Identification

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Name
Phentermine
Accession Number
DB00191  (APRD00093)
Type
Small Molecule
Groups
Approved, Illicit
Description

Phentermine is a sympathomimetic amine anorectic agent and it was introduced in 1959 as part of an anti-obesity combination drug.[1, 2] It is chemically related to amphetamine and it is commonly referred to as an atypical amphetamine.[4] Phentermine has not been reported an addictive potential which allows this agent to be classified under the Schedule IV drugs (low abuse potential).[3]

Phentermine was FDA approved for short-term weight management in 1959 and it became widely used in 1960. This initial product, formed by the combination of phentermine with fenfluramine and dexfenfluramine was discontinued after finding several reports of abnormal valves in nearly 30% of the consumers.[6, 8] Later on, phentermine was approved alone and in combination with topiramate in 2012 as a new alternative that required lower doses of phentermine to obtain the desired effect.[5]

Structure
Thumb
Synonyms
  • alpha,alpha-Dimethylphenethylamine
  • Fentermina
  • Phentermine
  • Phentermine resin
  • Phenterminum
Product Ingredients
IngredientUNIICASInChI Key
Phentermine hydrochloride0K2I505OTV1197-21-3NCAIGTHBQTXTLR-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fastin Cap 30mgCapsule30 mgOralSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1993-12-311999-02-02Canada
IonaminCapsule15 mg/1OralUCB Manufacturing Inc1959-05-042006-04-01Us
IonaminCapsule30 mg/1OralUCB Manufacturing Inc1959-05-042007-01-01Us
IonaminCapsule15 mgOralSanofi Aventis1958-12-312007-10-17Canada
IonaminCapsule30 mgOralSanofi Aventis1958-12-312007-10-17Canada
Phentermine HydrochlorideTablet37.5 mg/1OralVintage Pharmaceuticals, LLC2007-01-262007-01-26Us
SuprenzaTablet, orally disintegrating37.5 mg/1OralAkrimax Pharmaceuticals, LLC2012-12-142018-09-30Us
SuprenzaTablet, orally disintegrating30 mg/1OralAkrimax Pharmaceuticals, LLC2012-12-142018-09-30Us
SuprenzaTablet, orally disintegrating15 mg/1OralAkrimax Pharmaceuticals, LLC2012-12-142018-09-30Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Adipex-PTablet37.5 mg/1OralPhysicians Total Care, Inc.2009-08-142013-06-30Us
Adipex-PTablet37.5 mg/1OralTeva Select Brands1990-09-30Not applicableUs
Adipex-PCapsule37.5 mg/1OralTeva Select Brands1990-09-30Not applicableUs57844 0019 01 nlmimage10 8445420a
Adipex-PTablet37.5 mg/1OralA-S Medication Solutions1990-09-302015-04-30Us50090 028420180907 15195 1xoz9m4
Adipex-PTablet37.5 mg/1OralPD-Rx Pharmaceuticals, Inc.1990-09-30Not applicableUs
Adipex-PTablet37.5 mg/1OralA S Medication Solutions1990-09-30Not applicableUs57844 0009 01 nlmimage10 95354aba
LomairaTablet8 mg/1Oralbryant ranch prepack2016-09-12Not applicableUs
LomairaTablet8 mg/1OralKVK-Tech, Inc.2016-09-12Not applicableUs
PhentermineCapsule15 mg/1OralA-S Medication Solutions2017-03-20Not applicableUs
PhentermineCapsule30 mg/1OralA-S Medication Solutions2017-03-20Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
QsymiaPhentermine hydrochloride (3.75 mg/1) + Topiramate (23 mg/1)Capsule, extended releaseOralVIVUS, Inc.2012-09-17Not applicableUs
QsymiaPhentermine hydrochloride (7.5 mg/1) + Topiramate (46 mg/1)Capsule, extended releaseOralVIVUS, Inc.2012-09-17Not applicableUs
QsymiaPhentermine hydrochloride (15 mg/1) + Topiramate (92 mg/1)Capsule, extended releaseOralVIVUS, Inc.2012-09-17Not applicableUs
QsymiaPhentermine hydrochloride (11.25 mg/1) + Topiramate (69 mg/1)Capsule, extended releaseOralVIVUS, Inc.2012-09-17Not applicableUs
International/Other Brands
Dapex (Fernidale Labs) / Duromine (iNova Pharmaceuticals) / Fastin (Hi-Tech Pharmaceuticals) / Obenix (Jones Pharma) / Obestin-30 (Fernidale Labs) / Oby-trim (Rexar) / Phentercot (Truven Health Analytics Inc) / Phentride (Truven Health Analytics Inc) / Umi-Pex (Fernidale Labs)
Categories
UNII
C045TQL4WP
CAS number
122-09-8
Weight
Average: 149.2328
Monoisotopic: 149.120449485
Chemical Formula
C10H15N
InChI Key
DHHVAGZRUROJKS-UHFFFAOYSA-N
InChI
InChI=1S/C10H15N/c1-10(2,11)8-9-6-4-3-5-7-9/h3-7H,8,11H2,1-2H3
IUPAC Name
2-methyl-1-phenylpropan-2-amine
SMILES
CC(C)(N)CC1=CC=CC=C1

