PHENTERMINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H15N.ClH
Molecular Weight	185.6941
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(Cc1ccccc1)N.Cl

InChI

InChIKey=NCAIGTHBQTXTLR-UHFFFAOYSA-N

InChI=1S/C10H15N.ClH/c1-10(2,11)8-9-6-4-3-5-7-9;/h3-7H,8,11H2,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.4609
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C10H15N
Molecular Weight	149.2332
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00191
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/dosage/phentermine.html

Phentermine is an amphetamine that stimulates neurons to release or maintain high levels of a particular group of neurotransmitters known as catecholamines; these include dopamine and norepinephrine. High levels of these catecholamines tend to suppress hunger signals and appetite. The drug seems to inhibit reuptake of noradrenaline, dopamine, and seratonin through inhibition or reversal of the reuptake transporters. It may also inhibit MAO enzymes leaving more neurotransmitter available at the synapse. Phentermine (through catecholamine elevation) may also indirectly affect leptin levels in the brain. It is theorized that phentermine can raise levels of leptin which signal satiety. It is also theorized that increased levels of the catecholamines are partially responsible for halting another chemical messenger known as neuropeptide Y. This peptide initiates eating, decreases energy expenditure, and increases fat storage. Phentermine is indicated in the management of exogenous obesity as a short term (a few weeks) adjunct in a regimen of weight reduction based on caloric restriction. Phentermine hydrochloride is a sympathomimetic amine with pharmacologic activity similar to the prototype drugs of this class used in obesity, the amphetamines. Actions include central nervous system stimulation and elevation of blood pressure. Tachyphylaxis and tolerance have been demonstrated with all drugs of this class in which these phenomena have been looked for.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine transporter 92 Target ID: CHEMBL238 Sources: http://www.drugbank.ca/drugs/DB00191	Inhibitor 3315	0.31 µM [EC50]
Monoamine oxidase A 13 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11911838	Inhibitor 3315	498.0 µM [Ki]
Monoamine oxidase B 24 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11911838	Inhibitor 3315	375.0 µM [Ki]
Norepinephrine transporter 96 Target ID: CHEMBL222 Sources: http://www.drugbank.ca/drugs/DB00191	Inhibitor 3315

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 84 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/085128s065lbl.pdf	Primary		Approved 4033	ADIPEX-P Approved Use ADIPEX-P® is a sympathomimetic amine anorectic indicated as a short-term adjunct (a few weeks) in a regimen of weight reduction based on exercise, behavioral modification and caloric restriction in the management of exogenous obesity for patients with an initial body mass index ≥ 30 kg/m2, or ≥ 27 kg/m2 in the presence of other risk factors Launch Date -3.47241611E11

