Details of the Drug

General Information of Drug (ID: DMTFK3O)

Drug Name

Phenylpropanolamine

Synonyms

Norephedrine; phenylpropanolamine; Rhindecon; dl-Norephedrine; (+)-Norephedrine; Propagest; Dexatrim; Mucron; d-Norephedrine; Propadrine; 1r,2s-phenylpropylamine; Super Odrinex; 14838-15-4; (1S,2R)-2-amino-1-phenylpropan-1-ol; Fenilpropanolamina; dl-1-Phenyl-2-aminopropanol-1; UNII-7875H6443P; Phenylpropanolaminum; (+-)-Norephedrin; dl-Phenylpropanolamine; dl-2-Amino-1-hydroxy-1-phenylpropane; CHEBI:36; Naldecon; Cathinum [INN-Latin]; (+-)-Phenylpropanolamine; NSC9920; DLNKOYKMWOXYQA-VXNVDRBHSA-N; 37577-28-9; Cathina [INN-Spanish]; Acutrim; Cathina; Cathine; Cathinum; Codimal; Conex; Contuss; Despec; Exponcit; Fansia; Fugoa; Gentab; Guaipax; Katine; Minusine; Mydriatin; Myminic; Nolex; Norpseudoephedrine; Partuss; Phenoxine; Phenyldrine; Phenylfenesin; Phenylpropanolamina; Pseudonorephedrine; Rhymed; Snaplets; ULR; Vanex; Cathine [INN]; Fugoa Depot; Ami-Tex; D-Norpseudoephedrine; Dl-Norephedrine; Dura-Vent; Fansia (TN); L-Norephedrine; Proin (TN); Propalin (TN); Psi-Norephedrine; TAVIST-D; USAF CS-6; D-Nor-psi-ephedrine; L-Nor-psi-ephedrin; L-Nor-psi-ephedrine; D-(+)-Norephedrine; L-(-)-Norephedrine; (+-)-Norephedrine; (+/-)-Norephedrin; (+/-)-Norephedrine; (-)-Norephedrin; (-)-Norephedrine; (1R,2S)-Norephedrine

Indication

Disease Entry	ICD 11	Status	REF
Allergic rhinitis	CA08.0	Approved	[1]
Common cold	CA00	Approved	[1]
Cough	MD12	Approved	[1]
Rhinitis	FA20	Approved	[1]
Seasonal allergic rhinitis	CA08.01	Approved	[1]
Vasomotor/allergic rhinitis	CA08	Approved	[1]
Obesity	5B81	Withdrawn from market	[2]
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Therapeutic Class

Appetite Depressants

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

151.21

Logarithm of the Partition Coefficient (xlogp)

0.8

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability: 95% of drug becomes completely available to its intended biological destination(s) [4]
Elimination: 65% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 2.1 - 3.4 hours [5]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 15.2219 micromolar/kg/day [6]

Chemical Identifiers

Formula: C9H13NO
IUPAC Name: (1S,2R)-2-amino-1-phenylpropan-1-ol
Canonical SMILES: C[C@H]([C@H](C1=CC=CC=C1)O)N
InChI: InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m1/s1
InChIKey: DLNKOYKMWOXYQA-VXNVDRBHSA-N

Cross-matching ID

PubChem CID: 26934
ChEBI ID: CHEBI:36
CAS Number: 37577-28-9
DrugBank ID: DB00397
TTD ID: D09JXM

