feet, sexual dysfunction, erectile dysfunction (impotence), hair loss, mental/mood changes, trouble breathing, cough, and increased thirst. Other highly unlikely symptoms include easy bruising or bleeding, persistent sore throat or fever, yellowing skin or eyes, stomach pain, dark urine, and persistent nausea. Symptoms of an allergic reaction include: rash, itching, swelling, severe dizziness. Taking it with alcohol might cause mild body rashes and therefore is not recommended.[3]

References

  1. ^ "Effect of metoprolol CR/XL in chronic heart failure: Metoprolol CR/XL Randomised Intervention Trial in Congestive Heart Failure (MERIT-HF)" (June 12 1999). Lancet 353 (9169): 2001–7. doi:10.1016/S0140-6736(99)04440-2. PMID 10376614. 
  2. ^ Zhang Q, Jin H, Wang L, Chen J, Tang C, Du J (April 2008). "Randomized comparison of metoprolol versus conventional treatment in preventing recurrence of vasovagal syncope in children and adolescents". Medical science monitor : international medical journal of experimental and clinical research 14 (4): CR199–203. PMID 18376348. 
  3. ^ a b Canadian Online Pharmacy website: Metoprolol

External links

v • d • e
Adrenergic antagonists
α
Non-selective α
reversible (Phentolamine) · irreversible (Phenoxybenzamine)
Ungrouped
β
β1 selective
(cardioselective)
Mixed α1/β
Indirect
tyrosine hydroxylase inhibitor (Metirosine) · vesicle storage inhibitor (Reserpine) · neurotransmitter release blocker (Guanethidine, Bretylium)

Wikipedia content modification information:

  • This page was last modified on 5 October 2008, at 16:32.

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