phentolamine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	2142	50-60-2

Description:

Molecule

Description

Molfile Inchi Smiles Synonyms: phentolamine fentolamine phentolamine mesylate phentolamine mesilate phentolamine hydrochloride phentolamine HCl

A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of RAYNAUD DISEASE and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease. Molecular weight: 281.36 Formula: C17H19N3O CLOGP: 3.81 LIPINSKI: 0 HAC: 4 HDO: 2 TPSA: 47.86 ALOGS: -3.02 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Drug dosage:

Dose	Unit	Route
10	mg	O
10	mg	P

ADMET properties:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	15.23 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Hosey CM, Chan R, Benet LZ
CL (Clearance)	42 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	2.50 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Jan. 30, 1952	FDA	NOVARTIS

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

Source	Code	Description
ATC	C04AB01	CARDIOVASCULAR SYSTEM PERIPHERAL VASODILATORS PERIPHERAL VASODILATORS Imidazoline derivatives
ATC	V03AB36	VARIOUS ALL OTHER THERAPEUTIC PRODUCTS ALL OTHER THERAPEUTIC PRODUCTS Antidotes
MeSH PA	D018663	Adrenergic Agents
FDA EPC	N0000175553	alpha-Adrenergic Blocker
MeSH PA	D000317	Adrenergic alpha-Antagonists
MeSH PA	D018674	Adrenergic Antagonists
CHEBI has role	CHEBI:37890	alpha-adrenergic antagonist
CHEBI has role	CHEBI:35620	vasodilator agent
MeSH PA	D000959	Antihypertensive Agents
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D018377	Neurotransmitter Agents

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Paroxysmal hypertension	indication	23130000
Cerebral ischemia	indication	287731003
Pheochromocytoma	indication	302835009
Peripheral vascular disease	indication	400047006
Prevention of Hypertension in Pheochromocytoma	indication
Hypertensive Emergencies	indication
Diagnostic Test for Pheochromocytoma	indication
Dermal Necrosis	indication
Hypertension Secondary to Pheochromocytoma	indication
Extravasation injury	off-label use	371100002
Impotence	off-label use	397803000
Sinus tachycardia	contraindication	11092001
Myocardial infarction	contraindication	22298006	DOID:5844
Glaucoma	contraindication	23986001	DOID:1686
Complete atrioventricular block	contraindication	27885002
Conduction disorder of the heart	contraindication	44808001
Low blood pressure	contraindication	45007003
Angina pectoris	contraindication	194828000
Disease of liver	contraindication	235856003	DOID:409
Chronic myocardial ischemia	contraindication	413844008	DOID:3393
Disorder of coronary artery	contraindication	414024009
Cardiac Conduction Delay	contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.33	acidic
pKa2	7.33	Basic
pKa3	5.88	Basic

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
0.4MG/1.7ML	ORAVERSE	SEPTODONT HOLDING	N022159	May 9, 2008	RX	INJECTABLE	INJECTION	6764678	May 11, 2021	A METHOD OF REVERSING SOFT-TISSUE ANESTHESIA I.E. ANESTHESIA OF THE LIP AND TONGUE, AND THE ASSOCIATED FUNCTIONAL DEFICITS RESULTING FROM AN INTRAORAL SUBMUCOSAL INJECTION OF A LOCAL ANESTHETIC
0.4MG/1.7ML	ORAVERSE	SEPTODONT HOLDING	N022159	May 9, 2008	RX	INJECTABLE	INJECTION	7569230	Oct. 17, 2023	A METHOD OF REVERSING SOFT-TISSUE ANESTHESIA I.E. ANESTHESIA OF THE LIP AND TONGUE, AND THE ASSOCIATED FUNCTIONAL DEFICITS RESULTING FROM AN INTRAORAL SUBMUCOSAL INJECTION OF A LOCAL ANESTHETIC

