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phentolamine 🐶 Veterinary Use | 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

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:

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Property	Value	Reference
S (Water solubility)	50 mg/mL	Bocci G, Oprea TI, 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
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

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Approvals:

Date	Agency	Company	Orphan
Jan. 30, 1952	FDA	NOVARTIS

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Neutrophil count increased	59.34	52.91	15	281	29381	79714711
Blood urea increased	56.31	52.91	16	280	48774	79695318

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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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
CHEBI has role	CHEBI:35620	vasodilator agents
CHEBI has role	CHEBI:37890	alpha-adrenergic receptor blockaders
FDA EPC	N0000175553	alpha-Adrenergic Blocker
FDA MoA	N0000000099	Adrenergic alpha-Antagonists
MeSH PA	D018663	Adrenergic Agents
MeSH PA	D000317	Adrenergic alpha-Antagonists
MeSH PA	D018674	Adrenergic Antagonists
MeSH PA	D000959	Antihypertensive Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID
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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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)

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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	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

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN	ANTAGONIST	Ki	8.77	CHEMBL	CHEMBL
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN	ANTAGONIST	Ki	8.39	CHEMBL	CHEMBL
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN	ANTAGONIST	Ki	8.12	CHEMBL	CHEMBL
Alpha-2C adrenergic receptor	GPCR	P18825	ADA2C_HUMAN	ANTAGONIST	Ki	8.08	CHEMBL	CHEMBL
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN	ANTAGONIST	Ki	7.71	CHEMBL	CHEMBL
Alpha-1B adrenergic receptor	GPCR	P35368	ADA1B_HUMAN	ANTAGONIST	Ki	7.32	CHEMBL	CHEMBL
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN		Ki	6.68	DRUG MATRIX
Histamine H1 receptor	GPCR	P35367	HRH1_HUMAN		Ki	5.40	PDSP
Cytochrome P450 2D6	Enzyme	P10635	CP2D6_HUMAN		IC50	5	DRUG MATRIX
Sodium channel alpha subunits; brain (Types I, II, III)	Ion channel	P35498 Q99250 Q9NY46	SCN1A_HUMAN SCN2A_HUMAN SCN3A_HUMAN		IC50	5.08	CHEMBL

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External reference:

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ID	Source
001845	NDDF
001846	NDDF
001847	NDDF
11705	MMSL
22	INN_ID
227240	RXNORM
32436002	SNOMEDCT_US
372863003	SNOMEDCT_US
4018791	VANDF
4019892	VUID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Oraverse	HUMAN PRESCRIPTION DRUG LABEL	1	0362-0101	INJECTION, SOLUTION	0.24 mg	SUBMUCOSAL	NDA	25 sections
Phentolamine Mesylate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9564	INJECTION, POWDER, FOR SOLUTION	5 mg	INTRAMUSCULAR	ANDA	18 sections
Phentolamine Mesylate	HUMAN PRESCRIPTION DRUG LABEL	1	51224-012	INJECTION	5 mg	INTRAMUSCULAR	ANDA	19 sections
PHENTOLAMINE MESYLATE	HUMAN PRESCRIPTION DRUG LABEL	1	68094-101	INJECTION	5 mg	INTRAVENOUS	ANDA	16 sections

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