Pharmacology

Indication

Phentermine is indicated, alone or in combination with topiramate, as a short-term adjunct, not pass a few weeks, in a regimen of weight reduction based on exercise, behavioral modifications and caloric restriction in the management of exogenous obesity for patients with an initial body mass index (BMI) greater than 30 kg/m2 or greater than 27 kg/m2 in presence of other risk factors such as controller hypertension, diabetes or hyperlipidemia.[Label]

Exogenous obesity is considered when the overweight is caused by consuming more food than the person activity level warrants. This condition commonly causes an increase in fat storage. It is an epidemic condition in the United States where over two-thirds of adults are overweight or obese and one in three Americans is obese. In the world, the incidence of obesity has nearly doubled.[7]

Associated Conditions
Pharmacodynamics

It is reported that the main mechanism of action of phentermine is the generation of appetite suppression, maybe due to the increase in leptin, but it is considered that other mechanisms should be involved.[4] Some reports have indicated that the weight loss effect is mainly due to the increase in resting energy expenditure.[3]

In clinical studies where phentermine was used as a monotherapy and as combination therapy, this drug has shown an average weight loss of 3.6 kg when compared with the placebo in 2-24 weeks. Patients treated with phentermine also showed increased maintenance of the weight after treatment discontinuation.[3] As well, even though it is a derivative of the amphetamines, it has not been registered to produce any of the effects of amphetamine such as central nervous system stimulation, elevation of blood pressure, tachyphylaxis or QTc prolongation.[4]

Mechanism of action

Phentermine is an indirect-acting sympathomimetic agent that acts by releasing noradrenaline from the presynaptic vesicles in the lateral hypothalamus. This increase in noradrenaline concentration in the synaptic cleft results in the stimulation of beta2-adrenergic receptors.[3] Phentermine is classified as an indirect sympathomimetic due to the increase in the level of norepinephrine, dopamine and its indirect effect towards serotonin.[10] Some reports have indicated that phentermine inhibits the neuropeptide Y which is a principal signaling pathway for the induction of hunger.[8] This combined effect produces a continuous flight-or-fight response in the body which reduces the hunger signal as this state is on the immediate need for energy.[8]

Lastly, some reports have indicated that phentermine is a weak inhibitor of monoamine oxidase but this mechanism does not tend to produce a clinically significant response.[9]

