Amlodipine

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1 : 1 mixture (racemate)

Systematic (IUPAC) name
(RS)-3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
Identifiers
CAS number	88150-42-9
ATC code	C08CA01
PubChem	2162
DrugBank	APRD00520
ChemSpider	2077
Chemical data
Formula	C20H25ClN2O5
Mol. mass	408.879 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	64 to 90%
Metabolism	Hepatic
Half life	30 to 50 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	C(AU) C(US)
Legal status	POM(UK) ℞-only(US)
Routes	Oral (tablets)
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Amlodipine (as besylate, mesylate or maleate) is a long-acting calcium channel blocker (dihydropyridine class) used as an anti-hypertensive and in the treatment of angina. Like other calcium channel blockers, amlodipine acts by relaxing the smooth muscle in the arterial wall, decreasing total peripheral resistance and hence reducing blood pressure; in angina it increases blood flow to the heart muscle.

[edit] Indications

• Hypertension
• Angina pectoris

[edit] Cautions

• hepatic impairment
• pregnancy

[edit] Contraindications

• cardiogenic shock
• unstable angina
• aortic stenosis
• breast feeding

[edit] Side effects

Some side effects of the use of amlodipine may be:^[1]

• Very often: peripheral edema (feet and ankles) - in 1 of 10 users
• Often: dizziness; palpitations; muscle-, stomach- or headache; dyspepsia; nausea - in 1 in 100 users
• Sometimes: blood disorders, development of breasts in men (gynecomastia), impotence, depression, insomnia, tachycardia - in 1 in 1,000 users
• Rarely: erratic behavior, hepatitis, jaundice - in 1 in 10,000 users
• Very rarely: hyperglycemia, tremor, Stevens-Johnson syndrome - in 1 in 100,000 users

[edit] Dose

• Hypertension or angina: 2.5 to 10 mg once daily (initial treatment can start as low as 2.5 mg per day, titrate up to 10 mg/day as necessary).

[edit] Salts

In the United Kingdom tablets of amlodipine from different suppliers may contain different salts. The strength of the tablets is expressed in terms of amlodipine base, i.e., without the salt. Tablets containing different salts are therefore considered interchangeable.

The efficacy and tolerability of a fixed-dose combination of amlodipine 5 mg and perindopril 4 mg, an angiotensin converting enzyme (ACE) inhibitor, has recently been confirmed in a prospective, observational multicenter trial of 1250 hypertensive patients.^[2]

[edit] Drug metabolism and excretion

Amlodipine is almost entirely metabolised to inactive metabolites. 10% of the parent substance and 60% of the metabolites are excreted in urine.

[edit] Patent loss

Pfizer patent protection on Norvasc lasted until 2007. Total patent expiration occurred later in 2007.^[3] A number of generic versions are now available.

[edit] Brand names

Amlodipine is marketed as:

• Norvasc by Pfizer in North America and some European countries
• Norvasc and Perivasc in Australia
• Istin in the United Kingdom and Ireland
• Amlodine in the Philippines by Westfield Pharmaceuticals, a division of InnoGen
• Amdepin by Cadila Pharmaceuticals in India
• Dailyvasc by Xeno Pharmaceuticals
• Aken in Mexico by Kendrick Farmaceutica
• Amdipin in Colombia by Laboratorios Lafrancol

[edit] See also

• Amlodipine/benazepril

[edit] References

[edit] External links

• Norvasc
• Istin - Summary of Product Characteristics from the electronic Medicines Compendium