C_max

Value	Dose	Co-administered	Analyte	Population
44.78 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25668796	7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered: TOPIRAMATE	TOPIRAMATE	PHENTERMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
49.1 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: TOPIRAMATE	TOPIRAMATE	PHENTERMINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2057.33 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25668796	7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered: TOPIRAMATE	TOPIRAMATE	PHENTERMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2000 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: TOPIRAMATE	TOPIRAMATE	PHENTERMINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
20.63 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25668796	7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered: TOPIRAMATE	TOPIRAMATE	PHENTERMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
20 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: TOPIRAMATE	TOPIRAMATE	PHENTERMINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
82.5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: TOPIRAMATE	TOPIRAMATE	PHENTERMINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
37.5 mg 1 times / day single, oral Recommended Dose: 37.5 mg, 1 times / day Route: oral Route: single Dose: 37.5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202088Orig2s000MedR.pdf Page: nda/2012/202088Orig2s000MedR.pdf - p.12	healthy, 18 - 45 years old n = 17 Health Status: healthy Age Group: 18 - 45 years old Sex: M+F Population Size: 17 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202088Orig2s000MedR.pdf Page: nda/2012/202088Orig2s000MedR.pdf - p.12	Other AEs: Abdominal pain, Dizziness... Other AEs: Abdominal pain (6%) Dizziness (6%) Early satiety (6%) Intermittent headache (6%) Nausea (6%) Swollen lips (6%) Upper respiratory infection (6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202088Orig2s000MedR.pdf Page: nda/2012/202088Orig2s000MedR.pdf - p.12
37.5 mg 1 times / day single, oral Recommended Dose: 37.5 mg, 1 times / day Route: oral Route: single Dose: 37.5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202088Orig2s000MedR.pdf Page: nda/2012/202088Orig2s000MedR.pdf - p.12	healthy, 18 - 45 years old n = 17 Health Status: healthy Age Group: 18 - 45 years old Sex: M+F Population Size: 17 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202088Orig2s000MedR.pdf Page: nda/2012/202088Orig2s000MedR.pdf - p.12	Other AEs: Anorexia, Back pain... Other AEs: Anorexia (6%) Back pain (6%) Chapped lips (6%) Dry skin (6%) Dyspepsia (6%) Early satiety (6%) Irregular pulse (6%) Nausea (6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202088Orig2s000MedR.pdf Page: nda/2012/202088Orig2s000MedR.pdf - p.12
390 mg 1 times / day single, oral Studied dose Dose: 390 mg, 1 times / day Route: oral Route: single Dose: 390 mg, 1 times / day Sources: https://www.koreascience.or.kr/article/JAKO201429638663634.pdf	healthy, mean age 30 years n = 2 Health Status: healthy Age Group: mean age 30 years Sex: M+F Population Size: 2 Sources: https://www.koreascience.or.kr/article/JAKO201429638663634.pdf	Other AEs: Tachycardia, Hypertension... Other AEs: Tachycardia Hypertension Visual disorders NEC Nausea Insomnia Anxiety Sources: https://www.koreascience.or.kr/article/JAKO201429638663634.pdf
15 mg 1 times / day multiple, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Co-administed with:: topiramate(92 mg; 1/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000MedR.pdf Page: nda/2012/022580Orig1s000MedR.pdf - p.105	unhealthy, mean age 51.9 years n = 295 Health Status: unhealthy Condition: obesity Age Group: mean age 51.9 years Sex: M+F Population Size: 295 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000MedR.pdf Page: nda/2012/022580Orig1s000MedR.pdf - p.105	Disc. AE: Amnesia, Judgement impaired... Other AEs: Disorder sleep, Depression... AEs leading to discontinuation/dose reduction: Amnesia (0.3%) Judgement impaired (0.3%) Memory impairment (0.3%) Paraesthesia (0.3%) Depression (1%) Anxiety (0.3%) Vision blurred (0.3%) Eye pain (0.3%) Abdominal pain (0.3%) Tuberculosis skin test positive (0.3%) Nephrolithiasis (0.3%) Other AEs: Disorder sleep (12.9%) Depression (8.1%) Anxiety (9.5%) Cardiac arrhythmia (4.1%) Ischemic heart disease (1%) Disturbance in attention (3.1%) Memory impairment (2%) Cognitive disorders (1.4%) Language disorder (0.3%) Ocular disorders NEC (4.1%) Dyskinesias and movement disorders NEC (1.4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000MedR.pdf Page: nda/2012/022580Orig1s000MedR.pdf - p.105

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 753 substrate 882	inhibitor 825	inhibitor 894

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 725 CYP2E1 424		CYP 44

Drug as perpetrator

Target	Modality	Activity
CYP 82	inducer 772 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf#page=17 Page: 17.0	no
CYP1A2 805	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf#page=39 Page: 39.0	no
CYP2C9 851	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf#page=39 Page: 39.0	no
CYP2D6 908	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf#page=39 Page: 39.0	no
CYP2E1 467	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf#page=39 Page: 39.0	no
CYP3A4 920	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf#page=39 Page: 39.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 882	substrate 1689 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf#page=39 Page: 39,38	major		weak (co-administration study) Comment: In the presence of topiramate, phentermine Cmax and AUC0-inf increased 13 and 42%, respectively Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/022580Orig1s000ClinPharmR.pdf#page=39 Page: 39,38

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8080	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8080
ZINC	ZINC000008403947	http://zinc15.docking.org/substances/ZINC000008403947
eMolecules	1846375	https://www.emolecules.com/cgi-bin/more?vid=1846375