TargetActionsOrganism
ASodium-dependent noradrenaline transporter
inhibitor
Humans
ASodium-dependent serotonin transporter
inhibitor
Humans
ASodium-dependent dopamine transporter
inhibitor
Humans
AAmine oxidase [flavin-containing] A
antagonist
Humans
AAmine oxidase [flavin-containing] B
antagonist
Humans
APro-neuropeptide Y
inhibitor
Humans
Absorption

Phentermine shows a dose-dependent pharmacokinetic profile. After oral administration of a dose of 15 mg, the maximal concentration was achieved after 6 hours and its bioavailability was not affected by the consumption of high-fat meals.[4] The reported plasma concentration at steady-state is of around 200 ng/ml as observed in clinical trials.[9]

Volume of distribution

The reported volume of distribution for phentermine is reported to be of 5 L/kg.[11]

Protein binding

The protein binding of phentermine is determined to be of 17.5%.[4]

Metabolism

Phentermine undergoes minimal p-hydroxylation, N-oxidation and N-hydroxylation followed by conjugation. The total proportion of the drug that goes under metabolism only represents about 6% of the administered dose where about 5% is represented by the N-oxidized and N-Hydroxylated metabolites.[9]

Route of elimination

Phentermine is excreted mainly in the urine from which about 70-80% of the administered dose can be found as the unchanged drug.[4]

Half life

The mean terminal half-life of phentermine is reported to be of approximately 20 hours.[4] In conditions where there is acidic urine (pH <5), the elimination half-life is of 7-8 hours.[9]

Clearance

The reported clearance when administered orally is 8.79 L/h as observed in pharmacokinetic population studies.[13]

Toxicity

The reported LD50 after oral administration of phentermine in rats is reported to be of 151 mg/kg.[12] Reports of acute overdose include restlessness, tremors, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations and panic state followed by fatigue, and depression. In the cardiovascular system, there are reports of tachycardia, arrhythmia, hypertension, hypotension, circulatory collapse. In the GI tract, there are symptoms of nausea, vomiting, diarrhea and abdominal cramps. The management of acute overdosage includes symptomatic treatment as well as lavage and sedation with barbiturates.[Label]

On the other hand, chronic overdosage is marked by dermatoses, insomnia, irritability, hyperactivity and personality changes. In severe cases, it can derive into a schizophrenia-like psychosis.[Label]

Studies regarding the carcinogenic potential have not been performed. On the case of mutagenic assays, phentermine was shown to not be mutagenic nor clastogenic.[Label]

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Phentermine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Phentermine.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when Phentermine is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe therapeutic efficacy of 1-benzylimidazole can be decreased when used in combination with Phentermine.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Phentermine.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Phentermine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Phentermine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Phentermine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acidThe risk or severity of adverse effects can be increased when Phentermine is combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Phentermine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
Food Interactions
  • Limit caffeine intake.
  • Take without regard to meals.

