Responsive image

Common name


Phentolamine

IUPAC name


3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol

SMILES


CC1=CC=C(C=C1)N(CC1=NCCN1)C1=CC(O)=CC=C1

Compound class


Antihypertensive Agents; Adrenergic alpha-1 Receptor Antagonists; Adrenergic alpha-Antagonists; Antidotes; Cardiovascular System; Peripheral Vasodilators; Imidazoline Derivatives;

Therapeutic area


Used as an aid for the diagnosis of pheochromocytoma, and may be administered immediately prior to or during pheochromocytomectomy to prevent or control paroxysmal hypertension resulting from anesthesia, stress, or operative manipulation of the tumor. Phentolamine has also been used to treat hypertensive crisis caused by sympathomimetic amines or catecholamine excess by certain foods or drugs in patients taking MAO inhibitors, or by clonidine withdrawal syndrome. Other indications include the prevention of dermal necrosis and sloughing following IV administration or extravasation of norepinephrine, decrease in impedance to left ventricular ejection and the infarct size in patients with MI associated with left ventricular failure, treatment of erectile dysfunction through self-injection of small doses combined with papaverine hydrochloride into the corpus cavernosum, and as an adjunct to the management of cocaine overdose to reverse coronary vasoconstriction following use of oxygen, benzodiazepines,and nitroglycerin.

Common name


Phentolamine

IUPAC name


3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol

SMILES


CC1=CC=C(C=C1)N(CC1=NCCN1)C1=CC(O)=CC=C1

INCHI


InChI=1S/C17H19N3O/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15/h2-8,11,21H,9-10,12H2,1H3,(H,18,19)

FORMULA


C17H19N3O

Responsive image

Common name


Phentolamine

IUPAC name


3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol

Molecular weight


281.352

clogP


3.136

clogS


-4.169

HBond Acceptor


3

HBond Donor


2

Total Polar
Surface Area


47.86

Number of Rings


3

Rotatable Bond


4

Drug ID Common name Structure CAS SMILE Frequency
FDBF00011 imidazole Responsive image [nH]1ccnc1 0.0175
FDBF00023 toluene Responsive image c1(ccccc1)C 0.1268
FDBF00641 4-methylaniline Responsive image Cc1ccc(cc1)N 0.0024
FDBF01610 3-aminophenol Responsive image c1(cc(ccc1)O)N 0.0007
FDBF01611 2-methyl-1H-imidazole Responsive image Cc1[nH]ccn1 0.0038
FDBF01612 3-(methylamino)phenol Responsive image c1(cc(ccc1)O)NC 0.0003
FDBF01614 3-(4-methylanilino)phenol Responsive image c1(cc(ccc1)O)Nc2ccc(cc2)C 0.0003
FDBF01615 3-(N,4-dimethylanilino)phenol Responsive image c1(cc(ccc1)O)N(c2ccc(cc2)C)C 0.0003
FDBF01616 N-(1H-imidazol-2-ylmethyl)-4-methyl-aniline Responsive image c1(ccc(cc1)C)NCc2[nH]ccn2 0.0003
12 , 2