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Alpha-2C adrenergic receptor	GPCR	P18825	ADA2C_HUMAN	ANTAGONIST	Ki	8.08		CHEMBL	CHEMBL
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN	ANTAGONIST	Ki	8.77		CHEMBL	CHEMBL
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN	ANTAGONIST	Ki	7.71		CHEMBL	CHEMBL
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN	ANTAGONIST	Ki	8.12		CHEMBL	CHEMBL
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN	ANTAGONIST	Ki	8.39		CHEMBL	CHEMBL
Alpha-1B adrenergic receptor	GPCR	P35368	ADA1B_HUMAN	ANTAGONIST	Ki	7.32		CHEMBL	CHEMBL
Cytochrome P450 2D6	Enzyme	P10635	CP2D6_HUMAN		IC50	5		DRUG MATRIX
Sigma non-opioid intracellular receptor 1	Membrane receptor	Q99720	SGMR1_HUMAN		IC50	6.26		CHEMBL
Nischarin	Membrane receptor	Q9Y2I1	NISCH_HUMAN		Ki	7.94		CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III)	Ion channel	P35498 Q99250 Q9NY46	SCN1A_HUMAN SCN2A_HUMAN SCN3A_HUMAN		IC50	5.08		CHEMBL
Histamine H1 receptor	GPCR	P35367	HRH1_HUMAN		Ki	5.40		PDSP
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	5.61		PDSP
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN		Ki	5.67		PDSP
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		Ki	4.78		DRUG MATRIX
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		Ki	5.62		DRUG MATRIX
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN		Ki	6.68		DRUG MATRIX
Alpha-1B adrenergic receptor	GPCR		ADA1B_RAT		Ki	7.35		DRUG MATRIX
Alpha-1B adrenergic receptor	GPCR		ADA1B_MESAU		Ki	6.66		CHEMBL
Adrenergic receptor alpha-2	GPCR		ADA2A_RAT ADA2B_RAT ADA2C_RAT		Ki	8.85		CHEMBL
Alpha-1A adrenergic receptor	GPCR		ADA1A_BOVIN		Ki	8.17		CHEMBL
Alpha-2A adrenergic receptor	GPCR		ADA2A_BOVIN		Ki	9.03		CHEMBL
Alpha-2A adrenergic receptor	GPCR		ADA2A_RAT		Ki	8.33		CHEMBL
Histamine H1 receptor	GPCR		HRH1_RAT		IC50	4.90		CHEMBL
Alpha-1D adrenergic receptor	GPCR		ADA1D_RAT		Ki	7.35		CHEMBL
Alpha-1A adrenergic receptor	GPCR		ADA1A_RAT		IC50	7.96		CHEMBL

External reference:

ID	Source
4019892	VUID
N0000147977	NUI
C0031448	UMLSCUI
D00509	KEGG_DRUG
82165003	SNOMEDCT_US
4019892	VANDF
8153	RXNORM
372863003	SNOMEDCT_US
d00733	MMSL
001845	NDDF
86DRW83R1H	UNII
73-05-2	SECONDARY_CAS_RN
CHEBI:8081	CHEBI
CHEMBL597	ChEMBL_ID
DB00692	DRUGBANK_ID
22	INN_ID
5775	PUBCHEM_CID
CHEMBL1200873	ChEMBL_ID
CHEMBL1204146	ChEMBL_ID
D010646	MESH_DESCRIPTOR_UI
502	IUPHAR_LIGAND_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Phentolamine Mesylate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9564	INJECTION, POWDER, FOR SOLUTION	5 mg	INTRAMUSCULAR	ANDA	12 sections
Oraverse	HUMAN PRESCRIPTION DRUG LABEL	1	0362-0101	INJECTION, SOLUTION	0.24 mg	SUBMUCOSAL	NDA	17 sections
Phentolamine Mesylate	HUMAN PRESCRIPTION DRUG LABEL	1	51224-012	INJECTION	5 mg	INTRAMUSCULAR	ANDA	12 sections
PHENTOLAMINE MESYLATE	HUMAN PRESCRIPTION DRUG LABEL	1	68094-101	INJECTION	5 mg	INTRAVENOUS	ANDA	11 sections