References

General References
  1. Johnson DB, Quick J: Topiramate And Phentermine . [PubMed:29489234]
  2. Ryder JR, Kaizer A, Rudser KD, Gross A, Kelly AS, Fox CK: Effect of phentermine on weight reduction in a pediatric weight management clinic. Int J Obes (Lond). 2017 Jan;41(1):90-93. doi: 10.1038/ijo.2016.185. Epub 2016 Oct 24. [PubMed:27773937]
  3. Kiortsis DN: A review of the metabolic effects of controlled-release Phentermine/Topiramate. Hormones (Athens). 2013 Oct-Dec;12(4):507-16. [PubMed:24457398]
  4. Garvey WT: Phentermine and topiramate extended-release: a new treatment for obesity and its role in a complications-centric approach to obesity medical management. Expert Opin Drug Saf. 2013 Sep;12(5):741-56. doi: 10.1517/14740338.2013.806481. Epub 2013 Jun 6. [PubMed:23738843]
  5. Bersoux S, Byun TH, Chaliki SS, Poole KG: Pharmacotherapy for obesity: What you need to know. Cleve Clin J Med. 2017 Dec;84(12):951-958. doi: 10.3949/ccjm.84a.16094. [PubMed:29244650]
  6. Weigle DS: Pharmacological therapy of obesity: past, present, and future. J Clin Endocrinol Metab. 2003 Jun;88(6):2462-9. doi: 10.1210/jc.2003-030151. [PubMed:12788841]
  7. Adebonojo FO: Primary exogenous obesity. A conceptual classification. Clin Pediatr (Phila). 1974 Sep;13(9):715-8. doi: 10.1177/000992287401300901. [PubMed:4415200]
  8. May S. (2009). Weight-Loss Drugs. Chelsea House Publishers. [ISBN:978-1-60413-204-5]
  9. Barceloux D.G. (2012). Medical toxicology of drug abuse: Synthesized chemicals and psychoactive plants.. Wiley.
  10. EmpowerPharmacy [Link]
  11. Inchem [Link]
  12. FDA reports [Link]
  13. QSYMIA (phentermine/topiramate) FDA label [File]
External Links
Human Metabolome Database
HMDB0014337
KEGG Drug
D05458
KEGG Compound
C07438
PubChem Compound
4771
PubChem Substance
46508515
ChemSpider
4607
BindingDB
50246598
ChEBI
8080
ChEMBL
CHEMBL1574
Therapeutic Targets Database
DAP000719
PharmGKB
PA164748099
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Phentermine
ATC Codes
A08AA01 — Phentermine
FDA label
Download (306 KB)
MSDS
Download (48.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentBMI >30 kg/m2 / High Blood Pressure (Hypertension)1
1CompletedNot AvailableSubstance Abuse1
1CompletedTreatmentBMI >30 kg/m21
1CompletedTreatmentBinge Eating Disorder (BED) / Bulimia Nervosa (BN)1
1CompletedTreatmentHealthy Volunteers / Substance Abuse1
1CompletedTreatmentHepatic Impairment1
1CompletedTreatmentImpaired Renal Function1
1RecruitingBasic ScienceCocaine Use Disorders1
1WithdrawnBasic ScienceHealthy Volunteers / Substance Abuse1
2Active Not RecruitingTreatmentBariatric Surgery Procedures / BMI >30 kg/m2 / Metabolic Surgery / Obese experiencing rapid weight loss1
2CompletedTreatmentBMI >27 kg/m2 / BMI >30 kg/m21
2CompletedTreatmentBMI >30 kg/m21
2CompletedTreatmentBMI >30 kg/m2 / Heart Diseases / Vascular Diseases1
2CompletedTreatmentBinge Eating Disorder (BED)1
2CompletedTreatmentDiabetes Mellitus (DM)1
3CompletedTreatmentBMI >30 kg/m22
3RecruitingTreatmentBMI >30 kg/m21
3RecruitingTreatmentBMI >30 kg/m2 / Polycystic Ovaries Syndrome1
4Active Not RecruitingTreatmentBMI >30 kg/m21
4CompletedTreatmentBMI >30 kg/m23
4CompletedTreatmentObesity, Childhood / Pediatric Obesity1
4RecruitingTreatmentBMI >30 kg/m2 / Non-alcoholic Fatty Liver / Obese experiencing rapid weight loss / Obesity, Morbid / Post-gastrointestinal bypass surgery1
4Unknown StatusNot AvailableBMI >30 kg/m21
Not AvailableCompletedBasic ScienceBMI >27 kg/m2 / BMI >30 kg/m2 / Metabolic Diseases1
Not AvailableWithdrawnTreatmentBMI >30 kg/m21

