Details of the Drug

General Information of Drug (ID: DMJMVKI)

Drug Name

Metipranolol

Synonyms

Disorat; Methypranol; Metipranololum; Trimepranol; Turoptin; BM-01004; Betanol (TN); Disorat (TN); Metipranololum [INN-Latin]; OptiPranolol (TN); Trimepranol (TN); VUAB-6453; VUFB-6453; Metipranolol (USAN/INN); Metipranolol [USAN:BAN:INN]; [4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-2,3,6-trimethylphenyl] acetate; Phenol, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-2,3,6-trimethyl-, 1-acetate; Phenol, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-2,3,6-trimethyl-, 1-acetate (9CI); Phenol,4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-2,3,6-trimethyl-, (+-)-, 1-acetate; (+-)-1-(4-Hydroxy-2,3,5-trimethylphenoxy)-3-(isopropylamino)-2-propanol 4-acetate; (RS)-4-(2-Hydroxy-3-isopropylaminopropoxy)-2,3,6-trimethylphenyl acetat; 1-(4-Acetoxy-2,3,5-Trimethylphenoxy)-3-Isopropylamino-2-Propanol; 1-(4-Hydroxy-2,3,5-trimethylphenoxy)-3-(isopropylamino)-2-propanol 4-acetate; 2-Propanol, 1-(4-hydroxy-2,3,5-trimethylphenoxy)-3-(isopropylamino)-, 4-acetate; 4-(2-Hydroxy-3-((1-methylethyl)-amino)propoxy)-2,3,6-trimethylphenol 1-acetate; 4-[2-hydroxy-3-(isopropylamino)propoxy]-2,3,6-trimethylphenyl acetate; 62164P

Indication

Disease Entry	ICD 11	Status	REF
Ocular hypertension	9C61.01	Approved	[1]
Open-angle glaucoma	9C61	Approved	[2]
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Therapeutic Class

Antihypertensive Agents

Affected Organisms

Humans and other mammals

ATC Code

S01ED04: Metipranolol

S01ED: Beta blocking agents

S01E: ANTIGLAUCOMA PREPARATIONS AND MIOTICS

S01: OPHTHALMOLOGICALS

S: SENSORY ORGANS

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

309.4

Logarithm of the Partition Coefficient (xlogp)

2.7

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C17H27NO4
IUPAC Name: [4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-2,3,6-trimethylphenyl] acetate
Canonical SMILES: CC1=CC(=C(C(=C1OC(=O)C)C)C)OCC(CNC(C)C)O
InChI: InChI=1S/C17H27NO4/c1-10(2)18-8-15(20)9-21-16-7-11(3)17(22-14(6)19)13(5)12(16)4/h7,10,15,18,20H,8-9H2,1-6H3
InChIKey: BQIPXWYNLPYNHW-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 31477
ChEBI ID: CHEBI:6897
CAS Number: 22664-55-7
UNII: X39AL81KEB
DrugBank ID: DB01214
TTD ID: D0L5FY
INTEDE ID: DR1066

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adrenergic receptor beta-1 (ADRB1)	TTR6W5O	ADRB1_HUMAN	Antagonist	[3]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Metipranolol (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Bepridil	DM0RKS4	Moderate	Increased risk of cardiac depression by the combination of Metipranolol and Bepridil.	Angina pectoris [BA40]	[5]
Dronedarone	DMA8FS5	Moderate	Increased risk of atrioventricular block by the combination of Metipranolol and Dronedarone.	Angina pectoris [BA40]	[6]
Atracurium	DM42HXN	Moderate	Additive neuromuscular blocking effects by the combination of Metipranolol and Atracurium.	Corneal disease [9A76-9A78]	[7]
Mivacurium	DM473VD	Moderate	Additive neuromuscular blocking effects by the combination of Metipranolol and Mivacurium.	Corneal disease [9A76-9A78]	[7]
Pancuronium	DMB0VY8	Moderate	Additive neuromuscular blocking effects by the combination of Metipranolol and Pancuronium.	Corneal disease [9A76-9A78]	[7]
Pasireotide	DMHM7JS	Moderate	Increased risk of bradycardia by the combination of Metipranolol and Pasireotide.	Cushing syndrome [5A70]	[8]
Levamlodipine	DM92S6N	Moderate	Increased risk of cardiac depression by the combination of Metipranolol and Levamlodipine.	Hypertension [BA00-BA04]	[5]
Clevidipine butyrate	DMW4M97	Moderate	Increased risk of cardiac depression by the combination of Metipranolol and Clevidipine butyrate.	Hypertension [BA00-BA04]	[5]
Siponimod	DM2R86O	Major	Increased risk of atrioventricular block by the combination of Metipranolol and Siponimod.	Multiple sclerosis [8A40]	[9]
Fingolimod	DM5JVAN	Moderate	Increased risk of bradycardia by the combination of Metipranolol and Fingolimod.	Multiple sclerosis [8A40]	[10]
Ozanimod	DMT6AM2	Moderate	Increased risk of bradycardia by the combination of Metipranolol and Ozanimod.	Multiple sclerosis [8A40]	[11]
Polythiazide	DMCH80F	Moderate	Increased risk of hypertriglyceridemia by the combination of Metipranolol and Polythiazide.	Oedema [MG29]	[12]
Silodosin	DMJSBT6	Moderate	Additive hypotensive effects by the combination of Metipranolol and Silodosin.	Prostate hyperplasia [GA90]	[13]
Pipecuronium	DM5F84A	Moderate	Additive neuromuscular blocking effects by the combination of Metipranolol and Pipecuronium.	Tonus and reflex abnormality [MB47]	[7]
Vecuronium	DMP0UK2	Moderate	Additive neuromuscular blocking effects by the combination of Metipranolol and Vecuronium.	Tonus and reflex abnormality [MB47]	[7]
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⏷ Show the Full List of 15 DDI Information of This Drug

References

1	Metipranolol FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7239).
3	Invited review: Neuroprotective properties of certain beta-adrenoceptor antagonists used for the treatment of glaucoma. J Ocul Pharmacol Ther. 2005 Jun;21(3):175-81.
4	Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432.
5	Henry M, Kay MM, Viccellio P "Cardiogenic shock associated with calcium-channel and beta blockers: reversal with intravenous calcium chloride." Am J Emerg Med 3 (1985): 334-6. [PMID: 2860911]
6	Product Information. Multaq (dronedarone). sanofi-aventis , Bridgewater, NJ.
7	Harrah MD, Way WL, Katzung BG "The interaction of d-tubocurarine with antiarrhythmic drugs." Anesthesiology 33 (1970): 406-10. [PMID: 5512329]
8	Canadian Pharmacists Association.
9	Cerner Multum, Inc. "Australian Product Information.".
10	Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
11	Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.
12	Dean S, Kendall MJ, Potter S, Thompson MH, Jackson DA "Nadolol in combination with indapamide and xipamide in resistant hypertensives." Eur J Clin Pharmacol 28 (1985): 29-33. [PMID: 3987783]
13	Chrysant SG "Experience with terazosin administered in combination with other antihypertensive agents." Am J Med 80 (1986): 55-61. [PMID: 2872808]