Details of the Drug

General Information of Drug (ID: DMIJATC)

Drug Name

Benzphetamine

Synonyms

Benzaphetamine; Benzfetamina; Benzfetamine; Benzfetaminum; Benzofetamina; Benzphetaminum; Benzylamphetamine; Benzfetamina [DCIT]; Benzfetamina [Spanish]; Benzfetaminum [Latin]; U 0441; Benzfetamina [INN-Spanish]; Benzfetamine (INN); Benzfetamine [INN:BAN]; Benzfetaminum [INN-Latin]; Benzofetamina [INN-Spanish]; Benzphetaminum [INN-Latin]; D-Benzphetamine; Didrex (TN); N-Benzylmethamphetamin; N-Benzyl-N,alpha-dimethylphenethylamine; N,alpha-Dimethyl-N-(phenylmethyl)benzeneethanamine; D-N-Methyl-N-benzyl-beta-phenylisopropylamine; N,alpha-Dimethyl-N-(phenylmethyl)-benzeneethanamine; N-Benzyl-N-methyl-1-phenyl-2-propanamine; N-benzyl-N-methyl-1-phenylpropan-2-amine; N-methyl-1-phenyl-N-(phenylmethyl)propan-2-amine; Benzeneethanamine, N,alpha-dimethyl-N-(phenylmethyl)-, (+)-(9CI); (+)-N,alpha-dimethyl-N-(phenylmethyl)-benzeneethanamine; (+)-N-benzyl-N,alpha-dimethylphenethylamine; (+)-benzphetamine; (2S)-N-benzyl-N-methyl-1-phenylpropan-2-amine; (R,S)-N-Benzyl-alpha,N-dimethylphenethylamin; (S)-(+)-N-benzyl-N,alpha-dimethylphenethylamine; (S)-(+)-benzphetamine; (S)-benzphetamine; (alphaS)-N,alpha-dimethylphenethylamine

Indication

Disease Entry	ICD 11	Status	REF
Obesity	5B81	Approved	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

239.35

Logarithm of the Partition Coefficient (xlogp)

4.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Half-life: The concentration or amount of drug in body reduced by one-half in 16 - 31 hours [2]
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 10.44436 micromolar/kg/day [3]

Chemical Identifiers

Formula: C17H21N
IUPAC Name: (2S)-N-benzyl-N-methyl-1-phenylpropan-2-amine
Canonical SMILES: C[C@@H](CC1=CC=CC=C1)N(C)CC2=CC=CC=C2
InChI: InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1
InChIKey: YXKTVDFXDRQTKV-HNNXBMFYSA-N

Cross-matching ID

PubChem CID: 5311017
ChEBI ID: CHEBI:3044
CAS Number: 156-08-1
DrugBank ID: DB00865
TTD ID: D0T5UL
INTEDE ID: DR0198
ACDINA ID: D00063

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
N-methyl-D-aspartate receptor (NMDAR)	TT9IK2Z	NOUNIPROTAC	Antagonist	[4]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[5]
Cytochrome P450 2B6 (CYP2B6)	DEPKLMQ	CP2B6_HUMAN	Substrate	[6]
NADPH-cytochrome P450 reductase (CPR)	DE3N2FM	NCPR_HUMAN	Substrate	[7]
Docosahexaenoic acid omega-hydroxylase (CYP4F11)	DEIZLTN	CP4FB_HUMAN	Substrate	[8]