Pharmacoeconomics

Manufacturers
  • Baxter healthcare corp anesthesia critical care
  • Teva pharmaceuticals usa inc
  • Glaxosmithkline
  • Ferndale laboratories inc
  • Shire richwood inc
  • Mm mast and co
  • Abc holding corp
  • Able laboratories inc
  • Actavis totowa llc
  • Barr laboratories inc
  • Camall co inc
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Ivax pharmaceuticals inc
  • Kvk tech inc
  • Lannett co inc
  • Lannett holdings inc
  • Mutual pharmaceutical co inc
  • Sandoz inc
  • Tg united inc
  • Tg united labs llc
  • Usl pharma inc
  • Vitarine pharmaceuticals inc
  • Watson laboratories inc
  • Actavis elizabeth llc
  • Caraco pharmaceutical laboratories ltd
  • Vintage pharmaceuticals inc
  • Solvay pharmaceuticals
  • Ucb inc
  • Quantum pharmics ltd
Packagers
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Blenheim Pharmacal
  • Bryant Ranch Prepack
  • C.O. Truxton Inc.
  • Calvin Scott and Co. Inc.
  • Caraco Pharmaceutical Labs
  • Carlisle Laboratories Inc.
  • Corepharma LLC
  • Darby Dental Supply Co. Inc.
  • DispenseXpress Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • EMS Acquisition Corp.
  • Eon Labs
  • Gate Pharmaceuticals
  • H.J. Harkins Co. Inc.
  • Keltman Pharmaceuticals Inc.
  • Kraft Pharmaceutical Co. Inc.
  • KVK-Tech Inc.
  • Lake Erie Medical and Surgical Supply
  • Lannett Co. Inc.
  • Macnary Ltd.
  • Major Pharmaceuticals
  • MCR American Pharmaceuticals Inc.
  • Medisca Inc.
  • Mutual Pharmaceutical Co.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharma Pac LLC
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Qualitest
  • Quality Research Pharmaceutical Inc.
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Superior Pharmeceuticals
  • Teva Pharmaceutical Industries Ltd.
  • UCB Pharma
  • United Research Laboratories Inc.
  • Vintage Pharmaceuticals Inc.
Dosage forms
FormRouteStrength
CapsuleOral30 mg
CapsuleOral15 mg
TabletOral8 mg/1
CapsuleOral15 mg/1
CapsuleOral30 mg/1
CapsuleOral37.5 mg/1
TabletOral30 mg/1
Capsule, extended releaseOral15 mg/1
Capsule, extended releaseOral30 mg/1
TabletOral37.5 mg/1
Capsule, extended releaseOral
Tablet, orally disintegratingOral15 mg/1
Tablet, orally disintegratingOral30 mg/1
Tablet, orally disintegratingOral37.5 mg/1
Prices
Unit descriptionCostUnit
Phentermine hcl powder10.71USD g
Ionamin 30 mg capsule sa2.87USD capsule
Adipex-P 37.5 mg capsule2.2USD capsule
Adipex-p 37.5 mg tablet2.15USD tablet
Phentermine 37.5 mg tablet1.54USD tablet
Phentermine HCl 15 mg capsule1.18USD capsule
Phentermine HCl 30 mg capsule1.17USD capsule
Ionamin 15 mg capsule sa1.15USD capsule
Phentermine HCl 37.5 mg capsule1.0USD capsule
Phentermine HCl 37.5 mg tablet1.0USD tablet
Phentermine 8 mg tablet0.54USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6071537No2000-06-062017-06-23Us
US8895057No2014-11-252028-06-09Us
US7056890No2006-06-062020-06-14Us
US7553818No2009-06-302020-06-14Us
US7659256No2010-02-092020-06-14Us
US7674776No2010-03-092020-06-14Us
US8580299No2013-11-122029-06-14Us
US9011906No2015-04-212028-06-09Us
US9011905No2015-04-212028-06-09Us
US8895058No2014-11-252028-06-09Us
US8580298No2013-11-122029-05-15Us
US6149938No2000-11-212018-07-23Us
US8440170No2013-05-142029-03-14Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)205 °C'MSDS'
boiling point (°C)206 ºCBarceloux D. (2012). Medical Toxicology of Drug Abuse.
water solubility18.6 g/LGravey W. (2013). Expert Opin Drug Saf.
logP1.90Barceloux D. (2012). Medical Toxicology of Drug Abuse.
