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Details

Stereochemistry ACHIRAL
Molecular Formula C20H21NO4
Molecular Weight 339.385
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PAPAVERINE

SMILES

COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1

InChI

InChIKey=XQYZDYMELSJDRZ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H21NO4
Molecular Weight 339.385
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. Papaverine is a vasodilating agent. Papaverine is used for the treating certain conditions that are accompanied by smooth muscle spasms (eg, blood vessel, urinary, gallbladder, or intestinal spasm). Papaverine is a nonxanthine phosphodiesterase inhibitor for the relief of cerebral and peripheral ischemia associated with arterial spasm and myocardial ischemia complicated by arrhythmias. The main actions of Papaverine are exerted on cardiac and smooth muscle. Like qathidine, Papaverine acts directly on the heart muscle to depress conduction and prolong the refractory period. Papaverine relaxes various smooth muscles. This relaxation may be prominent if spasm exists. The muscle cell is not paralyzed by Papaverine and still responds to drugs and other stimuli causing contraction. The antispasmodic effect is a direct one, and unrelated to muscle innervation. Papaverine is practically devoid of effects on the central nervous system. Papaverine relaxes the smooth musculature of the larger blood vessels, especially coronary, systemic peripheral, and pulmonary arteries. Papaverine is a potent, specific inhibitor of PDE10A. Papaverine for treatment of erectile dysfunction (ED) is excluded from coverage.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
36.0 nM [IC50]
60.0 µM [IC50]
0.58 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Papaverine

Cmax

ValueDoseCo-administeredAnalytePopulation
54.7 ng/mL
3 mg single, intravascular
PAPAVERINE plasma
Homo sapiens
583 ng/mL
150 mg single, oral
PAPAVERINE plasma
Homo sapiens
117 ng/mL
150 mg single, oral
PAPAVERINE plasma
Homo sapiens
536 ng/mL
150 mg single, oral
PAPAVERINE plasma
Homo sapiens
218 ng/mL
200 mg single, oral
PAPAVERINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1760 mg × h/mL
80 mg single, intravenous
PAPAVERINE plasma
Homo sapiens
375 mg × h/mL
80 mg single, oral
PAPAVERINE plasma
Homo sapiens
1965 mg × h/mL
80 mg single, intravenous
PAPAVERINE plasma
Homo sapiens
855 mg × h/mL
80 mg single, oral
PAPAVERINE plasma
Homo sapiens
1308 ng × h/mL
150 mg single, oral
PAPAVERINE plasma
Homo sapiens
409 ng × h/mL
150 mg single, oral
PAPAVERINE plasma
Homo sapiens
1247 ng × h/mL
150 mg single, oral
PAPAVERINE plasma
Homo sapiens
800 ng × h/mL
200 mg single, oral
PAPAVERINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.9 h
80 mg single, intravenous
PAPAVERINE plasma
Homo sapiens
3.4 h
80 mg single, intravenous
PAPAVERINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Papaverine Hydrochloride may be administered intravenously or intramuscularly. The intravenous route is recommended when an immediate effect is desired, but the drug must be injected slowly over the course of 1 or 2 minutes to avoid uncomfortable or alarming side effects. Parenteral administration of papaverine hydrochloride in doses of 1 to 4 mL is repeated every 3 hours as indicated. In the treatment of cardiac extrasystoles, 2 doses may be given 10 minutes apart.
Route of Administration: Parenteral
In Vitro Use Guide
In bovine cauda epididymal and ejaculated spermatozoa, the major cAMP-PDE activity was papaverine-sensitive (44.5% and 57.5%, respectively, at 400 nm of papaverine).
Substance Class Chemical
Record UNII
DAA13NKG2Q
Record Status Validated (UNII)
Record Version