PubMed

Title	Date	PubMed
Detailed examination of fenfluramine-phentermine users with valve abnormalities identified in Fargo, North Dakota.	1999 Aug 1	10496440
Serial echocardiographic and clinical evaluation of valvular regurgitation before, during, and after treatment with fenfluramine or dexfenfluramine and mazindol or phentermine.	1999 Jul	10440587
Dose-effect of fenfluramine use on the severity of valvular heart disease among fen-phen patients with valvulopathy.	1999 Sep	10490797
[Obesity: principles of drug therapy].	2000 Aug	11026090
Complex vascular lesions at autopsy in a patient with phentermine-fenfluramin.	2000 Jun	10835505
A concise review on the therapeutics of obesity.	2000 Oct	11054601
Long-term pharmacotherapy of obesity 2000: a review of efficacy and safety.	2001 Aug 13-27	11493122
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.	2001 Jan	11071707
Pharmacologic options for the treatment of obesity.	2001 Jul 15	11471477
Fatal 4-MTA intoxication: development of a liquid chromatographic-tandem mass spectrometric assay for multiple matrices.	2001 Nov-Dec	11765028
Operation for anorexigen-associated valvular heart disease.	2001 Oct	11581595
High performance liquid chromatography with UV detection for the simultaneous determination of sympathomimetic amines using 4-(4,5-diphenyl-1H-imidazole-2-yl)benzoyl chloride as a label.	2001 Oct	11559922
Clinical and echocardiographic follow-up of patients previously treated with dexfenfluramine or phentermine/fenfluramine.	2001 Oct 24-31	11667938
Acute anorectic effect of single and combined drugs in mice using a non-deprivation protocol.	2001 Sep	11594445
The relationship between health-related quality of life and weight loss.	2001 Sep	11557837
Effects of anorexinogen agents on cloned voltage-gated K(+) channel hKv1.5.	2001 Sep	11504808
Pharmacotherapy of obesity: currently marketed and upcoming agents.	2002	14727970
Effect of fenfluramine-derivative diet pills on cardiac valves: a meta-analysis of observational studies.	2002 Dec	12486432
Pharmacological management of obesity.	2002 Dec	12472368
Morphology of anorexigen-associated valve disease by transthoracic and transesophageal echocardiography.	2002 Dec 1	12450616
Autopsy findings of heart and lungs in a patient with primary pulmonary hypertension associated with use of fenfluramine and phentermine.	2002 Feb	11834685
[Syncope - a systematic overview of classification, pathogenesis, diagnosis and management].	2002 Feb	11823926
Automated headspace solid-phase microextraction and in-matrix derivatization for the determination of amphetamine-related drugs in human urine by gas chromatography-mass spectrometry.	2002 Jan	11866382
Reversal of Phen-Fen associated valvular regurgitation documented by serial echocardiography.	2002 Jun	12050608
Effects on serotonin in rat hypothalamus of D-fenfluramine, aminorex, phentermine and fluoxetine.	2002 Jun 7	12065196
Prevalence of drug use in commercial tractor-trailer drivers.	2002 May	12051337
Enantiomeric separation of methamphetamine and related analogs by capillary zone electrophoresis: intelligence study in routine methamphetamine seizures.	2002 Nov	12455645
Anorexigen-induced cardiac valvulopathy and female gender.	2003 Apr	12628081
Noradrenergic modulation of ephedrine-induced hypophagia.	2003 Apr	12557268
Do these doctors give medicine a black eye?	2003 Dec	14733056
Ischemic colitis after weight-loss medication.	2003 Dec	14679420
Internet pharmacy prescription and phentermine overdose.	2003 Feb	12633132
Obesity drug pipeline not so fat.	2003 Feb 7	12574616
Risk of valvular heart disease associated with use of fenfluramine.	2003 Jun 11	12801402
The "steroid dementia syndrome": an unrecognized complication of glucocorticoid treatment.	2004 Dec	15677408
Pharmacological and surgical treatment of obesity.	2004 Jul	15526396
Relationship between collagen fibrils, glycosaminoglycans, and stress relaxation in mitral valve chordae tendineae.	2004 Jul	15298435
Pharmacotherapy for weight loss in adults with type 2 diabetes mellitus.	2005 Jan 25	15674929

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Weight Loss 15 to 37.5 mg orally once a day before breakfast or 1 to 2 hours after breakfast. Usual Pediatric Dose for Weight Loss 17 years or older: 15 to 37.5 mg orally once a day before breakfast or 1 to 2 hours after breakfast.

Route of Administration: Oral

In Vitro Use Guide

Phentermine inhibited serotonin-metabolizing (MAO-A) activity in rat lung, brain, and liver with K(i) values of 85-88 uM.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 20:55:53 UTC 2021` Edited by `admin` on `Fri Jun 25 20:55:53 UTC 2021`
Record UNII	0K2I505OTV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENTERMINE HYDROCHLORIDE

Common Name

English

PHENTERMINE HYDROCHLORIDE [MI]

Common Name

English

OBESTIN-30

Brand Name

English

PHENTERMINE HYDROCHLORIDE CIV

Common Name

English

PHENTERMINE HYDROCHLORIDE [VANDF]

Common Name

English

.ALPHA.,.ALPHA.-DIMETHYLPHENETHYLAMINE HYDROCHLORIDE

Systematic Name

English

FASTIN

Brand Name

English

QSYMIA COMPONENT PHENTERMINE HYDROCHLORIDE

Brand Name

English

PHENTERMINE HYDROCHLORIDE COMPONENT OF QSYMIA

Brand Name

English

PHENTERMINE HYDROCHLORIDE [WHO-DD]

Common Name

English

OBY-TRIM

Brand Name

English

PHENTERMINE HCL

Common Name

English

NSC-44090

Code

English

PHENTERMINE HYDROCHLORIDE [MART.]

Common Name

English

SUPRENZA

Brand Name

English

ADIPEX-P

Brand Name

English

PHENTERMINE HYDROCHLORIDE [USP-RS]

Common Name

English

ONA-MAST

Brand Name

English

TORA

Brand Name

English

PHENTERMINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

ZANTRYL

Brand Name

English

PHENTERMINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

BENZENEETHANAMINE, .ALPHA.,.ALPHA.-DIMETHYL-, HYDROCH

Common Name

English

WILPO

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29728