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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 Benzphetamine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Sodium bicarbonate	DMMU6BJ	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Benzphetamine caused by Sodium bicarbonate mediated altered urine pH.	Acidosis [5C73]	[9]
Tromethamine	DMOBLGK	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Benzphetamine caused by Tromethamine mediated altered urine pH.	Acidosis [5C73]	[9]
Methylene blue	DMJAPE7	Major	Increased risk of hyperpyrexia by the combination of Benzphetamine and Methylene blue.	Acquired methaemoglobinaemia [3A93]	[10]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Benzphetamine and Droxidopa.	Autonomic nervous system disorder [8D87]	[11]
Ethanol	DMDRQZU	Moderate	Additive CNS depression effects by the combination of Benzphetamine and Ethanol.	Cystitis [GC00]	[12]
Selegiline	DM6034S	Major	Increased risk of hyperpyrexia by the combination of Benzphetamine and Selegiline.	Depression [6A70-6A7Z]	[10]
Isocarboxazid	DMAF1NB	Major	Increased risk of hyperpyrexia by the combination of Benzphetamine and Isocarboxazid.	Depression [6A70-6A7Z]	[10]
Esketamine	DMVU687	Major	Additive hypertensive effects by the combination of Benzphetamine and Esketamine.	Depression [6A70-6A7Z]	[13]
SODIUM CITRATE	DMHPD2Y	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Benzphetamine caused by SODIUM CITRATE mediated altered urine pH.	Discovery agent [N.A.]	[9]
Procarbazine	DMIK367	Major	Increased risk of hyperpyrexia by the combination of Benzphetamine and Procarbazine.	Hodgkin lymphoma [2B30]	[10]
Didanosine	DMI2QPE	Moderate	Decreased absorption of Benzphetamine due to altered gastric pH caused by Didanosine.	Human immunodeficiency virus disease [1C60-1C62]	[14]
Sodium acetate anhydrous	DMH21E0	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Benzphetamine caused by Sodium acetate anhydrous mediated altered urine pH.	Hypo-osmolality/hyponatraemia [5C72]	[9]
Polyethylene glycol	DM4I1JP	Moderate	Increased risk of lowers seizure threshold by the combination of Benzphetamine and Polyethylene glycol.	Irritable bowel syndrome [DD91]	[15]
Glycerol phenylbutyrate	DMDGRQO	Moderate	Decreased metabolism of Benzphetamine caused by Glycerol phenylbutyrate mediated inhibition of CYP450 enzyme.	Liver disease [DB90-DB9Z]	[16]
Ozanimod	DMT6AM2	Major	Additive hypertensive effects by the combination of Benzphetamine and Ozanimod.	Multiple sclerosis [8A40]	[10]
Promethazine	DM6I5GR	Moderate	Antagonize the effect of Benzphetamine when combined with Promethazine.	Nausea/vomiting [MD90]	[17]
Bupropion	DM5PCS7	Major	Decreased metabolism of Benzphetamine caused by Bupropion mediated inhibition of CYP450 enzyme.	Nicotine use disorder [6C4A]	[18]
Rasagiline	DM3WKQ4	Moderate	Additive hypertensive effects by the combination of Benzphetamine and Rasagiline.	Parkinsonism [8A00]	[10]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Benzphetamine caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[19]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Benzphetamine caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[20]
Levomepromazine	DMIKFEL	Moderate	Antagonize the effect of Benzphetamine when combined with Levomepromazine.	Psychotic disorder [6A20-6A25]	[17]
Temsirolimus	DMS104F	Moderate	Increased plasma concentrations of Benzphetamine and Temsirolimus due to competitive inhibition of the same metabolic pathway.	Renal cell carcinoma [2C90]	[21]
Mesoridazine	DM2ZGAN	Moderate	Antagonize the effect of Benzphetamine when combined with Mesoridazine.	Schizophrenia [6A20]	[17]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Benzphetamine caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[22]
Sirolimus	DMGW1ID	Moderate	Increased plasma concentrations of Benzphetamine and Sirolimus due to competitive inhibition of the same metabolic pathway.	Transplant rejection [NE84]	[21]
Methdilazine	DMAUHQX	Moderate	Antagonize the effect of Benzphetamine when combined with Methdilazine.	Vasomotor/allergic rhinitis [CA08]	[17]
Trimeprazine	DMEMV9D	Moderate	Antagonize the effect of Benzphetamine when combined with Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[23]
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⏷ Show the Full List of 27 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
D&C red no. 30	E00456	3000709	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Calcium stearate	E00244	15324	lubricant
Crospovidone	E00626	Not Available	Disintegrant
FD&C red no. 3	E00629	Not Available	Colorant
Hexahydric alcohol	E00083	5780	Diluent; Flavoring agent; Humectant; Plasticizing agent
Hypromellose	E00634	Not Available	Coating agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Cellulose microcrystalline	E00698	Not Available	Adsorbent; Suspending agent; Diluent
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⏷ Show the Full List of 20 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Benzphetamine 50 mg tablet	50 mg	Oral Tablet	Oral
Benzphetamine 25 mg tablet	25 mg	Oral Tablet	Oral
Benzphetamine Hydrochloride 50mg tablet	50mg	Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3	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
4	Amphetamine inhibits the N-methyl-D-aspartate receptor-mediated responses by directly interacting with the receptor/channel complex. J Pharmacol Exp Ther. 2002 Mar;300(3):1008-16.
5	Identification of the human and animal hepatic cytochromes P450 involved in clonazepam metabolism. Fundam Clin Pharmacol. 1993;7(2):69-75.
6	Mechanistic analysis of the inactivation of cytochrome P450 2B6 by phencyclidine: effects on substrate binding, electron transfer, and uncoupling. Drug Metab Dispos. 2009 Apr;37(4):745-52.
7	On the mechanism of the inactivation of the major phenobarbital-inducible isozyme of rat liver cytochrome P-450 by chloramphenicol. J Biol Chem. 1985 Jul 15;260(14):8397-403.
8	Expression and characterization of human cytochrome P450 4F11: putative role in the metabolism of therapeutic drugs and eicosanoids. Toxicol Appl Pharmacol. 2004 Sep 15;199(3):295-304.
9	Anggard E, Jonsson LE, Hogmark AL, Gunne LM "Amphetamine metabolism in amphetamine psychosis." Clin Pharmacol Ther 14 (1973): 870-80. [PMID: 4729903]
10	Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
11	Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
12	Product Information. Suprenza (phentermine). Akrimax Pharmaceuticals, Cranford, NJ.
13	Cerner Multum, Inc. "Australian Product Information.".
14	Product Information. Adderall (amphetamine-dextroamphetamine) Shire Richwood Pharmaceutical Company, Florence, KY.
15	Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
16	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
17	Achor MB, Extein I "Diet aids, mania, and affective illness" Am J Psychiatry 138 (1981): 392. [PMID: 7468847]
18	Canadian Pharmacists Association.
19	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
20	Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
21	Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
22	Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.
23	Lake CR "Manic psychosis after coffee and phenylpropanolamine." Biol Psychiatry 30 (1991): 401-4. [PMID: 1912131]