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adrenergic receptor Alpha-1 (ADRA1)	TTG28O6	NOUNIPROTAC	Agonist	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Methylene blue	DMJAPE7	Major	Increased risk of hyperpyrexia by the combination of Phenylpropanolamine and Methylene blue.	Acquired methaemoglobinaemia [3A93]	[8]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Phenylpropanolamine and Droxidopa.	Autonomic nervous system disorder [8D87]	[9]
Linezolid	DMGFPU2	Major	Additive hypertensive effects by the combination of Phenylpropanolamine and Linezolid.	Bacterial infection [1A00-1C4Z]	[10]
Selegiline	DM6034S	Major	Increased risk of hyperpyrexia by the combination of Phenylpropanolamine and Selegiline.	Depression [6A70-6A7Z]	[8]
Isocarboxazid	DMAF1NB	Major	Increased risk of hyperpyrexia by the combination of Phenylpropanolamine and Isocarboxazid.	Depression [6A70-6A7Z]	[8]
Phenelzine	DMHIDUE	Major	Additive hypertensive effects by the combination of Phenylpropanolamine and Phenelzine.	Depression [6A70-6A7Z]	[8]
Ergotamine	DMKR3C5	Major	Additive hypertensive effects by the combination of Phenylpropanolamine and Ergotamine.	Headache [8A80-8A84]	[11]
Procarbazine	DMIK367	Major	Increased risk of hyperpyrexia by the combination of Phenylpropanolamine and Procarbazine.	Hodgkin lymphoma [2B30]	[8]
Polyethylene glycol	DM4I1JP	Moderate	Increased risk of lowers seizure threshold by the combination of Phenylpropanolamine and Polyethylene glycol.	Irritable bowel syndrome [DD91]	[12]
Ozanimod	DMT6AM2	Moderate	Increased risk of hyperpyrexia by the combination of Phenylpropanolamine and Ozanimod.	Multiple sclerosis [8A40]	[8]
Prochlorperazine	DM53SRA	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Prochlorperazine.	Nausea/vomiting [MD90]	[13]
Promethazine	DM6I5GR	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Promethazine.	Nausea/vomiting [MD90]	[13]
Bupropion	DM5PCS7	Major	Increased risk of lowers seizure threshold by the combination of Phenylpropanolamine and Bupropion.	Nicotine use disorder [6C4A]	[14]
Rasagiline	DM3WKQ4	Moderate	Additive hypertensive effects by the combination of Phenylpropanolamine and Rasagiline.	Parkinsonism [8A00]	[8]
Lindane	DMB8CNL	Moderate	Increased risk of lowers seizure threshold by the combination of Phenylpropanolamine and Lindane.	Pediculosis [1G00]	[15]
Ergonovine	DM0VEC1	Major	Additive hypertensive effects by the combination of Phenylpropanolamine and Ergonovine.	Postpartum haemorrhage [JA43]	[11]
Levomepromazine	DMIKFEL	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Levomepromazine.	Psychotic disorder [6A20-6A25]	[16]
Fluphenazine	DMIT8LX	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Fluphenazine.	Psychotic disorder [6A20-6A25]	[13]
Mesoridazine	DM2ZGAN	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Mesoridazine.	Schizophrenia [6A20]	[16]
Thioridazine	DM35M8J	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Thioridazine.	Schizophrenia [6A20]	[16]
Haloperidol	DM96SE0	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Haloperidol.	Schizophrenia [6A20]	[13]
Perphenazine	DMA4MRX	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Perphenazine.	Schizophrenia [6A20]	[13]
Chlorpromazine	DMBGZI3	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Chlorpromazine.	Schizophrenia [6A20]	[13]
Trifluoperazine	DMKBYWI	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Trifluoperazine.	Schizophrenia [6A20]	[13]
Methdilazine	DMAUHQX	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Methdilazine.	Vasomotor/allergic rhinitis [CA08]	[16]
Trimeprazine	DMEMV9D	Moderate	Antagonize the effect of Phenylpropanolamine when combined with Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[16]
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References

1	Phenylpropanolamine FDA Label
2	Pharmacotherapy for obesity. Drugs. 2005;65(10):1391-418.
3	BDDCS applied to over 900 drugs
4	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	Synthesis and structure-activity studies on N-[5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an imidazole-containing alpha(1A)-adrenoceptor agonist. J Med Chem. 2004 Jun 3;47(12):3220-35.
8	Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
9	Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
10	Hendershot PE, Antal EJ, Welshman IR, Batts DH, Hopkins NK "Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr." J Clin Pharmacol 41 (2001): 563-72. [PMID: 11361053]
11	Barthel W, Glusa E, Koth W "Interactions of dihydroergotamine with etilefrine in human leg veins in vitro and in situ." Int J Clin Pharmacol Ther Toxicol 25 (1987): 63-9. [PMID: 2881898]
12	Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
13	Achor MB, Extein I "Diet aids, mania, and affective illness" Am J Psychiatry 138 (1981): 392. [PMID: 7468847]
14	Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA.
15	Matsuoka LY "Convulsions following application of gamma benzene hexachloride." J Am Acad Dermatol 5 (1981): 98-9. [PMID: 6168673]
16	Lake CR "Manic psychosis after coffee and phenylpropanolamine." Biol Psychiatry 30 (1991): 401-4. [PMID: 1912131]