pKa9.84Suprenza - package insert. (2014)
Predicted Properties
PropertyValueSource
Water Solubility0.757 mg/mLALOGPS
logP2.32ALOGPS
logP2.08ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)10.25ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.34 m3·mol-1ChemAxon
Polarizability17.87 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9964
Blood Brain Barrier+0.959
Caco-2 permeable+0.7688
P-glycoprotein substrateNon-substrate0.6477
P-glycoprotein inhibitor INon-inhibitor0.934
P-glycoprotein inhibitor IINon-inhibitor0.9801
Renal organic cation transporterNon-inhibitor0.8236
CYP450 2C9 substrateNon-substrate0.8411
CYP450 2D6 substrateSubstrate0.7204
CYP450 3A4 substrateNon-substrate0.6493
CYP450 1A2 substrateNon-inhibitor0.7962
CYP450 2C9 inhibitorNon-inhibitor0.8861
CYP450 2D6 inhibitorInhibitor0.7825
CYP450 2C19 inhibitorNon-inhibitor0.8996
CYP450 3A4 inhibitorNon-inhibitor0.7348
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8782
Ames testNon AMES toxic0.9681
CarcinogenicityNon-carcinogens0.6949
BiodegradationNot ready biodegradable0.9303
Rat acute toxicity2.8400 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9867
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.33 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-9100000000-7037d3f1fad22de72c33
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ue9-0900000000-f2eb273dfd0ec45869c5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-2900000000-f527ee48b9e2784c178c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0159-4900000000-548f73a83354267c9f81
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-c7ab0aa268d14ae3da39
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1900000000-ce1c08c021fbc1cc5c8c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-2900000000-94b2b38953d359938c0a
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Aralkylamines / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Amphetamine or derivatives / Phenylpropane / Aralkylamine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Primary amine / Organonitrogen compound / Primary aliphatic amine / Amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
primary amine (CHEBI:8080)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Stephens LC, Katz SG: Phentermine and anaesthesia. Anaesth Intensive Care. 2005 Aug;33(4):525-7. [PubMed:16119498]
  4. Samanin R, Garattini S: Neurochemical mechanism of action of anorectic drugs. Pharmacol Toxicol. 1993 Aug;73(2):63-8. [PubMed:7902561]
  5. Proietto J, Fam BC, Ainslie DA, Thorburn AW: Novel anti-obesity drugs. Expert Opin Investig Drugs. 2000 Jun;9(6):1317-26. [PubMed:11060745]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. John CE, Jones SR: Voltammetric characterization of the effect of monoamine uptake inhibitors and releasers on dopamine and serotonin uptake in mouse caudate-putamen and substantia nigra slices. Neuropharmacology. 2007 Jun;52(8):1596-605. Epub 2007 Mar 16. [PubMed:17459426]
  2. Johnson GJ, Leis LA, Dunlop PC, Weir EK: The effect of the anorectic agent, d-fenfluramine, and its primary metabolite, d-norfenfluramine, on intact human platelet serotonin uptake and efflux. J Thromb Haemost. 2003 Dec;1(12):2663-8. [PubMed:14675103]
  3. Mekontso-Dessap A, Brouri F, Pascal O, Lechat P, Hanoun N, Lanfumey L, Seif I, Benhaiem-Sigaux N, Kirsch M, Hamon M, Adnot S, Eddahibi S: Deficiency of the 5-hydroxytryptamine transporter gene leads to cardiac fibrosis and valvulopathy in mice. Circulation. 2006 Jan 3;113(1):81-9. Epub 2005 Dec 27. [PubMed:16380550]
