Papaverine

Papaverine

Clinical data
Pronunciation	/pəˈpævəriːn/
Trade names	Pavabid, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682707
Pregnancy category	AU: A US: C (Risk not ruled out)
Routes of administration	Oral, intravenous, intramuscular, rectal, intracavernosal
ATC code	A03AD01 (WHO) G04BE02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	80%
Protein binding	~90%
Metabolism	Hepatic
Biological half-life	1.5–2 hours
Excretion	Renal
Identifiers
IUPAC name 1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinoline
CAS Number	58-74-2 Y 61-25-6 (hydrochloride)
PubChem (CID)	4680
DrugBank	DB01113 Y
ChemSpider	4518 Y
UNII	DAA13NKG2Q Y
KEGG	D07425 Y
ChEBI	CHEBI:28241 N
ChEMBL	CHEMBL19224 Y
ECHA InfoCard	100.000.361
Chemical and physical data
Formula	C20H21NO4
Molar mass	339.385 g/mol
3D model (Jmol)	Interactive image
SMILES COc1ccc(cc1OC)Cc2c3cc(c(cc3ccn2)OC)OC
InChI InChI=1S/C20H21NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-8,10-12H,9H2,1-4H3 Y Key:XQYZDYMELSJDRZ-UHFFFAOYSA-N Y
NY (what is this?)

Papaverine (Latin papaver, "poppy") is an opium alkaloid antispasmodic drug, used primarily in the treatment of visceral spasm, vasospasm (especially those involving the intestines, heart, or brain), and occasionally in the treatment of erectile dysfunction. It is used in the treatment of acute mesenteric ischemia. While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the analgesic (morphine-related) opium alkaloids (opiates).

Papaverine was discovered in 1848 by Georg Merck (1825–1873). Merck was a student of the German chemists Justus von Liebig and August Hofmann, and he was the son of Emanuel Merck (1794–1855), founder of the Merck corporation, a major German chemical and pharmaceutical company.

Papaverine is approved to treat spasms of the gastrointestinal tract, bile ducts and ureter and for use as a cerebral and coronary vasodilator in subarachnoid hemorrhage (combined with balloon angioplasty) and coronary artery bypass surgery. Papaverine may also be used as a smooth muscle relaxant in microsurgery where it is applied directly to blood vessels.