phentolamine ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2142 50-60-2

Description:

MoleculeDescription

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:

DoseUnitRoute
10 mg O
10 mg P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 15.23 ยตM/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:

DateAgencyCompanyOrphan
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)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Neutrophil count increased 60.13 57.91 15 251 25159 64473307

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC C04AB01 CARDIOVASCULAR SYSTEM
PERIPHERAL VASODILATORS
PERIPHERAL VASODILATORS
Imidazoline derivatives
ATC V03AB36 VARIOUS
ALL OTHER THERAPEUTIC PRODUCTS
ALL OTHER THERAPEUTIC PRODUCTS
Antidotes
FDA MoA N0000000099 Adrenergic alpha-Antagonists
FDA EPC N0000175553 alpha-Adrenergic Blocker
MeSH PA D018663 Adrenergic Agents
MeSH PA D000317 Adrenergic alpha-Antagonists
MeSH PA D018674 Adrenergic Antagonists
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
CHEBI has role CHEBI:35620 vasodilator agents
CHEBI has role CHEBI:37890 alpha-adrenergic receptor blockaders

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.33 acidic
pKa2 7.33 Basic
pKa3 5.88 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent 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

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Alpha-2A adrenergic receptor GPCR ANTAGONIST Ki 8.77 CHEMBL CHEMBL
Alpha-1A adrenergic receptor GPCR ANTAGONIST Ki 8.39 CHEMBL CHEMBL
Alpha-2B adrenergic receptor GPCR ANTAGONIST Ki 8.12 CHEMBL CHEMBL
Alpha-2C adrenergic receptor GPCR ANTAGONIST Ki 8.08 CHEMBL CHEMBL
Alpha-1D adrenergic receptor GPCR ANTAGONIST Ki 7.71 CHEMBL CHEMBL
Alpha-1B adrenergic receptor GPCR ANTAGONIST Ki 7.32 CHEMBL CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 6.68 DRUG MATRIX
Histamine H1 receptor GPCR Ki 5.40 PDSP
Cytochrome P450 2D6 Enzyme IC50 5 DRUG MATRIX
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.08 CHEMBL
Nischarin Membrane receptor Ki 7.94 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor IC50 6.26 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 4.78 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 5.67 PDSP
5-hydroxytryptamine receptor 2A GPCR Ki 5.61 PDSP
5-hydroxytryptamine receptor 2B GPCR Ki 5.62 DRUG MATRIX
Histamine H1 receptor GPCR IC50 4.90 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 9.03 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 6.66 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 8.85 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 7.35 DRUG MATRIX
Alpha-1A adrenergic receptor GPCR IC50 7.96 CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 7.35 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 8.33 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 8.17 CHEMBL

External reference:

IDSource
4019892 VUID
N0000147977 NUI
D00509 KEGG_DRUG
65-28-1 SECONDARY_CAS_RN
4018791 VANDF
4019892 VANDF
C0031448 UMLSCUI
CHEBI:8081 CHEBI
CHEMBL597 ChEMBL_ID
DB00692 DRUGBANK_ID
CHEMBL1200873 ChEMBL_ID
D010646 MESH_DESCRIPTOR_UI
5775 PUBCHEM_CID
502 IUPHAR_LIGAND_ID
22 INN_ID
73-05-2 SECONDARY_CAS_RN
Z468598HBV UNII
227240 RXNORM
11705 MMSL
5280 MMSL
d00733 MMSL
001845 NDDF
001846 NDDF
001847 NDDF
32436002 SNOMEDCT_US
372863003 SNOMEDCT_US
82165003 SNOMEDCT_US
CHEMBL1204146 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Phentolamine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9564 INJECTION, POWDER, FOR SOLUTION 5 mg INTRAMUSCULAR ANDA 18 sections
Oraverse HUMAN PRESCRIPTION DRUG LABEL 1 0362-0101 INJECTION, SOLUTION 0.24 mg SUBMUCOSAL NDA 25 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