  4. Rothman RB, Ayestas MA, Dersch CM, Baumann MH: Aminorex, fenfluramine, and chlorphentermine are serotonin transporter substrates. Implications for primary pulmonary hypertension. Circulation. 1999 Aug 24;100(8):869-75. [PubMed:10458725]
  5. Zolkowska D, Rothman RB, Baumann MH: Amphetamine analogs increase plasma serotonin: implications for cardiac and pulmonary disease. J Pharmacol Exp Ther. 2006 Aug;318(2):604-10. Epub 2006 Apr 27. [PubMed:16644904]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. John CE, Jones SR: Voltammetric characterization of the effect of monoamine uptake inhibitors and releasers on dopamine and serotonin uptake in mouse caudate-putamen and substantia nigra slices. Neuropharmacology. 2007 Jun;52(8):1596-605. Epub 2007 Mar 16. [PubMed:17459426]
  2. Gruner JA, Marcy VR, Lin YG, Bozyczko-Coyne D, Marino MJ, Gasior M: The roles of dopamine transport inhibition and dopamine release facilitation in wake enhancement and rebound hypersomnolence induced by dopaminergic agents. Sleep. 2009 Nov;32(11):1425-38. [PubMed:19928382]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Rothman RB: Is phentermine an inhibitor of monoamine oxidase? A critical appraisal. Synapse. 1999 May;32(2):141-5. [PubMed:10231134]
  2. Ulus IH, Maher TJ, Wurtman RJ: Characterization of phentermine and related compounds as monoamine oxidase (MAO) inhibitors. Biochem Pharmacol. 2000 Jun 15;59(12):1611-21. [PubMed:10799660]
  3. Kilpatrick IC, Traut M, Heal DJ: Monoamine oxidase inhibition is unlikely to be relevant to the risks associated with phentermine and fenfluramine: a comparison with their abilities to evoke monoamine release. Int J Obes Relat Metab Disord. 2001 Oct;25(10):1454-8. [PubMed:11673765]
  4. Nandigama RK, Newton-Vinson P, Edmondson DE: Phentermine inhibition of recombinant human liver monoamine oxidases A and B. Biochem Pharmacol. 2002 Mar 1;63(5):865-9. [PubMed:11911838]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Rothman RB: Does phentermine inhibit monoamine oxidase? Lancet. 1999 Apr 17;353(9161):1362-3. [PubMed:10218558]
  2. Rothman RB: Is phentermine an inhibitor of monoamine oxidase? A critical appraisal. Synapse. 1999 May;32(2):141-5. [PubMed:10231134]
  3. Ulus IH, Maher TJ, Wurtman RJ: Characterization of phentermine and related compounds as monoamine oxidase (MAO) inhibitors. Biochem Pharmacol. 2000 Jun 15;59(12):1611-21. [PubMed:10799660]
  4. Kilpatrick IC, Traut M, Heal DJ: Monoamine oxidase inhibition is unlikely to be relevant to the risks associated with phentermine and fenfluramine: a comparison with their abilities to evoke monoamine release. Int J Obes Relat Metab Disord. 2001 Oct;25(10):1454-8. [PubMed:11673765]
  5. Nandigama RK, Newton-Vinson P, Edmondson DE: Phentermine inhibition of recombinant human liver monoamine oxidases A and B. Biochem Pharmacol. 2002 Mar 1;63(5):865-9. [PubMed:11911838]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Receptor binding
Specific Function
NPY is implicated in the control of feeding and in secretion of gonadotrophin-release hormone.
Gene Name
NPY
Uniprot ID
P01303
Uniprot Name
Pro-neuropeptide Y
Molecular Weight
10851.29 Da
References
  1. May S. (2009). Weight-Loss Drugs. Chelsea House Publishers. [ISBN:978-1-60413-204-5]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. QSYMIA (phentermine/topiramate) FDA label [File]

Drug created on June 13, 2005 07:24 / Updated on April 13, 2019 21:04